Judd Apatow On Comedy, Creativity, And Embracing Your Inner Weirdo

One of the most acclaimed filmmakers of his generation, today Judd Apatow graces the podcast to discuss his fascinating perspective on filmmaking, storytelling, creativity, and more. From directing This Is 40, Knocked Up, and The 40-Year-Old Virgin, to serving as producer for Anchorman and executive producer for Freaks and Geeks, Judd has made an indelible mark on Hollywood. Today we unpack the experiences, philosophies, and strategies that have shaped him into the unparalleled creator he is today. We explore his creative process, his approach to storytelling, the lessons he’s learned from working with some of the biggest names in the business, and how he pays it forward. This conversation left me with a newfound appreciation of comedy not only as an art form—but as a powerful means of grappling with the complexities of the human experience. I hope you enjoy this one as much as I did. Show notes + MORE Watch on Youtube Newsletter Sign-Up Today’s Sponsors: BetterHelp: BetterHelp.com/RICHROLL Timeline Nutrition: Timelinenutrition.com/RICHROLL Momentous: LiveMomentous.com/RICHROLL Babbel: Babbel.com/RICHROLL Whoop: WHOOP.com Plant Power Meal Planner: https://meals.richroll.com Peace + Plants, Learn more about your ad choices. Visit podcastchoices.com/adchoices

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

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• 1:13Rich Roll?

  The Rich Roll Podcast.

• 1:17Speaker 01

  You can't think yourself into writing, but you can write yourself into thinking. So just start.

• 1:24Speaker 02

  Emmy-winning writer, producer, director Judd Apatow. The man behind almost at least half of the funny movies and TV shows you've seen this century.

• 1:32Rich Roll?

  Looking at your IMDb, I mean, it's 100 miles long. From where you sit right now, do you reflect back on it and think, "My life is a dream"?

• 1:40Speaker 01

  I moved to LA and I met all the other people in comedy. Adam Sandler and Rob Schneider and David Spade and Jim Carrey. And that was our world and our crew back then. It was like running a race with all your friends. People are interested in the struggles of people that we're all struggling. We root for people to do better because we're trying to do better. How do you survive high school? How do you survive having a baby? How do you make your marriage work? You have to be willing to be vulnerable and put yourself out there. The greatest gift you can give people is your story.

• 2:14Rich Roll?

  I've got a couple more things I would very much like to mention before we dig into this one, but first.

• 2:24Rich Roll?

  One of the most acclaimed screenwriters, filmmakers, and comedic minds of his generation, today Judd Apatow joins the podcast to share his experience and wisdom on filmmaking, on storytelling, comedy, creativity, mentorship, parenting, and basically, life. Over the course of his much storied career, Judd has worked alongside some of the industry's brightest stars, helping to catapult their careers to new heights. His ability to identify and nurture talent is unmatched, and his keen eye for storytelling has made him a sought-after mentor and creative collaborator. Judd has also made a significant impact as a documentary filmmaker, a stand-up comedian,

• 3:08Rich Roll?

  and as an advocate for many causes, including mental health awareness. He fearlessly explores the human condition, often shining a light on the poignant and vulnerable aspects of our lives with his trademark blend of humor and honesty. So today, we unpack the experiences, philosophies, and strategies that have shaped Judd into the unparalleled force he is today. We explore his creative process, his approach to storytelling, the lessons he's learned from working with some of the biggest names in the business, and how he pays it forward. Not gonna lie, this one was a thrill. I hope you enjoy it as much as I did. So, without further ado, this is me and Judd Apatow.

• 3:53Rich Roll?

  Super nice to meet you. Thank you for making the time to do this, inviting me into your beautiful offices here. Just for, you know, the person who's listening or watching, who has a creative impulse, and they feel like they have something to say, or there's something deep in them that feels like they want to express, an emotion, a thought, a story, how do you speak to that person who is trying to, you know, bring forth some expression into the world?

• 4:22Speaker 01

  I mean, I I struggle with it too. I mean, I think the best advice is, you know, writers write, you just gotta write. You have to be willing to throw it out. You have to be willing to do it just for yourself. And everybody is interesting. It took me a long time to think anything about me was interesting. I always wrote for for people like Jim Carrey, who were seemed fascinating. And I always thought, God, I'm so boring. What about this life is interesting? And then when I finally realized, maybe what I'm going through is interesting, my career completely took off. The moment I just accepted that, like the forty old virgin, it's just an expression of my own anxieties. And people

• 5:04Speaker 01

  really connected with it. So you have to have some confidence that your story is interesting. You know, someone said, you know, the greatest gift you can give people is your story. And that was a big thing for me, because I really thought, who the hell wants my story? And so you have to be willing to be vulnerable and put yourself out there. I mean, there's a lot of work that you have to do. But you have to do the same thing that I do every day, which is, can I just let it go? Just see what comes out of me? And, you know, there's simple things that are really helpful. You know, one is from, what is her name? She has that book, Bird by Bird.

• 5:45Rich Roll?

  Oh, Anne Lamott.

• 5:47Speaker 01

  Anne Lamott. And she has, she had the line in one of her books where she said, it's a down up theory. You got to get it down, then fix it up. George Saunders said a version of that, which is, you know, I can write a really mediocre short story, but give me five years to punch it up, and it'll be great. You know, you have to just like, see what comes out, and trust that. And then you you switch gears. Like, for me, creativity is always, there's one mode, which is spewing, and then one mode, which is assessing and editing. And you can't do it at the same time. And I think a lot of people, the reason why they're not creative is they try to do it at the same time. They're judging every sentence as it's coming out. And you have to just kind of blow it all out. And then

• 6:28Speaker 01

  the next day, look at it and go, what's of value here? And I feel like that's maybe the most important lesson that I've learned.

• 6:38Rich Roll?

  Yeah, beautifully put. I mean, I think even the precursor to that, the thought that I don't have anything worth saying, or my life isn't interesting enough. Like overcoming that hurdle to even get to the point where you're sitting down, ready to write anything down and understanding that your experience has value. You know, the specific is the universal, like the more specific you are about it, the more opportunity there is to connect with something universally human about all of us. And, you know, you, growing up in suburban, you know, Long Island and having the experiences that you had and the fact that you, you know, kind of had to go to war with yourself

• 7:19Rich Roll?

  over the value of your own experience is, I think, interesting and instructional and inspirational that you had to do that for yourself to get to that place of like freedom to express.

• 7:33Speaker 01

  Yeah, it took a long time. And I worked with people who did it, like Shanling and Paul Feig on Freaks and Geeks. And on Freaks and Geeks, I started pitching some more personal stuff and I saw that those scenes were good.

• 7:44Rich Roll?

  Yeah.

• 7:45Speaker 01

  I wrote a lot of stuff about divorce on the show and Bill's mom dating the gym teacher and Neil's obsession with ventriloquism as a way to deal with his parents divorce. You know, and I saw, oh, that stuff seems to be working and it's small. I mean, even like, if you think of like the moment you first tried to kiss a girl, is there anything more dramatic than that? But we all have that moment.

• 8:07Rich Roll?

  Right.

• 8:08Speaker 01

  And all these moments are, can be fascinating. I mean, I think a lot of my best work is just, someone's pregnant, what do we do? I mean, they're not, it's not Ghostbusters.

• 8:19Rich Roll?

  Right.

• 8:19Speaker 01

  It's, it's just the simplest thing.

• 8:22Rich Roll?

  In Recovery, there's a saying, like, the facts of someone else's experiences may be different, but the kind of emotional landscape, the emotions are what, you know, you can connect with when people share their stories, et cetera. And even if you think, and you were talking about this with respect to a 40-year-old virgin, like, it's really a story about, like, Shame and guilt, you know, which is something most people can connect with in various ways. And it's draped on this very heightened story about this extreme character. But part of the reason why I think it's a big hit is because beneath the surface, it's grappling with something that everybody can relate to.

• 9:03Speaker 01

  Yeah, it's about, am I lovable? Am I a freak? And how that can get enlarged and shut down your whole life. So when we started writing that, Steve Kral and I, we said, let's just write it real. Like, what would this feel like? How would it have happened if you tried to face it? And you didn't know how? What disasters would happen along the way? But that is why people connect to it, because Steve does such a good job being really honest about how scared he is to be found out. And that there's no way at the end of the day, you would want to be with him. And I think everybody on some level has that voice.

• 9:42Rich Roll?

  If he really knew what I was like, you would run.

• 9:46Speaker 01

  Yes. And then at the end, he says, I'm a virgin. I always have been.

• 9:54Rich Roll?

  I am having, I will admit, like in a moment of vulnerability to begin this, I'm having a little bit of an outer body experience. You're somebody who's like been in my life, you know, in a parasocial way for, you know, and I'm sure you have this experience a lot. So it's, you know, it's meaningful for me to meet you and for you to be open to doing this. And it happens to be occurring on an important day for me because 25 years ago, this day, I was like broken and on my way to rehab and thinking like my life was completely over. And so I'm very present at the moment, reflecting back on this arc that I've been on.

• 10:32Speaker 01

  Congratulations.

• 10:33Rich Roll?

  And so to be sitting with you here today is sort of a punctuation mark on that, which is cool.

• 10:37Speaker 01

  I feel like it's going to be your best podcast ever.

• 10:39Rich Roll?

  You think so? We are holding that vision.

• 10:42Speaker 01

  Yes. It has to be. We can't have the 25th anniversary with a really lame podcast.

• 10:47Rich Roll?

  Yeah, let's not do that.

• 10:51Rich Roll?

  One thing, you know, we lived very different lives, but I think one thing that we share is a curiosity about other people. You have plied that curiosity and created a career out of it that began at a very young age interviewing comedians when you were in high school for your radio show. My aperture is a little wider, like I just talk to all different kinds of people that fascinate me and inspire me in different ways. And in thinking about kind of your origin story and how you started with this obsession and fascination with comedy and comedians and the kind of gumption to reach out to, you know, these people as a young person and having them be receptive. Had it been the era that it is now, 100% you would have had a podcast, right?

• 11:32Speaker 01

  Exactly.

• 11:33Rich Roll?

  This would have been, this would have been a podcast, not a high school radio show. And then that continues to this day with the books that you do and, you know, you've been able to kind of maintain that level of curiosity, that fascination with comedians and comedy, despite the fact that you're, you know, at the kind of apex of that ecosystem, that world. Like, what is it about other comedians and comedy that you still, you still want to like learn from these people? You still want to figure out what makes them tick?

• 12:04Speaker 01

  I just always had this weird instinct to get in the room with people. I think it's because I was just such a fan to start. So the idea of meeting anyone was a big thing for me as a little kid. Oh, you could meet Robert Conrad? I remember Robert Conrad from Black Sheep.

• 12:22Rich Roll?

  Yeah.

• 12:23Speaker 01

  When I was a little kid.

• 12:23Rich Roll?

  That's possible.

• 12:24Speaker 01

  We were on vacation and like, there he is. Oh, my God, let's chase him. Let's, let's find him. And so I collected autographs and my grandmother was friends with this comedian, Todi Fields, who was, you know, a Joan Rivers-like comedian. She sang and, and it always seemed like she was the coolest person that we knew. People talked about her in a grand way. Like, there was this special person in our lives, Todi Fields. And she, you know, was a, you know, a not classically beautiful woman. That's what she talked about on stage, but loved herself, self-deprecating, hilarious, amazing singer. And at one point, she, she had diabetes and she had to have her leg amputated. And I went to see her when I was 10.

• 13:11Speaker 01

  And I always look back at it and think it just must have had a massive impact to see her get all of these standing ovations and the crowd loved her so much and I probably felt other and weird and a nerd and to see this woman who was so wonderful get that type of reaction, I think it had a big effect.

• 13:30Rich Roll?

  Like locked in on your brain.

• 13:32Speaker 01

  I think somewhere I just I just saw like, oh, there's other paths to success. You don't have to be the quarterback. You don't have to be the most handsome guy in the room. There's a way to connect with people. And so I always loved watching comedians on the talk shows and was always tracking them like they were athletes. And it just never ended. After I interviewed people in high school, I met Dave Edgar, Dave Edgar's the writer and he has a charity eight two six, which raises money for literacy programs around the country. And I said, well, I have all these old interviews, maybe we can put them in a book and I'll give all the money to you and I'll do a couple of new ones.

• 14:14Speaker 01

  And it just sold a lot and I noticed that it had a big impact on young, creative people. So then I said, well, maybe I'll do another one of almost all new ones. And then it's just an excuse for me to just say what I said when I was a kid, how do you do it? Why do you do it? How do you feel? And now that I'm in the same profession as everyone, it's like, how are we doing? Here's, here's my experiences. Are you okay? Are you falling apart or are you insane? Are we evolving? And so the conversations get much richer than when I was 15.

• 14:45Rich Roll?

  Right, right, right. And do you feel like you're still learning about comedy?

• 14:50Speaker 01

  Oh, yeah.

• 14:51Rich Roll?

  That there's no end to what you can discover.

• 14:53Speaker 01

  No end because there's no answers to anything in comedy. I mean, you know how they know like there are certain beats in music that will always make you dance. There's just themes that are consistent with comedy. It's really an experiment and you just don't know if something's going to work ever. No matter how much you think you know, you might make a movie, go in a movie theater, you're sure it's rocking and there are places where it just. Bombs and you were completely wrong.

• 15:20Rich Roll?

  Right.

• 15:20Speaker 01

  And there was no way to anticipate that.

• 15:22Rich Roll?

  Do you find that exciting or frustrating after all these years? I mean, there is, yeah, that, that sort of quality of comedy, the elusiveness of it. You just don't know. It's, it's something you can't quite, I mean, there's rules, I'm sure. And there's structure and all of that is wrote for you, I'm certain. But on some level, the mystery of it all, you know, persists. And there's something about stand up where you can get up and practice it and you get the feedback in real time and you refine, et cetera. But when you're making a TV show or a movie, you don't, you're, you're operating a bit in a vacuum.

• 15:56Speaker 01

  Yeah.

• 15:56Rich Roll?

  Cause you don't know how it's ultimately going to play, even if you're laughing. Or I guess you just have to trust your instinct and surround yourself with talented people and.

• 16:04Speaker 01

  And why do people laugh? Cause I'm not very intellectual about it. There are people who could really talk about laughs and why it happens and surprise. And they understand the psychology. I have no idea. I'd never talk about it in those terms.

• 16:16Rich Roll?

  Really? So when people say, what is comedy or try to get philosophical about it?

• 16:20Speaker 01

  Yeah, I know nothing. I, I really do know nothing other than instincts. And I know that people are interested in the struggles of people that we're all struggling. And watching other people struggle in ways that we relate to, uh, makes us laugh. And we root for people to do better because we're trying to do better. So I understand, you know, the, the core emotional rules of it. But why, you know, Maya Rudolph, uh, in a wedding dress, go to the bathroom in the middle of the street? That's a big laugh. I can't really scientifically explain it or anticipate it because what we usually do is we shoot something like that. And if it doesn't work, we cut it out. Yeah, a year later, you're like, didn't get a laugh. And if it didn't, that's just not in the movie.

• 17:03Rich Roll?

  Uh huh.

• 17:03Speaker 01

  You know, so I always overshoot and shoot a lot of extra things because I don't know.

• 17:08Rich Roll?

  On top of that, there's this added layer of timeliness to the whole thing. Like, it's rare for a comedy to hold up over decades. A lot of comedy, you go back, you thought it was hilarious, you can't wait to share it with your friend. You're like, wait, you know, you're not laughing anymore. Um, you know, for every Life of Brian, there's a, you know, tons of movies out there and TV shows that, you know, just don't, for whatever reason, hold up in that way. Like, what is it about comedy that roots itself to the moment in a way that, you know, drama seems to be able to transcend a little bit more easily?

• 17:45Speaker 01

  I mean, sometimes the pace of things change.

• 17:47Rich Roll?

  Now I'm asking you to answer questions that you said you don't want to answer.

• 17:50Speaker 01

  I mean, I think about things that haven't held up. I mean, things don't hold up usually because they're not authentic in some way. I feel like if you're true to your time and true to the characters and the story, they have a better chance of holding up. If you see The Apartment, the Billy Wilder movie, you know, with Jack Lemmon and Shirley MacLaine, it completely holds up. And there's a lot of movies like that. But sometimes when you're taking big swings or doing sillier things, maybe as time passes, you go, oh, that was too broad, or we don't get those references anymore. But I'm pretty sure if you watch Airplane today, you would laugh your ass off.

• 18:22Rich Roll?

  Yeah, that, that holds up still, yeah.

• 18:24Speaker 01

  And anytime, you know, something of mine airs somewhere or is on a new streamer, I love going online to see what people make of it now. So Funny People, which we made in 2009, it just went up on Netflix. It was number five on Netflix.

• 18:39Rich Roll?

  Uh huh.

• 18:40Speaker 01

  And so that's probably, it could be more people than saw it when it came out.

• 18:43Rich Roll?

  Right. That's a weird thing about the streamers. I'm sure it's a love-hate relationship that you have. But the ability for those platforms to resurface older material and suddenly put it in front of way more eyeballs that ever saw it in the, you know, on its initial run.

• 18:58Speaker 01

  It's remarkable because that's all you want is for your things

• 19:02Rich Roll?

  Yeah.

• 19:03Speaker 01

  to not disappear down the algorithm in some digital black hole. This is 40 has been on Netflix and people walk up to me more than they did when it when it came out. And that's great because I feel like people don't watch it as if it's old. They really watch it like it's brand new.

• 19:21Rich Roll?

  Yeah.

• 19:21Speaker 01

  Content. And if you, you know, other than sometimes the phones are larger.

• 19:25Rich Roll?

  Right.

• 19:27Speaker 01

  Everyone's good. Why does Adam Sandler have a flip phone? I mean, you know, I always try to dress people in clothes that I think will not age badly. So, you know, Seth Rogen's in a T shirt. Yeah, he could be in a T shirt today. It doesn't make it look like it's the 40s.

• 19:40Rich Roll?

  Freaks and Geeks is like that. I mean, my kids love that, you know, that that that felt like it. It got new life during the pandemic. Maybe not to the extent of something like, you know, The Office or Friends, but, you know, to have new generations discovering stuff that you did a long time ago has to be cool as well.

• 19:58Speaker 01

  Yeah, I mean, no one watched Freaks and Geeks when it was on. That's why we were canceled. So the fact that, you know, that was 24 years ago, that people are watching it right now. And yeah, I rarely meet young people that haven't seen it, which is crazy.

• 20:13Rich Roll?

  Right.

• 20:14Speaker 01

  And lately I've been trying to think, can I let go of my sense of time? So like I made things in many different eras, many different years. Can I look at it like they all are from the same moment? Like, why do I have to think of it as something 24 years old? Could I think of Freaks and Geeks like we did it this year?

• 20:37Rich Roll?

  So when you're, when you're making it, you're conscious of that timelessness quality.

• 20:42Speaker 01

  Yeah. And I, and for myself too, in my emotional relationship to it, things that are in the distant past, can I refresh it in my own mind and go, what's the difference if I made that in 2005 or in 2023?

• 20:56Rich Roll?

  Yeah. Well, you mentioned authenticity. I mean, that's certainly a, you know, a huge recurring like sort of trademark or theme and everything that you do. And, you know, the work that you've done that that has stuck with me and we're like the same age. So the work that really resonates with me is the more personal stuff like this is 40 and funny people. And, um, and I feel like you.

• 21:18Rich Roll?

  Like if I had to think of what distinguishes you or a hallmark of everything that you do, it's it's sort of taking those mundane quotidian moments that are highly relatable, telling those stories in a very specific way that's authentic to you, like that idea of the the specific is the universal, like the more specific in a counterintuitive way becomes the thing that connects with the most number of people and telling stories that kind of fall in the gaps between what we're used to seeing, like in between the highlights, like what's going on, you know, at breakfast or whatever, you know, and in a way that is probably, you know, very specific to your life and yet you're touching on something

• 22:02Rich Roll?

  that, you know, we can all connect with.

• 22:04Speaker 01

  It's funny you say that because when we did this TV show Love on Netflix with Paul Rust and Gillian Jacobs, the whole idea was to show every single step in a relationship. So if they bumped into each other and then didn't talk for a few weeks, let's show the few weeks. Let's show the pauses in between. If they break up, let's show what they do when they're broken up and who else they go out with. And then before then later they come together. I mean, that's always something that I'm interested in. At some point, someone said, you know, these are movies where you take the supporting actors or actresses and make them the leads. These are the characters. It's like if there was a movie about Bruno Kirby and Carrie Fisher from When Harry Met Sally, you'd love that movie.

• 22:49Rich Roll?

  Right.

• 22:49Speaker 01

  Like, I want to go home with them for a little while.

• 22:51Rich Roll?

  Right. The the side story over there. Like, that's the more interesting thing. Is that a conscious thing when you're reviewing material and trying to figure out what you want to be involved in, like the process of deciding where you're going to invest your time and your energy for the next, you know, however many years it takes to get something onto a screen?

• 23:08Speaker 01

  I think I just relate to those people. And so I'm always in that space because I don't relate to the super handsome hero. I like that kind of movie, but I I relate to the goofy person next to them who's too tired to keep up as they're going up the mountain. That's, you know, I'm a John Candy guy.

• 23:28Rich Roll?

  Yeah.

• 23:28Speaker 01

  And so, and I always feel, you know, a little bit insecure in spaces. And so most of the comedy comes from. You know, whatever my anxieties, things I'm trying to get over, things I'm trying to learn about or deal with. And so it inherently isn't heroic. It's just, how do you survive high school? How do you survive having a baby? How do you make your marriage work? You know, the simple things to me have so much drama in them because that that is the the most rewarding stuff, but also the most challenging stuff.

• 24:00Rich Roll?

  Mm hmm. And the weirdo, making heroes out of the weirdos or the people that are in between, like in the cracks.

• 24:07Speaker 01

  Yeah, I mean, I I remember we were promoting Knocked Up and Seth was always really funny about the fact that the poster was just his face. And it said, what would you do if this guy got you pregnant?

• 24:17Rich Roll?

  Uh huh.

• 24:18Speaker 01

  And Seth, Seth said like, so like, that's enough to sell the movie like just my face is enough, you know? And and he was like, it doesn't make any sense because everyone is like me. He's like, the world is like me. No one's like Brad Pitt.

• 24:32Rich Roll?

  Uh huh.

• 24:33Speaker 01

  They're like me. I'm not the exception. And and I think that's true, that we all, you know, feel like that.

• 24:41Rich Roll?

  Yeah.

• 24:41Speaker 01

  I know how many people feel strong and fantastic.

• 24:44Rich Roll?

  Yeah.

• 24:44Speaker 01

  They're accomplishing their goals and feel mentally strong. We all feel like a mess, so it's fun to write about people who are a mess.

• 24:51Rich Roll?

  Yeah, that's the same thing with the show Girls. Like I was reading that HBO, what's that HBO book?

• 24:57Speaker 01

  Oh.

• 24:58Rich Roll?

  The kind of like the history. Yeah, yeah, yeah, Tinderbox. And there's a whole section on there on on how girls came to be. And at one point, Lena shares her like two page brief or whatever about the show. And it's all about like the people that she grew up like there's Sex in the City and there's these other shows or Gossip Girl. But like, what about like my friends? And what happens when you graduate college and you go to New York City and you're trying to figure things out? Like, I've never seen that on television. Those are the, those are the people that I relate to, my generation, et cetera, that are kind of have been overlooked in the media landscape. And, you know, I'm sure a big reason why that show was so special is because it was telling those stories that had yet been told.

• 25:38Speaker 01

  Yeah, I mean, she always thought it was funny to have people. Who feel like they're owed the world. So they get out of college and they think, here it comes. Life is about to be handed to me on a silver platter and then nothing goes right. And they're not as smart as they thought they were. The jobs don't come as easily. And that's what she found hilarious about, you know, that premise and all the weird relationships and friendships that you have at that time in your life.

• 26:05Rich Roll?

  Yeah. In terms of, of you, you mentioned like, you like to write to whatever you're going through, or, you know, kind of staring in the mirror, looking at your neuroses or whatever kind of issue you're trying to, you know, work your way through. I know that, that like self-help books and all that kind of stuff has been, you know, kind of a touchstone in terms of how you think about this stuff and try to develop characters out of what you're reading. Like, what is, how is that played into your work? Like, what are the, I mean, I, I texted Pete Holmes earlier and I was like, I'm going to talk to Judd, which he's like, he loves Eckhart Tolle. He's a deeply spiritual dude, you know?

• 26:44Speaker 01

  That's so funny. I think, you know, I, my history with self-help is funny. I remember my dad, when he was a younger man, married to my mom, at some point read the Wayne Dyer book, Your Erogenous Zones. And then very quickly after that, my parents got divorced.

• 27:09Rich Roll?

  Did you have like, were there like Erica Jong books laying around your house? Remember, I'm okay, you're okay? Like, you know?

• 27:16Speaker 01

  Yeah, the early era of that. I think that was really the only book that was in the house, but it had an effect on my dad. I think him and my mom went to the therapy and on the first day, he said to me, the therapist went too hard at your mom and so she won't go back. And so, so that was the first time I heard about self-help. But when I was a kid, I was home a lot. My, my friends all played sports and I didn't. And I would go home every day and watch Donnie You. I would watch Phil Donnie You every day. And there would, all these self-help people would be on or just, you know, shows about people's problems in the pre Oprah era.

• 27:54Rich Roll?

  Right.

• 27:55Speaker 01

  And Stanley Siegel's another guy who had a, a show like that that was edgier. And so it was always interesting to me. But then I met Gary Shannen and he introduced me to Buddhism, and he gave me this book, A Feather on a Fan, and another one called Turning Your Problems Into Happiness. And that was the first time I paid any attention to it as a, as a young person, because my parents didn't really teach me anything about any of it. And it wasn't really in the culture. So I probably should have gone to a therapist as a teenager, but no one did.

• 28:28Rich Roll?

  No, nobody was doing that. And if you, and if you were to go, it was pathologized. You were something, there was something tremendously broken about you.

• 28:36Speaker 01

  It's funny, looking back, because I, you know, I graduated high school in 85.

• 28:40Rich Roll?

  Me too.

• 28:41Speaker 01

  And back then, I mean, I really don't remember one person who went to a therapist. There was nobody out of the closet. You know, our school couldn't have been less diverse on Long Island. And there was just so much we didn't know anything about. That

• 28:59Rich Roll?

  Right.

• 28:59Speaker 01

  We just, it's, it's like when David Sedaris writes about the fact that he went to a speech therapist, where he just realized that everyone there was gay.

• 29:09Rich Roll?

  Right.

• 29:10Speaker 01

  That's what, that's what it was like back then. Like, people weren't tuned into who you were.

• 29:14Rich Roll?

  No.

• 29:15Speaker 01

  And how to help you with your problems.

• 29:16Rich Roll?

  And it was a big deal when Kramer vs. Kramer came out, or Terms of Endearment, like, oh, my God, these are movies that are dealing with, you know, challenging emotions.

• 29:25Speaker 01

  Sure.

• 29:26Rich Roll?

  It's sort of like, it was like a watershed. Like, we don't talk about that stuff.

• 29:30Speaker 01

  I just watched Kramer vs. Kramer again. I can't say it fully wholesome. It's really rough on Meryl Streep. I mean, you watch it through the lens of today. And it, it's like, the, the great ending, the triumphant ending, is that the kid leaves his mom to stay with the dad.

• 29:50Rich Roll?

  The dad.

• 29:50Speaker 01

  And she gives up her child.

• 29:52Rich Roll?

  Yeah, that would not get greenlit today, I don't think. But, but that's what you did, right? You, well, you stayed with your dad.

• 30:00Speaker 01

  I was with my dad.

• 30:01Rich Roll?

  When your parents split up, right?

• 30:02Speaker 01

  My mom moved out, and I just wanted to stay in the same town.

• 30:04Rich Roll?

  Uh huh.

• 30:04Speaker 01

  I didn't, I didn't want to leave. And I just thought, I don't care what you do, I'm staying in this house. Like, my friends are here. You're not going to separate me.

• 30:13Rich Roll?

  Right. So it wasn't a choice of parents as much as location.

• 30:17Speaker 01

  Yeah. And, and that consistency, just the, and the consistency of my, of my friends. And it was, you know, Middle of junior high school. And it was a funny time because everyone's parents got divorced at some point during our childhood. Literally no, there were no kids whose parents can get divorced. And in our neighborhood, it was pretty upper middle class, middle class in most of the town. And then you would, your parents would get divorced and then you would move into an apartment complex.

• 30:51Rich Roll?

  Right.

• 30:51Speaker 01

  Down the street, literally like a mile away. You'd see like, oh, look, they moved into Hidden Ridge. That's where we moved. And that's how you knew that people's parents got divorced.

• 31:02Rich Roll?

  Yeah, it was an interesting time because it was sort of the first era where there was acceptance around divorce, but all those people got married too young.

• 31:14Speaker 01

  Yeah.

• 31:14Rich Roll?

  In an era in which you're just expected to get married as soon as you graduate college or, you know, your high school sweetheart or whatever.

• 31:20Speaker 01

  I was looking at a picture of my parents' wedding this week and I would, it was a party and I literally thought it was my mom's sweet 16.

• 31:30Rich Roll?

  Right, they're so young.

• 31:31Speaker 01

  They're just, they're so young and they're like, no, this is their engagement party. They met in summer camp. But yes, it was just a different time and no one knew how to talk about anything. You know, my dad, when my parents split up, you know, I was living with him. It was just me and him for a while and I saw a book, it was called Growing Up Divorced. And I picked it up and looked at it and, and it was kind of helpful. It was like explaining what the parents were going through and I never talked to my dad about it. I just thought it was like some book that he had to deal with me.

• 32:08Rich Roll?

  He sort of placed it there quietly for you to discover.

• 32:12Speaker 01

  He placed it there. But, but I said to my dad recently, when I realized that he placed it there. Cause I said to him once, you never talked to me about. How it was going, my feelings, you never explained anything to me. And I think he thought the good thing that I'm doing is I'm not going to, you know, to war with your mom, you know, she's mad at me, but I'm not going to say anything bad about her. But we didn't really talk emotionally because I don't think people really knew how back then. So he left out this book and so recently I said to him, but you never asked me if I read the book. So just because like I moved it, maybe I would have read one page. Like, don't you think you should have followed up?

• 32:53Rich Roll?

  Well, I mean, there's a lot of, a lot of threads he could have pulled. You know what I mean? Like, I'm sure in his mind, he's like, look what I did, you know? Like, that's, you know.

• 33:00Speaker 01

  The book's in his room.

• 33:01Rich Roll?

  Right.

• 33:02Speaker 01

  He's fine now. I don't have to ask him if he's depressed.

• 33:08Rich Roll?

  Oh, that's amazing.

• 33:10Speaker 01

  But to me, that's hilarious. Like, that's comedy.

• 33:12Rich Roll?

  Right.

• 33:13Speaker 01

  Like, I think it's so funny, and I've, I've, I've tried to figure out how to tell that in stand up. I've never really worked it out. But that is what I find funny about life. Like, you're a kid, your parents are getting divorced, they're at war, your dad doesn't know how to communicate with you. He leaves a book out on a coffee table and then never, ever asks you till you're like 50 years old if you picked it up.

• 33:34Rich Roll?

  And what did you, what did he say when you finally raised it with him?

• 33:37Speaker 01

  He's like, I figured you read it. And I'm like, but you don't know. He's like, yeah, but I saw that you, you took it.

• 33:48Rich Roll?

  Meanwhile, your mom, I read that, like, that, so she worked in this comedy club, but you didn't find out until later that she actually took that job out of, you know, this understanding that she had about what you were interested in.

• 34:04Speaker 01

  Well, I assume that. It's nothing that she ever said or I ever asked about, but I'm sure it's the case because, you know, my mom was so mad when her and my dad split up. She really, like, enjoyed her middle-class life and playing tennis and taking care of the kids and suddenly. You know, she's in the middle of this divorce and she has to get a job and she, everything about her life changed. Her parents were both, after being very wealthy, were also having serious financial problems. And so she waited tables, she sold ads at a, at a radio station.

• 34:46Speaker 01

  But my mom was hilarious because she really didn't want to do any of it. Like, you know, she, she would just say like, this is a nightmare. You know, she wasn't like, I'm really learning about hard work and connecting with the new people. And it's really putting me in, in a, in a new space, which I'm enjoying. It was just like, this sucks.

• 35:02Rich Roll?

  Right. Upper middle class, uh, single mom.

• 35:05Speaker 01

  Yeah.

• 35:05Rich Roll?

  Work.

• 35:06Speaker 01

  And, uh, I didn't really understand it till years later, you know, close to when she died, we started talking for real about some of it about 12 years ago. And then after she died, my aunt told me that my grandfather would be on the road. He was a jazz producer and he would leave for a week or weeks at a time. And he would always come back and bring her a dress. And he, he did that because he felt bad about leaving. And in a way, love became presence, became materialism. And so my mom had that thing where she, it, it meant a lot to her to have a nice pair of shoes.

• 35:47Speaker 01

  And I never understood it my whole life. Like, I, you know, I lent her money once and she, she would get a, like a, she'd lease like a Mercedes. But then she'd have no, no food to eat.

• 36:00Rich Roll?

  Right.

• 36:00Speaker 01

  And I'd say, why don't, why didn't you get like a Camry? And she said, cause I'm not an animal. And it was like, that was her in a nutshell, but I didn't understand that it was really connected to, love is materialism. It's a, these gifts, uh, how, uh, that's what her makeup was. And so now she's in Southampton, living in a guest house, uh, of, of someone because she can't afford anything but a guest house. And she takes this job seating people at a comedy club. Because my parents owned a restaurant and the, the bartender left and he's

• 36:42Speaker 01

  became, uh, an owner of comedy clubs. And then he was Tim Allen's manager and Drew Carey. And he became very successful. But at that time, he had just started opening up some comedy clubs and. I always thought, how much could they have paid her? I mean, what do you get paid in 1983 to seat people for a few hours? It's just at night, it's not even like a full-time job. And, and then I thought, she must have done it because she knew I wanted to see that world.

• 37:10Rich Roll?

  Right.

• 37:11Speaker 01

  Consciously or unconsciously, it was almost the most important moment in my life that my mom took that. And so for one summer, I could go to every show all summer, go see Paul Prevenza and Jay Leno and all of these people. And someone showed me there was some pictures of the club. And I literally found a picture of a show that I was at and it was Paul Prevenza and he had taken a giant umbrella and he, he was doing an impression of E.T. in the woods, turning like an umbrella into a satellite dish. And I was like, I was in the back of the room when this photo was taken in 1983. And so I'm always very thankful to my mom and to my dad who drove me to comedy clubs at night. I mean, when I was in high school, I started doing stand-up and he would drive me to Chuckles

• 37:56Speaker 01

  and Mini Olin, come and pick me up in the middle of the night. So they always, as much as they weren't getting along, both of them believed I could succeed. They never had any doubt. And I think that their belief that this was worth doing made me confident enough to take big risks.

• 38:14Rich Roll?

  That's really beautiful. You know, that's a, like, what a, what a gesture on your mom's part. And then that belief that your parents had in you, like this kid who knew very early on what he wanted to do, what he was obsessed with. I mean, that's a, that could be a gift and a curse. That's something I'd be curious to ask you about, to have that conviction at such a young age about what you wanted to do with your life. But to have that support and not be, not have parents trying to talk you out of it, or you should be a dentist, or, you know, like, that's the more typical, you know, especially with comedian, you know, comedians, right? Like, that's a tough road. But to have that, you know.

• 38:55Rich Roll?

  To have that like vote of confidence in your parents. So when you reflect back on your life from where you sit right now, do you reflect back on it and think my life is a dream or I can't believe I'm here? Or do you feel some sense of like inevitability or pre? Yeah, of course I'm here. I deserve to be here. My parents believed in me. I had the conviction to do it. I worked hard. Yes, I own this. I own this spot. Like where does the where does the confidence and the ego like crash into the neurosis? And you know what I mean? Like, what does that like stew look like?

• 39:31Speaker 01

  Well, comedy was the only place that I ever felt really confident. It's the only place I

• 39:37Rich Roll?

  And there was never a plan B?

• 39:39Speaker 01

  There was no plan B. There's never a plan B. I just thought there's there's some place for me in this world. Maybe I'll be a writer. Maybe I'll be a comedian. Maybe I'll act. Maybe I'll direct. I just knew there's got to be something. But, you know, back then, there were 50 comedy clubs in the country and no one in my high school wanted to be in comedy. So I thought

• 40:00Rich Roll?

  And comedy is not was not like it is now.

• 40:02Speaker 01

  Not

• 40:02Rich Roll?

  You know, it's not there's this industrial complex around comedy that like

• 40:06Speaker 01

  There's no internet.

• 40:07Rich Roll?

  Yeah, yeah.

• 40:08Speaker 01

  There's no podcasts. I mean, now all the comedians are playing, you know,

• 40:13Rich Roll?

  Arenas.

• 40:14Speaker 01

  Arenas. It's then it was like just Steve Martin and there weren't that many clubs. And so it really felt like, oh, there's room for me in this world.

• 40:22Rich Roll?

  It was accessible.

• 40:24Speaker 01

  Yeah. And then no one else was interested in it. You know, so I thought, I'm kind of lame in high school. But this thing that I'm interested in that no one else is interested in, I know it's cool.

• 40:35Rich Roll?

  Yeah.

• 40:36Speaker 01

  But no one here thinks it's cool.

• 40:37Rich Roll?

  Yeah.

• 40:37Speaker 01

  Even one of my friends said to me, at some point in the last 10 years, I finally get what you were doing back there.

• 40:45Rich Roll?

  Now, like, yeah.

• 40:47Speaker 01

  Now I know why you're.

• 40:48Rich Roll?

  It took that long to, yeah.

• 40:49Speaker 01

  Now I know why you were watching the Dinah Shore Show every day in Murph Griffin. They did, like, no one really got it, but that made me feel like, okay, there's a, there's a place for me in this space. And then I moved to LA and I met all the other people in comedy. And suddenly I had all these friends who had basically lived the same life as me in their little town. And.

• 41:09Rich Roll?

  There was no subreddit, though, where you guys could all, like, chat about, like, your weird obsession that no one else had.

• 41:15Speaker 01

  No, you'd have to show up at a comedy club and do open mic nights and you'd meet all the aspiring comedians. I used to start out, you know, I started out with people like Doug Benson and Andy Kindler. And, you know, we would just go to the clubs every night. Then I met, you know, Adam Sandler and Rob Schneider and David Spade and Jim Carrey. And that was our, our world and our, our crew back then. And we all had the same, same dream and also the same path to do it, which is write jokes during the day, get on stage, see if they worked. Every night, maybe that set will be a little bit better. And then maybe one night someone important will see you do it. And that was the whole path of comedy, which I love that it was that simple. Like, get funny, get noticed.

• 41:59Speaker 01

  And it seemed very fair. You know, none of us really had any advantage. It was just, we had to make Bud Friedman like us, so he'd put us on stage at the improv. And then if he did, maybe the Tonight Show would show up or maybe they'd put us on Evening at the Improv. And it was really fun. It was like running, you know, like a race with all your friends.

• 42:25Rich Roll?

  It happened, I mean, the way it appears, it looks like it all happened pretty quickly for you. I mean, you move out to LA, you go to USC for a year, two years.

• 42:35Speaker 01

  Year and a half.

• 42:36Rich Roll?

  Year and a half, drop out, move in with Adam Sandler. Do you just met him at the comedy clubs or how did that, like, happen?

• 42:43Speaker 01

  I met him at the comic strip one night and then, then he moved to LA and I met him when he first moved out to LA and he had just graduated NYU. And it's funny because I was at USC, my parents couldn't afford my tuition. I wasn't doing well because I. I got there when I was seventeen and I was in over my head and I was very immature. And creatively, I hadn't even begun to understand anything. And then I went on the dating game and I won. So they said, you have to go on this trip to Acapulco, which happened in December during like the last two weeks of finals. And I couldn't afford to go to school anymore. I was tired of begging my parents to try to figure out how to get the tuition.

• 43:27Speaker 01

  So I just went to Acapulco and quit college.

• 43:34Speaker 01

  I just was like, just bailed so hard on the whole thing.

• 43:37Rich Roll?

  What was the impulse to go on the dating show, though? Do you just went and stood in that line, like by the studio? Or how does it, you know, like back then, just something fun to do?

• 43:46Speaker 01

  I think we were all scouted that the shows like that would want comedians, young comedians, and I wasn't a good comedian at that point. But they just wanted people who were comfortable with themselves on those shows. And, but that's how I felt at the time, like this is not working here at school and I can't afford it. And everyone here seems way better at me than this, than I am. And so I did that and said, okay, I'm just going to focus full time on stand up. And then, you know, a couple of years later, I met Adam. And we were doing the same thing, just trying to figure out how to be funnier.

• 44:20Rich Roll?

  Yeah. It was an interesting time. I feel like that period was an inflection point in comedy and how the entertainment industry sort of interfaced with comedy in a similar way to, you think of these like places and periods of time that are special, like Seattle in nineteen ninety-two, or like, what would it have been like to live in downtown New York when David Byrne was, you know, like, like where you know there's like a certain energy, you know, something's happening that's interesting. And did you have a sensibility like, oh, this is like, there's something cool going on that, that like contemporaneously with this community and kind of culture at large?

• 45:02Rich Roll?

  And that's meeting up with like my obsession that's creating a potential energy? Or were you just like, I don't care, I'm here, I love this stuff. I'm just meeting these people and trying to work it out.

• 45:13Speaker 01

  I think somewhere in me was the dream of. You know, having a community like Saturday Night Live always felt like a community.

• 45:20Rich Roll?

  Yeah.

• 45:20Speaker 01

  Oh, they were all friends. I mean, maybe they weren't, but in your head, you'd watch the show or you'd see Monty Python or Second City TV and they had these, these groups. And so the idea of finding your people and, you know, working in the thing that you love was very appealing to me. I don't know if at the time we really understood how well so many people were going to do.

• 45:42Rich Roll?

  Uh huh.

• 45:43Speaker 01

  Looking back, it seems kind of crazy. Rob Schneider lived across the street from me and Adam and down the street was David Spade and over the hill, you know, Jim Carrey, who was ahead of us by a bunch of years, but, you know, was just coming back to stand up after having a movie and a TV show not do well. And he was trying to figure out who he was as a creative voice. You know, these were the people that we were around. And then, you know, one by one, people got these opportunities and then people did really well. And it was so fun. I mean, me and Adam look back on it and we just talk about it like it was the greatest time ever.

• 46:20Rich Roll?

  Right.

• 46:21Speaker 01

  We're very nostalgic about it. I mean, we'll, we'll talk on the phone and go, oh, remember when we went to Red Lobster that time?

• 46:28Speaker 01

  We were so excited we could afford Red Lobster. So.

• 46:31Rich Roll?

  There's those videos of him crank calling people from that apartment.

• 46:34Speaker 01

  Yeah, that is what our life was like. We, we didn't have jobs. So way too much time was spent doing goofy things like making phony phone calls because we didn't have an outlet for our creativity.

• 46:46Rich Roll?

  Uh huh.

• 46:46Speaker 01

  And Adam had so much chi, he had so much energy to be funny. So he would be, he would, he'd be funny with you. He'd be funny with anyone around because it was just there.

• 46:59Rich Roll?

  Yeah. And there had to be a sense of inevitability with him though. Like everybody must have known, like there's this.

• 47:04Speaker 01

  There were certain people you just.

• 47:06Rich Roll?

  Knew.

• 47:06Speaker 01

  Thought this is unlimited. What could happen here? And it hasn't happened much since then, but certainly at the time, Adam and Jim Carrey, at least in my mind and in a lot of people's minds, were going to be.

• 47:21Rich Roll?

  Yeah.

• 47:21Speaker 01

  The biggest stars in the world.

• 47:23Rich Roll?

  Yeah.

• 47:24Speaker 01

  Even when they were bombing, even when it wasn't going well, you would just see them up there and go, there's something magical in what they're doing and their personality and their, their charisma. And they're also the two of the hardest working people of everyone. They did outwork everybody.

• 47:38Rich Roll?

  Hmm. I knew that about Carrie. I didn't know that about Adam Sandler though.

• 47:42Speaker 01

  I mean, Adam was writing screenplays for himself.

• 47:46Speaker 01

  Immediately, before he had any jobs, before he even had a decent job when he was just happy to get a commercial, he was writing a screenplay with my friend Joel Madison, who lived down the street. I mean, there was a sense of, I need to learn how to do this. And so, and a bunch of us did that. I wrote a pilot. No one really wanted me to write a pilot. We just started writing. We're like, I think we need to learn how to write. And we saw some people succeed around us, like Jim Carrey with Ace Ventura. And we noticed, oh, Jim and Tom Shady, I found this script and they rewrote it. And they created an opportunity for themselves. They didn't wait to get cast. They-

• 48:24Rich Roll?

  Yeah. And you're like, I know these guys. This is doable.

• 48:27Speaker 01

  Yeah, you have to, it's what I preach to everyone. Like, you're gonna, you have, most of the time, you have to write your future. And you have to show people what you do. So, when I worked with, you know, Jason Segel, and he talks about it all the time, I just, you know, he, this becomes like a story he tells, but it is true. I said, you know, you're, you're, you're a weird guy. You're funny and you're, you're super unique. And people aren't just gonna hand you a script that captures that. You need to write it. And then he wrote Forgetting Sarah Marshall, was the first screenplay he ever wrote.

• 48:56Rich Roll?

  Yeah.

• 48:56Speaker 01

  But it was so true to him. And he understood himself in a way that nobody else ever could have. And so, we all were trying to figure out how to do that.

• 49:06Rich Roll?

  Right. The community piece seems to loom large for you. Like, everything that you, that you've done, and your best work is all about this sort of esprit de corps. And, and trying to kind of recapture what it was like living with Adam in that apartment, you know, like, just having a lot of cool, funny people around all the time. And, you know, the, the sort of lore, the mythos of Saturday Night Live is that, that's what that is, right? So, you know, it's, it is, you would have fit in well with that, I think, as a writer. But, but short of that, like, you recreating that in, in, in other ways.

• 49:41Speaker 01

  Yeah. I mean, Adam, you know, one day, Adam just says, I'm going to Chicago to-

• 49:48Speaker 01

  Audition for Saturday Night Live.

• 49:49Rich Roll?

  Uh huh.

• 49:49Speaker 01

  He didn't like do characters. They just saw him do stand up. And then afterwards, a few days later, he's like, yeah, I'm leaving. So suddenly I'm in the apartment by myself.

• 49:57Rich Roll?

  That era is over.

• 49:59Speaker 01

  Yeah, that era is over. I'm in the, I move out. Do I stay in this apartment? And Adam, you know, kept paying rent for a while and then slowly I was like, I guess I should leave. I live alone. He's not coming back. I talked to him yesterday because he left his wallet. On the Mark Twain Awards, I showed his driver's license because he literally left his driver's license and his fake ID that he had when he was a kid. But yesterday I was just going through some stuff and I found his wallet, which had a receipt from Ralph's supermarket. And I just looked at it because this is what Adam just bought, his groceries. It was literally chocolate pudding and frosted flakes. It was the most unhealthy.

• 50:40Rich Roll?

  You still have this?

• 50:41Speaker 01

  Yeah, I just, I just, because I always thought it was funny that he left his wallet. Not only did he leave wallet.

• 50:46Rich Roll?

  Fake ID?

• 50:46Speaker 01

  I have his fake ID. Is that he never asked if it was there. He didn't just leave it. He never said, did I leave my wallet? I mean, that's how forward thinking he was. He just moved to a new city with no ID and started his new life. Never looked back at all. Left most of his clothes. But, um, so then I, you know, we would all help each other and, you know, try to help Adam write sketches and then hope that one day we could get hired. And some of us did get hired. Tim Hurley, who, who, who wrote, you know, most of Adam's movies with Adam,

• 51:23Speaker 01

  who is as funny as anybody ever, you know, he got a job there. He was a lawyer and he left to write for Saturday Night Live. He was Adam's roommate in college. And then I had a packet and I was trying to get in. I just never got in. And then Jim, I was helping Jim write some sketches for Living Color. And then I did a meeting to try to get a job there. I couldn't get a job there. So then I met Ben Stiller and we created the Ben Stiller Show. And that's how I got in at a sketch show because I couldn't get a staff job. And then just through just this weird.

• 51:59Speaker 01

  Moment where I bumped into Ben Stiller, who I didn't know, and but people were interested in him doing a sketch show and we just thought of an idea for it. And two weeks later, we sold it. People thought that we were friends forever. We had met two weeks before.

• 52:10Rich Roll?

  Wow.

• 52:11Speaker 01

  And so without really any useful experience, you know, I was

• 52:17Rich Roll?

  Right.

• 52:18Speaker 01

  Helping Ben.

• 52:19Rich Roll?

  Right. And that really, you know, sort of kicks off you and like everything that follows. You know, that show, how many seasons did that go? It didn't go very long, right?

• 52:27Speaker 01

  Half a season.

• 52:28Rich Roll?

  One or two. Oh, only half a season.

• 52:29Speaker 01

  Thirteen episodes.

• 52:29Rich Roll?

  Yeah.

• 52:30Speaker 01

  You know, up against 60 Minutes.

• 52:33Rich Roll?

  Uh huh.

• 52:34Speaker 01

  And all the commercials that we shot, we wrote all these commercials was Ben playing an agent and he was talking to different celebrities in the different commercials and telling them not to go on the Ben Stiller show because it's definitely going to get canceled because it's up against 60 Minutes.

• 52:49Rich Roll?

  Yeah.

• 52:49Speaker 01

  I mean, our ad campaign was predicting our cancellation, which followed soon after. But that's where, you know, we worked with Bob Odenkirk and Andy Dick.

• 52:58Rich Roll?

  Yeah.

• 52:59Speaker 01

  Jenny Graffalo. And that's really where I learned most of the first stuff that I needed to learn how to do this was was from Ben, who had already done a sketch show for MTV and was brilliant and had a real vision.

• 53:11Rich Roll?

  Right.

• 53:11Speaker 01

  About what he wanted comedy to look like. He wanted to do these cinematic sketches.

• 53:18Rich Roll?

  It's interesting to see what he's doing now. I mean, you know, was Severance like, you know, in your, in your, in your deck for something that he, you know, he would be interested in doing, like so cinematic, so weird and, and kind of heavy on the drama and, you know, Dan Amora, like these serious, you know, cinematic shows that he's working on.

• 53:40Speaker 01

  No, he's, uh, he's really fulfilling all the potential.

• 53:45Rich Roll?

  Yeah.

• 53:45Speaker 01

  You know, that he had, because back then, you know, he was developing Reality Bites and Danny DeVito was one of the producers. And he said, you know, you're doing this sketch show, you should really go nuts with the camera and really learn

• 53:56Rich Roll?

  Uh huh.

• 53:57Speaker 01

  How to be a director. And then Ben did. He did these sketches like this TJO Pooter Toots Twilight Zone type episode that David Cross wrote and, and he, he pushed himself. And now, you know, he's like Sidney Lumet or

• 54:13Rich Roll?

  I know, it's crazy. I mean, you could see Bill Hader doing that too, with the stuff that he's doing on Barry. You know, you could see that trajectory.

• 54:20Speaker 01

  And we always say to people, hey, If you have your own show, really push to direct it because it's not impossible to do. You could really learn how to be a great director. Aziz Ansari directed a lot of Masters of None and has become an amazing director. And Amy Schumer's done a lot of directing and is great. So I think that's what we all look for, opportunities to figure out how to do that next step. I learned at the Larry Sanders Show, Gary let me direct an episode. And then when we did Freaks and Geeks is when I really started doing a bunch of it.

• 54:53Rich Roll?

  I want to talk about Gary, but you know, and looking at your IMDB, I mean, it's, you know, it's 100 miles long. There are so many movies, we can't talk about all your movies. But if I kind of glance at it at 10,000 feet, what jumps out at me is this period between around 2004 to 2015, where it's just an insane amount of output, like just an incredible number of movies. I mean, how many movies, like, you know, 15 movies or something, you know, like just TV shows, movies, producer, writer, director, et cetera.

• 55:31Rich Roll?

  And I can't help but think, despite it being like just an absolute tear, that there has to be some level of like obsessive workaholism in that. Like, like what was your life like for that 10 year period where you were hitting your stride and like just the output was like beyond?

• 55:53Speaker 01

  You know, I'm only beginning now to have any perspective about it. I do think that when you're younger, you have like a ridiculous amount of belief in yourself that is completely unwarranted. And that I think it's almost in your genetic makeup to take risks and to leap in. And when I look back, I think, yeah, I mean, there was a moment of feeling like. We were all in a crazy groove, but also being very collaborative with each other. We were all reading each other's scripts and giving notes and going to table reads. And, you know, there was a, there really was a community there. So if there was a table read, we all would go. Right.

• 56:38Speaker 01

  And you would get notes from everybody. And I remember the Forty Year Old Virgin table read and Adam McKay was there. And he's like, you know, when they're talking, maybe they should all be like hitting each other with fluorescent lights. I used to do that when I worked at this place. And you put it in or, you know, Gary Shandling would come to the table read and give remarkable notes way deeper than, than we knew how to do. And, and, you know, he would tell us what the core emotional ideas were that we needed to pay attention to. Uh huh. And I recently found in Gary's stuff, the script for the Forty Year Old Virgin with Gary's notes all throughout. So he called me with his notes, but I found the actual scripts. And he said, you know, it's, this is about love.

• 57:21Speaker 01

  This is about the fact that he falls in love and, and because he's in love, his sex is better than all of his friends' sex. Right. And he's like, you have to find a way to, to show that. And I didn't know how to do it because I'm like, I can't end it with just like the greatest sexy.

• 57:39Speaker 01

  But as a friend, we were all there for each other. And a lot of ways, you know, still are, but more, you know, distant because people have their own worlds and, and new people they, they work with. That all happened in the, in the normal, natural way. But for a while, you know, almost like a music scene, everyone was in Seattle. Yeah. And I think it helped all of us, you know? Seth and Evan, you know, were producers in addition to Seth acting in the movies. So they would be there. Right. For all the punch ups and all the creative conversations and, and, you know, I produced movies for, you know, a lot of people. And then friends who had nothing to do with it would come and just pitch. Yeah. And help.

• 58:24Speaker 01

  Yeah. I remember, uh, we did a Pineapple Express table read and.

• 58:30Speaker 01

  People had such incredible notes. One friend of ours was like, this is about the fact that Seth Rogen doesn't know if he wants to be friends with his dealer, but his dealer really wants to be friends with him. It was in there, but we didn't really know that that's what it was about. And as soon as someone-

• 58:47Rich Roll?

  That unlocks like the whole movie.

• 58:48Speaker 01

  Yeah, then suddenly the whole movie was funny because this one friend said, this is what you just wrote.

• 58:53Rich Roll?

  Right.

• 58:54Speaker 01

  And, and so it was definitely a really special time. And I think, you know, I had two young daughters and, you know, I was working and Leslie was working, but I also made a point of trying to shoot almost all of it in town, sometimes down the street. You know, one movie we shot on our block. So there was a real, real intention to not be the dad that disappears.

• 59:23Rich Roll?

  Right.

• 59:23Speaker 01

  So we shot Walk Hard in town and Knocked Up and Forty Old Virgin and Funny People. I mean, we, you know, people don't usually shoot movies in LA because it's cheaper out of town and whatever power we had, we used a lot of it to stay in LA.

• 59:36Rich Roll?

  Yeah, yeah, yeah.

• 59:37Speaker 01

  And be normal human beings.

• 59:38Rich Roll?

  Yeah, it's interesting. I mean, you, you know, a typical perspective on Hollywood is, you know, cutthroat, everybody's stabbing each other in the back, everybody's lying to you, they're telling you what they want to hear. It's like this sort of like a succession sort of situation where, you know, you can't trust anybody. Everybody's, you know, screwing around on their partners and spouses and all of that. And you're a guy who's, you know, making tons of movies and TV shows, living a pretty traditional fan, you know, like, you know, child of divorce, clearly, you know, went into your marriage with a commitment to do it differently and you've been with your wife forever and you have two daughters that, you know, it, it appears that you have great

• 1:00:20Rich Roll?

  relationships with and you've been able to have like a, you know, a really kind of conventional family upbringing in an insane town while doing tons of work with a perspective that, you know, the pie is unlimited, like the best idea wins, let's do this as a community, as a family, bring more people in, like that is, that, you know, that, that sort of like camaraderie team approach, I think would surprise people who have like a projected idea of what it's like to make a movie in Hollywood.

• 1:00:52Speaker 01

  Everybody does it differently. This came organically out of-

• 1:00:58Speaker 01

  Freaks and Geeks and Undeclared, where we met all these people. The shows were canceled, but we all felt like we haven't really tapped this. And we knew that so many of the people involved were special. And not just the actors, the production designer, Jeff Sage, who did Undeclared and Freaks and Geeks, did tons of movies with us and still does. And just people in all positions, Russ Alsobrook, our DP on Freaks and Geeks, you know, did Forgetting Sarah Marshall and did, you know, Superbad. And so we just wanted to keep working together.

• 1:01:32Rich Roll?

  Right.

• 1:01:33Speaker 01

  And so.

• 1:01:34Rich Roll?

  The traveling circus that doesn't leave town.

• 1:01:36Speaker 01

  Yeah, and I encourage everyone to write, and oddly, they did. And so.

• 1:01:42Rich Roll?

  But when you look at the cast of Freaks and Geeks and Undeclared, you know, obviously, you have this keen eye for emerging talent or who would be good. Or you see Lena, I know you came into that project later. And, you know, keeping those people close and sort of fostering their careers and believing in them in a way that, you know, I can't help but think was your relationship with Gary Shandling, right? Like this idea, you meet him very young. He gives you this job to write jokes for the, it was the Grammys, right? Was that the first thing? And he plays this incredibly powerful role in your life as like a mentor, like just a force of nature. So talk a little bit about, like, I'm interested in the kind of mentorship piece

• 1:02:27Rich Roll?

  and how you think about returning the incredible, you know, sort of favor that he did for you with all the young people that you work with.

• 1:02:37Speaker 01

  Well, I met Gary doing stand-up with him at the Comedy Magic Club. And my manager, Jimmy Miller, was like, hey, Gary, you should use Judd to write you some jokes. And Gary didn't seem to show any interest. And then a few months later, I got a call. He's hosting the Grammys and he needs jokes. And I was at the improv in Tempe, Arizona. And I just stayed up all night and wrote like 100 jokes. I just thought, I need to write enough jokes so I'm indispensable to him. And in the morning, we went through the jokes on the phone and we just got along great. He rewrote every single joke, but I think I was presenting ideas that lit him up. So here's the premise, here's a setup, and then he would just top the punchline every single time.

• 1:03:22Speaker 01

  But I think it really worked for him and I understood music and what all the issues were. He didn't really know that much about music. And then he invited me to go to the show and to be there for rehearsals and be on stage during the show, giving him jokes. And then we became very close friends and then that becomes like, you know, a fantasy come true. I interviewed him when I was in high school.

• 1:03:44Rich Roll?

  Right.

• 1:03:44Speaker 01

  After he hosted The Tonight Show for the first time, before he did a TV show. And the fact that he would let me hang around with him and suddenly like, I'd go over to his house and have dinner with him and his girlfriend Linda and we'd watch TV. And then he was writing The Larry Sanders Show and he would let me read the drafts and he was casting it and he would show me tapes and I would open up for him on the road sometimes. I opened up when he shot his HBO special. And there was a part of me that's like, why is this guy so nice to me? And as someone who came from a divorce, it was very impactful for me because it's someone that had my interest, was the best in the world at it, who wanted to teach me.

• 1:04:28Rich Roll?

  And created a home for you.

• 1:04:30Speaker 01

  Yeah, it was very kind. Yeah, and, uh, you know, became just a really close, close friend. And I tried to come through for him. So if he needed writing done, I really worked hard and I, but I also think I understood him and I think some people didn't understand him. I think he was a very unique, neurotic person. And for whatever reason, probably just having similarities in complicated moms.

• 1:04:57Speaker 01

  Something like that. Yeah, yeah. I just spoke his language. I wasn't anywhere near as talented as him. I don't think I was providing him with something that came close to what he could do at that time. But I was, I was a good hang and I was a good sounding board and I helped him stir the pot. And he said something funny, I wrote it down and wouldn't lose it. Uh huh. And so that's a big. That's an underrated skill probably. Oh, that's, that's a big skill when you're with funny people because they're funny all day long, but they let it all disappear into the ether. So if you're the person that goes, remember you said that thing and it's a great joke? You know, that's, that's a real, a real gift. And the thing about Gary is he continued to do that.

• 1:05:41Speaker 01

  So I did the sketch show with Ben. I asked him if he would be on the pilot doing a cameo. And he said, yes, which I think is part of the reason why I got picked up. Him and Roseanne and Tom were in the pilot and it made us look like we really were connected. When we really didn't know that many people. Uh huh. We just got everyone we knew on the pilot. Right. Um, then he hosted an episode of the Still Show or was the guest on one of the shows. And at the same time, he was doing Larry Sanders Show. And that's how he, he mentioned Groffola because I was showing him tapes of her. And then he put her on the Larry Sanders Show. Yeah. And then Bob Odenkirk was on the Larry Sanders Show. So there was a lot of cross pollination. Right, right, right, right. Happening.

• 1:06:24Speaker 01

  And then he, then when my show got canceled, he said, why don't you come work for me? He's like, you're gonna learn, you'll learn a lot. And he, and I always say, he didn't, he didn't say, you're gonna be so helpful to me. He said, you're gonna learn a lot. Uh, but over the course of five or six years, I got better. And then he asked me to direct and he asked me to run the show with Adam Resnick the last season. And so he continued to give me opportunities and believe in the next stage of my career. He didn't ask anyone else to direct the show, uh, that wrote for the show. When I look back at that now, that's crazy because they were some of the great comedy writers of all time there. Mm hmm. But he had some instinct that I could do it. And then when I started directing elsewhere.

• 1:07:07Speaker 01

  He'd read the script, he'd look at the cuts. I mean, it's harder now, honestly, without him. I have to really imagine that I'm talking to him and I just finished a script and I really thought like, okay, this is just write like it's an episode of the Larry Sanders Show. Just think, just put it through the Gary filter.

• 1:07:25Rich Roll?

  Right.

• 1:07:25Speaker 01

  Be tough on it the way Gary would be. Ask the questions Gary would ask.

• 1:07:28Rich Roll?

  Or go back and read his journals about how he thought about his own work.

• 1:07:32Speaker 01

  Yeah. And what is, what are these stories really about? What, what kind of lessons are in there? Cause I think Gary, underneath the satire was him exposing all the ways people have trouble connecting and all the masks we wear and how hard it is to be close to people when you're insecure and broken or when you're very ambitious. And I try to get his, you know, his, his voice in my head and, and I can, you know, in most situations, if I think about what Gary would say, I usually think I'm pretty close.

• 1:08:06Rich Roll?

  Yeah. I love the documentary that you, that you made about him. And I think he was, you know, on the one hand, like in terms of his work, like so pioneering, not just in how he thought about standup and the evolution of how he kind of arrived at his style, which was to be himself and to be authentic and to try to find those specific things that he was going through that would connect with the universal that obviously is influential in your work, but also reinventing and reimagining the form of television in that original sitcom, like It's, It's Gary Shandling Show or whatever, where he was breaking the fourth wall. And then the show that you worked on with him over the years, like, you know, does

• 1:08:49Rich Roll?

  Curb Your Enthusiasm happen without that? Like, you know, like the ripple effect of like him sort of pushing the envelope of what television could be, I think is probably underestimated, not to you, but maybe a lot of people. And then beyond that, just the impact that he had on people personally, obviously like this hugely important figure for you, but you're not alone. Like he impacted a lot of people, like when he, I mean, it was like, you know, all of Hollywood, you know, there were so many people who have so many stories about how he touched them in really meaningful ways with his.

• 1:09:27Rich Roll?

  You know, desire to be connected and to be helpful and to be this sort of mentor and the undercurrent of kind of spirituality that he, you know, brought to his work and to other people that I guess began when he had this near death experience in this car accident when he was young?

• 1:09:45Speaker 01

  Yeah, he was, he got into a fender bender and he got out to look at the damage and a car hit one of the cars in the fender bender and he got crushed between the two cars and had to have his gallbladder removed. And he had one of those stories where he said, during the operation, I looked down and I saw everything that was happening and there was a white light and I walked to it and they said, you want to continue living Gary Shandling's life? And he said, yes. And then the next day he could say what happened in the room. And as neurotic as he was, he didn't seem to have a fear of death. That's what is so fascinating about Gary because he's still-

• 1:10:23Rich Roll?

  More afraid of commitment than death.

• 1:10:24Speaker 01

  Yeah, really, right? Like afraid of engulfment and afraid of losing his freedom. Afraid of being with the wrong person by accident. And yet, you know, there were journals where he was heading into, you know, life threatening surgeries and he's, he's just very courageous and, you know, he writes in his journal. If you live another year, be grateful. If you live another day, be grateful. And that's what I love about the documentary because, because Gary on some levels is such a mess. The beauty of someone like him working so hard to understand himself, to grow and then

• 1:11:09Speaker 01

  to get to a place of just wanting to be grateful and to give to other people. On another, on another page in his, in his journal, it said,

• 1:11:18Speaker 01

  Give, give with no hope of getting anything in return. And those were things that he was writing to himself to try to make himself believe them.

• 1:11:29Rich Roll?

  Remind him, yeah.

• 1:11:30Speaker 01

  And to try to live them. But just the fact that he was trying. And he did walk the walk in a lot of ways where he was giving to me and to a lot of people. And he, you know, maybe in relationships, he never quite figured that out. But he was really trying. And then, you know, he got sick and I think he was diminished in some ways near the end of his life and had some, some problems. But you know, when I went through all the emails from him after he died, every single time I asked him if he could help me with something, he said, yes. Can you go to this thing? Yes. And like, it was literally a hundred times.

• 1:12:08Rich Roll?

  Wow.

• 1:12:08Speaker 01

  Every single time, what time? And that's the thing, as a mentor, I took from him. I tried to take both from the bad stuff, like, don't do that, or try not to torture yourself in that way. And I tried to learn from the, the great things that he did. So for me, mentoring people, I don't even think I ever thought about it, other than it just seemed like that's what you do. It's like, if you're like a baby and you know to breastfeed, and then you have a baby and you know, okay, now I'm, I'm the breastfeeder. Like, I guess that's how it works, right? Like, people help me and now it's my job to collaborate and help other people. And, you know, the main reason I always do it and did it is because I like it.

• 1:12:52Speaker 01

  I just, I'm impressed with creative people. I love the collaboration. I love the friendship of it.

• 1:12:57Rich Roll?

  Yeah.

• 1:12:58Speaker 01

  It's not like a noble effort.

• 1:13:00Rich Roll?

  Yeah, like, being a supporter feels like that's your design naturally.

• 1:13:05Speaker 01

  Yeah.

• 1:13:05Rich Roll?

  It's not like you're, you have to force yourself to

• 1:13:07Speaker 01

  No.

• 1:13:08Rich Roll?

  Wear that costume.

• 1:13:09Speaker 01

  And it's not like, isn't it so great that I'm doing this, or aren't I a great person for doing this? Because I don't think it really works that way. I think you're entering into collaboration. It's like starting a band with each person. And so you're like, oh, I play drums on this one. You play guitar on that one. And that's really what it is. I'm giving as much as I'm getting. Sometimes I'm getting more, you know, than I'm giving from the experience or the work. I'm playing a small role in the work. Maybe I'm just getting this thing made, but someone's doing all the creative work.

• 1:13:38Rich Roll?

  Yeah.

• 1:13:39Speaker 01

  So each situation is very unique.

• 1:13:41Rich Roll?

  Right. But is there, like, when you're writing a script and you're thinking, what would Gary say? Or how would, what would his notes be? Do you think, what would Gary do in this situation when, you know, somebody calls me and says, do you have, you know, 15 minutes where I can run an idea by you? Some young, you know, writer or something?

• 1:14:01Speaker 01

  Yeah, you try to be generous with your, with your time.

• 1:14:04Rich Roll?

  Yeah. I mean, when you think about legacy, and this is a legacy obsessed town, right? What are the projects that are gonna live beyond you, et cetera? And then you reflect on Gary Shandling's legacy. I mean, his legacy is, is the impact, how he made people feel. I mean, he has this great body of work, but really what people talk about and revere about him is the time that he invested in all of these people out of the kindness of his heart.

• 1:14:31Speaker 01

  Absolutely. I mean, that is the, the, the main impact of his life. I mean, he inspired people. And in the documentary, everyone at The Simpsons was like, It's Gary Shandling Show was where many of them started.

• 1:14:43Rich Roll?

  Yeah, exactly.

• 1:14:44Speaker 01

  And they said, like, he showed us how far you can go, how creative you can be. And it lit up their imaginations. You know, the other person that was an important mentor to me was David Milch, who created Deadwood and co-created NYPD Blue with Steven Bochco. And he was another one that, you know.

• 1:15:06Rich Roll?

  Everybody talks, I mean, reveres him as a genius.

• 1:15:11Speaker 01

  I mean, it's ridiculous.

• 1:15:13Rich Roll?

  Like, like the ultimate television writer.

• 1:15:15Speaker 01

  Yeah, and you watch Deadwood and it's a different kind of genius because sometimes you watch things and you think, I could do something in the universe of that. And when you watch Deadwood, you think, there's no chance that me or anyone else on earth could do this. It's just on a completely different level. But David Milch, he has Alzheimer's now. And so it's been a long time, you know, since he found out. And, and I go visit him and, you know, one day I was talking to him and he said, we should write something together. And it's very emotional because, you know, he's far down that road.

• 1:15:55Rich Roll?

  Right.

• 1:15:56Speaker 01

  And I said, what would he write? And he said, something about someone in my situation. And I said, well, what would it be about? And he said, regrets. And I said, what, what would he regret? And he goes, failures of generosity. And I, I literally, it was hard to not just start crying hard right there. But it was a reminder that that's really all that you're left with, which is, you know, how did I treat people? How did I treat myself? Was I good to the people in my life? How could I have been better? You know, it was just a gift to even have that moment with him.

• 1:16:39Speaker 01

  And, and he's talked about that at other moments, which is that's, that's his main concern is to be a giving person. And I think all of us as creative people, there's something so self-involved about it and it, it takes a lot of your bandwidth. And you're always trying to figure out, how do I balance this? How do I be a good parent? How am I available to the people in my life while still doing this work, which just sucks so much out of you.

• 1:17:05Rich Roll?

  Right. Yeah, when I look at that decade period where you were a maniac, I'm sure you're thinking like, I, I'm creating all of these things and this is what my life will, will mean, right? Or if you're David Milch, who was, he was, I mean, he's like a hard ass, right? Like, he was a tough guy?

• 1:17:23Speaker 01

  Well, he, he, I mean, I never worked with him on those shows, but he definitely.

• 1:17:29Rich Roll?

  Like a hard boiled writer type dude.

• 1:17:31Speaker 01

  I mean, he.

• 1:17:34Speaker 01

  You know, he taught at Yale, but he also, you know, had a lot of issues with addiction and gambling. And, you know, he was one of those people that would, he would lay on the ground, there'd be a microphone on the ground, and he would dictate the show. And people would wait around while he channeled the show. And he believed, he used to say, inspiration comes to prepared souls. And his whole thing was about that connection. Can you open yourself up and be so present and available that the creativity comes? And to trust that. And I learned so much from him about that. You know, to be in that place.

• 1:18:16Rich Roll?

  Do you practice that? When you pair that with, you know, Gary's passion for meditation and all, does that like trickle down into the

• 1:18:24Speaker 01

  It does.

• 1:18:25Rich Roll?

  Apatow daily routine?

• 1:18:27Speaker 01

  I try to, I try to understand it. I, you know, I recently took a flow course. You know, Stephen Kotler, who I'm sure you've had on, you know, has these online programs about like flow research, which I highly recommend. It was great. But I had this instinct like, oh, I'm too distracted. I need to get my focus back. So I, so I did this online course.

• 1:18:52Rich Roll?

  Breath work and stuff like that, or?

• 1:18:55Speaker 01

  It's just explaining where the distractions come from, how to prevent them and how to get into a state of flow and how to stay there, you know, for a while and to know how to give yourself a break and get back to it, just to really understand how that works in your mind. And, you know, I've heard him on so many of the podcasts talking about it. I said, you know what? What if I just committed to doing this? And I'd never done that in my whole life. And they said, and we have coaches who you can speak with, which I did.

• 1:19:25Speaker 01

  And it was, you know, it was very simple stuff, but the stuff you just don't do. And a lot of stuff that you've talked about in a lot of podcasts, you know, just wake up in the morning and don't check your phone. Just get your ass in the chair.

• 1:19:37Rich Roll?

  Yeah.

• 1:19:37Speaker 01

  Tell everyone not to interrupt you for four hours. Take a break every half an hour for five minutes, but don't go on your phone in the break. You know, just all the things interiorly and exteriorly, which will stop your creative.

• 1:19:49Rich Roll?

  Right. Like you can't necessarily manufacture a flow state, but you can create circumstances to that make it, make it conducive. And, and being in that state is like the holy grail of a writer.

• 1:20:02Speaker 01

  It's like when Bob Dylan talks about, you know, a song just happened in 10 minutes. Well, that's what that is.

• 1:20:09Rich Roll?

  Right.

• 1:20:10Speaker 01

  There are moments in your life where you can just see it. Like the screenplay I just wrote, I took a hike. I never do that. I never take a hike. It's like rare. And so I said, I'm going to take a hike alone. And like 30 minutes in, like the entire movie just came to me. And then I, then I took this class. Then I wrote the movie. I mean, I hadn't written a movie alone in 10 years. I'd been writing with other people because I got lonely. I got so bored of being alone. I said, this time I'm going to write it alone. I'm going to get used to being alone again. And everything about the course completely worked. It was hilarious. I mean.

• 1:20:47Rich Roll?

  Did it make you mad that it worked?

• 1:20:51Speaker 01

  Well, sometimes I think, well, you know, should I have been doing more writing alone? But I, I really cherish those times with other people.

• 1:20:59Rich Roll?

  More.

• 1:20:59Speaker 01

  And the work, and the work. But yes, I should hike more and I do. I do take like a 90 minute walk, like four or five times a week. But sometimes I listen to a podcast and sometimes I go, I'm just going to do it in silence and see what comes. Or, you know, one of the David Milch things is to, you know, to, to just start writing. You know, he, he always says.

• 1:21:18Speaker 01

  You can't think yourself into writing, but you can write yourself into thinking. So just start and it'll, it'll just come. And so that was a, a real lesson for me. There are ways I could be better at this. That's why, when you get back to, you know, self-help. You know, I'm, I'm always looking for something that will make me, you know, open up in some way, heal in some way, learn something that will make me more efficient. And, and sometimes I'm drowning in self-help because I just read and listen.

• 1:21:54Rich Roll?

  Yeah, that, that creates its own paralysis.

• 1:21:56Speaker 01

  Yes, yeah, because I'm a hoarder a bit, so I'll, I'll listen to too much. But with this, I just said, okay, this is, this is really simple. Just get your ass in a chair.

• 1:22:06Rich Roll?

  And then, and then amazement at it, at it actually working.

• 1:22:10Speaker 01

  Yeah, because you go like, how creative am I? Do I have any jokes left in this brain? And to see it happen was really rewarding and made me think, oh, maybe I could do that three more times this year.

• 1:22:31Rich Roll?

  How do you balance the collaborative aspect of the creation and writing process versus that like, ass in a chair alone at home? You know, what is the daily, you know, do you set it up with a schedule?

• 1:22:44Speaker 01

  Well, once the script is done, then I just send it to everybody and just go, what do you think? What do you think? And then at some point I'll sit alone and, you know, or with a writer's assistant and just rewrite it. And then I try to read it out loud and then, then I can watch it like a movie and see if it works for me as a movie. And then rewrite it, then read it out loud again. And then at some point, if someone will let me make it, we go into rehearsals and then it changes a lot. Once the actors bring their stuff into it.

• 1:23:14Rich Roll?

  How do you know when you're, when you have an idea? I think I asked you this earlier, but like that, that, you know, it's like, once you commit to an idea, there's a long road ahead, right? Is there like something, does something light up in your brain where you're like, this is it? Or this is the thing I like, or is that an instinct or?

• 1:23:33Speaker 01

  You have an instinct, but then you just keep like telling it to people. And so you're like,

• 1:23:38Rich Roll?

  If they like it, if it stays with you.

• 1:23:40Speaker 01

  Yeah, it seemed funny and it's just like a movie about like, Guy gets girl pregnant and he hangs out with those stone friends and he's a nightmare, but she wants to see if maybe he could be a good boyfriend and you know, and then you, then you start showing the outline to some friends and you're looking for some reinforcement that you're not in a crazy place.

• 1:24:01Rich Roll?

  Uh huh.

• 1:24:01Speaker 01

  And then at some point you think, am I really gonna do this? Okay, maybe I'll write five pages. Let me just see if it comes to life. And then usually you go, oh, yeah, this seems funny.

• 1:24:15Rich Roll?

  Does it start generally with a conceit for you or with a person, like a character? Like this, this person, what would this person, what adventure would this guy go on?

• 1:24:26Speaker 01

  I mean, each, each time is different, but I like working from some very passionate idea or truthful idea. You know, when Leslie and I, uh, we were at the hospital, having our second, uh, our, our second child, just everything went wrong, uh, other than she's beautiful and healthy.

• 1:24:47Rich Roll?

  But the doctor was mean, right?

• 1:24:49Speaker 01

  The doctor was mean. The other doctor just didn't show up, just left town to go to a bar mitzvah. And I just took notes that night. I was like, this is so crazy how weird this night is. So in the back of my head, I'm like, there's probably a way to tell this story. And then you back into it, you know, eventually, uh, you know, with, with Pete Davidson, with the king of Staten Island, we had worked on a different idea for a while. And then usually it, you just say, what should we really be writing about? And then it just comes out. Like, are you willing to explore what we probably should explore? And Pete was, and so then we started writing that version.

• 1:25:28Rich Roll?

  Yeah, yeah, yeah. It's interesting. Like knowing when, you know, it's time to pull the thread a little bit further versus moving on.

• 1:25:39Speaker 01

  And it's really hard to start a script for me because I think one of the things I always have to get over is by, by writing, I'm finding out if I'm terrible. So it's very easy to not write because if I don't write, I won't find out if I'm bad.

• 1:25:54Rich Roll?

  Do you still go to war with yourself in that way, though?

• 1:25:56Speaker 01

  I think so. I think it's subtle, but it's just, just because.

• 1:26:02Speaker 01

  There's a little, there's a critical voice that you are always wrestling with that basically says, just don't do it. Just go watch TV. Like, you don't have to suffer through this. And to try to turn it into a pleasurable experience, I'm still almost in hyperventilation or anxiety. Most of the time, I'm actually writing. I'm just, my breath gets short. I'm so nervous and I'm trying to like, open a spigot. And I have to relax to let it come out. But there's just a weird part of me that's just scared, scared it's gonna be bad, scared I'm gonna- That like Steven Pressfield resistance war of art kind of thing.

• 1:26:42Speaker 01

  It's totally that. And, and that's what the flow thing helped me with, which is, you know, I can toss it all. I don't have to, I can throw out all the, I can throw out all the work today. Just, just trust it might be, there might be something good. Like if you, I wrote this script kind of fast. And I just said, I'm gonna write straight through to the end. I'm not even gonna reread yesterday's pages till I get to the end. And then I got to the end and then I started reading it and I was like, I don't even remember writing almost anything. Like, I remember the story, but the language and the jokes. And I was really pleasantly surprised by it. But I, I just forced myself to, to just go to, you know, that part of my imagination and just followed wherever it led me. And

• 1:27:25Speaker 01

  that's not how I always wrote. I think I was more methodical. And I just thought, maybe I'll just kind of, you know, go into the trance and see what bubbles up. Make it sort of like morning pages, no stakes. Exactly. And I did those, I mean, the Julie Cameron artist way, you know, I did that in the early 90s. Yeah, I think I started that in 90. When did that book come out?

• 1:27:53Rich Roll?

  Ninety seven, ninety eight?

• 1:27:55Speaker 01

  I mean, I could have done that in the

• 1:27:57Rich Roll?

  No, it was early.

• 1:27:57Speaker 01

  No, no, because I did it early nine.

• 1:27:59Rich Roll?

  Yeah, you're right. Yeah.

• 1:28:01Speaker 01

  I could have even done it late eighties, but you know, so that idea of morning pages to just write, don't judge, just whatever comes out, it doesn't matter. Which was also David Milch exercise where he said, to get your creative juices going for two weeks, write for 20 minutes a day, print it and then tear it up. Just to get used to your brain being creative and

• 1:28:25Rich Roll?

  Like the Zen Buddhist sand mandala.

• 1:28:28Speaker 01

  Exactly. But he said, you'll, you'll open up, you know, that part of your brain and it'll fire up. And I'd never done that, but I understand what he's talking about.

• 1:28:40Rich Roll?

  Precious, not being too attached.

• 1:28:43Speaker 01

  There's, it's like having a baby, like suddenly your body knows how to make a baby. Right? Like your whole life is not making a baby, then one day like this machine builds itself. And you have a baby. Well, this is a part of your brain or your mind that you could turn on and it builds itself to be creative.

• 1:29:02Rich Roll?

  Yeah.

• 1:29:03Speaker 01

  If you just start doing it.

• 1:29:04Rich Roll?

  There's something about consistency and momentum also.

• 1:29:08Speaker 01

  Yes.

• 1:29:08Rich Roll?

  Build a little momentum and then you're kind of, then suddenly there's something real about it. And then you're like, oh, this is a real thing.

• 1:29:16Speaker 01

  Yeah. And I always think if I'm on page 60, I can finish, finish it in a weekend.

• 1:29:20Rich Roll?

  Wow.

• 1:29:20Speaker 01

  I don't always do it in a weekend, but I think if I get to 60, I could write 20 pages a day for two days and have a really shitty draft and then I'll fix it up.

• 1:29:29Rich Roll?

  How often do people ask you about when you're gonna write, this is 50?

• 1:29:37Speaker 01

  People have been asking because it's been on Netflix and, and, and I have an idea for it.

• 1:29:43Rich Roll?

  Oh, you do?

• 1:29:44Speaker 01

  And so, you know, I'd have to sit down and do it, which I've thought about maybe trying to do that before I shoot the next movie to take a few buns and, and write that and try to do that in a year or so.

• 1:29:57Rich Roll?

  You're, you're leaving soon. Are you going to work on something? Like you're leaving town to go work or is that just?

• 1:30:03Speaker 01

  Oh, I'm going to London. My daughter is in Cabaret in the West End. So that's what you do when your kids move out is you just go to where they are and just stalk them.

• 1:30:15Rich Roll?

  We're in your office right now. We're in the middle of a strike.

• 1:30:19Speaker 01

  Yes.

• 1:30:20Rich Roll?

  You've shared thoughts and opinions on what's going on right now, but maybe you could kind of explain the conflict that's happening right now between the Writers Guild and the industry at large.

• 1:30:32Speaker 01

  Well, when technology changes, the way people get paid needs to change. But what is tricky about it is for this industry, it really only works if the writers can survive. So if the way people are paid makes it so that writers can't survive, then the writers won't be writers, or they'll disappear. And the way that writers survive gig to gig is that in between gigs, they get paid for the reruns of previous work. And when that's not fair, writers can't eat. And then, you know, a lot of these shows, they're not 22

• 1:31:13Speaker 01

  episodes anymore, they're six, or they're eight. So right there, a lot of people are not making what they used to make, because that means you have to get two jobs a year, or three jobs. And it never times out that you could fill your year for most writers. And it's a big problem, and it only gets solved because the streamers want the writers to be solid. They have to have the intention, because if the writers aren't working and getting residuals, money doesn't go into their health plans and their pension plans. And then suddenly, none of the writers have healthcare, or the actors have healthcare. So hopefully, they'll figure it out.

• 1:31:52Rich Roll?

  And it's an exacerbation of what was already lopsided in favor of the studios versus the writers. The writers have always been sort of shortchanged. It appears like in this equation of being equitably treated. And it's a little bit different, whether you're talking about movies or TV. Like, in movies, there was always home video and DVD and all these ancillary markets, foreign territories, et cetera. So all these revenue streams were kind of percolating in over time. And then in television, which heralds the writer a little bit better, especially on Big shows than it does in movies. There, you know, you have these showrunners. There's, it seems like there's a little, I'm interested in this, like,

• 1:32:33Rich Roll?

  there are like a lot of these really big showrunners, right, who have massive deals with streamers and networks and et cetera. And then you have legions of writers who are, you know, semi-employed, sometimes employed, et cetera. At some point, what is the political heft of those showrunners who are like, they can wait it out, they're getting paid plenty of money, to say, you know, enough's enough, we gotta get back to work.

• 1:32:59Speaker 01

  That's usually how, how, how it, how it ends is.

• 1:33:04Rich Roll?

  I mean, Mike White's over in Thailand right now, sitting around, you know, interrupted in the middle of White Lotus. At some point HBO's gotta go, we gotta, we gotta, we gotta get this show made.

• 1:33:16Speaker 01

  Well, I mean, I think people start noticing that they're not getting anything but reality shows. And I think it, it probably affects stock prices at some point when you go Stranger Things isn't coming anytime soon now. And a lot of these programs that everyone loves and wait for, they're not in production. So you hope that this gets resolved before people suffer a lot. And the thing that always frustrates me is whatever the solution is, they could have thought of it three months ago. There's nothing.

• 1:33:47Rich Roll?

  But you had said, and I think you're right, like, they already know. They already know what they're gonna settle for.

• 1:33:53Speaker 01

  Yeah, they know their numbers. And so a lot of people suffer, a lot of the support people in the community, the restaurants, the other studios and, you know, people on the, on the crews suffer and they really don't need to. What the, what the end result of this will be will not be shocking. And, and that's what the drag of the whole thing is because it really is unnecessary. If they wanted to, to solve it, they definitely could have. And that's what I think is awful. But it is an enormous amount of companies who have to agree on the solution. And that some of these companies, they're not really entertaining companies. You know, they're computer companies that have a little tiny entertainment business to them.

• 1:34:30Rich Roll?

  Yeah.

• 1:34:31Speaker 01

  So I think it's much more complicated. And then they all say, oh, we're suffering, we're suffering. But then all the heads of the companies are making so much money. And you're like, well, if you're getting paid that much, I think your business is working.

• 1:34:45Rich Roll?

  Yeah.

• 1:34:45Speaker 01

  You can't say the business isn't working if you could justify your salary. So if the business is working, then we're doing a good job too. But we're not actually being paid for the job that we're doing. You know, it's also about creativity. You know, what people don't like to talk much about is like all the metadata leads you to a very bland place.

• 1:35:08Rich Roll?

  They know exactly what people are watching, how long they're watching, when they tune out. They use all of that to decide what kind of stories they're going to green light.

• 1:35:17Speaker 01

  The great stuff is the unexpected stuff. You can't use an algorithm to make Taxi Driver. They're never going to ask you to do Taxi Driver. They're never going to ask you to do Raging Bull. They're always going to ask you to do a very middle of the road action film. And that's a big problem because then they go, all right, well, now we'll only use the biggest stars in the world and we'll pay them 35, 40 million dollars to be in it, which is fine for those to exist. But when you put all of your energy into those types of movies, then you're not really looking to make Moonlight. You're not looking to, you know, break ground. And so they don't trust their own innovation and creativity.

• 1:36:00Speaker 01

  They really only trust more than ever a super famous worldwide star to attract subscribers. So it's the worst version of bean counting. And it took a few years for it to happen. But now they have so much information, they're like, yeah, people don't like this type of movie. But if you were to pitch Midnight Cowboy, nothing about their metadata would say, you know, this is what the world wants.

• 1:36:25Rich Roll?

  Yeah.

• 1:36:26Speaker 01

  They really want this movie about these hustlers in New York. Like, they would never, ever make it. And that, I think, is the tragedy of all of this, which is it's so money driven. And it wasn't in the beginning, when the streaming started, some of the appeal was we're taking crazy chances. And a lot of that is beginning to disappear.

• 1:36:47Rich Roll?

  Yeah, that's gone. And it's not even about how good is the movie or how many people are watching that particular piece of content. What it's really about is, is this driving subscribers, new subscribers to come? And as they penetrate, you know, North America and what blah, blah, blah, and they're moving into all these other parts of the world, it becomes about creating for those audiences to tap into that subscriber base. And it has nothing to do with storytelling necessarily. It's detached in a certain way. And then on top of that, you have an industry at large that's become so conglomerized and, you know, sort of superheroified. Like, how do you think about just that beyond like the streamer aspect of it?

• 1:37:30Rich Roll?

  Just the way that the movie theaters operate in terms of the kind of movies that people go to the movies to see, how that's changed and evolved over time? And how you fit in as a comedy producer, writer, director?

• 1:37:45Speaker 01

  I just think you need all of it. It's just the, what are the proportions? We love action movies. We love sci-fi. We love horror movies. We love romantic comedies and comedies. But if it used to be 25% comedies and it goes down to 4%, we pay a price for that. I mean, if you look at the world right now, because there's not an enormous amount of support from the studios for comedies, and a lot of the big comedy stars aren't in the theaters anymore, we almost don't have the next generation of comedy stars. And then it becomes something that you can't stop because we haven't trained the audience to watch comedies and we haven't introduced them to people who become the next Kristen Wiig

• 1:38:30Speaker 01

  or Sandler. And so, you know, that funk happens. And then people are like, do we even need it? And that's the problem because if you notice on all streamers, everything leads to like murder, you know?

• 1:38:48Rich Roll?

  True crime.

• 1:38:49Speaker 01

  True crime, kids being abused, women being abused. And they get huge numbers for that. So you go, wow, there's a lot of that on there.

• 1:38:57Rich Roll?

  Right. A lot of serial killer docu-style stuff.

• 1:39:01Speaker 01

  Like if it bleeds, it leads. It becomes such an enormous part of it because...

• 1:39:09Speaker 01

  I don't think that everyone is focused enough on let's do something good that we're all proud of. Like, just because people would watch a lot of that, do we have to make that much of it? And I think the stock market and the financial forces say, yes, yes, you're not allowed to try to make these other movies. You're not allowed to try, you know, to, to make Boogie Nights. You, you need to stay mainly on the topics that our metadata says people like. And that's a natural part of business, but it's way worse than it used to be. It used to be, you know, there was, there was always the, you know, popcorn movies and then challenging movies. But, you know, when streamers lose interest in independent

• 1:39:54Speaker 01

  film, they, and they think, well, we're not getting enough viewers. And it's not in the theaters. It can completely disappear. That, and that part's really scary. So what is the antidote to that? Well, like, for me, as a fan of all the streamers, and I work with all the streamers, I just think the mistake that they're making is they want everything to be flashy. So you'll get the streamer to see the show, right? I want you to see this because it looks wild. But a lot of great stuff is more muted and it's subtler. And so you lose all of that. So for a TV show, they want a big loud show. They always say, we want it to be sticky. That's what they'll say. And then they also think that the amount of people watching it generally goes down year to year. And they don't really need more than two or three

• 1:40:39Speaker 01

  seasons of it. So the audience doesn't have that relationship. And they also don't trust the streamers because they think, well, I don't want to fall in love with this show because I'm not going to get six seasons out of it. I'm not going to get that relationship. And so what I think everyone should do is like, why don't you just make it so your streamer has good stuff? And it, it doesn't have to be like, everything conquers the world. There should be things on the streamers that don't make economic sense. And I think in the old days, someone like Brandon Tartikoff would go, I believe in Cheers. I'm just not going to cancel it. I believe in Seinfeld. And that would happen. Shows sometimes it took two, three years to find their audience. And those are the shows that all the streamers want to re-air.

• 1:41:24Speaker 01

  Right. Or all those shows that were believed in when they weren't doing great. And I think you should watch, like, a streamer and think,

• 1:41:36Speaker 01

  I bet you no one watches this show, but the head of the streamer loves it. That was what was great about some things on network TV. Like you knew, like, oh, like even with movies, I know even from studio heads are like, I make this movie. So I'm allowed to make this one. I'll take the hit on this small one because I really am proud of it. And we need more of that, things that don't make economic sense.

• 1:41:58Rich Roll?

  Right.

• 1:41:59Speaker 01

  And then we would love our streamers more because it would have a little more heartbeat to it.

• 1:42:03Rich Roll?

  There's still a little bit of that, though, isn't there with prestige directors? They know the movies aren't going to make a lot of money. Maybe they'll even lose money, but they want to be in business with this person. And perhaps there's Oscars attached to it and that kind of thing. But I, it's almost like you need a new streaming service where the mission statement isn't growth necessarily. It's just like, let's just.

• 1:42:25Speaker 01

  Quality.

• 1:42:26Rich Roll?

  Like a criterion collection for just cool shit that's new, you know?

• 1:42:30Speaker 01

  Yeah, I mean, it, it feels like all these places just want to be. Not in the worst way, but they just, they just want to be Walmart. They just want to have everything on it so you never go to the other streamer.

• 1:42:42Rich Roll?

  Yeah.

• 1:42:43Speaker 01

  And as a result, they lose some personality and everyone's spread too thin. It's, everyone doesn't make too much, you know? It takes people to, to help you with, with these things. And so, you know, how many people know how to develop comedy? How many people know how to develop shows? How do you learn how to do it? Do you have enough time on one or two shows? Say you're covering 30 shows. Can you really learn how to do it versus if you just had three shows or four shows? And you were responsible for as an executive. So there's all sorts of reasons why things get, get flattened out and all the people involved there. Everyone is, you know, they're all like good people. They're all smart and funny and, and interesting.

• 1:43:24Speaker 01

  It's just the system is so dominant and the people who control the levers of it.

• 1:43:32Speaker 01

  I don't know if enough of the time they're pushing for experimentation because that's how you get The Sopranos. That's how you-

• 1:43:41Rich Roll?

  Right. And you need the, you know, every once in a while, the Squid Game comes along to remind everyone like, oh, it's something really good. That's brand new and completely out of the box.

• 1:43:50Speaker 01

  Beef.

• 1:43:50Rich Roll?

  Gets people excited about, yeah, beef.

• 1:43:52Speaker 01

  Beef is an amazing show.

• 1:43:53Rich Roll?

  Yeah.

• 1:43:54Speaker 01

  Remarkable. But we just need more of that.

• 1:43:57Rich Roll?

  Yeah.

• 1:43:57Speaker 01

  Right? Like, like, how did that even happen? When I watch them, like, how did this even happen?

• 1:44:02Rich Roll?

  It's the craziest shit that show.

• 1:44:04Speaker 01

  And White Lotus happened because there was a pandemic and they needed a show and Mike said, I have an idea. And they let him do it at a time when no one else really could get into production.

• 1:44:12Rich Roll?

  And it wasn't meant to be more than a season.

• 1:44:14Speaker 01

  Yeah.

• 1:44:15Rich Roll?

  And now it's-

• 1:44:16Speaker 01

  And so they trusted him.

• 1:44:17Rich Roll?

  Cornerstone of HBO.

• 1:44:18Speaker 01

  Yeah. And so it's those weird flukes. So you have to create an environment for flukes. You have to let creative people really take big risks to have that reward. And so that's the danger of, of a system that really rewards the, what they perceive as successful because things can get a lot of viewers. But this is my new thought. You can have things that a lot of people watch, but it also doesn't mean they liked it. You know, they talk a lot about completion rate. Oh, well, they completed it. I complete a lot of shit I like.

• 1:44:53Rich Roll?

  Yeah.

• 1:44:54Speaker 01

  You know, it doesn't-

• 1:44:54Rich Roll?

  Are you a guy who's just gonna see it through no matter what? Or do you pull the ripcord like on episode two of something that's not?

• 1:45:01Speaker 01

  I tend to only pull the ripcord because my wife has advanced ahead of me. And then, you know, I'll come home and we're on episode two and she's like, I watched five today. And I'm like-

• 1:45:11Rich Roll?

  He's that little white line at the bottom.

• 1:45:14Speaker 01

  And then I can't find the time alone to watch the, the rest of the series. But I do think that's a big, you know, a big part of it, which is pride in the work above all, above the numbers. That, that's what people can feel. You can feel someone at this place, wherever it is, some, they love this. You could feel the love of it and the passion for it. It's not just a placeholder. It's not filling a need.

• 1:45:46Rich Roll?

  You mentioned beef. Is there anything else that you've seen recently that you thought this is really excellent and new and fresh?

• 1:45:57Speaker 01

  What else have I been watching? I mean, I'm mainly a documentary fan. I do documentaries, but I just everything in the world of documentary. I tend to watch, you know, series wise. What do we watch? Watch Daisy and the Six was very good. We enjoyed that a lot. You know, Barry and Succession are pretty remarkable. And it's sad that they're gone. That's two giant holes in television. My daughter's on the TV show Euphoria, which I think is really special.

• 1:46:27Rich Roll?

  I mean, that is just a juggernaut and such an iconic cultural memento for that generation. You know, obviously, I have kids as well, and they love it. I love watching Euphoria with them. As rough as that can be. Yes. I know you've been asked about that, like, what's that like to have your daughter on that show? I mean, it's intense, but it's real. And I think it's cool to watch that show with teenagers. And it opens up, you're meeting them where they where they live and where they are. And I've just found that like the communication that you can have after that is, you know, really a unique thing.

• 1:47:09Speaker 01

  I think it's it's an amazing show. And I love what Sam Levinson did with it over the two seasons. Because by the end of the second season, you realize what his whole point was. He really stuck the landing on the idea of those two seasons. I think I meet way too many adults with kids who say, I can't do it. You know, they'll watch one. And maybe the first one was too scary for most people, because I think there's a fair amount of people who didn't get to the second one. And they really are missing out on something.

• 1:47:40Rich Roll?

  I mean, it is a lot. It is a lot. I'm empathetic to that impulse.

• 1:47:44Speaker 01

  If you had a film camera, shooting me sexually in high school, you'd be disgusted by that, too.

• 1:47:55Rich Roll?

  It wouldn't look like Euphoria, though.

• 1:47:57Speaker 01

  It wouldn't look like Euphoria. So like anytime you show that explicitly, you know, especially as a parent, that's rough, but you do have to get over that. And I think in terms of all the issues about addiction, there's important messages in there. I think some parents were like, well, does this make them want to do it? And I'm like, I don't know. They're all in hell. It doesn't seem like that's the fun party. For kids who watch the whole thing, there's a huge price to be paid for all of it. And I think that he finds the cinematic language to connect with kids and then to get a lot of very important ideas through.

• 1:48:33Rich Roll?

  I agree 100%. I think it's really potent and powerful. And, and, you know, to cast a, you know, just to say, put your blinders on and say, I don't want to look at that is to not engage with, on some level, you know, the reality of, of that time for young people that is very, I mean, we live in an urban place, you know, maybe we're exposed to stuff that wouldn't exist if you lived in some small town in the middle of the country. But, you know, I think a lot of the themes that they explore, I mean, there's a reason why that show is so big. It's because it is tapping that nerve of truth for that generation.

• 1:49:12Speaker 01

  Oh, absolutely. And you can't really look away from it when you have kids.

• 1:49:18Rich Roll?

  Yeah.

• 1:49:19Speaker 01

  Because they're having a completely different experience of reality than we had when we were young. It's just completely different. And just the fact that they like it makes it worth watching to just get a sense of how do you grow up with this much social media, this much judgment of you. I mean, when I was a kid, I don't think I even knew what I looked like half the time.

• 1:49:39Rich Roll?

  Can you imagine like having this thing in your pocket that was reflecting back to you, the good and the bad of everybody that you know, what they're saying about you, what they're doing when you're not around, what you've been disincluded from?

• 1:49:53Speaker 01

  Yeah, that's the thing I noticed with my kids. The hard part was they knew what everyone was doing. They knew when they weren't invited. I never knew, I wasn't invited to anything, but I didn't know it.

• 1:50:07Rich Roll?

  But the psychic pain of that.

• 1:50:10Speaker 01

  And also to just feel like you need to be attractive all the time. I mean, if I had to put up a picture every day during high school of what I looked like and tried to make it look good, or to make it look like I'm having fun, or to try to be funny, and then I'm going to judge based on how people responded, if people like me. I mean, I have issue with that now. I'll laugh with Leslie because I could go through the photos on my Instagram and I'm fascinated by what people heart and don't heart. And usually the things that are kind of just me, I don't get almost any. If I put up a picture like me and my wife, I got like 180,000 hearts. I'm like, people really like you and not me. But, but that's, that's a lot of pressure for kids and how they navigate.

• 1:50:54Speaker 01

  All the things that we hear about is so important. And how do we know? Like, if you can't watch that, how do you even know what your kid is experiencing?

• 1:51:05Rich Roll?

  Yeah.

• 1:51:06Speaker 01

  Not that it's exactly that.

• 1:51:07Rich Roll?

  Right, and we're running this unprecedented experiment on everyone. And we're doing it to young people while their, their brains are, you know, barely formed. And what does that mean? And how is that going to play out over time?

• 1:51:19Speaker 01

  I mean, how many times I've had to say to my kids, it doesn't matter what people say about you. Like someone said, you shouldn't care about anyone's opinion who you wouldn't ask for their opinion.

• 1:51:31Rich Roll?

  Right, which is true. And, you know, coming from dad, like, that's not connecting.

• 1:51:38Speaker 01

  I'll say it every day.

• 1:51:39Rich Roll?

  They don't, you know, like, they're now, they have these careers and they're in the, you know, in the public eye and, you know, they've been part of all, many of your projects over the years as, as young people. Do they look to you and Leslie for, like, how do you help guide them through that process? Having had some experience? Or do they just say, you know, are you like, you know, out to pasture? I guess is what I'm asking. You know, as a parent, like, when you have a 19 year, like, they're, you know, they can hear exactly what you would say from some other person that they trust, but they can't necessarily hear it from you as the parent.

• 1:52:18Speaker 01

  I mean, they drift in and out of interest in our opinions. But we do have an ongoing conversation about it. And I think. It's similar to, I was listening to your previous podcast and you were talking about the show and why you do the show and how you feel about advertisers and just staying in touch with the original reason why you're doing the show, your vision for it, not getting off track. And that's what I talk to my kids about all the time. You know, why are you in the business? You should have something that you want to say. You should have a reason and a passion for creativity and that's what matters most. Way down the line is how do

• 1:53:02Speaker 01

  people feel about you. It's really important to have mentors who don't care about the audience. It's not your main thought, but I always read interviews with John Cassavetes because he's always like, I don't care if it bugs them. I know, he's like, all I care about is if in 10 years, you're still thinking about it a little bit. He's like, I don't even need every scene to work. Maybe a couple of scenes work for you. Like you need those avant garde people who have a little disdain for the audience. You need that voice in your head in addition to your voice that wants to connect with everybody. Because that's part of being a creative person or an artist is I don't need everyone to like

• 1:53:43Speaker 01

  it. I mean, if you look at the top 10 movies of the year, how many do you like? Maybe zero.

• 1:53:48Rich Roll?

  Yeah, there's a lot of people in the world.

• 1:53:50Speaker 01

  Yeah, we're not supposed to like the same stuff.

• 1:53:52Rich Roll?

  But that's goes back to the whole streamer thing. Like they're trying to create for everybody all the time, everywhere. And that's death.

• 1:53:59Speaker 01

  Yeah. I mean, I like certain movies. They're, you know, like there are people who love Marvel. And then there's some people who will never watch any of it. And they're both, they're both legitimate point of views about that. But say you're a Marvel person and you're just like destroyed by the people who aren't interested in superheroes. I mean, that's what we're all doing in our own way, which is, yeah, I have a certain genre of what I make. And every once in a while, I'll read from someone who just like doesn't like my stuff. You know, I'll go online and go, oh, funny people is up. I wonder what people think. And, you know, it's usually about like 80, 90% positive and then like 10%.

• 1:54:37Rich Roll?

  Do you seek that out? You go, you're like, I'm gonna expose myself to that?

• 1:54:41Speaker 01

  Occasionally, because I'm just interested, how's it holding up?

• 1:54:44Rich Roll?

  Uh huh.

• 1:54:45Speaker 01

  And I won't go to town with it, but I'll just kind of buzz through and, and I'm always happy with people who, who were like, oh, I watch this movie once a year and, and they tell stories about when they watched it or when they first saw it. And then there's just a few people are like, it's so long and boring. Oh my God, this is your worst movie. Can you go back to your other stuff?

• 1:55:04Rich Roll?

  The ad hominem, you know, Judd's a tool.

• 1:55:08Speaker 01

  And I always say to my kids, look up Tom Hanks. 10 to 20% of people will be like, Tom Hanks is the worst. Like, look at the Dalai Lama, someone slamming the Dalai Lama. Like, there's 10 to 20% of people who don't like every single thing. It doesn't matter what it is. Tom Cruise, Garth Brooks, Shania Twain, you know, you know, me, Sandler, like, there's a percentage of people, and that's fine. It's supposed to be that. But if you go online and you're devastated by the people who don't like you, then you're in big trouble because it might shut you down. And if it, if your self-esteem isn't strong enough to understand that you're not supposed to win everybody over. You're just supposed to find your crowd.

• 1:55:53Rich Roll?

  And when you deliver that to Maude and Iris, how does that land? I mean, do they, do they get that?

• 1:56:00Speaker 01

  Yeah.

• 1:56:00Rich Roll?

  I mean, for Maude to be in Euphoria, I mean, she's, you know, it's, it's, you know, charting, challenging territory, and I'm sure there's a lot of people who have a lot of issues with that show. And she's at a young age to be on the receiving end of any kind of criticism, but it's also so artistically celebrated.

• 1:56:21Speaker 01

  Yeah, it's, it's, it's everything. And so it does require, you know, a constant conversation about art. You know, why do people like this painting versus that painting? You're part of a painting. And also, people love to debate stuff. So the main thing I always say is, it's a miracle to be on something that everyone's talking about.

• 1:56:39Rich Roll?

  People are talking about, yeah.

• 1:56:40Speaker 01

  Because no one watches most things, and the things they watch, they kind of forget about five minutes later. So the fact that you're part of something that's such a giant conversation, that will be one of those things that people remember forever, that is a really fantastic opportunity. Because it's just, it's hard, especially now. There's 500 TV shows, and maybe 10 are the ones that get talked about a ton.

• 1:57:07Rich Roll?

  Yeah. Have you had that experience where you're scrolling on your thing, trying to figure out, oh, I'm gonna watch, maybe I'll watch this. You click on it, and you're like, I already watched it.

• 1:57:16Speaker 01

  Yes, yes, yeah, no.

• 1:57:17Rich Roll?

  And I didn't remember watching it.

• 1:57:18Speaker 01

  I used to do a joke on stage about that, where I said, I got three episodes in, and then I turned to Leslie, and I'm like, I think we've seen this. It took three episodes to realize we've seen it. Or the other thing is, you watch a series that takes a year and a half to come back, and then you don't remember any of it, and you're like, is Escobar a good guy or a bad guy?

• 1:57:43Rich Roll?

  Yeah, I've had that experience where it's been, yeah, like a year and a half, and I can't remember anything that happened. And that mental calculus is, well, I'm gonna have to go back and at least watch two or three of the last ones, just to get ready. And I'm like, I'm not doing that.

• 1:57:57Speaker 01

  I gotta Google, I gotta read the wiki page for the last season, try to understand it. I have a question for you, though. So you do ultra marathons and things like that. That's the opposite of what I do. Because I have all sorts of issues around that, like emotional issues around being physical, exercise, jocks, like so much of what

• 1:58:25Speaker 01

  My world always was, was resenting the jocks because I was so little. I was the youngest kid in the grade and then bad at sports. And then you wouldn't be allowed in. So they'd throw you in right field. The ball would never come to you. And so you would never would have an opportunity to prove that you deserved a better position. And that would just happen for a decade.

• 1:58:47Rich Roll?

  Yeah.

• 1:58:48Speaker 01

  And so I think that's what a lot of Freaks and Geeks was about. Like these, these kids who weren't being accepted and they resented. So they become what we always said were cocky nerds. You know, you become kind of funny, but like you're scared of the athletes as a kid and the jocks. But you're also condescending to them.

• 1:59:09Rich Roll?

  Yeah.

• 1:59:10Speaker 01

  And, and that for me has been a big thing to get over. As I've gotten older, you have to exercise to not die. I never wanted to be around anyone who exercised.

• 1:59:22Rich Roll?

  No, I get it. Yeah, I get it. You know, it's interesting. I was, I was listening to the podcast that you did with Brene Brown a while back. And she said something like, what do people not know about you? Or something like that. And, and you said that I'm an athlete. Your friend tells you, Chud, you're an athlete.

• 1:59:40Speaker 01

  My friend, Brett Forrester, who, who was a great writer from, you know, The Simpsons and The Office. We take like 90 minute walks a bunch of times a week. And he's always like, people don't know, Chud's an athlete. Chud's an athlete. How fast you're walking today, people don't even know. But I have to put so much effort into staying consistent with any type of physical exercise. Because there's some part of me that so resents, I have to, to do it. And before the pandemic, I said, I signed up to this really expensive gym. And I'm like, this is really expensive, but I'm going to do it because then I have to go. And then for about a year or two, I did go and it worked. And then I said, how can I not hate this?

• 2:00:26Speaker 01

  There must be a way to not hate doing this because I not only hate this, I hate everyone in here. I hate every person who tells me what to do. And I'm like, so my goal is, could I ever want to come here? And I read a book, you probably know what the book is. It was a book written by Kobe Bryant's trainer.

• 2:00:48Rich Roll?

  Hmm, I don't think I've read that.

• 2:00:50Speaker 01

  It was all about how Kobe looked at his workouts and just what his mental approach was. And so in my head, I would-

• 2:01:00Rich Roll?

  The Mamba mentality thing, yeah.

• 2:01:02Speaker 01

  And in my head, I just thought, okay, when I'm here, I'm going to pretend I'm Kobe. What would he say? So if I want to get off the treadmill in three minutes, he'd be like, I'm gonna stay out here as long as I need to. I love it. Or, or just like, I want to go farther or faster than I did last time. And I would, in my head, pretend. And strangely, it started working, where after like two years, I had a little feeling of like, I want to go to the gym. And I'm not mad at everybody here. And then the pandemic hits.

• 2:01:37Rich Roll?

  And then it all fell to shit.

• 2:01:38Speaker 01

  And then it all fell to shit.

• 2:01:39Rich Roll?

  Yeah, yeah, yeah. Well, uh, there's a lot in there. I mean, the first thing I would say to your first question, the freaks and geeks aspect of it. You know, I relate to that sentiment or that kind of archetype deeply, because I was bullied in junior high and high school. I was not an athlete. I can't do anything with eye-hand coordination or a ball. And I was very much an outcast throughout high school. I grew up in suburban Maryland and, uh, and found swimming. And swimming was like an oasis away from the terrible experience of being in high school. And, and kind of like a womb-like, like underwater, like I can't hear all of that.

• 2:02:24Rich Roll?

  And I, I'm safe, you know, I'm not going to get beat up. And it was the only sport that I actually was any good at, at all. I had some, I wasn't like super talented, but I was okay. But it was one thing that I could do. And it was also a way to, you know, I wasn't the, the funny kid. I wasn't the, you know, it was like the one thing that I, I found kind of a home at, where there were other kids who were kind of like me. And so I just doubled down on that. And, you know, I wasn't a good student. I didn't know how to make friends. I certainly- We didn't have a girlfriend or anything like that, but it taught me discipline and it taught me this equation between hard work and like achievement or moving forward. And I realized

• 2:03:06Rich Roll?

  like, oh, I'm not as good as these other kids. But if I, if I actually work harder or I do more, like I can like bridge that gap and I could be with them, like create some parity. And that started to spill into into my school work and I got better at school. And then I got quite good at swimming. And by the time I graduated high school, I was like getting recruited at colleges and all that kind of stuff. But have always been that kind of bookish, sensitive outsider who felt like everybody else had a rulebook for life that I couldn't connect with them, like never the cool kid. But then I go to Stanford and the swimmers were the cool kids. So this was like, you know,

• 2:03:49Rich Roll?

  my version of you moving to LA and, you know, like being in the comedian community. And then alcohol fucked it all up, all of that. But to your point of, of, you know, being an outsider, I've always had that same relationship with bullies and with like football, basketball, like traditional sports guys and that like kind of archetype of what that personality is.

• 2:04:16Rich Roll?

  And then rediscovering fitness and kind of moving my body later in life was really a function of an existential crisis that I was having as much as anything else. Like the same impulse that made you go hike, you know, and then you realize what that script was is kind of how it started for me as well. But I ended up enjoying it. So that just was one foot in front of the other of kind of, you know, putting the Legos together and then realizing like, I actually like this and I'm actually good at this. And like, where could I take this? Let's see. But it was really from a place of like joy and curiosity. So when you go to the gym and you're trying to force yourself to like enjoy this thing that you don't enjoy, and you're trying to run

• 2:05:00Rich Roll?

  like some kind of mind trick, like I think that's backwards. You should find something that you that is fun like, you know, shooting hoops or pickleball or like what, you know, even walking or whatever it is. And then building on that, because that's how you create a sustainable habit that you look forward to. And you're not having to try to convince, some days you're not going to want to do it. But fundamentally, it's like, it's like this thing that, you know, nourishes you and isn't something that you're constantly dreading.

• 2:05:30Speaker 01

  Yeah. Yeah, it's a tough one. I think part of it also was it's connected to not wanting to be in my own head. So when I hear about you, you know, running for a great distance, all I think of is like, oh, but then you're just sitting with yourself.

• 2:05:44Rich Roll?

  Yeah. But that's like, there is something about like, if you can just get your heart rate up a little bit, like more than it would be if you were walking, but not like out of breath, that quiets the mind. And yeah, it's uncomfortable, but it's just like pushups. And then, you know, you can go a little bit further and then you sort of look for, it's sort of like meditation, like your mind's attacking you. This is the most painful thing ever. All suffering is because we can't sit alone by ourselves for fucking two seconds.

• 2:06:14Rich Roll?

  But there's a peace that comes with that. And I think also as a way to nourish your creativity, you already know the relationship between what that experience can be in terms of how you do your work. So I think there's something cool there for you to maybe explore.

• 2:06:33Speaker 01

  Lately, I keep thinking, I feel like I'm almost beginning to get it, just like a general get it, you know, like just lately, I feel like, oh, I almost understand, not, not completely, but more, but of kind of all of it. Like I almost feel like a circle closing and then right when I get it, my body will fall apart.

• 2:06:59Rich Roll?

  It is that thing, but it is like, it's also that momentum thing. Like when you're go- when you're in the, when you're doing it, it's easier to do it. And then something happens, you have to go out of town or whatever, and then you're fucked. And like, you never find your way back. Like, that's just, that's human. That's just being human, too. You know? I don't know. Um, I have faith in you, though.

• 2:07:19Speaker 01

  One day I'll get-

• 2:07:19Rich Roll?

  Come on, dude. We're like, how old are you? I'm 56.

• 2:07:22Speaker 01

  I'm 55.

• 2:07:23Rich Roll?

  Yeah, so, you know, we can't fuck around anymore.

• 2:07:25Speaker 01

  No, no.

• 2:07:26Rich Roll?

  You know?

• 2:07:26Speaker 01

  That's the drag. When I realized like, I needed to exercise to stay healthy, it was easier to start exercising. I hated the idea of exercising to look good. I don't know why. I was just like, I didn't like the like, guys in the gym trying to get ripped. And-

• 2:07:41Rich Roll?

  But what about the feel, like, oh, I feel better?

• 2:07:44Speaker 01

  I, I had gotten to that a little bit. Like, I don't love doing like, the cold plunge, but I started doing it.

• 2:07:49Rich Roll?

  Do you have one at your house?

• 2:07:50Speaker 01

  No, but I started doing it at the gym. And then I was able to do it for like, five minutes, and I did it a few times. And then I realized, oh, this strangely put me in a good mood for like, four hours. Like, a really good mood.

• 2:08:01Rich Roll?

  I mean, on the flow state thing, like, the cold plunge, in terms of being an antidepressant, and just something to kind of calm you down and clear the mind, like, it's pretty effective.

• 2:08:11Speaker 01

  But isn't it terrible that like, that's what you have to do?

• 2:08:14Rich Roll?

  I know, I know.

• 2:08:15Speaker 01

  That's how the world works. Like, you'll feel great, just freeze for five minutes.

• 2:08:19Rich Roll?

  Yeah, but it's like, is it any different than like, isn't it awful that I have to pull my hair out to like, get this idea on paper?

• 2:08:25Speaker 01

  Yes.

• 2:08:26Rich Roll?

  And it takes years, and it's like, horrible?

• 2:08:28Speaker 01

  Yeah.

• 2:08:28Rich Roll?

  You know, it's rigged that way.

• 2:08:30Speaker 01

  I know. I've been, there's so many things that aren't pleasant that now I have no choice but to do.

• 2:08:39Rich Roll?

  That's, I just came up with the inspirational quote from the podcast.

• 2:08:45Speaker 01

  All right, I get it. I gotta meditate, then I get in that cold plunge, then I gotta find a sauna somewhere, then I gotta raise my heart rate.

• 2:08:53Rich Roll?

  The four-hour morning routine.

• 2:08:54Speaker 01

  I mean, it's a lot of morning routine. And that, that was a big thing with writing the script, like, someone was saying, you know, it's okay to do all of your exercise at the end of the day. You don't have to do it first thing because sometimes you're just wiped out from that. Like, you know, write for four hours, then go do it. And even learning that was a game changer because there was no part of my brain that could have figured that out because I'm just so dumb. Like, wait, jog in the afternoon. Like, it would take me 30 years to do that math.

• 2:09:23Rich Roll?

  It's harder to do that in the afternoon, though. But the tension is, if I sit down and write, I'll have something that's permanent. And this is actually what I do. And, you know, the exercise stuff, that's not necessarily critical. I can do that later. But you know, if you do the exercise first, you'll actually feel better. And maybe the writing that you do afterwards will be a little bit crisper.

• 2:09:48Speaker 01

  Yeah, but then you gotta, then you gotta wake up early. Now I gotta sleep well and get up early. Yeah, sleep well and get up early.

• 2:09:56Rich Roll?

  The pressure.

• 2:09:57Speaker 01

  So many things.

• 2:09:58Rich Roll?

  Anxiety disorder about being well.

• 2:10:00Speaker 01

  Exactly, right? Like, the whole day, all right, and then, but don't eat till lunch. Okay, so sleep great, get up early, don't eat till lunch. There's so many things.

• 2:10:14Rich Roll?

  I'm like weirdly kind of uplifted and encouraged by the fact that you are struggling with that equation.

• 2:10:22Speaker 01

  But you know, I, but I kind of get it a little bit. So I, I, I mean, I don't think I, till the pandemic, I don't think I took a walk my whole life. Where like I said, oh, I'm gonna do a walk for an hour and a half. Never, would never go on a hike, wouldn't even think to do it. The treadmill, but would never think like, oh, maybe it's just fun to get outside. It took the world shutting down for me to realize there was an outside, you know?

• 2:10:46Rich Roll?

  I've heard you tell stories, though, about like walking around your neighborhood and knocking on your neighbor's doors unannounced.

• 2:10:52Speaker 01

  I started doing that during the pandemic. I would just knock on people's doors because everyone was just stuck in the house, especially the scariest part of it.

• 2:10:59Rich Roll?

  Yeah.

• 2:10:59Speaker 01

  I just knock on people's doors and they would like, sometimes they wouldn't even open the gate. They'd like talk to me through the gates, like people were really freaked out. And I'm like, how you doing? Just people I hadn't seen in a long time. And people I wasn't even that close with, but someone I admire, like, how's it going over the other side of that fence?

• 2:11:18Rich Roll?

  Yeah, that's cool. All right. Well, we're going off the rails here.

• 2:11:23Rich Roll?

  Thank you, Chad. That was a pleasure and an honor to talk to you. I really appreciate it, man.

• 2:11:27Speaker 01

  Pleasure.

• 2:11:28Rich Roll?

  Great. You have, well, we're in a writer's strike. It's not like you have a movie coming out right now or anything.

• 2:11:33Speaker 01

  I have a book.

• 2:11:33Rich Roll?

  But like you have this book, you have Sick in the Head and Sicker in the Head.

• 2:11:36Speaker 01

  Yes.

• 2:11:37Rich Roll?

  Please watch the documentaries. If you've seen all of his big movies already, the George Carlin doc and the Gary Shandling doc. You have the Avnet Brothers documentary.

• 2:11:46Speaker 01

  The Avnet Brothers, yes.

• 2:11:48Rich Roll?

  Yeah, Avnet, sorry.

• 2:11:48Speaker 01

  On HBO, that's on HBO. Doc and Daryl.

• 2:11:52Rich Roll?

  Yeah.

• 2:11:52Speaker 01

  ESPN 30 for 30.

• 2:11:54Rich Roll?

  I haven't seen that.

• 2:11:55Speaker 01

  Oh, that's, you like that one.

• 2:11:56Rich Roll?

  All right. Anything else you want to draw attention to? Your wife on Instagram?

• 2:12:01Speaker 01

  My wife.

• 2:12:02Rich Roll?

  Get the likes.

• 2:12:03Speaker 01

  My wife, we all need our likes. Funny people on Netflix.

• 2:12:08Rich Roll?

  Good deal.

• 2:12:08Speaker 01

  Let's pretend that's a brand new. The Bubble is also on Netflix.

• 2:12:11Rich Roll?

  The Bubble, yeah. I haven't seen The Bubble. Usually I have like six or eight weeks where these things are scheduled and I can marinate. You know, but I, this came about pretty quick, so I haven't yet.

• 2:12:20Speaker 01

  It'll always be there for you. It's waiting for you.

• 2:12:24Rich Roll?

  Thanks, Chad. Cheers.

• 2:12:26Speaker 01

  Thanks.

• 2:12:38Rich Roll?

  That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guest, including links and resources related to everything discussed today, visit the episode page at richroll.com where you can find the entire podcast archive, as well as podcast merch, my books, Finding Ultra, Voicing Change, and The Plant Power Way, as well as the Plant Power Meal Planner at meals.richroll.com. If you'd like to support the podcast, the easiest and most impactful thing you can do is to subscribe to the show on Apple Podcasts, on Spotify. And on YouTube and leave a review and/or comment.

• 2:13:22Rich Roll?

  Supporting the sponsors who support the show is also important and appreciated. And sharing the show or your favorite episode with friends or on social media is of course awesome and very helpful. And finally, for podcast updates, special offers on books, the meal planner, and other subjects, please subscribe to our newsletter, which you can find on the footer of any page at richroll.com. Today's show was produced and engineered by Jason Camiolo. The video edition of the podcast was created by Blake Curtis with assistance by our creative director, Dan Drake. Portraits by Davy Greenberg. Graphic and social media assets courtesy of Daniel Salis. Thank you Georgia Whaley for copywriting and website management.

• 2:14:06Rich Roll?

  And of course, our theme music was created by Tyler Pyatt, Trapper Pyatt, and Harry Mathis. Appreciate the love, love the support. See you back here soon. Peace. Blinds. Namaste. [music] [laughing] [music] [laughing] [music]