Working It Out With Mike Birbiglia: Comedy & Creativity, Podcasting & The Pope

Mike Birbiglia is a master storyteller, acclaimed comedian, and the creative force behind Netflix specials including "The Old Man & the Pool" and his newest, "The Good Life." This conversation explores the quiet architecture of story—how to shape it, live it, and share it in a way that matters. We talk about finding empathy for the parents who couldn’t fully show up, embracing feedback without losing your voice, and why the creative process might just be as simple and profound as “letting your brain go for a walk.” It’s not about performance. It’s about presence. Mike illuminates our shared humanity. This conversation is medicine for our divided times. Enjoy! Show notes + MORE Watch on YouTube Newsletter Sign-Up Eight Sleep: Get $350 off your Pod 5 Ultra w/ code RICHROLL👉eightsleep.com/richroll On: High-performance shoes & apparel crafted for comfort and style 👉on.com/richroll Bragg: Get 20% OFF your first order with code RICHROLL👉 Bragg.com BetterHelp: Get 10% OFF the first month👉BetterHelp.com/richroll PPMP: Get $10 OFF your membership with code RICHROLL👉mealplanner.richroll.com ROKA: Unlock 20% OFF your order with code RICHROLL👉ROKA.com/RICHROLL AG1: Get a FREE bottle of Vitamin D3+K2 AND 5 free AG1 Travel Packs 👉drinkAG1.com/richroll Check out all of the amazing discounts from our Sponsors 👉 richroll.com/sponsors Find out more about Voicing Change Media at voicingchange.media and follow us @voicingchange 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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• 1:04Rich Roll?

  Mike Birbiglia is pretty hilarious.

• 1:07Speaker 01

  Wife and I hate going to parties, but we love driving away from parties.

• 1:13Rich Roll?

  But what separates Mike from other very funny people is story.

• 1:18Speaker 01

  Stories are one of the world's oldest art forms. It's the way we understand ourselves. I remember the first time I got emotional on stage, and I didn't know what to do. Every night I walk on stage, whatever happens tonight is the show.

• 1:37Rich Roll?

  Hey, everybody, welcome to the podcast. My guest today is the great Mike Birbiglia. Mike is a comedian, which if you've heard of him, then you already know that. I certainly have been a fan of his for a very long time. But what he really is, is a master storyteller. Story is the foundation of everything that Mike does, from performing live onstage to behind the mic on This American Life, which is where I first discovered him many years ago, on his own podcast called Working It Out, and on screen in films like Sleepwalk With Me, which he wrote and directed based on his bestselling book and his one-man show about his crazy experiences with a sleep disorder. Story is something that I think about a lot because story is something that's innately human.

• 2:22Rich Roll?

  It's hardwired into us. It's a primordial need, and that informs how we learn, how we make sense of the world, and serves as the primary way we connect ourselves to and feel connection with other people and the world. So in many ways, the way we experience reality is a story. So fundamental is storytelling, in my opinion, that the stories we tell ourselves about ourselves, who we are, what we're capable of or not, and tell others about ourselves and other people, whether they're true or not, create and inform our reality. And only by changing those stories can we change our experience of reality. Mike is also an actor. He's appeared in movies like Trainwreck and The Fault in Our Stars, and a bunch of TV

• 3:05Rich Roll?

  shows like Girls, Billions, and Orange is the New Black. He also has a couple Netflix specials under his belt, including The Old Man and the Pool, which I got to see live. Quite amazing. So today, we're going to get into all of it, and we're going to do what Mike does best, which is work it out, from comedy and creativity to parenting and podcasting, and even some stories about the Pope. But more than anything, this is about storytelling, why it's vital, and how to do it well. The Good Life is his new Netflix special. It's out now, so check it out, because it's super good. But right now, check this out, which is Mike Birbiglia sharing stories about storytelling and vice versa, but mostly me doing what you do when someone is telling a really great story, which is sit back and listen.

• 3:52Rich Roll?

  Dude, we worked it out.

• 3:53Speaker 01

  We made it happen. We worked it out.

• 3:55Rich Roll?

  After many years of back and forth, it finally happened. And today, we're gonna work it out.

• 4:00Speaker 01

  Yep, we're gonna work it out also.

• 4:03Rich Roll?

  It's great to have you here. I've been a fan for a long time. And I thought, when The Old Man in the Pool came out, I was like, oh, this is like, the perfect set of circumstances for us to talk, like swimming, midlife, you know, health and all this sort of thing. But actually, your new special is sort of hitting the bullseye of like, stuff I'm going through right now with my parents. And I thought it was, you know, really beautiful, this expression that you're now, that you're now sharing, and the honesty and the vulnerability, and how that impacts how you think about parenting. And it's just a highly relatable story.

• 4:41Speaker 01

  Dang.

• 4:42Rich Roll?

  Yeah, really well done. I'd seen some of the pieces of it, because I saw you at Largo and you were kind of, you were working out the show, I assume, at that time.

• 4:51Speaker 01

  Yeah.

• 4:51Rich Roll?

  So I'd heard a couple of those stories before, but like, to have it all come together as this woven together like fabric, where you go from A to Z, it's like, you're really a master storyteller.

• 5:03Speaker 01

  I appreciate it. It's, I think for me, the experience of this one, what made it different from the other specials is that the story is the story I'm living in the present. Like, my dad is still, you know, in care and had an acute stroke, and it's really struggling. And so the pain is still there. Like, a lot of the things, it's like, things that I've dealt with in the past, having a sleeping disorder, sleepwalking disorder, but I've dealt with it to some degree. I had bladder cancer when I was 20, you know, it hasn't come back. Like, I've been doing well in that front. This is like, oh, this is my life now, and this is hard.

• 5:47Speaker 01

  And it was, it was interesting, because I started out writing a show two years ago about what can I teach my daughter, who at the time was eight. And I was having this thing where I thought, you know, when you're, when the kids are little... This is a joke in the special, but I go, that doesn't, you don't have to know that much, because the, you know, it's a lot of layups. It's like, it's like, what's that? That's an egg. I'm a genius, you know? And, and then at a certain point, you're like, oh, I think my ceiling of intel, for intelligence, might be like age seven.

• 6:19Rich Roll?

  Right.

• 6:20Speaker 01

  You know what I mean? And, and, and, and then you don't know the answers. And then the thing happened with my dad, where he had a stroke. And I'm trying to explain to my daughter what a stroke is. I'm going, I'm sure I can't really explain this. This is hard to explain. And, and, and that's what the show became ultimately about, which is, what can I teach my daughter? And then what have I learned from my dad? And to do that, I had to be, I think, more empathetic with my dad than I had been previously. So it was a good exercise, in the sense that my dad has always felt distant to a degree, even though our family's close. But it forced me to just go, well, as, as a writer of a

• 7:05Speaker 01

  play, you want to have, you want to care about all the characters and do justice to all the characters. Because otherwise, it just feels cartoonish. And I was like, yeah, he was angry and he had a temper, but also, he was a great doctor and he was very compassionate in these ways. And, and, so it was an interesting challenge for me. And like, I think made me understand my father more.

• 7:31Rich Roll?

  Well, the low hanging fruit, from a comedy perspective, is all the anger and resentment that you've stored over many years of like, why didn't he do this? And why was he like that? And here's why I'm this way.

• 7:42Speaker 01

  Yes.

• 7:43Rich Roll?

  But the real arc of the story, and the, the kind of spiritual aspect of it, is traveling from that place to a place of like, love and compassion and forgiveness and, to your point, empathy. Like, seeing him, maybe for the first time, as a, as a, like a holistic person who did the best that he could with what he had.

• 8:05Speaker 01

  Yeah, I mean, truly, like, when I was a kid, I really viewed my dad as like this, this mythological creature, like, in hindsight. And, and as, as I've, in the last few years, I feel like I've just understood him as a person.

• 8:20Rich Roll?

  How old is he?

• 8:21Speaker 01

  He's eighty-four. So he's born in nineteen forty.

• 8:24Rich Roll?

  So was my dad.

• 8:25Speaker 01

  Yeah.

• 8:26Rich Roll?

  Yeah.

• 8:26Speaker 01

  Oh, really? I mean, my dad grew up in 1940 in Bushwick, Brooklyn. Was, you know, it was really unlikely for him to have the life he had. Like, he, he got, I mean, I asked him about this. So much of this stuff is like in the condition he's in. He can't remember what's happened in the last year, but he can remember things from the distant past. So I've asked him all these things that I had never asked him about his life. And, you know, one of the things was I, I go, how'd you end up going to Xavier High School in New York? And, and Holy Cross College and med school and all this?

• 9:08Speaker 01

  And he goes, you know, it was like some kid at school was going to take the entrance exam for Xavier and this Jesuit school in Manhattan. And, and I go, I'll try that. And then he, he like scored really well and got a scholarship. And he ended up leading him on this path that I think he never imagined for his life at all.

• 9:33Rich Roll?

  My favorite joke is when you say, um, you know, he was this great doctor, uh, but then that wasn't enough. So he went to law school. That's how much he didn't want to be a dad.

• 9:45Speaker 01

  In his free time, he went to law school. It's crazy.

• 9:49Rich Roll?

  But that is an amazing thing. But you're this kid who's vying for attention and never able to get it. I mean, there has to be a connection between that and you becoming this comedian.

• 10:00Speaker 01

  Oh, yeah, certainly. Yeah. I think part of it is, and maybe this is the reason why I'm the comedian of the, you know, four children is like, I was youngest of four and I think I was like the oops baby of family. And I think my dad was kind of done with parenting at that point.

• 10:20Rich Roll?

  Like whatever attention he had available to him to give to the kids had been long past spent.

• 10:26Speaker 01

  Yeah, yeah, yeah, exactly. So, you know, it's like he would come to soccer games and he would come to, you know, but it's not like I was good at soccer. You know what I mean? It's like, no, come to my, my plays. But he would, yeah, he would show up to things, but he wasn't around a lot. And it was, and I do think that, like you're saying, like the correlation between that and becoming a performer is not lost on me.

• 10:52Rich Roll?

  Being the youngest, you get free rein to kind of be who you want to be though also, right? Like, so there's not the pressure that the eldest has to like follow in the footsteps or the expectations. It's sort of like, you go do whatever you want to do, right? Like, so was that part of it too, where you felt like you could go into this, you know, off kilter world and profession without the intensity of your parents judging it?

• 11:17Speaker 01

  A hundred percent. So much of my childhood, and it's so confusing, the way we, you know, me and others raise our children now, it's like, it really was, there weren't a ton of rules. We were just in the forest. We would be at the park. We would, it was, it's that cliche people say, come back by dark. You know what I mean? When it's dark?

• 11:42Rich Roll?

  Yeah.

• 11:42Speaker 01

  And of course, parenting is not like that now for almost anyone. But, um, but yeah, so it did give me free rein. And then, and then the other thing is, you know, it's not lost on me that my, you know, my mom is extraordinarily loving. And so that gave me a stability also to feel comfortable in trying things. And she's a good storyteller. And I think that, that I had always admired that and kind of copied that in a certain way. So, I don't know. Yeah. But it's, it's definitely, it's all part of the alchemy that leads one to being, doing something so odd as being a comedian.

• 12:24Rich Roll?

  Yeah. Have you ever had your dad on your podcast?

• 12:28Speaker 01

  No. My dad, like, it's so hard to describe, like, how, how uninterested he is in show business.

• 12:37Rich Roll?

  But I, I raised that because I had my dad on. And there was a reason for that. He, he was a lawyer, but then when he retired from his profession, he started writing these really dense, uh,

• 12:54Rich Roll?

  Historical biographies, you know, on like historical figures and he had written this book and it's like, I'll have him on, but obviously this is my opportunity to like, you know, like let's, let's go into it, you know, but the formality of podcasting allowed us to talk about his life in a way that I don't know if I ever would have taken the opportunity to sit down with him across the breakfast table and engage with him in that way.

• 13:19Speaker 01

  I have definitely tried to interview my parents over the years about different things and they just, they just don't really want to engage in it.

• 13:29Rich Roll?

  Yeah.

• 13:30Speaker 01

  And I just have to go, okay, sure.

• 13:33Rich Roll?

  And of course, we do, uh, we do, you know, we do the opposite as parents, right? We let that pendulum swing way too far in the other direction. And you talk about that in the special as well. Like, we're gonna try to do all the things that, you know, give our kids all the things that we feel like we were deprived of, but as a result of the stoic, you know, kind of unemotional, um, you know, landscape of, you know, intimacy being, you know, something impossible to get.

• 14:02Speaker 01

  Yeah. No, and exactly. It's like whatever, whatever we're doing wrong, my wife and I parenting, we're gonna find out when she's an adult. And you can't get, you can't even guess what it is.

• 14:16Rich Roll?

  So Una is 10, right?

• 14:18Speaker 01

  Yeah.

• 14:19Rich Roll?

  Okay, so I'm way further down this path and I can report back to you that, you know, most assuredly, you know, these, it'll be, there's gonna be a whole laundry list of, of, you know, things to, you know, grievances that, you know, why did you do it this way?

• 14:33Speaker 01

  Sure.

• 14:34Rich Roll?

  And like, you know, all those choices that you make that you feel like are the right ones. Like, it's wired such that it's always gonna be the wrong choice from their perspective for some reason later in life.

• 14:43Speaker 01

  No, absolutely. And, and I will say, like, I, you know, my parents have, while they haven't been extremely supportive of my comedy career, like, they don't come to a lot of my shows, et cetera. They also haven't complained a lot. I mean, apparently, they complained to other members of my family. Like, they complained to my brother and sisters about stuff I'm talking about. But they don't, it's not to the point where they say, like, you can't talk about that. You know, I think, like, in some ways, if, like, the lineage of my comedy does go back to, like, another theme in the, in the show, which is I went to the Vatican last year and met

• 15:24Speaker 01

  the Pope, and which is so lucky, you know, before he passed. And, um, and that was my strict upbringing, was Catholicism. And I do feel like there was, at least in that 1980s Massachusetts Catholicism, a sense of, like, don't talk about things. And I feel like, in a lot of ways, my comedy is, like, talk about everything.

• 15:46Rich Roll?

  Right. So, that's what I'm always thinking about when I watch your stuff, because you're naming names and you're talking about the people that you're closest to in your life. And it's, it's like deeply uncomfortable to me as a people pleaser. Like, how does he just do that? You know, there must be a whole domino effect to that. You know, you talk about your wife, and, you know, they're, they're getting wind of whatever you're saying.

• 16:08Speaker 01

  No, no, certainly. And, I mean, fortunately, yeah, there's a little bit of a hack to it if you look at, if you deconstruct sort of who are the main players in my shows, which is to say that, like, I talk about my brother Joe a lot, and he's a collaborator of mine. We've worked together for 20 years. And I talk about my wife a lot, and she's a collaborator of mine, and we've worked together for probably almost 20 years. So, they have a lot of input on, you know,

• 16:37Rich Roll?

  The line.

• 16:37Speaker 01

  The depiction of, yeah, the line and the depiction of themselves. Sometimes, you know, in the case of my special a few, three specials ago, the new one, I included poetry from my wife about the birth of our child. And that was my depiction of her feelings about how it was, because it's so sensitive for her. So I was like, oh, I'll read it verbatim and just say, this is a poem that Jen wrote. So there's that. And then, and then there's, I mean, mostly, in my comedy, I try to make myself the butt of the joke. I try to find the humor of, you know,

• 17:21Speaker 01

  That I was talking about this with Conan recently. It's like the comedy of like, we're the ones in the mud with everybody. You know, and that there's something fun about that of being, being part of the joke, being part of what the joke is as opposed to looking down at people who are in the mud.

• 17:40Rich Roll?

  Yeah, no, there's nothing condescending about it. You're, you're in the middle of the whole thing. And you're the one who created the disaster and, you know, has to find their way out of it.

• 17:50Speaker 01

  That's right.

• 17:50Rich Roll?

  Yeah.

• 17:51Speaker 01

  No, completely. And I will say like, as I've gotten older, the most rewarding part of being a comedian has become that people, people feel connected to the personal experiences. Like the stuff that you're describing of like, that this is similar to what you're experiencing in your life. For me, that's the most rewarding part of being a comedian more than anything, more than any part of it. Like, which is so different from what got me into it. What got me into it was like, look at me. And I feel like as I've gotten older, it's like, no, no, look at everybody.

• 18:28Rich Roll?

  Yeah, the connection.

• 18:30Speaker 01

  Yeah.

• 18:31Rich Roll?

  Creating.

• 18:32Speaker 01

  Yeah, look at all, look, look at all of us.

• 18:34Rich Roll?

  And, and just telling jokes or making fun of yourself or, or, you know, pointing a finger at other people, that doesn't accomplish that. What accomplishes it is storytelling, like a story well told where every member of the audience can see themselves and feel themselves somewhere in that narrative. Even though the facts of their life are very different from yours, the emotional experience of whatever you're traversing is something highly relatable. So I wanted to talk about storytelling. I mean, that is the defining feature of, of what you do, and I think you're a master at it. Why do you see this as so central to your work? Like, what is it about storytelling and how do you think about it?

• 19:18Speaker 01

  So. I started out writing jokes when I was in high school. I, it was the fir-, I, I was, my brother Joe took me to see Steven Wright, who's like a great, classic, one-liner comedian from Boston. We saw him at the Cape Cod Melody Tent in Massachusetts, and I was entirely transfixed. I was like, oh my God, I can't believe people think like this. This is, you know, kind of like the illusion of stand-up comedy, which is like, that's what I think. He's saying what I think, you know? And of course, because I've never experienced that before, I'm thinking, this is only me. You're the only one. And, and so, I, I went home, just like a notebook like this, to just start writing jokes. And they're all like one-liner jokes.

• 20:03Speaker 01

  So in college, I entered the Funniest Person on Campus contest, and I won that, and I worked the door at the Washington DC Improv. And I like studied all these comedians. And then it, probably when I was about 24, I did the, I was asked to do the Moth Storytelling Series. And it was the first time I told a story. And it was, I told this story that ended up being eventually in my special called My Girlfriend's Boyfriend, about how when I was in high school, I had my first, like, serious girlfriend. And she told me that I, I couldn't tell anyone that she, she was my girlfriend because she had another boyfriend in another town or whatever. And so, I was like, okay.

• 20:46Speaker 01

  And then eventually she invites me to meet her parents. And I was like, this is my moment. And I went over and I met her parents. And this other guy is like hanging around the house. And I'm slowly realizing like, that's the other boyfriend. And he seems nice. And then he invites us to meet his parents. And I goes, very strange thing, meeting your girlfriend's boyfriend's parents for the first time. And it's, uh, and, and that was the first time. I told that on stage. It was in Aspen, Colorado. And it was the first time where I was like, Oh, this is deep. Like, what's happening in this room is pretty deep. Because I, you know, like, the thing I just said to you, the version I just said to you, that's a joke.

• 21:27Speaker 01

  But then there's, there's also moments of silence where it's, it's like, people are really feeling something in the room of, oh, my God, I've had that. I've lived that.

• 21:39Rich Roll?

  Or it's their worst fear.

• 21:41Speaker 01

  Or it's their worst fear. Or they've lived something like it. And I was like, really hooked. I was like, oh, I should tell a story like this. And then I told, for the moth, I told my sleepwalking story where I jumped through a second-story window, sleepwalking. And then Ira Glass from This American Life heard about it and asked me to put it on This American Life.

• 22:04Rich Roll?

  I think that was the first time that I, that I heard you.

• 22:07Speaker 01

  Yeah. And, and that, in a lot of ways, changed my whole career because Ira really kind of taught me how to tell stories. And the more that I would tell stories, the more I was just interested in that format of like, there's something about, you know, stories are, you know, one of the world's oldest art forms. It's the way we understand ourselves. You know, that's, that, I mean, I mean, look, it's like, people always say, filmmakers say this, playwrights say this. It's like, make the movie you want to see. You know, not the movie you think people want, make the movie you want to see.

• 22:50Speaker 01

  It's like, for me, I, I, when I was a kid, I would watch, I'm trying to think of a movie that like, really captures that, like, it's, it's funny, like, the James L. Brooks movies for me, like, you know, or the Woody Allen movies. But like, I'm thinking of like, broadcast news, where it's like, it's so funny, the Albert Brooks character is so funny and sweating, and he's, he's in love with this woman, and she's not in love with him. And it's funny, I'm saying that now, like, that's my girlfriend's point.

• 23:24Rich Roll?

  Yeah.

• 23:25Speaker 01

  It's literally my girlfriend's boyfriend.

• 23:26Rich Roll?

  The context of the story is irrelevant. It's just.

• 23:29Speaker 01

  That's right.

• 23:30Rich Roll?

  The idea that even though he's sweating on camera and all of that, like, we all have had some version of that experience in our own private lives.

• 23:38Speaker 01

  That's right. And so when I watch movies like that, or like more recently, Jesse Eisenberg's movie, A Real Pain, I like so deeply connected with that movie. Cause I'm like, yeah, I've had, I've been in that relationship that he and Culkin are in, their characters are in. And it's like, yeah, the way that we see ourselves through stories is powerful. And it's like, when it works, it's amazing. When it doesn't work, it's brutal.

• 24:19Rich Roll?

  When it works, it's transcendent.

• 24:20Speaker 01

  Yes.

• 24:21Rich Roll?

  And it lives forever.

• 24:22Speaker 01

  Yeah.

• 24:23Rich Roll?

  You know, it really is an incredibly powerful thing. And Ira is like the ultimate mentor guru of storytelling. And you have this opportunity to like, learn the craft with him.

• 24:35Speaker 01

  Unbelievable.

• 24:36Rich Roll?

  You talk about it all the time in your podcast, but you know, this guy has x-ray vision when it comes to story and what works and what's not working about it in ways that, you know, mere mortals can't, can't see. Like, what is it that he has? And how does he deconstruct stories?

• 24:52Speaker 01

  He would, if he were here, he would say, it's the sheer amount of stories that he's edited that has made him so sharp. He's one of these, he's one of these like fierce believers of like, it's not talent. Like, it's like, I worked for this. I figured this out. I do it over and over and over again, like that. And I think he's of course a genius. So I, you know, I'll argue with him about that. But, but, but I think, you know, his.

• 25:25Speaker 01

  He has like five or 10 things that he believes about what should be in a story. And he's just very rigorous about making sure that that is there. And, you know, one of the biggest things he's taught me over the years is, is that the best way to tell a story is you tell a little bit of plot and then how you feel about the plot, and then a little more plot, and then how you feel about the plot. And he said to me years ago, he goes, "You have this lucky thing, which is you have jokes, and jokes is your version of how I feel about the plot." So, so the time where you might lose the audience, they're actually laughing, and so they're engaged.

• 26:05Rich Roll?

  Right. The other thing that he talks about and that you talk about all the time is, is this idea of structuring the story so there's never a situation in which it's an "and then." It's always a "so then." Like, everything is propelling the next thing forward.

• 26:23Speaker 01

  Yeah, that's like a, that's the thing he talks about. I think Pixar talks about that, that's in their storytelling book, which is great. It's, whenever a young storyteller asks me for advice, I always say, "Just get really nerdy on the causality of the story." It's like, I jumped, I jumped through the second story window sleepwalking, "So then, I walked, you know, to the front desk and explained what happened. So then, he told me to go to the hospital. So then, I got into the rental car. So then, I drove to the hospital. So then, I flew home and I saw a doctor."

• 27:04Speaker 01

  So then, if a story essentially has a "so then" structure, the audience is always waiting for what the next thing is, and they're always, and the key thing is, like, when you're breaking apart a story is, if the audience gets ahead of the story and they know what's gonna happen, it actually becomes boring.

• 27:25Rich Roll?

  Yeah.

• 27:26Speaker 01

  And so that's why, like, I workshop this show, The Good Life, in 70 cities. And what I'm looking for a lot of times is, where are the laughs? And where is the audience ahead of me?

• 27:36Rich Roll?

  Hmm.

• 27:37Speaker 01

  When do they know?

• 27:39Rich Roll?

  They can anticipate.

• 27:40Speaker 01

  Where this is going.

• 27:41Rich Roll?

  The predictability of it. There's also the part of identifying which stories or what aspects of these stories are actually important and which aren't. And when you're talking about yourself, it's, there's many things that you could say, "Well, I could tell this story, this story, this story." But what is the story that actually is driving forward, like, the theme or the point that I'm trying to make?

• 28:05Speaker 01

  Yes.

• 28:05Rich Roll?

  And being rigorous in saying, "Yeah, this story's really funny, but it actually isn't, like, speaking to the underlying, kind of, like, idea that I'm trying to get to."

• 28:15Speaker 01

  Yeah, so, so when I'm developing these shows, I probably, I probably write about three or four hours of material in a show that ends up being about an hour fifteen. So it's essentially like, three times as much material as ends up being in, in the show. And a lot of the, the bits that I cut are pretty good. Some of them are great. You know, some of them, you know, my brother Joe collaborates with me on, on some of the shows, and, and sometimes he'll just be like, "You're taking out the rap song about drugs?" You know, and I'm like, "Yeah, it's a funny story, but it's..."

• 28:52Rich Roll?

  But stories king, you can't, like, hold on to the funny thing if it's not moving the story forward, right?

• 28:56Speaker 01

  Absolutely.

• 28:57Rich Roll?

  Like, every, every, like, comedy director will, will tell you that, right?

• 29:00Speaker 01

  No, absolutely. And, and my director Seth Baeresh, who's directed, you know, my last five specials and, and all of these solo shows, um, he and I will have painful conversations about, you know, he'll go, "You know, I just don't, this story, like, I don't get anything from it. Like, I get that it's funny, but I don't get how it relates to the story you're telling." And he won't say, "You have to cut it," but he'll just go, "That's how I'm experiencing."

• 29:29Rich Roll?

  Yeah.

• 29:30Speaker 01

  And it's, it's, those are painful conversations.

• 29:32Rich Roll?

  Well, this gets to the idea of, of, of working it out. Like, everything you learned from Ira and the way that you, uh, you know, workshop and, and craft these shows, you solicit input and feedback from other people.

• 29:46Speaker 01

  True.

• 29:46Rich Roll?

  Um, and then you created this podcast, working it out.

• 29:49Speaker 01

  Yeah.

• 29:50Rich Roll?

  During COVID, is that when you started it?

• 29:51Speaker 01

  Yeah, yeah, five years old.

• 29:52Rich Roll?

  Where you bring On your buddies and other people, other creative people who are working on things. And you share what you're working on and you give each other feedback. And I think like it's funny and it's just enjoyable on a surface level to like,

• 30:06Speaker 01

  Oh, thanks.

• 30:07Rich Roll?

  You know, here you like talk to all these people. But I actually think it's a real public service because you're modeling this practice of being open to other people's perspectives on your work.

• 30:20Speaker 01

  Yeah.

• 30:20Rich Roll?

  Which is something that is essential if you're a creative person in order to, you know, make the best version of your, your project. But is a real life skill that I think most people lack because we over identify with whatever we're doing. And we're defensive. We're not receptive or open to other people saying, hey, maybe don't do this and look at this instead.

• 30:43Speaker 01

  Right.

• 30:43Rich Roll?

  And when you and you know, whether it's whoever it is, John Mulaney or Pete Holmes or Judd Apatow, to watch you guys kind of get together and say, you know what, that thing, that's not working. Here's why and be excited about that. Like, oh, cool. Tell me more about that. Is a way of showing people like this is a way of being in the world also.

• 31:07Speaker 01

  Yeah.

• 31:07Rich Roll?

  With like your own behavior, because I don't think you can grow or change or evolve or, or, you know, achieve your goals or manifest whatever it is you're trying to do unless you can learn how to model that very behavior.

• 31:20Speaker 01

  It's funny. Yeah, it is a little bit like the Silicon Valley version of open sourcing. Where you just say like, here's the code, here's how we did it. You can do your version of it. It's basically like, and, and, and it's something that comedians

• 31:40Speaker 01

  for many years and myself included are, have been very resistant to, which is like showing people how it's done and what it looks like along the way. Because you're, it's a vulnerability. If, when you go out and you perform your best 10 minutes of standup comedy, you don't do versions of the jokes that just aren't there yet. And as a result, if you go out and you kill for 10 minutes, people just go, oh, that guy's a genius, right? They go like, he doesn't, that guy doesn't miss. That guy's just home runs all day.

• 32:15Rich Roll?

  Yeah.

• 32:16Speaker 01

  And if you show an audience. That, oh, they don't start like that? The jokes don't start like that? There's a vulnerability that you're risking where people go, oh, no, he's not a genius. He's actually like me. He's just someone thinking about this and working on it and trying and failing. And it was during COVID that I was like, well, I don't want to give away my jokes, but I, like in their early form, but why not? Why not try it? And then what happened was by the time I, people started performing again in front of audiences, my audiences were like two or three times as big as they were before the podcast.

• 33:01Speaker 01

  Because people wanted to see where this jokes started and where they ended. And so it was like a kind of an awesome experience.

• 33:10Rich Roll?

  But as a comedian, you have to have a healthy relationship with failure and imperfection. Because you're constantly getting up and working on stuff that isn't working. And you have to deal with people who aren't laughing and all of that. So I feel like more than most people, like you're, you're engaging with your own limitations, like publicly in a way that most people don't or don't have to.

• 33:33Speaker 01

  Yeah, but with typically smaller audiences. So like I would, like I would go to the Comedy Cellar for years and work on jokes that I thought were pretty good, but could be great. And then once they got great, I would bring them out to the theater tour. But this is like recording and filming, working out things that are just not done.

• 33:55Rich Roll?

  Yeah.

• 33:56Speaker 01

  And it's a weird level of trust. It's, it's a trust that the audience is smart enough at home to go, no, no, we've seen him do it well. So we're comfortable seeing him do it not well and not judge him for it.

• 34:14Rich Roll?

  Yeah, what I take away from it is just. Leaning into being open to, like, you have to choose your, the people who you're gonna expose your work to, right? Like, you can't just do it to everyone. But how vital it is to be receptive to other people's perspectives and to be objective about your own blind spots, to like, have the humility. Like, in order to create something great, you have to have, you have to believe in yourself, but you have to have the humility to know that you don't, you can't see all of it, and there are other people who, who can make it better.

• 34:47Speaker 01

  Oh, absolutely. I mean, I think like, that was why, in some ways, like, when I first moved to New York, I wanted to have comedians who were mentors, and I didn't really have that as much, but that's why, when Ira came along, Ira became something of a mentor, and I feel like that's why my comedy veered in that direction.

• 35:14Rich Roll?

  Uh huh. Do you feel that your success in, in doing your comedy in this way is now influencing other comedians to follow in suit with their version? I mean, Andrew Sholes's show is, you know, follows a, you know, a narrative through line in a way that is a little bit different than most of what you see in these comedy specials.

• 35:34Speaker 01

  Yeah, and I talked to him when he was developing that, and I gave him a couple thoughts on, on, on, you know, things he could do, but...

• 35:44Rich Roll?

  Yeah, I think it's, I think it's out there.

• 35:46Speaker 01

  I think like, I think, I think that I've been part of a, a, a series of Hannah Gadsby's shows or like that, you know? I've been part of, I would say the last decade of comedy has moved towards narrative storytelling, much more than when I started. And, you know, when I moved to New York in 2000, it was like, no one was really doing stories.

• 36:08Rich Roll?

  But you come out of Georgetown, you, when did you graduate Georgetown?

• 36:12Speaker 01

  2000.

• 36:13Rich Roll?

  2000. You moved to New York right after that. But at Georgetown, you're, you're at Georgetown at the same time, or in the same range as Mulaney, John Mulaney and Nick Kroll, which is insane.

• 36:25Speaker 01

  Even beyond that, Bradley Cooper...

• 36:28Rich Roll?

  Oh, that's right.

• 36:29Speaker 01

  Um, so Bradley Cooper was in a theater company called Nomadic Theater Company. We were the Georgetown Players Improv Group. In my screenwriting class was Joan Nolan, who has co-

• 36:40Rich Roll?

  Oh, I didn't know that.

• 36:41Speaker 01

  ... one of those Batman movies and The Prestige and all these brilliant things. He was in my screenwriting class.

• 36:49Rich Roll?

  It's like, it's so funny, though, because Georgetown, it's not like, you know, USC or NYU. It's like, you don't go to Georgetown to be in the entertainment industry. You go there to become a senator, you know? And so here you-

• 37:04Speaker 01

  It's so, it is so confusing.

• 37:06Rich Roll?

  And it hasn't been repeated. It's not like, oh, you know, every couple of years, amazing talent is coming out of Georgetown and making its way to Hollywood.

• 37:13Speaker 01

  No, it was so utterly strange. And because I remember in college thinking like, everyone's really good.

• 37:24Speaker 01

  And then cut to like, like a ton of people are like luminaries in the businesses, like, you know, the director of my improv group was James Murray, who now has a show Impractical Jokers that's like a mega hit, um, TV, like prank TV series. And like, they were just that, for whatever, it's like a bumper crop of people. It's like the Malcolm Gladwell theory of, I think, outliers, which is like the groups of people are overachieving is good for each other because it kind of demonstrates that for the other person and they kind of see a through line for it.

• 38:00Rich Roll?

  Yeah, like, like Seattle and grunge music.

• 38:02Speaker 01

  That's right, that's right. So like even like Mulaney wasn't, he was a year after I graduated. So, so, so I cast Nick Kroll and then Nick Kroll cast John Mulaney. But then I came back to visit Georgetown, like a year later. I met John, I met Jacqueline Novak, who's another one who's a brilliant comedian. And, um-

• 38:25Speaker 01

  It just, we all became friends and then when John moved to New York, he like opened for me for a little bit and he, you know, he said this before, it's like, it's a thing where you see, you see someone else do it, something that's unorthodox as a job and you go, oh, I guess that could be a job.

• 38:44Rich Roll?

  Mm-hmm.

• 38:44Speaker 01

  Which I think is a huge part of it.

• 38:47Rich Roll?

  But it's not like it's set in motion a wave, right? Where then, you know, the, the people who were younger than John then saw that and then they came up.

• 38:56Speaker 01

  Yeah.

• 38:57Rich Roll?

  It did become a, you know, a self-perpetuating situation.

• 39:00Speaker 01

  Yeah.

• 39:01Rich Roll?

  So, so this is where I ask the question that Ira, Ira Glass would ask, which is like, what do you make of that?

• 39:05Speaker 01

  Yeah, what do you make of that? The, I think it is the outliers phenomenon, which is, there was a bunch of people, I mean, for starters, like my screenwriting, playwriting professor is a guy named John Glavine, who has taught for so many years at Georgetown, revered, also a little feared. Like, I, like my first week in class, I, he told me I was late or something and then I, I think he told me not to come back and it was kind of like, it felt like West Point or something. Like, he was just like, no, no, you're not in the class anymore. I was like, I went to office hours, like, no, this is really important to me, I really

• 39:50Speaker 01

  want to pursue screenwriting. His classes were so hard, you know, you'd hand him a script, you'd hand him a screenplay or short film and he would write things like, no, on the top. And you just feel like, this is crazy. But then like, but, but I kind of-

• 40:09Rich Roll?

  Did he do that on Jonathan Nolan scripts?

• 40:11Speaker 01

  Maybe. I, I mean, you'd have to ask, but I think so. Like, like he was so tough. But then it was interesting because I remember sitting in, in John Glavine's office hours one day and we're talking about the different people in class and, and he goes, Jonah, he goes, Jonah's gonna be a major screenwriter. I was like, oh. And I, you know, I'm like 20 years old. I'm in Washington DC, kind of, okay. You know what I mean? Jonah Nolan, who, you know, works at Eagle Liquors and, you know what I mean? Like, is just the guy.

• 40:52Rich Roll?

  But then you moved to New York and you're almost immediately on Letterman.

• 40:55Speaker 01

  Almost immediately felt like a long time.

• 40:58Rich Roll?

  Well, it was two years, maybe.

• 40:59Speaker 01

  Two years. It was.

• 41:01Rich Roll?

  But still to be that young.

• 41:03Speaker 01

  After a year of being in New York, I got a thing that's hard to get, which is Montreal Comedy Festival New Faces, which in comedy is a big deal because, like, Ray Romano got it and then he got a sitcom. There was seemingly a pathway for that to be how you get introduced to the industry. In my group was like Kevin Hart, Demetri Martin, like a bunch of people. We were the new faces that year. Yeah, I was like 20, 23 years old. And then the Booker of Letterman, Eddie Brill, saw me at Montreal and he said, I think we could put together a set for Letterman. And it's gonna take a while. We're gonna have to work on it.

• 41:46Speaker 01

  And we did. We worked on it for about a year and then I was on it at 24. And that really, yeah, really changed my career.

• 41:53Rich Roll?

  So it was still in the period of time in which something like that could be an incredible lever.

• 41:59Speaker 01

  Yeah, it was, I mean, I was touring, I was touring the country as quote unquote, "the youngest comedian to ever be on Letterman." This is not, I don't even think it's true.

• 42:13Rich Roll?

  I'm sure that went over really well when you would show up at the comedy clubs with the other comedians.

• 42:17Speaker 01

  I don't even think it's true. Actually, I looked it up once. I think, I think the other, the two younger people were Chappelle and Bobcat Goldthwait.

• 42:26Rich Roll?

  Wow.

• 42:26Speaker 01

  And, and I think Chappelle did it when he was like 19 or something. And Bobcat maybe when he was 20 or 22. But, uh, no, it didn't go over well. It was, it was, that was a hard era for me because it was, I had a lot of success fast and then there was some, there were some resentments and I was too young to navigate it well. And so I ended up.

• 42:55Speaker 01

  I don't know, just in like stickier conversations with people that I wish I'd never had. And I feel like I'm still kind of at age 46, like reliving those conversations.

• 43:06Rich Roll?

  Is this like, like a situation in which, you know, you and Marc Maron have to sit down and rehash some bullshit from way back?

• 43:13Speaker 01

  I talked to Maron last week on the phone and we're talking about stuff that happened 20 years ago. I mean, it's, well, cause I was, I, my first solo show is called Sleepwalk with Me. And it was at the Baker Street Theater and he was doing a solo show in the basement of that theater at the same time. And then I invited him to come see the show and he was like, fuck you. And you know, it's like the whole thing. And, and of course, you know, Mark and I, I put him in my movie. I made my, made Sleepwalk with Me in a movie. He's like the mentor comedian character. But yeah, I mean, it's like those relationships you have in your twenties, like you somehow never lived down.

• 43:54Speaker 01

  You never lived down how immature you were, the ways that you put your foot in your mouth and all that.

• 43:59Rich Roll?

  Yeah. I feel like Maron's podcast could have also been called Working It Out. You know, it's like he started it to, you know, basically repair all the, all the, all the, all these relationships.

• 44:11Speaker 01

  No, completely. And, and it's, uh, so I, but what was interesting about my twenties was that I got that big break and I was touring the country. And then I, that's when I started to tell stories, probably when I was like 25, 26, 27 years old. And so this thing where I, I got into it and with that look at me energy of like, oh, I'm funny. Look at me. I started to tell stories and really connect with people and go, oh, this is really kind of like, just a meaningful experience, like.

• 44:44Rich Roll?

  But wasn't necessarily a path well trodden at that point. Like the paradigm was go on Letterman and then, you know, develop a sitcom.

• 44:52Speaker 01

  That's right.

• 44:53Rich Roll?

  There's a parallel universe where, you know, there was a, I think this even almost happened, right? Where there was going to be, you know, a sitcom and then you could have spent 10 years doing that.

• 45:02Speaker 01

  A hundred percent. Yeah. I got a sitcom deal with CBS. Well, first it was with NBC, then it was CBS. You know, it was that whole thing that go, you're the next Seinfeld and you're the next this, you're the next that. And I was, I was believing it. I was like, yes, yes, this is true. You know, and then we shoot the pilot and it doesn't get picked up to series. And it was that kind of death by a thousand cuts artistically thing where you write the script based on your life and then they say, change this, change this. And you go, okay. And then you give it back and then they say, change this, change this. By the time the thing gets filmed, it's nothing like what you had written. And, and then it didn't get picked up. And thank God it didn't get picked up because it ended up,

• 45:45Speaker 01

  literally three months later, I came back to New York and I produced Sleepwalk with Me off Broadway. My friend Eli Gonda produced it and then Nathan Lane was willing to present it. And, and it was a big hit and it kind of changed my whole, a big hit, a humble, a humble off Broadway hit in New York City, but a hit in relation to what I had done previously.

• 46:08Rich Roll?

  But also it gives you this opportunity to flex your muscles in all these different ways. I mean, The Moth to This American Life to the, you know, The One Man Show and then the book and then the movie that you wrote and directed.

• 46:21Speaker 01

  Yeah. And I'd always wanted to direct movies since I was basically studying screenwriting in college. And so, so that was a huge thing. And then, and then four years later, I was able to direct Don't Think Twice. And, and now I'm actually, I'm getting ready. I'm writing my next movie. And so that's been, that's kind of a dream because honestly, like this, The Good Life special is so close to the bone personally, that I'm just like, I need to write fiction. Like this is too much. Like I can't do this all the time.

• 46:55Rich Roll?

  How many times have you performed that show?

• 47:00Speaker 01

  I mean, 70 cities on the on the tour and in some cities, you know, two or three shows. So I would say I would guess probably 400 times.

• 47:09Rich Roll?

  Wow. It seemed like the old man in the pool was touring forever.

• 47:14Speaker 01

  Yeah.

• 47:15Rich Roll?

  Like you were on the road incessantly with that.

• 47:18Speaker 01

  I think Old Man Pool was like 120 cities. That that was probably something in the universe of like 600 or 800 performances.

• 47:24Rich Roll?

  Wow. And when I'm watching the new one, there's moments where I feel your emotion is is real, like, and I'm wondering, like, is he is he is he a really good actor? Or is he still able to emotionally connect with this after performing it so many times? And maybe just because now it's being filmed for Netflix?

• 47:46Speaker 01

  No, no, no, no, it's certainly like, I remember the first time I got emotional on stage and it was in Sleepwalk with me in 2008 at the Bleecker Street Theater. And I didn't know what to do, you know, because it oh, it came, it was like just choked up talking about, you know, the doctor in the emergency room taking glass out of my legs and how close the glass was to my femoral artery and all this stuff. And I really was choked up. And I said to my director, Seth Baerish, who's directed tons of plays, I go, what should I do if I feel like I'm getting choked up? And he he goes, yeah, just live it, you know, like, that's what we're here for. Like, that's what live theater is for. We're for what happens.

• 48:29Speaker 01

  And so like with with with The Good Life, it's it really is me. Every night I walk on stage and I think, I would think, whatever happens tonight is the show. And yes, I have this line and this line and this this story follows this story. And but whatever happens with this audience is that's for all like all of us.

• 49:05Rich Roll?

  And is the special one singular performance? Or did you, is it edited together from multiple?

• 49:12Speaker 01

  It was mostly one we stole. We filmed for three nights, Thursday, Friday, Saturday, the Beacon Theater. And then the Friday one was like the circle. And then the circle take. And then the other ones, we've just like taken little patches from, because it was like a nice inspired moment.

• 49:27Rich Roll?

  I won't spoil it, but the long-term married couple in the audience, I mean, that was a gift from God. That can't happen every night, every time you do that.

• 49:36Speaker 01

  It's always different. I can say what the question is to the audience. I always ask, who's been married the longest? And then when people say how long they've been married, I say, if you're in a conversation with your wife or husband, and it's kind of, there's a silence, or there's something in the air, and you don't know what it is, do you probe or do you let it lie? And what's amazing is people's answers are never the same. The one in the special is hilarious, but like every night is hilarious in a way. Like people's, when you get an insight into people's marriages behind closed doors, it is fascinating.

• 50:20Speaker 01

  I feel like I might do a show just on that.

• 50:22Rich Roll?

  Yeah, the idea that everybody's marriage is, you know, impossible to understand.

• 50:29Speaker 01

  Yeah, one night, a guy goes, I probe. And I go, oh, you probe? He goes, I probe relentlessly. I'm like, what does that look like?

• 50:37Rich Roll?

  It must be fun to live with that guy.

• 50:40Speaker 01

  Well, there's a lot of people, when they answer that question, you're like, oh, this person's a lot. And then you're like, everyone's a lot, maybe.

• 50:48Rich Roll?

  But it's all in the context of trying to understand how to be married. Like, nobody taught me how to be married.

• 50:53Speaker 01

  Completely. Yeah, that's what I bring up in the show, is this idea of like, I'm trying to teach my daughter all these things, but like, no one taught me how to be married. No one gave me a sex talk. No one told me about drugs. No one told me, like, so in a certain way, we're all just winging it all the time. But with marriage particularly, I mean, I just like, I have no idea.

• 51:13Rich Roll?

  Meanwhile, we want our parents to answer these questions or like lead the way. But it's our kids who are our real teachers. Like Una is the sort of in between the lines in your show is she's the teacher because she's pointing out your the things that you need to learn and explore.

• 51:33Speaker 01

  Yeah.

• 51:33Rich Roll?

  And so as much as you wanted your dad to do that, or you lament the fact that he didn't, she's right there to kind of highlight the journey that you need to go on.

• 51:44Speaker 01

  No, that's right.

• 51:44Rich Roll?

  And that's what kids do.

• 51:46Speaker 01

  Yeah, no, and it's powerful.

• 51:47Rich Roll?

  Yeah.

• 51:48Speaker 01

  And it's something I never would have expected in my life. I mean, that's what my whole show, which was called The New One on Broadway, was about how I never wanted to have a child and all the reasons I never wanted to have a child. And I how I had a child and how why I was right. And then ultimately, why I was wrong.

• 52:05Rich Roll?

  Yeah.

• 52:05Speaker 01

  That's sort of the emotional turn of that one.

• 52:07Rich Roll?

  I mean, your relationship with your daughter is borderline, you know, an obsession.

• 52:13Speaker 01

  I tell you.

• 52:14Rich Roll?

  You know, that's how it comes across sometimes.

• 52:16Speaker 01

  No, that's why I'm taking a break from the Autobycraft and stuff and making a movie where people can go, okay, enough Mike Birbiglia for now. We can just see his movies.

• 52:25Rich Roll?

  She asks you a question, you know, that that is the kind of inciting incident for the show. But how would you answer this question if Una put it to you? Daddy, what is creativity?

• 52:39Speaker 01

  Oh, what's creativity? Yeah, yeah. Oh, man. You know, my brother Joe has this great one, a great answer for that, which is, he always describes comedy writing as letting your brain go for a walk. You know, and it's like, in some ways, I think that's what it is in a way. That's what creativity is.

• 52:58Rich Roll?

  What does that mean?

• 53:00Speaker 01

  Letting go of essentially like, what is the are the stringent aspects of your life? I have to be at this appointment at this time. I should eat at this time. And just going, I'm just gonna let my imagination run wild. You know, like, sometimes my, my daughter will be like daydreaming and, and Jenny and I, my wife and I are always like, great. You know what I mean? Like, daydreaming is great. Daydreaming is everything. Like Mitch Hedberg is one of my favorite comedians of all time and sadly passed many years ago. But like, he always said that daydreaming is what is what joke writing is.

• 53:40Rich Roll?

  Yeah, that's the juice. So how do you hold on to that? I mean, you've got a journal in front of you.

• 53:46Speaker 01

  Yeah, yeah.

• 53:47Rich Roll?

  It's all like dog ear. Like, what is the practice?

• 53:50Speaker 01

  The practice?

• 53:50Rich Roll?

  The daily practice?

• 53:51Speaker 01

  This is just like me writing in my journal every morning about how I feel. A lot of it's how I feel, you know? So it's like, you know, this is what I've been doing. This is what my day is like. This is what I always say, like, this is, in The Old Man in the Pool, I say, I find that if I write in my journal what I'm saddest about or angriest about, I can start to see my life as a story. And if you see your life as a story, you can start to encourage the main character to make better decisions.

• 54:23Rich Roll?

  Uh huh.

• 54:23Speaker 01

  And I feel like that's like, that's like this in a nutshell. And then what happens is, is you write down what happened. And often, like, when you write it, the moment you write it, it is infuriating. It's the thing you're mad about. And you read it a couple of months later and you go, oh, that's pretty funny. Like, the guy who wrote that doesn't know what's gonna happen the next day.

• 54:47Rich Roll?

  Mm hmm. And how do you know when an idea has legs to take it further?

• 54:53Speaker 01

  A lot of it-

• 54:53Rich Roll?

  If you're just writing tons of stuff all the time?

• 54:56Speaker 01

  A lot of it's conversational. So like, you know, it's so funny, because I like, so much of it is iterative with the way that my stand-up comedy is iterative. Like, like, doing in front of, like, with jokes, it's like, doing in front of audiences, seeing, seeing what is getting laughter, and then, and then writing towards that, writing in that direction. And even with my movies, it's like, Don't Think Twice was a really basic idea. It's like, what if there's a group of friends in an improv group, and one of them gets cast on Saturday Night Live, and then the rest of them don't? And what happens in those friendships when that happens? And I would say that to people casually. I'm working on this movie, and that's the premise. And they would go, oh, my God, that's just like my life.

• 55:41Speaker 01

  That's just like me and my band. That's just like me and, and, and my friend group from college, whatever. And that's when I knew, I was like, oh, okay, this isn't just me. This is like everybody. Yeah.

• 55:51Rich Roll?

  That's interesting. Is that something you've just developed over time? Or is it like you do it in the morning, or you just take it with you and you're doing it throughout the day?

• 56:00Speaker 01

  Yeah, and what's funny is I have like, you know, I have 50 of these and they're just around my house.

• 56:06Rich Roll?

  And you go back and you read them and stuff?

• 56:08Speaker 01

  Some of them, yeah, yeah.

• 56:10Rich Roll?

  I'll journal tons, but then I never go back and look at them.

• 56:13Speaker 01

  Sometimes I do, sometimes I don't.

• 56:15Rich Roll?

  Yeah, that's a lot.

• 56:17Speaker 01

  Yeah, it's a lot.

• 56:19Rich Roll?

  I want to hear about the Pope story.

• 56:21Speaker 01

  Okay.

• 56:22Rich Roll?

  I don't want to spoil the special.

• 56:24Speaker 01

  Yeah, sure.

• 56:25Rich Roll?

  Whatever you're willing to share about this, because this is kind of an amazing thing.

• 56:29Speaker 01

  Well, the Pope, Pope Francis, had this thought, which was, he wanted to invite comedians to the Vatican to speak about comedy, which I make the joke in the special, I go, "He talked to us about comedy," which is, which is a great example of power corrupting. If you get, you know, so confident as a priest, you're like, "I should invite Chris Rock over and tell him my thoughts about comedy."

• 56:59Rich Roll?

  Right.

• 56:59Speaker 01

  Because that's who it was. It was like Chris Rock and Conan O'Brien and, you know, Julia Louis-Dreyfus, Whoopi Goldberg, all these people. I mean, it was crazy.

• 57:08Rich Roll?

  This was like a year ago, right?

• 57:10Speaker 01

  Exactly a year ago. And Jim Gaffigan called me, I think Colbert, Stephen Colbert had called him, and he said, "Hey, you're on this list," and, you know, my first inclination was like to say no. I mean, I just thought like Catholic Church, like I grew up in the 80s in Massachusetts. I mean, I wasn't abused, but like, but, you know, if you read anything about this stuff, it's so many people. And it's, you know, one of the most powerful movies I've ever seen is, is Tom McCarthy's movie Spotlight about that, which is, if people haven't seen that, is I think one of the great movies of the last 25 years.

• 57:47Rich Roll?

  So the reluctance has to do with your own personal relationship to Catholicism, but also you don't want to be like involved in the, in the, you know, like laundering of its new image?

• 58:00Speaker 01

  A hundred percent. And then what happened was, is I was with my dad and I told my dad this, and he was like, "Oh," you know, he was like, you know, Grandpa Joe from Charlie and the Chocolate Factory, like he couldn't believe it. And then I, and then I start-

• 58:17Rich Roll?

  Now you might finally be able to get, you know, the attention of your dad.

• 58:21Speaker 01

  Exactly.

• 58:21Rich Roll?

  All your, all your ethics and moral principles go out the window.

• 58:24Speaker 01

  It's funny you should say that. Ira pointed that out. Ira Glass pointed that out. He goes, you know, the thing you're not saying in your show is that your dad wouldn't have done that for you, but you did it for your dad. He goes, he wouldn't have, it was some comedy legend or something. He wouldn't have gone to, to see the comedy legend for you because you're interested in comedy. But yeah, I was, uh, there was that. There was the my dad of it, who had been through a stroke and all that. And then there was, uh, I just started doing research on Pope Francis and I'm just going, okay. Well, everything is compared to everything else. And, you know,

• 59:08Speaker 01

  he, compared to other popes, this guy's great. You know what I mean? But only compared to other popes. If you met him at a party, you'd be like, this fucking guy, you know, but compared to other popes, um, he's amazing. And, uh, you know, he blessed gay couples in the church and he, uh, he, he was advocated for refugees and he was very critical of America in these ways that were very bold. And I just thought, you know, this guy's really special. And this is an unbelievable invitation. The idea that someone would invite me to something like this is a real honor. And I went and, and I, and I, I say it in the special, like the things he said,

• 59:50Speaker 01

  but a lot of it had to do with like, humor has the power to unite people, bring people together. When you make a joke and one audience member laughs, that, that God laughs, which is sweet. And, and I, I thought it was very moving. I thought it was very heartfelt. And I thought being in his presence, we went up and he shook his hand and, and took it, took a photo and, you know, said two words and, and it was, I just thought, this is a peaceful person who, who, who, who believes in-

• 1:00:23Speaker 01

  Or seemingly believes in the real message of Jesus Christ. And I, and I, and I do think that that's very good. I think that what's happened to various churches from Jesus Christ's message, I think, is wild. But I think that at its core, this idea of selflessness and self-sacrifice and, and, being kind to people who are sick and downtrodden is, is beautiful.

• 1:00:50Rich Roll?

  And perhaps the Vatican did a very good job in, in, with its propaganda machine. And changing their perspective.

• 1:00:58Speaker 01

  The PR machine over there is strong.

• 1:01:00Rich Roll?

  But you, you had finished, I assume you'd already taped the special by the time he passed away. He just passed away recently, right?

• 1:01:06Speaker 01

  Exactly. So then we thank him, we thank him in the credits.

• 1:01:09Rich Roll?

  Yeah, I was gonna say, had you, you know, had you still been on tour with this and not yet taped it, would you have added a button to that that might have had something to do with shady dance?

• 1:01:18Speaker 01

  That's really funny. Maybe.

• 1:01:21Rich Roll?

  There is a, there is a low hanging fruit joke in there somewhere.

• 1:01:24Speaker 01

  I almost never reference people who are cultural figures, especially ones who one might hope might be short-term cultural figures. And so, yeah, I wouldn't have included that probably.

• 1:01:40Rich Roll?

  Yeah, we didn't get that. I had, I saw your movie, Sleepwalk with Me, and I've heard you tell that story a bunch of times. But for some reason, I didn't know something about that story that you talk about in the new special, which is the fact that for 20 years, you've been taking Klonopin, basically, every night.

• 1:02:00Speaker 01

  Yeah, yeah.

• 1:02:01Rich Roll?

  That is wild.

• 1:02:02Speaker 01

  It is, right?

• 1:02:03Rich Roll?

  That is such a powerful drug.

• 1:02:06Speaker 01

  Are you, what are your concerns?

• 1:02:07Rich Roll?

  I don't know. I went to, dude, I went to rehab with people who were there strictly because of their Klonopin habit.

• 1:02:15Speaker 01

  Do you know what their dosage was?

• 1:02:17Rich Roll?

  I don't know.

• 1:02:17Speaker 01

  Okay.

• 1:02:18Rich Roll?

  I'm sure it was, well, of course, it was more intense, but it's also highly addictive.

• 1:02:22Speaker 01

  No, I know.

• 1:02:23Rich Roll?

  And so you're able to take, what do you take? A milligram and a half?

• 1:02:26Speaker 01

  A milligram, yeah. Well, I used to take, I used to take one and a half, but I taper. I used to take two, and then I took one and a half. I've tapered it down to one. I take one milligram. I don't know.

• 1:02:36Rich Roll?

  But this is to treat the rapid eye movement disorder that caused you to sleepwalk?

• 1:02:41Speaker 01

  That's right, yeah.

• 1:02:41Rich Roll?

  And you're able to do that and, and like, not be dysfunctional? That's, that's, that's really something.

• 1:02:47Speaker 01

  I'll have a coffee in the morning.

• 1:02:49Rich Roll?

  That one milligram would have escalated quickly in my life.

• 1:02:52Speaker 01

  Oh, really?

• 1:02:53Rich Roll?

  What do you do if you have that disorder, but you're like a, you know, a drug addict in recovery?

• 1:02:58Speaker 01

  Oh, God.

• 1:02:59Rich Roll?

  Is there another treatment for that?

• 1:03:00Speaker 01

  What's amazing is like, there wasn't, it's not like there was a case study for people jumping through second story windows, sleepwalking. It's not, I was the guy. That, that's why, you know, I'm in the, I'm in the DSM as the example. Cause they don't have a ton of examples of, of people doing stuff like this. So, and, and then weirdly like, and I say this in the special, they don't even know for sure if that's what I have, because it's such a young field of medicine. You know, sleep medicine is, I think it's from the seventies. You know what I mean? Like, it's not that recent, or it's not that old.

• 1:03:40Rich Roll?

  There's something interesting about the fact that, you know, fundamentally, it's a neurological disorder of some form, right? And your dad, a neurologist.

• 1:03:50Speaker 01

  Yeah. Cry for help.

• 1:03:53Rich Roll?

  What's happening, you know?

• 1:03:55Speaker 01

  Yeah, I know. No, sure. We could talk about this all day. I mean, I don't know what to say.

• 1:04:00Rich Roll?

  I know. But I am in this process of, of trying to find grace in my relationship with my parents, particularly my mother who's suffering. And, and, and it's challenging, man, to, to let go of all that baggage and, you know, find that place of empathy. And, you know, when they're in the later stages of life, or they're suffering health situations, it's easier to do that. And I still find, you know, I can still feel my own resistance around it.

• 1:04:32Speaker 01

  Yeah. I mean, with my dad, it's like, he would, he would shout when I was a kid, and that was very hard. And he had just a hot temper. And then, you know, the first joke that I was able to make, um, to, to even, you know, a lot of these things, you, as a comedian, you go like, well, maybe I could try talking about that as a topic. But then, like, your dad having a stroke, the audience goes silent. You bring that up as a topic, but that, my first joke was like, it's devastating, but I will say it has calmed him down. And it was funny because it was like that church laugh. It's that kind of like, not everyone's laughing, but a few people are laughing really hard at it.

• 1:05:15Speaker 01

  And I was like, okay, that's kind of my way in to this. And I will say like, you know, to your point about your mom, it's like, it's like, I have in a certain way gotten closer to my dad than I have been in my entire life through this horrible ailment.

• 1:05:34Rich Roll?

  How is he doing now?

• 1:05:37Speaker 01

  He's okay. I mean, he's, he had pneumonia and the flu a few weeks ago and, and it's, and so he's in and out of the hospital, but it, what's amazing is how sharp he is about, you know, I'll talk to him about, you know, me having a sickness or something like that, and he'll, he'll diagnose it. Like he's in, his doctor brain is sharp as a tack. His memory, particularly his memory of the last year is, is tough. But he doesn't have, what's interesting, he doesn't have the temper he did when I was a kid. And so you, so it's like you take out that thing and it, and you do start to see him more as a person.

• 1:06:23Rich Roll?

  Yeah. I think the practice of, of asking the questions you never asked about their life, you know, rather than waiting for them to be interested in yours, like showing interest in theirs. That's what, that's the mending, you know, energy.

• 1:06:41Speaker 01

  I think that that's, and, and yeah, I think that that's where, that's where the special lands as a, as an idea. And, and I think it's absolutely what I would recommend to people who have challenges with their parents is just ask, ask questions.

• 1:06:57Rich Roll?

  What about people who are challenged with their own creativity? Maybe they would like to be more creative or they're inspired by your storytelling, you know, talent and facility. Do you think everybody has a story to tell? And if so, what is the, what is the advice or the practice of helping people connect with the stories in their own lives that might be important for them to explore?

• 1:07:23Speaker 01

  I think like, yeah, I always tell people to journal. I think writing and.

• 1:07:33Speaker 01

  And rereading your own work and then repeating just over and over and over again is great. I think that like building a community of creatives and it could be as small as two or three people is great. I mean, I feel like my entire creative life changed when I met my improv group in college. I think that's why I ended up making the movie Don't Think Twice, kind of about this improv group, because I was so obsessed with this idea of like, oh, my God, there's people like me who just want to just goof around in this

• 1:08:10Speaker 01

  way that's just unfiltered and go in kind of wild directions and explore the creativity. And that can be in an improv class, you know, that could be, you know, asking a group of friends to read, you know, everyone could read their essays that they wrote or stories they wrote or screenplays or plays that they wrote and everyone can play a part. Like even like my last movie, it's like I invited a bunch of friends to come over and read the screenplay in my living room and people gave their thoughts and it was just a good hang. Like the thing about creativity is like you want it to get to a point where

• 1:08:55Speaker 01

  you're a productive and creating a lot of things because there's so much trial and error and it's mostly error. And then you want that to coincide with it being just kind of a fun hang with a few friends. Because then you're not alone in it.

• 1:09:15Rich Roll?

  Did you see that video that has been swirling around kind of virally the past couple of days of Jordan Peele talking about writing and storytelling?

• 1:09:22Speaker 01

  I think that was really interesting.

• 1:09:23Rich Roll?

  Where he's like, it's supposed to be fun.

• 1:09:25Speaker 01

  It's supposed to be fun.

• 1:09:26Rich Roll?

  And it gets to that idea you were saying of like, you know, writing like the story you wanna, you, you, you want to tell and you would like to read or watch on a screen.

• 1:09:35Speaker 01

  Yeah. No, I think Jordan Peele is, is one of the great visionaries of film and TV in the last 20, 30 years. And I think like, he completely has the right idea. Like when I saw Get Out in the theater, I think I saw it opening weekend and I just remember going, oh yeah, this is like, this is best picture, best screenplay, best, best movie. Like, this is like, this guy clearly wanted to make this movie.

• 1:10:08Rich Roll?

  Yeah.

• 1:10:08Speaker 01

  You know what I mean? Like, it has so much, just like, it's teeming with that kind of like inspiration.

• 1:10:14Rich Roll?

  Well, yeah, and it's just, it's undeniable.

• 1:10:17Speaker 01

  Yes.

• 1:10:17Rich Roll?

  You know, in a weird way.

• 1:10:19Speaker 01

  And I think like, my recommendation to people in the creative space is to not do the things you like, but do the things you love. Because no one's paying you anyway.

• 1:10:31Rich Roll?

  Yeah.

• 1:10:32Speaker 01

  You know what I mean?

• 1:10:33Rich Roll?

  And even if they are, nobody's really waiting for your thing.

• 1:10:36Speaker 01

  No. No, I feel like there's, I feel like in the creative spaces, a lot of times what ends up happening is, you have people who, they, they sign up for a lot of things that they sort of like, and they're sort of interested in, and, and that's fine. Like, when you're in the kind of early stages of trying to figure out what, what it is you love. But at a certain point, I think you gotta go hard at what you love, because that's the thing that's really rewarding.

• 1:11:04Rich Roll?

  Mm hmm. And all you have is your unique voice.

• 1:11:08Speaker 01

  That's it.

• 1:11:09Rich Roll?

  That's the only differentiator.

• 1:11:10Speaker 01

  Yeah, years ago, I wrote this piece for the New York Times, and it was called, Six Tips for Making It Small in Hollywood, which is how I view myself.

• 1:11:19Rich Roll?

  I looked on your website, you have an advice. Like, literally, it's like, bio, shows, schedule, advice.

• 1:11:25Speaker 01

  Advice. You know why? Because I got so many of my emails from people were asking for advice. I'm like, I just gotta put this up there.

• 1:11:31Rich Roll?

  Yeah, and you have these New York Times articles where you're like, here's what I would do.

• 1:11:34Speaker 01

  Six Tips for Making It Small in Hollywood. And, and, and one of them is do what, yeah, do what you love, instead of what you like. And, and this was Ira Glass's one, that he gave to me, which is, start now. It's like, there's, there's no reason to wait. And also, weirdly, like, no one's, like, if you're looking to pursue a creative job, it's like, just know, like, you're never gonna get rich from it, probably. And it doesn't matter. Like, because if you love doing it, it doesn't matter. You can have another job, and you can do that, too.

• 1:12:09Rich Roll?

  It reminds me of that speech that Mark Duplass gave at South by Southwest about like,

• 1:12:17Rich Roll?

  they're not, nobody's coming to save you.

• 1:12:19Speaker 01

  Yeah, yeah, yeah. Nobody's gonna save you. Nobody's gonna save you, yeah.

• 1:12:23Rich Roll?

  The moment is right now. Like, if you wanna make a thing, like, you're gonna have to, you know, the bad news is, is you're gonna have to make it yourself, but the good news is, you get to make it yourself, basically is the idea.

• 1:12:35Speaker 01

  No, and Mark is amazing. I remember seeing Puffy Chair, one of his first movies, at Nantucket Film Festival. My wife and I saw it, and it's brilliant, brilliant movie. And I didn't know him. I know, I know, he and I are friends now, but I didn't know him at the time. But that's, that's the other thing. It's like, go to film festivals, go to one-act play festivals. Like, if you're a creative and you wanna be in the world of it, it's like, just go to the things that, that the creatives are making and they're doing. It's like, I can't tell you how many people through the years I've seen in the audience of a UCB Theater show or interning at UCB Theater,

• 1:13:17Speaker 01

  Improv Theater in New York, and then, and then, and then one day you go, oh, they're on The Office.

• 1:13:25Rich Roll?

  Because when you're in it, you're just like, oh, that's, that's just whoever, right?

• 1:13:29Speaker 01

  No, absolutely. I remember, I remember I, I used to rent my, I had an office, like a real, you know, rinky-dank office in New York City, where I would do creative work, and then I would rent it out to improv groups to, to help pay for the rent. And Ellie Kemper used to come all the time, and, and like, had an improv group where she practiced, and she'd just be in my crazy improv space. And it's like, one day I'm like, she's on The Office? Like, this is crazy. She's on Bridesmaids. Like, she's like a major star. This is crazy. But it's like, what's weird is, is like, that, those kind of are the people, the people who are in the proximity of creative spaces consistently,

• 1:14:12Speaker 01

  and they're consistently like, getting better, making mistakes, learning. Those are the people that end up eventually getting the larger slots in art, in art culture.

• 1:14:23Rich Roll?

  Proximity, just making sure they, you know, push through that door and then stay there, you know? Like, a lot of it is just about, like, the refusal to stop doing it or walk away.

• 1:14:34Speaker 01

  A hundred percent, yeah.

• 1:14:36Rich Roll?

  You know, once you've been around for a while, then you're like, you look around and like, all these people, you know, that you, that you've, you know, you knew way back when are all, like, when you get older, these are the people who are now in charge.

• 1:14:49Speaker 01

  Yeah, no, it's crazy.

• 1:14:50Rich Roll?

  Which is like encouraging, but also like, we're in big trouble.

• 1:14:53Speaker 01

  Yeah, yeah, we're in big trouble. That guy.

• 1:14:55Rich Roll?

  Like, nobody knows anything, trust me, you know?

• 1:14:58Speaker 01

  A hundred percent, yeah.

• 1:15:00Rich Roll?

  Which maybe that is good, because it like lowers the bar, like.

• 1:15:03Speaker 01

  No, completely.

• 1:15:05Rich Roll?

  That's really funny. I, in a past life, I made a short film called Down Dog that I wrote and directed. That was sort of a parody of the LA yoga scene.

• 1:15:13Speaker 01

  Yeah, yeah.

• 1:15:13Rich Roll?

  And did it, did a little film festival circuit run. And I remember I was at the Bend Film Festival with this thing. And that's when the puffy chair was there and Mark was there. And, you know, I ended up meeting him and like, hanging out with him that weekend or whatever. And it's like, that was the inception of what, you know, what would become a really huge career for him and his brother.

• 1:15:34Speaker 01

  Unbelievable, yeah, truly.

• 1:15:35Rich Roll?

  Which is inspiring.

• 1:15:37Speaker 01

  Yeah.

• 1:15:38Rich Roll?

  Are you still swimming? How's the pool?

• 1:15:40Speaker 01

  Yeah, I swim, truthfully, like, because I'm on the East Coast, I swim mostly in the summer. But, but yeah, I do, I do swim. And now my daughter's great at swimming. So I go to like, the swim meets.

• 1:15:53Rich Roll?

  Oh, now you're a swim meet dad?

• 1:15:55Speaker 01

  I'm a swim dad.

• 1:15:56Rich Roll?

  Oh, my God.

• 1:15:58Rich Roll?

  Sitting, I mean, kids swim meets are, they're just interminably long.

• 1:16:04Speaker 01

  Yeah, yeah.

• 1:16:04Rich Roll?

  And you're sitting in these really chlorinated environments. My dad, I mean, my dad did this for me when I was a kid, you know, that's a way of me like, feeling compassion and empathy. I'm like, that poor guy.

• 1:16:16Speaker 01

  Yeah, no, absolutely.

• 1:16:18Rich Roll?

  No, but I. Just 10,000 heats of the 25 yard breaststroke.

• 1:16:22Speaker 01

  Yeah, I gotta get back to the YMCA. I've been doing different things physically, but yeah.

• 1:16:29Rich Roll?

  The health is okay, though?

• 1:16:30Speaker 01

  Health is good right now, yeah.

• 1:16:32Rich Roll?

  Cool.

• 1:16:32Speaker 01

  Yeah.

• 1:16:33Rich Roll?

  Well, this was great, man. I love talking to you. This is really fun. I think the new special is fantastic. And you are a master storyteller. And I think it's a real gift that you give all of us to, to show us how powerful story is. And the Pope is right, you know, like, not only comedy, but it is the storytelling aspect of your comedy in particular, that I think is. Needed connective tissue in our divided world at the moment.

• 1:17:02Speaker 01

  Thanks a lot, Rich. That means a lot to me, and I'm glad we did this.

• 1:17:05Rich Roll?

  It's super fun, man. Anytime. You're always welcome here. Maybe five years from now.

• 1:17:09Speaker 01

  Years in the making.

• 1:17:11Rich Roll?

  Cheers, dude. Thanks.

• 1:17:12Speaker 01

  All right. Thank you.

• 1:17:20Rich Roll?

  That's it for today. Thank you for listening. I truly hope you enjoyed the conversation. To learn more about today's guests, including links and resources related to everything discussed today, visit the episode page at richroll.com where you can find the entire podcast archive, my books, Finding Ultra, Voicing Change, and The Plant Power Way, as well as The Plant Power Meal Planner at mealplanner.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. And sharing the show or your favorite episode with friends or on social media is, of course, awesome and very helpful.

• 1:18:04Rich Roll?

  This show just wouldn't be possible without the help of our amazing sponsors, who keep this podcast running wild and free. To check out all their amazing offers, head to richroll.com/sponsors. 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 and Morgan McRae, with assistance from our creative director, Dan Drake. Content management by Shana Savoy, copywriting by Ben Pryor. And of course, our theme music was created, all the way back in 2012,

• 1:18:49Rich Roll?

  by Tyler Pyatt, Trapper Pyatt, and Harry Mathis. Appreciate the love, love the support. See you back here soon. Peace. Thanks.