Ben Stiller on the Price of Fame and the Power of Failure

Scott speaks with Ben Stiller, actor, director, and executive producer of the hit series Severance, to discuss the highs and lows of a four-decade career in Hollywood. They talk about growing up in a showbiz family, the lessons hidden in failure, and the creative risks that paid off. Ben also opens up about sobriety, balancing ambition with family, and why Severance almost didn’t get made. Follow Ben Stiller, @BenStiller. 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.

• 0:00Speaker 00

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• 0:30Speaker 01

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• 1:01Speaker 02

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• 1:31Scott Galloway?

  Episode 360. 360 is the area code serving western Washington. In 1960, the FDA approved the first birth control pill. True story, I have found this moisturizer that is a perfect birth control. After applying it for two minutes, I no longer need to have sex.

• 1:50Scott Galloway?

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• 2:06Scott Galloway?

  That's good. Go, go, go!

• 2:18Scott Galloway?

  Welcome to the 360th episode of the Prop G Pod. I mean, come on, come on. Birth control? That's why the people come here. What's happening? It's scot-free August, but we're still bringing you thoughtful conversations all month long. In today's episode, we speak with Ben Stiller, an actor, director and comedian responsible for many films, including Meet the Parents and Zoolander, as well as the TV series Severance. We discussed with Ben growing up in a showbiz family, making iconic films, and what he's learned about creativity, family and staying grounded. I've become friends with Ben Stiller. He's sort of my, is he my first celebrity friend? I think it is. He actually reached out to me and he's a very thoughtful, like impressive guy.

• 2:59Scott Galloway?

  Also, type in Ben Stiller filmography. This guy has an unbelievable body of work. Anyways, with that, here's our conversation with the immensely talented Ben Stiller.

• 3:28Scott Galloway?

  Ben, where does this podcast find you?

• 3:30Speaker 04

  I am at my house.

• 3:32Scott Galloway?

  Well, we need a little more detail than that. At my house.

• 3:37Speaker 04

  I'm in, I'm in Westchester, New York, about 45 minutes north of, of the city. You know, I guess in my old age, I like just being out in the country and hanging out. And, you know, when I do like going into the city, I grew up in the city, but I never had like the suburban experience as a kid. And I think I always kind of wanted that. And this is kind of, yeah, it's like, you know, something about just being somehow connected to nature that I really like.

• 4:01Scott Galloway?

  So people don't know this. Ben and I started at UCLA the exact same year and Ben dropped out. And, you know, things really haven't worked out for Ben, but Ben, can you, this is a bridge to.

• 4:15Speaker 04

  And things didn't really work out for you, Scott, either.

• 4:17Scott Galloway?

  Yeah, it took me a little bit longer. Anyways, give us your sort of origin story. I think people know you by your work, but they don't, tell us like becoming Ben Stiller.

• 4:28Speaker 04

  Yeah. Well, I mean, I'm a nepo baby, you know, I grew up around show business. I.

• 4:35Speaker 04

  Like my parents, my parents were a comedy team, still are in Mira. They uh and they acted separately together. And um I grew up around that in in New York in the seventies. And with my sister, we lived in an apartment on the Upper West Side. And yeah, like it was show business in our life, you know. And I knew from a young age, I wanted to be doing something having to do with making movies. I love making movies as a kid. You know, so I grew up around around show business. My parents weren't always making movies. They were performing, doing comedy, uh, you know, uh nightclub act and commercials and sitcoms. And uh but I knew movies were what I really wanted to do.

• 5:20Speaker 04

  Then I went to, you know, so I kind of grew up in this sort of like, you know, I guess you'd say privileged Upper West Side. You know, Manhattan. So I grew up in in, you know, New York in the seventies was much more, I think, uh, uh, rougher around the edges. So like I I grew up on Riverside Drive in Manhattan. But if you went up to Amsterdam or Columbus, it was, you know, a tougher neighborhood. And that upbringing for me was sort of, you know, it was uh you got a lot of tastes of different uh, you know, experiences of the world. As opposed to, I think, you know, maybe if I'd grown up in LA where my parents hated LA and, you know, and been in show business where you'd sort of like living, you know, wherever Brentwood or Beverly Hills or something like that, where it was so much more, um, you know, segregated, really.

• 6:05Speaker 04

  And this experience was, I think, for me, you know, kind of what I grew up with. I feel like I've seen New York change a lot over the years. Not that we're talking about that, but um I went out to LA to go be a director and an actor, went to UCLA, hated it.

• 6:21Scott Galloway?

  How did you end up at UCLA?

• 6:23Speaker 04

  I apply, I was not a great student, Scott. I didn't have great grades and UCLA somehow. Somehow I was able to squeak in there. I thought LA, movies, that world, I loved going to LA as a kid. I I kind of sort of like put it, you know, it was sort of this, you know, wonderful world of, you know, like, I love the history of the movies and the idea of, you know, going out there and becoming a director. But then, so UCLA, USC, Boston University and NYU were the four places I applied to. And I got into those four places except for USC.

• 7:01Scott Galloway?

  But you got into UCLA because when we applied, I know a lot about it. I applied the same year. UCLA had an acceptance rate of 76%, but at the time, SC was where rich kids who didn't get into UCLA went. Shocking you got into UCLA and not into USC.

• 7:12Speaker 04

  Well, the film school was a tough film school to get into, I think. And, uh, but my grades weren't great. And so I somehow got into UCLA and thought, okay, I'm going to do that. And it was such a, I went to this little private school on the Upper West Side of Manhattan, where there were like 60 kids in our whole class. And there were open classrooms where it was like the whole floor was basically every, the learning area was divided just by, you know, these sort of like dividers where you could hear everything going on. So to go to all of a sudden to like a history course at UCLA, where there were like 300 kids in the class and a teaching assistant and all that, it was like, I, I literally, I didn't know how to do it.

• 7:54Speaker 04

  And I was never a great student and I wasn't, I didn't really socialize when I was out there and I kind of, you know, it's interesting, my son's going, uh, to school now in New York and he's a freshman and he's just turned the corner. The last couple of weeks, his freshman year of like embracing it and loving it. And I never really opened myself up to that experience.

• 8:14Scott Galloway?

  And what was sort of your first gig? So you dropped out of UCLA. What did you do?

• 8:18Speaker 04

  I remember very well, uh, coming back to my parents' apartment, sitting on my bed on a red eye from LA and like, it was like six o'clock in the morning and, you know, got back to New York and sitting on the bed and going like, now what do I do? I'm at school. That moment where you have to figure it out. And basically, uh, I got, um, I got a job working as a busboy. I stayed at home with my parents and I started taking acting classes and I got an agent and auditioned for about three years. And started to get callbacks, you know, which is where they have to call you back for another audition and get closer and closer to get the part. But it took, it took about two years to even get to that point. I just was not great at auditioning.

• 9:00Speaker 04

  I don't think I was great at being an actor in front of the camera. It wasn't that comfortable. And after a couple of years of doing it, I finally got to a place where I, you know, started to get better at, at that process. And then I got a job in this play off Broadway called The House of Blue Leaves by John Guer. And it was at Lincoln Center Theater. And that production was, is a small part, but the character had a monologue at the beginning of the second act. And the production went to Broadway and ended up winning a bunch of Tony Awards. And I was in that and everybody came to see that. And from that, a couple of directors came and I got a small part in Empire of the Sun that Steven Spielberg was directing.

• 9:43Speaker 04

  And then I got another small part in another movie.

• 9:46Scott Galloway?

  Empire of the Sun, I forgot about that.

• 9:48Speaker 04

  Yeah, yeah.

• 9:49Scott Galloway?

  What was your, I remember Christian Bale, but I don't remember Ben Stiller.

• 9:53Speaker 04

  Yeah, Ben Stiller is one of the prisoners of war in that prison camp with John Malkovich. And I had maybe two lines.

• 10:04Scott Galloway?

  And what was, what was your quote unquote, big break? Like what sort of took you, what was a step change in your career?

• 10:13Speaker 04

  I feel like I had a bunch of little breaks that led to a bigger break. And so I was pursuing both wanting to be an actor and a director and, you know, and also not really knowing what I was doing, honestly, in terms of having a sense of like, like I wasn't somebody who came out of the box, like I'm gonna write and direct this movie and I know what it is. I was sort of finding it. And so I did these little parts in, in movies and then I got a chance to be on Saturday Night Live in 1988, I think. And I auditioned with a friend of mine. We made an audition tape. We were doing this little comedy act. So I was sort of like exploring.

• 10:54Speaker 04

  Making short films, you know, doing, being in comedy, which I had sort of really kind of not wanted to do for a long time, but then started to find a sense of humor, I guess, that I connected with in shows like SCTV and Saturday Night Live, too. And so I auditioned and got a job as a, I made a short film, actually, for them that I sold to them that was Take Off on the Color of Money with Tom Cruise, and then they hired me to be a writer and, or an apprentice writer. And that was at the end of the eighty-eight season, and I knew very quickly that I wasn't gonna do well there, because I wasn't great at live performing. I didn't love it.

• 11:39Scott Galloway?

  You weren't at US now very long, no?

• 11:41Speaker 04

  No, I was there like six weeks. And I, and then I had an opportunity to do a show at MTV. So MTV was just starting up in terms of like doing programming that wasn't videos. And that little comedy act I did with my friend Jeff Khan, we-

• 11:57Scott Galloway?

  You had a show, right, The Ben Stiller Show?

• 11:58Speaker 04

  Yeah, The Ben Stiller Show. It was on MTV for like thirteen episodes. And then somebody at the fledgling Fox Network, which was just starting, they didn't even have full programming then, saw it and they, and there was a guy named Chris Albrecht who ran HBO Comedy, and he produced, basically, this show that we worked on for a couple of years that we sold to Fox. And then that got canceled after about twelve episodes. But that was probably like my first, you know, like, I was doing a show, and I was working with Bob Odenkirk and Janine Garoppolo and Andy Dick and David Cross and like all

• 12:40Speaker 04

  these people, we were just sort of starting out. And that got canceled, but then somebody saw that, some of those sketches, and in Danny DeVito, Danny DeVito's a production company, and they were making a movie called Reality Bites, that they were developing with Helen Childress, who was a writer, a young writer. And they put us together, and we started to work on that movie together. And Winona Ryder signed on to it. And this was probably nineteen ninety-three, ninety-four, and we made that movie. So that was my first movie that I ever directed, thanks to Winona signing on to it.

• 13:16Scott Galloway?

  Ethan Hawke was in that, right?

• 13:17Speaker 04

  Exactly, yeah. Ethan was in it. And, and then-

• 13:23Speaker 04

  That movie came out and, you know, did okay, but I was also kind of, it's, it's, it's like, kind of interesting. I was like doing that as a director and an actor because I was in that too. But nobody was really like banging down the door, you know, for me to do the next thing. And then Judd Apatow, who I'd met when we started to work on the Ben Stiller Show on Fox a few years before, um, had been working with Jim Carrey. And Jim signed on to do The Cable Guy, and which originally was a Chris Farley vehicle. And then Jim said he was gonna do it and Judd was gonna rewrite it. And Judd suggested me to direct it to Jim. And then we all had a meeting and, you know, got along. And so this was a, you know,

• 14:07Speaker 04

  a point where Jim was just, you know, every movie he was doing was, you know, bigger and bigger. And so he had total freedom. And it was this weird sort of dark relationship comedy that probably was not a great summer movie for Sony. But, um, you know, we did it and it came out and was not super well received.

• 14:27Scott Galloway?

  Was there ever a moment where you thought, maybe this isn't the industry for me? Or what was, what was kind of, can you think of one moment that was sort of your lowest moment in?

• 14:36Speaker 04

  Well, I mean, I never thought it wasn't for me. I really never thought of doing anything else. And I think when you're younger and you have this sort of, you know, sense of what you want to do, or this ambition, or this, you know, kind of like blind sort of just, you know, uh, motivation to go towards something. Like, I wasn't self-aware back then to understand what was pushing me towards it. But I did definitely deal with, you know, Cable Guy. Cable Guy was a, you know, there was like an article in New York Times, like the first disaster movie of the summer has come out and it's a comedy called The Cable Guy. That was the review. So that was tough because, you know, in show business, when you

• 15:15Scott Galloway?

  I think you're being unfair. You've had a lot of negative reviews in movies. You've, I mean, Along Came Polly, like, I mean, there's definitely

• 15:23Speaker 04

  Oh, my God.

• 15:24Scott Galloway?

  Yeah. There's

• 15:25Speaker 04

  Well, I didn't get to those yet. This was

• 15:27Scott Galloway?

  I think you're being really hard on The Cable Guy.

• 15:31Speaker 04

  Well, I took that one personally because I directed it and somehow, and yeah, you're right. Like, I remember, I think David Denby came out once in The New Yorker and wrote like a seven-page article about why I shouldn't be in movies.

• 15:43Scott Galloway?

  The Heartbreak Kid, Starsky and Hutch, which I enjoyed. Syracuse, I mean, come on, this is, we're gonna need a bigger boat. I mean, this is, this is not your press tour, Ben. I'm not here to just blow you and talk about, ask you your vision for Severance. Wait, hold on. You were also in Mary Madagascar. Let's talk a little bit about that. Oh, my gosh. And then Madagascar 2, Escape to Africa.

• 16:07Speaker 04

  That's right. Oh, yeah.

• 16:09Scott Galloway?

  Night at the Museum, Battle of the Smithsonian. Yeah, I'm sure that wasn't for the money.

• 16:13Speaker 04

  Yeah, and Madagascar 3, too.

• 16:16Scott Galloway?

  Fresh Horses? I don't even know what that is. Of Lucy Fell.

• 16:19Speaker 04

  Well, I could tell you, I could tell you about all of these because each one has an amazing story to it.

• 16:25Scott Galloway?

  Oh, my God. If you type in Ben Stiller's worst movies, there's three pages.

• 16:33Scott Galloway?

  Oh, my God. You're literally, you're the advice, you are the living embodiment of the advice I give to young dudes. And I'm like, go up to everyone and ask them out, and eventually something's gonna work. Something's gonna work. You have taken so many shots here. Like, I, I, this, I'm a, I'm similarly, one out of seven businesses works, so I've started nine.

• 16:54Speaker 04

  Oh, right, right. Well, it's, yeah, it's the law of averages.

• 16:57Scott Galloway?

  Anyway, sorry, sorry.

• 16:58Speaker 04

  No, it's okay. I mean, you know, it was an interesting time in terms of, you know, like, all those movies, making those movies, because they were just sort of, you know, when, the first movie that I ever was in that really did well was There's Something About Mary. And, and that was in 1998. And, you know, I'd been doing it for a number of years. And then after Mary, I did get a lot of, you know, opportunities. And like, yeah, like, I think right after that is like, you didn't mention Duplex, too. Duplex, Envy.

• 17:33Scott Galloway?

  I was, I was holding that.

• 17:35Speaker 04

  But you know, that's a weird, it's a weird thing to go through for sure, though, right? When you're like, kind of given these opportunities and coming off of one that finally worked and then a couple of them that really didn't, you know, that didn't work was, you know, it's kind of like you have to look at yourself and go, what am I doing here?

• 17:53Scott Galloway?

  What pieces of work surprised you to the downside and that is you thought they were going to be? I've, I've never, I've started nine businesses, which is not nearly as romantic as cool as making a movie, but I couldn't tell you when I started a company, what was going to be successful and what wasn't. And sometimes I was surprised at the upside and sometimes surprised at the downside. What pieces of work surprised you that they weren't as successful as you thought they were going to be? And what other pieces of work you thought this is good, but it ended up being a huge commercial hit?

• 18:22Speaker 04

  You know, I don't know, it's, it's really hard to tell what's going to work and what's not going to work. Like I wouldn't have known, there's something about Mary was interesting because it didn't open at number one. This was in, in 98 when movies were, you know, in, for comedies in theaters. And that movie might've opened like number three or four or something like that. But over the course of the summer, it worked its way to number one after like nine weeks. And that hardly ever happens. And so that was a surprising thing for sure. And, but then to see how that movie worked and then for me, when I was surprised by how that changed all the opportunities for me, because at that point I'd already, you know, I'd done Reality Bites in 19, in 93, 94.

• 19:05Speaker 04

  So I'd been around for a while doing it and was actually really, I was really happy in my career, getting all these opportunities to do different things. But then being in a movie that was a box office success really changed then the sort of like, I think the, you know, lens that people looked at what I was doing. And because they were like, well, what's the next thing? And then all of a sudden people were paying attention. And yeah, you know, people were going to a lot of those movies. Some of them didn't work, but then some of them really did work and. Um, for the audiences and you know comedies critically have always been, you know, it's always a crap shoot in terms of whether critics will go for them or not, but I never ever had the feeling going into something like this is gonna be the one, you know what I mean?

• 19:46Speaker 04

  Except for maybe Fresh Horses, because Fresh Horses was, I was, it was, that was nineteen eighty seven and I was just, uh, you know, just starting out and it was Andrew McCarthy and Molly Ringwald and they were coming off of, you know, Breakfast Club and all these movies and it was like, this was the brat pack. And I was like, oh, man, I'm gonna be in the brat pack. I'm gonna be, and the movie just-

• 20:08Scott Galloway?

  This is it. This is my moment.

• 20:09Speaker 04

  The movie just tanked and, uh, but it was literally to this day, my favorite experience ever making a movie.

• 20:16Scott Galloway?

  Really?

• 20:16Speaker 04

  Yeah, cuz it was, you know, it was like six twenty something year old kids in a motel in Kentucky outside of Cincinnati for three months, making a movie and having fun and hanging out and hooking up and doing everything. It was just like, you know, it was, it was like the dream. It was, it was so much fun.

• 20:35Scott Galloway?

  So I know you're dying to know what my favorite, uh, works are of yours. Uh, first off, my, my partner is literally obsessed with Severance. For me, your two favorites, probably the Royal Tannenbaum's. Actually, you know what? I think Tropic Thunder. I think our friend, our friend wrote it, Justin Theroux, and then, uh, you directed and starred and Robert Downey Jr. was nominated. I thought that thing was so unusual. I can't even imagine pitching that movie. And then the Tom Cruise, um, character. Anyways, but I still like the Royal Tannenbaum's the most. I think also, I think it was one of Gene Hackman's kind of crowning performances. I, which leads me to my question, what, and don't say Robert De Niro. You've

• 21:20Scott Galloway?

  got a pretty deep body of work here. Who are some of the most talented actors that you have directed or worked with that may not be on the tip of our tongue? Like, we know, we know Gene Hackman's incredible, right? Who are some of the people you thought, wow, this person is not really appreciated for the depth of their talent?

• 21:41Speaker 04

  Well, I mean, I would start with saying that, you know, in Tropic Thunder, you know, he is appreciated. He just won an Oscar last year, but Downey, for sure, is a genius. And working with him on that movie, I felt like I was working with somebody who was sort of just channeling something in terms of that character, that actor playing that role. And the courage he had doing that, and also just the, like, he kind of just watching his process, working with him. I love working with him. I love him as a person. He puts this energy into his work that he's aware of the fact that he needs to sometimes be not aware of what he's doing. He has to allow it to flow and go and try things.

• 22:26Speaker 04

  And I think in movies, you have to be, feel free to try things because you're not going to know what works until you find it, but sometimes it's going to be bad. And you're going to put it out there and you have to feel that freedom. And I really felt like that's what he was doing with that character. And that real humility about the work, but also an incredible sense of confidence, too, in taking the chances. So I think with him in that movie, and I think everybody in that movie, like Jack Black, everybody was just kind of like doing that on a certain level where they're just kind of going for it. And that's not easy, I don't think, you know, especially in a, you know, because comedies can go bad, you know, and you, but you have to take those chances.

• 23:05Speaker 04

  I think, you know, working with Greta Gerwig and Greenberg with Noah Baumbach, which was like her first sort of role that people sort of, you know, discovered her in. And watching, you know, the simplicity of what she was doing was very, you know, that that helps when you're working with an actor who's so real in a scene, you know, that that changes everything for you because you're just, you know, I think so much of acting is reacting. And so that's why doing something like with De Niro is great because, you know, you have this amazing person giving you all this and you just have to kind of like take it in.

• 23:46Scott Galloway?

  We'll be right back after a quick break.

• 23:54Scott Galloway?

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• 24:39Scott Galloway?

  No new tabs, no switching apps, no losing your place. This is AI that works with you, not on top of you, so that you have the time and brain space to solve the problems that matter. Check it out, find out more at superhuman.com.

• 24:57Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch-up when audit season comes around again. Vanta works differently. The regentic trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year-round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

• 25:42Scott Galloway?

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• 26:04Scott Galloway?

  Support for the show comes from Vanta. As AI adoption grows, so does your company's security risks and requirements. New frameworks, audits, and vendors keep piling on, but your team isn't getting any bigger. Most compliance tools promise automation, but you're really stuck doing all the work by hand, chasing screenshots, validating controls, and playing catch-up when audit season comes around again. Vanta works differently. The regentech trust platform is built to scale with you, not slow you down. With over 1,400 automated tests across 400-plus integrations, Vanta collects evidence and monitors your controls year-round, cutting your audit prep by 82%. Plus, you can access the Vanta agent everywhere you work, whether your team is in Vanta every day or living in tools including Claude or Cursor. Want proof?

• 26:49Scott Galloway?

  Over 16,000 fast-growing companies like Ramp, Ryder, and Harvey save time and resources while scaling fast with Vanta. Learn more at vanta.com/profg and get $1,000 off. That's spelled V-A-N-T-A dot com slash profg for $1,000 off.

• 27:15Scott Galloway?

  Let's talk about

• 27:16Speaker 04

  Failures, more failures?

• 27:17Scott Galloway?

  Literally, everyone's glomming all over you on severance.

• 27:21Speaker 04

  I've heard you talk about failure. Let's talk about Madagascar Three. Come on.

• 27:25Scott Galloway?

  Dude, we only have an hour and a half here.

• 27:28Speaker 04

  Okay, all right. You know, when you talk about business, right? You do learn, you really do learn more from the things that don't go well, as we all know. That's very true.

• 27:39Scott Galloway?

  I don't know if you've heard this, but my vivico, Kara Swisher, has her own podcast called On, and you went on there before you went on my podcast, despite the fact that we're good, good friends, and I'm constantly talking you up and apologizing and saying that, no, Night at the Museum, The Smithsonian meets The Folkers meets whatever. Anyways, you said you had to make the show as soon as you read an early version in a writing sample from its creator, Dan Erickson. What drew you to this? Because when I, and this is why I would never be successful in your industry, when I've watched the show, it reminds me of Game of Thrones. Every time I watch Game of Thrones, one of the things I appreciate most, and I'm being serious now about severance, is what I appreciate about Game of Thrones, and that is, I can't even imagine pitching this to people and asking them for money to make this. It seems so

• 28:23Scott Galloway?

  If I, if I had read, if someone had pitched something about the seven realms and sword fighting with dragons, but there's, there's a, there's a red woman who's got mystical power. And then someone said, okay, I have this dystopian, this dystopian drama about relationships and our severing between our work and our personal lives. I would have, as a studio exec, thought this could be such a bomb. And the thing about Severance reminds me a little bit, and I think Apple's smart in terms of brand positioning, between the talent, you know, Christopher Walken, John Turturro and the production values. I mean, there's just some, there's some shots where I think I would just want to leave this shot for three minutes because it's so beautiful.

• 29:06Scott Galloway?

  You can see the money dripping off the screen, quite frankly, the talent, the production values. That show must have cost a lot of money to produce. And I would have thought there is a high probability of failure. It just really impressed me that you were able to talk them into this. What about it was so intoxicating for you that, as you said on ON, you thought, I gotta do this?

• 29:29Speaker 04

  I mean, it was, it all started with a script that Dan wrote, this, this, you know, script that he wrote on spec to send around to get people to meet with him. And it was so clear to me, the tone of it. And what, what it evolved into is probably its own thing that maybe wasn't quite on the page. But I think the combination of what Dan wrote and kind of what it sparked in me was this, you know, basically, you know, it reminded me of these workplace comedies that, that I really loved, like Office Space or The Office. And yet it was in this weird world. And that to me was the kind of hook of it.

• 30:12Speaker 04

  I give Apple credit for reading the script and saying, yeah, we like it, we want to do it. You know, they were starting up, it was like a weird confluence of events where Apple hadn't quite, wasn't streaming yet. It was all sort of theoretical in a way because they were, they were saying like, okay, you know, go ahead, develop these scripts, we like it. At first, I think they thought I was going to like find an office, like an abandoned office and just shoot it there. And then when we started to talk to them about, no, this is actually going to be, you know, like a kind of a weird surreal world that we have to create. It, it kind of evolved into something, but I think, you know, people say yes to things because. For some reason, they connect with it, but maybe what I was connecting with was maybe a little

• 30:54Speaker 04

  different than what Apple saw, but I think I have to give them credit for saying, yeah, let go ahead and do it. But it's I don't know how things evolve in this way where you're given the freedom. Maybe it's because of like stuff I'd done before where I was given a little more leeway to experiment. I think when we put together the cast we had, they were excited about that. But nobody knows, you know, you don't know what it's going to become. And yeah, and we never tested it. We never did any, you know, focus groups or anything like that, too, which is also kind of weird because all those comedies back in the day where you always did test screenings and focus groups and all that. And this was one of the first things I did where I didn't have to do any of that.

• 31:35Scott Galloway?

  There's, I mean, from an outsider standpoint, you look at the kind of the streaming wars and Netflix spending 18 billion and everybody having to massively increase their budgets. You wouldn't logically think, wow, there's never been a better time to be in the creative side of Hollywood. And yet you talk to people, you talk to creatives in Hollywood or in the business, and they say, it is awful here right now. Awful. So try and reconcile the two. You've been in the business a long time and you see and you've been a producer and you've had to pull the money together. You see the business side of this. You've worked with, I think, most of the major streamers, most of the major movie companies. What observations would you have about how the

• 32:17Scott Galloway?

  dynamics of the industry and the biggest shifts? How do how do you perceive it as a creative, having been in the business for pretty much 40 years now?

• 32:26Speaker 04

  Yeah, it feels to me that it's upside down in that nobody really knows how it's going to shake out with the streamers and movies and people are watching and what's a movie now and how do they make money from the streaming? You know, you know more about this than I do. But there's, I don't, there used to be this model that you make a movie and then you'd You know, you've released it in theaters, you make money there and then you go to DVD and VHS, right? And that that was the DVD streaming thing became like basically, you know, dead after when streaming happened DVDs died and that's changed everything. And I remember my agent telling me that like,

• 33:11Speaker 04

  I don't know, like eight, nine years ago, saying like, it's all going to change. It's all changing and it was kind of hard to believe, but it really has. I don't think anybody knows where it's going. So there's a lot of fear of, you know, what people are going to go and see in the movie theaters that those studios have. So they've just retreated to making, you know, things that are safe, that they know, you know, that that that, you know, that's what sequels are. That's what, uh, you know, known IP is. So it's become sort of polarized in a way where there are these giant movies. And then there are these movies like The Brutalist that are made for, you know, nine million dollars or whatever and win Academy Awards, but it's two different world and you have to struggle to make the, you know, the things that aren't going to be,

• 33:56Speaker 04

  you know, a slam dunk in in a pitch. So it's really hard because then post-strike, there's been so much retraction too. And the economy is really in a, in a tough place too. And that that affects, that affects everything. So it's, um, I would say it's, it's really tough. It's really tough to go out there and pitch an idea if you don't have, you know, some star attached or some IP that it's based on, or something that, you know, is going to basically, you know, guarantee the the streamer or the movie studio that they know they're going to get an audience. And as we all know in show business, nobody knows anything. And you never know what's going to work. So people, you know, are not taking as many chances and it's, it's really tough out there.

• 34:39Scott Galloway?

  So I don't know you well, but I've gotten to know you a little bit. And whenever we talk, uh, you inevitably. Bring up your parents and you bring up your kids. And I want to talk a little bit about, I mean, we all like to think of ourselves as being close with our parents, but you, you're making a documentary where you're literally going through, my understanding is old photos. And, and it feels like just sort of an ode or a nod to them in their life, lives. I believe your mom died in 15, your dad in 2020. Talk a little bit about your parents, their approach to raising you. And, you know, I don't want to say the impact they had on you, but I, I don't think I've ever been with you and within an hour, you don't reference your parents.

• 35:20Speaker 04

  Interesting. Yeah. Well, I mean, I think they've been in my mind a lot and just with me a lot because I've been working on the documentary. So the last five years I've been working on it and just, just mixing it and finishing it now. Um, so I think I've been, you know, looking at, at my relationship with them. I miss them. I think, uh, I think probably when they first, uh, passed away, I didn't know how to deal with it as much. And still I'm trying to figure out how to deal with it. I think anybody, when you lose your parents, there's such an, you know, important relationship in your life and I love my folks and, um, it's interesting when you have parents who are supportive and love you

• 36:02Speaker 04

  and you don't have something to rebel against or to say, you know, my dad was this awful person and I had to get out of the house or whatever, you know, my, they all, they both had their issues. Um, but they were very loving parents who were also actors and very much about the process of creativity for themselves, which I am too. And that's the thing I've been kind of thinking about a lot the last few years, working on this movie is how my own, you know, uh, process as a, as an actor and filmmaker and creative person affects my relationships with my kids because you have to have a certain amount of selfishness as

• 36:45Speaker 04

  a creative person where you go, I need to take this time to work on this thing because that's going to make me happy. But then how do you balance that with? Being there for your family. And that's what I experienced with my parents too. And I, you know, experienced it as a parent with my kids. And I think that's, um, you know, what I grew up around was my parents working all the time in an apartment on the Upper West Side. At Manhattan, where they had a room where they had an office and they'd write commercials and write sketches. And go off and do like a part in a sitcom or go do, uh, you know, do their act at a nightclub. Or, you know, do a little part in a movie or something like that, but they were constantly having to work because they weren't super rich or anything. They had to work for a living.

• 37:31Speaker 04

  And, um, they never wanted to move to LA and be a part of the whole kind of Hollywood world. My mom had a real aversion to that. Uh, my mom was a tough Irish Catholic, very acerbic, very funny. You know, still, you know, say she loved me, but it was, it was, it wasn't like warm and cozy. Like I, I think I'd share my mom's sense of humor more than my dad's. Um, and my dad was much more kind of, uh, of a soft touch. But he grew up, he grew up in the depression with parents who were not that supportive of what he was doing. My mom lost her mom at a young age. And my, then she was an only child.

• 38:13Speaker 04

  And I think she built up some walls, but, um, you know, she was committed to my dad and this, this work relationship that they had. And they were trying to make a living and they were trying to just kind of, you know, do well in, in show business. And as parents, they were, you know, there's a lot of laughing, a lot of fun, but it was also a lot of feeling the stress of, you know, what they had to do to, to make ends meet, really. Um, and yeah, so, so I, I feel like they were, um, I don't know, I, I, but I really, yeah, I really love them. I feel like I had issues with them when they were alive. With my dad, I always had um sort of this push-pull where I was like, I wanted him to treat me like an adult.

• 38:56Speaker 04

  And he kind of always coddled his kids and was overprotective. And that led to tension. And I think also part of it was, you know, my mom drank. Uh, and later got sober in her life and talked about it a lot. And I think my dad was always trying to like, you know, to, to balance that. And that, and I think that came out of the tension and stress of having to perform live, which she didn't love to do. My dad sort of drew her into comedy. Um, she was a dramatic actress who then was really good at comedy. And he said, hey, we could do an act together. We can do a comedy act. And that can make ends meet because they were starving, living in an apartment on the Upper West Side in the 50s, trying to, you know, make money.

• 39:41Speaker 04

  And then that act provided a living and an identity for them. And she never really loved doing it as much.

• 39:48Scott Galloway?

  So I, I didn't connect the dots. I didn't, I've never heard the story, the, the reference of your mom and drinking. Is that one of the reasons why you don't drink? That's one of the first things I noticed about you is that you, you don't drink.

• 40:00Speaker 04

  Yeah, I mean, about, I, I, I think I stopped drinking about seven years ago. Um. Yeah, I mean, there was always an awareness in our family. I mean, like I said, my mom was amazing in the last, you know, 10 years of her life. She got sober and quit smoking. She'd smoked her whole life and um and talked about it and was, you know, very committed to a program. And that in turn, for me, when I got into my twenties, you know, I started to realize what that dynamic was in our family. And went my own way to, to deal with that and, and find a program to help deal with that for myself. Um, and yeah, an awareness of that has always been part of, um, I, I think, you know, for me.

• 40:46Speaker 04

  You know, looking at the lens of how our relationships with our parents when we're young affect our, our current relationships. And I think for me, you know, Christine and I um separated about seven years ago and we were separated for about three, three or four years. And when we separated, that was when I stopped drinking.

• 41:06Speaker 04

  Because I felt like I wanted to just,

• 41:10Speaker 04

  you know, be present for whatever was going on, which was, you know, feeling a lot of feelings and it felt to me like I could go down a road that would not be dealing with the things I needed to deal with if I kept drinking.

• 41:24Scott Galloway?

  Do you think your sobriety led to ultimately some sort of recognition or realization in your life that resulted in your reconciliation?

• 41:33Speaker 04

  Well, I think, yeah, I think, you know, you have to be present for a relationship, you know, and be available and be, you know, I'm not saying you have to be completely sober and not drink to be in a relationship, but like you have to just, you know, you have to be who you are and acknowledge and take responsibility for, you know, for being there. And if someone isn't, then, you know, it's, it's hard. It takes two to tango. So I think both, you know, Christine and I, for us, when we came back together was, I think we'd both done work on ourselves on some level that was important so that we could be together.

• 42:15Speaker 04

  And, and the great thing is now I recommend if it's right to come back with somebody, because a lot of times it's not right to come back to somebody. I didn't know we were going to come back together. But now every day it's that, that acknowledgement of like, okay, this is good. I appreciate this and it could go away. So I'm gonna just, I'm gonna be, I'm gonna be grateful for it and I'm gonna be present. And then you figure out for yourself like what that means in terms of your own choices.

• 42:47Scott Galloway?

  We'll be right back.

• 42:52Speaker 00

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• 43:52Scott Galloway?

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• 45:04Scott Galloway?

  We're back with more from Ben Stiller.

• 45:09Scott Galloway?

  We have a lot of young men who listen to the podcast, and I'm curious what, and a lot of these men are starting families, what advice, and none of us have got this figured out, but in terms of your own approach to being a dad, the role that your parents have had on you, trying to straddle the line between that tension we're talking about around your own creative process and focusing on your own career, such that you can be a provider while being present as a parent, being separated for a few years, that always creates a different dynamic with your kids. What advice would you have for dads as they are thinking about or just starting their journey around fatherhood?

• 45:50Speaker 04

  Wow, that's a good question. Oh, man. Well, I would say that, you know, coming out the other end here with the kids who are in their twenties now, practically, my son's nineteen, daughter's twenty-three, it goes by quickly and there's a really short amount of time that you're able to really, you know, be connected to your kids before they go out into the world. It's not, it's not even when they're in their twenties, you know, it's by the time they're whatever, thirteen, fourteen years old, they're, they're socializing and, you know, there's so many other influences that are coming in. And I, I think when I was younger with

• 46:26Speaker 04

  my kids when they were that age, I was, I was a little bit daunted by, by parenting. And I might say that my mother, you know, talking about my mom's influence, my mom was daunted by parenting too. I think engaging with your kids, trying to set an example of what you do in terms of to be healthy for yourself, taking care of yourself, but also reaching out to your children and being open to what they're giving back to you in a way that might not be what you had imagined. In other words, like with my daughter,

• 47:09Speaker 04

  when she was younger, you know, I used to, we had a tougher relationship, but it was more because I wasn't meeting her where she was. I wanted, I'd like, I, you know, and I would want her to be interested in something that I was interested in. And she was interested in what she was interested in. And so having a willingness to, to go, to, to do that, it's, you have to kind of sacrifice a little bit of like what you think you're, you know, you, you want that relationship to be and, and, and be there and, and, and open to it and not run away from it. Because I, I think it's, you know, for some guys, it's, you

• 47:49Speaker 04

  know, having babies and infants and toddlers, it's really intimidating. And I, I think leaning into it and just knowing that it's a time that's going to go by very quickly, even if it's not the most comfortable for you, because it's a world that you're not that confident in. And being able to just, like, just be open to what your kids are giving you back is really important. It's not that easy, I don't think.

• 48:17Scott Galloway?

  Yeah, agreed. And what you said really resonates in that is I imagine that my sons would just naturally be fascinated by CrossFit and World War II history because they would have such a fascination with all things dad that they'd want to be into what I'm into. And then I found out, no, they have no interest in these things. And being a dad means you have to fake interest in what they're interested like, oh yeah, let's go get Pokemon cards.

• 48:38Speaker 04

  Totally, totally. And by the way, once you do that, you do get a lot back because all of a sudden you're engaged with your kids.

• 48:48Scott Galloway?

  How is your approach to your primary relationship different post reconciliation than it was pre reconciliation? What advice would you have for young men trying to have a fruitful and rewarding relationship with their partner?

• 49:01Speaker 04

  Well, a lot of it is, I think, compromise. And, you know, if you really care about this person, you have to figure out, again, like, how to meet them where they're at also. If you have a career or something that you're really focused on, or, you know, revolves around, you know, the things you want to do, you have to communicate and really talk about, you know, what's important to both of you. And that's the thing, I guess, like, I just said it before, but the gift of getting back together is that you realize that, you know, just because you're married, or just because you say you have a commitment to

• 49:41Speaker 04

  each other, it doesn't mean that it's going to work. You have to, you have to be present every day and have a back and forth where you can say like, you know, like, hey, you know, I want to do this thing for me. Can you be there for me? And then when they have something that they need you for, be willing to sacrifice it. I mean, I think, sacrifice your own stuff. And, I don't know, you know, like, things like, just, I think, a lot of human nature comes out of, you know, insecurity and jealousy in relationships. And, you know, if you can have that confidence of like, saying, okay, you know, I'm going to be okay with you going out and doing your thing.

• 50:22Speaker 04

  Um, if, if you're in a good relationship, that's gonna, you know, that's gonna help you so much. And it doesn't always work out because sometimes people are in different places and they're not doing what they should be doing. But if you're, you know, if you are a good couple, you're meant to be together, you have to give each other the freedom and have the trust.

• 50:40Scott Galloway?

  So I affectionately say we're the exact same age. Um, I affectionately say we're kind of on the back nine, kind of hanging out and waiting for the ass cancer. Like what, what is literally?

• 50:51Speaker 04

  I had the prostate cancer already.

• 50:53Scott Galloway?

  Oh, that's right. Oh, my God. That was so, that was so, that was so uncouth of me. That's right. You actually had prostate cancer.

• 50:59Speaker 04

  Yeah, yeah.

• 51:00Scott Galloway?

  Talk a little bit about that experience and how it, how, if and how it changed you.

• 51:04Speaker 04

  It, well, it's scary. It's scary.

• 51:07Scott Galloway?

  That makes sense. God, that was so awful. I make a, I make an irreverent reference to ass cancer and you raised your hand and said, oh, well, I did have ass cancer. I have prostate cancer.

• 51:16Speaker 04

  Scott, I've spent a little bit of time with you and I, as much as I talk about my kids and my parents, you talk about ass cancer.

• 51:24Scott Galloway?

  Look, I, I think we have the beginnings of a Madagascar six prostate cancer. I think it's coming.

• 51:30Speaker 04

  There it is. And didn't I tell you that if you get a colonoscopy, I think I told you this at the wedding, uh, you get a colonoscopy, you go to the right doctor, he explains to you why a colonoscopy is a good thing because it's, if there's stuff in there, they can get it before it gets bad. So anyway, uh, it was very scary because all of a sudden it's like, everything is like boom, stop. You know what I mean? Everything we're talking about is like, stop. You don't know if you're gonna be alive in, you know, six months if you don't, you know, if this doesn't get dealt with. It's, um, like your worst fear. And I had a bad diagnosis in terms like the doctor wasn't great when he told me, you

• 52:12Speaker 04

  know? He's like, uh, I'm gonna, you know, first of all, it's like, you know, you do a PSA test, which I recommend every, every guy who's like in forty five and up.

• 52:20Scott Galloway?

  Even that's kind of unreliable though.

• 52:22Speaker 04

  Yeah, but you have to watch it. And my doctor started testing me early. He was supposed to be fifty, but he started testing me around forty five and he saw it growing. And then you do a biopsy when they see something that's spiking up there, um, which is scary and they stick a needle in your, in that, your butt and it's not good. And then all of a sudden, you know, you're in a room with a guy saying like, yeah, yeah, it's cancer. So, uh,

• 52:49Scott Galloway?

  Wait, let me check my notes again. Yeah, yeah, it's definitely cancer.

• 52:52Speaker 04

  He's like, yeah, so it's cancer. Um, and it was, I got a different doctor. Cause I wanted a better.

• 53:00Scott Galloway?

  Hoping for a different diagnosis.

• 53:02Speaker 04

  Yeah. No, I just wanted a guy who was gonna actually like, just, you know, I felt was like a little more. Yeah, empathetic. But then I went to this amazing guy, Ted Schaper, Dr. Edward Schaper, who's now chief of oncology at Northwestern. He was at Johns Hopkins at the time, Johns Hopkins at the time. And he, you know, met with me and he laid it out and said, you know, you gotta do this operation. And that's the only choice. And did the operation and that was it.

• 53:31Scott Galloway?

  That was 10 years ago.

• 53:32Speaker 04

  Yeah.

• 53:33Scott Galloway?

  So cancer-free. So, but is it one of those things where it was a speed bump and you're back to what you do? Or are there certain instances where you think you approach it or perceive it differently kind of post that scare?

• 53:47Speaker 04

  Well, the great thing about human nature is that, you know, when you get further away from an event that's painful, you kind of, you know, you forget it a little bit. My first PSA test that came back, you know, zero after operation, whatever, when it was like, yeah, you're officially, you know, it's cancer-free. You know, that was, I cannot tell you like what a great feeling that was. So whenever anybody I know, or even somebody I see on Twitter or something says, hey, you know, just got my cancer-free diagnosed. That's to me, I know what that feeling is. And I tried to hold on to it. But if I'm being honest, as the years go by, you start to, you do put it in the rearview mirror. But you walk around with a sense of like, at any moment, something could happen.

• 54:31Speaker 04

  And, you know, this obviously just because you had cancer once doesn't mean you can't get cancer again. And or something else can happen to us, obviously. So it's an appreciation, I think. And something that you kind of carry with you. There's also, you know, it's traumatic. It's traumatic to go through anything like that. I was really lucky. I was really, really lucky. I have friends who have dealt with, you know, cancer where the treatments have gone on for years. Even successful treatments, but you know, put, put them through the wringer and you know what toll that can take. And the tough thing is being able to go forward and do all this stuff you want to do in your life and just not think about it, but getting, it's like in three months, I gotta get that scan, you know, and see if I'm, um, and I've had so,

• 55:15Speaker 04

  I mean, so many people, why, why can't we, Scott, why can't we cure cancer?

• 55:20Scott Galloway?

  That's a very good question.

• 55:21Speaker 04

  These like moon shots and money and like, could, you know, one of these billionaires just put, you know, all the money in the world.

• 55:29Scott Galloway?

  I think we're curing it slowly. I think just seven years ago, we passed a threshold where more people survive cancer now than die from it. So I don't think we ever cure it. I think we just get better at figuring out a way that you die from something else.

• 55:41Speaker 04

  Yeah.

• 55:41Scott Galloway?

  That we can treat it really well.

• 55:42Speaker 04

  But it's, it's also, I, you know, so it's just like, it takes such a toll on people, even when they're being, you know, it's just all, I mean, but look, it's also.

• 55:51Scott Galloway?

  And you had money. Think about what it's, you know, 40% of American households have some sort of medical or dental debt. It's like, hi, I've got bad news. Your wife has lung cancer. I've got worse news. It's going to bankrupt you.

• 56:02Speaker 04

  Yeah. I was incredibly lucky that I, I didn't have to worry about that at all. And when I think about, you know, just what, what people have to deal with, uh, you know, on, on a daily basis, when, when they do get these diagnoses and also like access to good doctors and, you know, people who care. Cause like, I was able to find a different doctor when I didn't like my doctor, but most people can't do that. You know, I have a friend who's involved with AI and I'm sure you know much more about AI than I do, who says that like in the seven, next seven or eight years, they'll be huge.

• 56:35Scott Galloway?

  They keep saying that, Ben. We keep waiting. The whole singularity, we're going to grow limbs and petri dishes and flying cars. I'm getting pretty cynical. We're just going to figure out.

• 56:43Speaker 04

  So you think AI is?

• 56:44Scott Galloway?

  We're just going to figure out new applications that depress our daughters. Uh, I've, I've become very cynical about it. I, I don't, I hope there's an, we've been on the age of this great dawn of discovery for what feels like 40 years now, where everyone's saying we're on the edge of unbelievable. So AI is obviously tremendous opportunity to speed the cycle time of testing and discovery. But yeah, so let's cross our fingers, but I'm, I'm, as you can tell, and you know me a little bit, I'm a glass half empty kind of guy. Just in our remaining time here, we only have a couple of minutes. You've been very generous. Where I was headed with our age, if you will, you got a good relationship. My sense is you have a good relationship with your kids. You've obviously like had a pretty, you know, other than, you know, several thousand misfires.

• 57:27Scott Galloway?

  You've had, you occasionally get lucky, occasionally with the buckshot of your career hit something. You know, you've had, you really have from all dimensions, you've had a pretty storied career. Like what, trying to, trying, literally just if you can, lowering your guard. What do you want to accomplish? And in 10 years, what are you hoping to accomplish that you haven't yet? Or is it just more of the same?

• 57:59Speaker 04

  That's a really good question, because I think about that a lot at this age. I'm sure you do too. It's like so clear that what the runway is, right? And like that's, it's, and it, it, it's, um, and time goes by so quickly.

• 58:18Speaker 04

  I feel like I want to make some more movies that are closer. Like this documentary is probably like the most personal thing I've worked on. And I realized, oh, for me, I, for a long time, I started working before I even knew why I was doing it. I just had this instinct to do it. And now I have a sense of wanting to,

• 58:43Speaker 04

  I guess, just explore filmmaking in a way for me that will allow me to get closer to expressing myself and, and trying things and not being afraid of failure and going out and just doing it because I love doing it. And so in 10 years, I hope that I continue to do that. And then also found the time to, to just do the things I love doing and be places I love being. But the creative process is really important to me. And honestly, like I just hope, you know, in 10 years, 20 years, I still have my faculties

• 59:23Speaker 04

  and I can enjoy the people I love and keep asking these questions of why we're here and what is it all about? And, um, and connect with people in some way through, through the creativity.

• 59:40Speaker 04

  You know, I, I love comedy too, because I find it really challenging.

• 59:46Speaker 04

  But when it's done well, it can really, you know, it really can unlock a lot for people. Um, but I, I don't know, like for me, I'm still trying to find my voice, I think, even at this late age, to tell you the truth.

• 1:00:00Scott Galloway?

  Ben Stiller is an actor, director and comedian responsible for many films, including Meet the Parents, Zoolander, Meet the Fokers. Fokers? Fokers?

• 1:00:10Speaker 04

  Fokers.

• 1:00:11Scott Galloway?

  The Fokers.

• 1:00:11Speaker 04

  Because it sounds like fuckers.

• 1:00:13Scott Galloway?

  Um, I mean, just, there's like Tropic Thunder, just, it's, it's staggering, the, the, the book of work here. And most recently, the hit TV series, which is, which is just kind of at least rocking the Galloway household, Jesus Christ, I'm sick of hearing about it. Uh, Severance, which is, uh, airing now on Apple Television. He joins us from his home in Westchester. Ben, you know, occasionally you meet people and you have this image of what they'd be like. You are literally, and this doesn't happen that often, you're exactly as I'd imagine. You're this nice man who has managed to maintain some semblance of humility. I remember when we went to the US Open together, every person that kind of walked by and saw you and was like, oh my gosh, that's Ben Stiller, and would stop.

• 1:00:58Scott Galloway?

  And this happened a dozen times. Every time you made an effort to be thoughtful, act really receptive and warm. And I can't imagine, and you seem like you like people, but that's at some point, that is an effort, but you make that effort. You're generous with your time and you never, I never got the sense that you took for granted you're a celebrity. So anyways, I've really enjoyed, obviously, your body of work, but I've enjoyed, um, it's just nice to meet someone who kind of is exactly as you would imagine and hope they would be. Uh, congratulations on all your success, man.

• 1:01:29Speaker 04

  Thanks, man. I appreciate you. I love what you do and I feel the same way about you.

• 1:01:33Scott Galloway?

  Thanks, brother.

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