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

Summary

The Prof G Pod with Scott Galloway: Episode Summary

Title: Ben Stiller on the Price of Fame and the Power of Failure
Host: Scott Galloway
Guest: Ben Stiller
Release Date: August 7, 2025

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Introduction

In the 360th episode of The Prof G Pod, host Scott Galloway engages in a candid and insightful conversation with acclaimed actor, director, and comedian Ben Stiller. The discussion delves into Ben's illustrious career, personal life, creative processes, and the challenges he's faced both professionally and personally.

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Ben Stiller’s Early Life and Career Beginnings

Ben Stiller opens up about his upbringing in a showbiz family. Growing up on the Upper West Side of Manhattan in the 1970s, Ben was immersed in the entertainment industry from a young age. His parents, a comedy duo, instilled in him a deep appreciation for creativity and performance.

Notable Quote:
"I grew up around show business. My parents were performers, doing comedy acts, commercials, and sitcoms. I knew from a young age I wanted to make movies."
— Ben Stiller [04:29]

Stiller shares his initial foray into acting and directing, highlighting his attendance at UCLA's film school despite not being a stellar student. His early career involved small roles, such as in Steven Spielberg’s Empire of the Sun, and participation in Off-Broadway productions, which laid the foundation for his future endeavors.

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Career Breakthroughs and Setbacks

Ben discusses the pivotal moments in his career, emphasizing that success often comes from a series of small breaks rather than a single defining moment. His role in Reality Bites marked an early recognition in his acting career, but it was There's Something About Mary (1998) that became a significant box office success, reshaping the trajectory of his career.

Notable Quote:
"There's Something About Mary didn't open at number one, but it worked its way to the top over nine weeks, which hardly ever happens."
— Ben Stiller [18:23]

He candidly addresses the challenges he faced with films like The Cable Guy, which received harsh criticism and negative reviews. Despite these setbacks, Ben remained resilient, understanding that failure is an inherent part of the creative process.

Notable Quote:
"In show business, you're being unfairly treated sometimes. 'The Cable Guy' was dubbed the first disaster movie of the summer, and I took it personally because I directed it."
— Ben Stiller [14:38]

Stiller also touches upon his work in animated films like the Madagascar series and the critical and commercial dichotomies these projects presented.

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Creative Process and Industry Insights

The conversation shifts to Ben's recent projects, particularly the critically acclaimed TV series Severance. He elaborates on the creative freedom afforded by Apple Television and the collaborative efforts involved in bringing the show to fruition without relying on traditional focus groups or test screenings.

Notable Quote:
"We never did any focus groups or test screenings for 'Severance.' It was one of the first things I did where I didn't have to rely on that traditional feedback."
— Ben Stiller [29:22]

Ben reflects on the current state of the entertainment industry, noting the challenges creatives face amidst the evolving dynamics of streaming services and traditional movie studios. He expresses concern over the industry's retreat to safe, proven IPs, limiting the space for innovative and risky projects.

Notable Quote:
"Nobody really knows how it's going to shake out with the streamers and movies. It's really tough to pitch an idea without some star attached or known IP."
— Ben Stiller [32:19]

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Personal Life: Family, Sobriety, and Relationships

Ben delves into his personal life, discussing his relationship with his parents and the profound impact their careers and personal struggles had on him. He speaks openly about his mother's battle with alcoholism and his own journey towards sobriety, which began seven years prior to the episode.

Notable Quote:
"I stopped drinking about seven years ago because I wanted to be present for my family and deal with my feelings without relying on alcohol."
— Ben Stiller [39:53]

He also shares his experiences navigating a separation and subsequent reconciliation with his partner, emphasizing the importance of personal growth, compromise, and mutual support in maintaining a healthy relationship.

Notable Quote:
"If you have a career that revolves around the things you want to do, you have to communicate and figure out what's important to both of you."
— Ben Stiller [49:28]

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Health Struggles: Overcoming Prostate Cancer

Ben opens up about his diagnosis with prostate cancer a decade ago. He details the emotional and physical toll the experience took on him and the importance of early detection and compassionate medical care.

Notable Quote:
"Being diagnosed with cancer was terrifying. It changes your perspective on life and makes you cherish every moment."
— Ben Stiller [51:31]

He emphasizes the value of reliable medical support and the ongoing fear that accompanies survivorship, even years after being declared cancer-free.

Notable Quote:
"Even years later, you carry the sense that something could happen at any moment. It’s an appreciation and a trauma rolled into one."
— Ben Stiller [54:14]

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Advice for Fatherhood and Relationships

Addressing the listeners, particularly young men navigating fatherhood and relationships, Ben offers heartfelt advice drawn from his own experiences. He underscores the fleeting nature of time with children and the importance of being present, adaptable, and open to their interests.

Notable Quote:
"Engage with your kids, set an example for taking care of yourself, and be open to what they're giving back to you."
— Ben Stiller [46:17]

For maintaining healthy relationships, he highlights the necessity of compromise, trust, and continuous effort to nurture the bond between partners.

Notable Quote:
"If you're in a good couple and meant to be together, you have to give each other freedom and have trust."
— Ben Stiller [49:28]

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Future Endeavors and Reflections

Looking ahead, Ben expresses a desire to continue exploring filmmaking in a way that allows for personal expression and creative risks. He aims to produce more personal projects, such as his documentary on his parents, and maintain a balance between his creative passions and personal life.

Notable Quote:
"In 10 years, I hope to continue making movies that allow me to express myself and stay connected with the people I love."
— Ben Stiller [58:25]

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Conclusion

The episode concludes with Scott praising Ben's humility, generosity, and the authenticity he brings both on and off the screen. Their mutual respect and camaraderie underscore the depth of the conversation, leaving listeners with a comprehensive understanding of Ben Stiller's multifaceted life and career.

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Key Takeaways:

• Resilience in Creativity: Ben emphasizes the importance of persevering through failures and viewing them as learning opportunities.

• Work-Life Balance: Maintaining meaningful relationships requires continuous effort, compromise, and presence.

• Health Awareness: Early detection and compassionate medical care are crucial in overcoming serious health challenges.

• Industry Insights: The evolving landscape of entertainment necessitates adaptability and creativity, especially amidst the dominance of streaming platforms.

Notable Quotes Highlighted:

• "I grew up around show business..." — Ben Stiller [04:29]
• "There's Something About Mary didn't open at number one..." — Ben Stiller [18:23]
• "We never did any focus groups..." — Ben Stiller [29:22]
• "I stopped drinking about seven years ago..." — Ben Stiller [39:53]
• "Being diagnosed with cancer was terrifying..." — Ben Stiller [51:31]
• "Engage with your kids..." — Ben Stiller [46:17]
• "In 10 years, I hope to continue making movies..." — Ben Stiller [58:25]

This episode offers a profound exploration of Ben Stiller’s journey, blending professional insights with personal reflections, making it a valuable listen for fans and aspiring creatives alike.

Transcript

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[Scott Galloway]

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[Ben Stiller]

Go, go, go.

[Scott 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 a TV series Severance. We discuss with Ben growing up in a showbiz family, making iconic films and what he's learned about creativity, family, and staying grounded. Um, 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. Also, type in Ben Stiller filmography. This guy has an unbelievable body of work.

[Advertisement Voice]

Anyways, with that, here's our conversation with.

[Scott Galloway]

The immensely talented Ben Stiller. Ben, where does this podcast find you?

[Ben Stiller]

I am at my house.

[Scott Galloway]

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

[Ben Stiller]

I'm in Westchester, New York, about 45 minutes north 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, you know, something about just being somehow connected to nature that I really like.

[Scott 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.

[Ben Stiller]

And things didn't really work out for you, Scott, either, did they?

[Scott 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.

[Ben Stiller]

Yeah, well, I mean, I'm a Nepo baby. You know, I grew up around show business. Like, my parents. My parents were a comedy team. Stiller and Mira, they. And they acted separately together. And I grew up around that in New York in the 70s, and with my sister, we lived in an apartment on the Upper west side. And, yeah, it was show business in our life. And I knew from a young age I wanted to be doing something having to do with making movies. I loved making movies as a kid. So I grew up around show business. My parents weren't always making movies. They were performing, doing comedy, nightclub act, and commercials and sitcoms. But I knew movies were what I really wanted to do. Then I went to. So I kind of grew up in this sort of, I guess you'd say, privileged Upper west side Manhattan. So I grew up in New York in the 70s was much more, I think, 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. You got a lot of tastes of different, 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 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 segregated, really. And this experience was, I think, for me, 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 I went out to LA to go be a director and an actor. Went to ucla. Hated it.

[Scott Galloway]

How did you end up at ucla?

[Ben Stiller]

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 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.

[Scott Galloway]

But you got into ucla. Because when we applied. I know a lot about. 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. It's shocking you got into UCLA and not into usc.

[Ben Stiller]

Well, the film school was a tough film school to get into, I think, but my grades weren't great. And so I somehow got into UCLA and thought, okay, I'm gonna do that. And it was such a. I went to this little private school on the Upper west side of Manhatt 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 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 literally. I didn't know how to do it. 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 to school now in New York, and he's a freshman, and he's just turned the corner the last couple weeks, his freshman year of, like, embracing it and loving it. And I never really opened myself up to that experience.

[Scott Galloway]

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

[Ben Stiller]

I remember very well coming back to my parents apartment, sitting on my bed on a red eye from LA and like it was like 6 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 out of school. That moment where you have to figure it out. And basically 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 to get closer and closer to get the part and. But it took about two years to even get to that point. I just was not great at auditioning. I don't think I was great at being an actor in front of the camera. I wasn't that comfortable. And after a couple of years of doing it, I finally got to a place where I started to get better at that process. And then I got a job in this play off Broadway called the House of Blue Leaves by John Guare. And it was at Lincoln Center Theater. And that production was a small part, but the character had a monologue at the beginning of the second act and the production went to Broadway, 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. And then I got another small part in another movie, Empire of the Sun.

[Scott Galloway]

I forgot about that.

[Ben Stiller]

Yeah, yeah.

[Scott Galloway]

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

[Ben Stiller]

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

[Scott Galloway]

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

[Ben Stiller]

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 going to 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 making short films, 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 I made a short film, actually, for them that I sold to them. That was Takeoff on the Color of Money with Tom Cruise. And then they hired me to be a writer or an apprentice writer. And that was at the end of the 88 season. And I knew very quickly that I wasn't going to do well there because I wasn't great at live performing. I didn't love it.

[Scott Galloway]

You weren't at SNL very long?

[Ben Stiller]

No, no. I was there, like six weeks. 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 Kahn, we had a show, right?

[Scott Galloway]

The Ben Stiller Show.

[Ben Stiller]

The Ben Stiller show that we were on that. It was on MTV for, like, 13 episodes. And then somebody at the fledgling Fox network, which was just starting, they didn't even have full programming then, saw it. And there's 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 12 episodes. But that was probably, like, my first. I was doing a show and I was working with Bob Odenkirk and Janine Garoppolo and Andy Dick and David Cross and, like, all these people, we were just sort of starting out, and that got canceled. But then somebody saw that, some of those sketches, and Danny DeVito, Danny DeVito's production company, and they were making a movie called Reality Bites that they were developing with Helen Childress, who was a writer, young writer, and they put us together and we started to work on that movie together. And Winona Ryder signed onto it. And this was probably 1993, 94. And we made that movie. So that was my first movie that I ever directed, thanks to Winona signing onto it.

[Scott Galloway]

Ethan Hawke was in that, right?

[Ben Stiller]

Is that exactly. Yeah, Ethan was in it. And then that movie came out and did okay. But I was also kind of. It's kind of interesting. I was doing that As a director and an actor. Cause I was in that too. But nobody was really banging down the door for me to do the next thing. And then Judd Apatow, who I met when we started to work on the Ben Stiller show on Fox a few years before, had been working with Jim Carrey. And Jim signed on to do the Cable Guy, which originally was a Chris Farley vehicle. And then Jim said he was going to do it and Judd was going to rewrite it. And Judd suggested me to direct it to Jim. And then we all had a meeting and got along. And so this was a point where Jim was just. Every movie he was doing was 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 we did it and it came out and was not super well received.

[Scott Galloway]

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

[Ben Stiller]

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 sense of what you want to do or this ambition or this kind of like blind sort of just motivation to go towards something. 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're being unfair.

[Scott Galloway]

You'Ve had a lot of negative reviews. Movies. I mean, along came Paulie. Like, I mean, there's definitely mv. Yeah, there's.

[Ben Stiller]

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

[Scott Galloway]

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

[Ben Stiller]

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.

[Scott Galloway]

The Heartbreak Kid, Starsky and Hutch, which I enjoyed. Sarah Cooper. I mean, come on, this is. We're gonna need a bigger boat. I mean, 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 are also in Mary Madagascar.

[Ben Stiller]

Let's talk a little bit about that.

[Scott Galloway]

Oh, my gosh. And then Madagascar 2. Escape to Africa.

[Ben Stiller]

That's right.

[Scott Galloway]

Oh, yeah. Night at the museum. Battle of the Smithsonian. Yeah, I'm sure that wasn't for the money. Hold on.

[Ben Stiller]

And Madagascar three, too.

[Scott Galloway]

Fresh horses. I don't even know what the fuck that is.

[Ben Stiller]

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

[Scott Galloway]

Oh, my God. If you type in Ben Stiller's Worst Movies, there's three pages. It's like, oh, my God. 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 this. I'm similarly. One out of seven businesses work. So I've started nine.

[Ben Stiller]

Right, let's. Yeah. It's a law of averages, anyway.

[Scott Galloway]

Sorry. Sorry.

[Ben Stiller]

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, it was like, dude, you didn't mention duplex, too. Duplex envy.

[Scott Galloway]

I was. I was holding that.

[Ben Stiller]

But, you know, that. That's a weird. It's a weird thing to go through. For sure, though, like, 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?

[Scott 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 we thought they were gonna be? And what other pieces of work. You thought, this is good. But it ended up being a huge commercial hit.

[Ben Stiller]

You know, I don't know, it's really hard to tell what's gonna work and what's not gonna 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 98, when movies were, you know, there were 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. But then to see how that movie worked and then for me, what. 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. 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 lens that people looked at what I was doing and because then 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 for the audiences. And, you know, comedies, critically have always been, you know, it's always a crapshoot in terms of whether critics will go for them or not. But I never, ever had the feeling going into something, this is gonna be the one. You know what I mean? Except for maybe Fresh Horses, because Fresh Horses was. That was 1987 and I was just, 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 in the movie.

[Scott Galloway]

Just this is it. This is my moment.

[Ben Stiller]

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

[Scott Galloway]

Really?

[Ben Stiller]

Yeah, because it was, you know, it was like 620 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 like the dream. It was so much fun.

[Scott Galloway]

So I know you're dying to know what my favorite works are of yours. First off, my partner is literally obsessed with severance. For me, your two favorites, probably the Royal Tannenbaums. Actually, you know what I think? Tropic Thunder, I think our friend wrote it, Justin Theroux. And then 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 character. Anyways. But I still like the Royal Tannenbaums the most, I think, also, I think it was one of Gene Hackman's kind of crowning performances. Which leads me to my question. And don't say Robert De Niro. You've 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 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?

[Ben Stiller]

Well, I mean, I would start with saying that in Tropic Thunder, he is appreciated. 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 of 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. And I think in movies, you have to 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, everyone 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, but you have to take those chances. 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.

[Scott Galloway]

We'll be right back after a quick break.

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[Ben Stiller]

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This episode is brought to you by Choiceology, an original podcast from Charles Schw. Choiceology is a show all about the psychology and economics behind our decisions. Each episode shares the latest research in behavioral science and dives into themes like can we learn to make smarter decisions? And the power of do overs. The show is hosted by Katie Milkman. She's an award winning behavioral scientist, professor at the Wharton School, and author of the best selling book how to Change in each episode. In this episode, Katie talks to authors, historians, athletes, Nobel laureates and everyday people about why we make irrational choices and how we can make better ones to avoid costly mistakes. Listen and [e-mail] podcast or find it wherever you listen.

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[Scott Galloway]

Let'S talk about failures.

[Ben Stiller]

Failures.

[Scott Galloway]

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

[Ben Stiller]

You want to talk about failure? Let's talk about Madagascar 3.

[Scott Galloway]

Come on, dude, we only have an hour and a half here.

[Ben Stiller]

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.

[Scott Galloway]

I don't know if you've heard this, but my Vivico host, 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 apologize and saying that no night at the museum, the Smithsonian meets the Fokkers 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? Cause 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 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 if I had read, if someone had pitched something about the seven realms and sword fighting with Dragons, but there's a red woman who's got mystical power. And then someone said, okay, I have 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. 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.

[Ben Stiller]

I mean, it was. It all started with a script that Dan wrote, 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 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. 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 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 kind of evolved into something. But I think people say yes to things because for some reason they connect with it. But maybe what I was connecting with was maybe a little different than what Apple saw. But I think I have to give them credit for saying, yeah, go ahead and do it. But I don't Know how things evolve in this way where you're given the freedom. Maybe it's because of 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.

[Scott 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 would 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'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 dynamics of the industry and the biggest shifts. How do you perceive it as a creative having been in the business for pretty much 40 years now?

[Ben Stiller]

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 more about this than I do. But there used to be this model that you'd make a movie and then you'd release it in theaters, you'd make money there. And then you go to DVD and vhs, right? And that was the DVD streaming thing became, like, basically dead after. When streaming happened, DVDs died. And that's changed everything. And I remember my agent telling me that, like, I don't know, like, eight, nine years ago, saying, like, it's all gonna 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, 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, $9 million or whatever and win Academy Awards. But it's two different worlds, and you have to struggle to make the, you know, the things that aren't going to be, you know, a slam dunk 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 tough place, too, and that affects. That affects everything. So it's. I would say 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 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 really tough out there.

[Scott Galloway]

So I don't know you well, but I've gotten to know you a little bit. And whenever we talk, 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 as old photos, 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 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.

[Ben Stiller]

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. So I think I've been looking at my relationship with them. I miss them. I think probably when they first 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 important relationship in your life. And I love my folks. And it's interesting when you have parents who are supportive and love you 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, they both had their issues, 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 last few years working on this movie is how my own process 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 a creative person where you go, I need to take this time to work on this thing, because that's gonna 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 experienced it as a parent with my kids. And I think that's what I grew up around was my parents working all the time in an apartment on the Upper west side in Manhattan where they had a room, where they had an office, and they'd write commercials and write sketches and go off and do a part in a sitcom or go do their act at a nightclub or 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. And 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. 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 share my mom's sense of humor more than my dad's. And my dad was much more kind of. 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, and I think she built up some walls. But, 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 show business. And as parents, they were, you know, there's a lot of laughing and 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. And, yeah, so I feel like they were. I don't know, 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 sort of this push pull where I was, like, I wanted him to treat me like an adult, 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 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 balance 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. 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 of me, because they were starving, living in an apartment on the Upper west side in the 50s, trying to make money. And then that act provided a living and an identity for them, and she never really loved doing it as much.

[Scott Galloway]

So I didn't connect the dots. I've never heard the story or 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 don't drink.

[Ben Stiller]

Yeah, I think I stopped drinking about seven years ago. Yeah, I mean, there was always an awareness in our family. I mean, like I said, my mom was amazing. In the last 10 years of her life, she got sober and quit smoking. She smoked her whole life and talked about it and was very committed to a program. And that in turn, for me, when I got into my 20s, I started to realize what that dynamic was in our family and went my own way to deal with that and find a program to help deal with that for myself. And, yeah, an awareness of that has always been part of, I think, for me, looking at the lens of how our relationships with our parents when we're young affect our current relationships. And I think for me, Christine and I 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 because I felt like I wanted to just, you know, be present for whatever I was, whatever was going on, which was, you know, feeling a lot of feelings. And. 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. If I kept drinking.

[Scott Galloway]

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

[Ben Stiller]

Well, I think, yeah, I think you have to be present for a relationship and be available and be. I'm not saying you have to be completely sober and not drink to be in a relationship, but you have to just. You have to be who you are and, and take responsibility for being there. And if someone isn't, then it's hard. It takes two to tango. So I think both 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. 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 with somebody. I didn't know we were going to come back together, but now every day it's that acknowledgment of like, okay, this is good, I appreciate this, and it could go away. So I'm going to just, I'm going to be. I'm going to be grateful for it and I'm going to be present. And then you figure out for yourself, like, what that means in terms of your own choices.

[Scott Galloway]

We'll be right back.

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[Scott Galloway]

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[Ben Stiller]

I'm always looking for ways to make.

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[Ben Stiller]

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[Ben Stiller]

Reynolds here from Mint Mobile. Now I was looking for fun ways to tell you that Mint's offer of unlimited Premium Wireless for $15 a month is back. So I thought it would be fun if we made $15 bills, but it turns out that's very illegal, so there goes my big idea for the commercial. Give it a [e-mail] Switch upfront payment.

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[Scott Galloway]

We're back with more from Ben Stiller. 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. Figured it 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?

[Ben Stiller]

Oh wow. That's a good question. Oh man. Well, I would say that, you know, coming out the other end here with kids who are in their 20s now practically my son's 19, daughter's 23. It goes by quickly. And there's a really short amount of time that you're able to really be connected to your kids before they go out into the world. It's not even when they're in their 20s. It's by the time they're whatever, 13, 14 years old, they're socializing. And there's so many other influences that are coming in. And I think when I was younger, with my kids, when they were that age, I was a little bit daunted by parenting. And I might say that my mother. 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, when she was younger, we had a tougher relationship, but it was more because I wasn't meeting her where she was. 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 go to do that, you have to kind of sacrifice a little bit of what you think you want that relationship to be and be there and open to it and not run away from it. Because I think it's. For some guys, it's having babies and infants and toddlers, it's really intimidating. And 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 be open to what your kids are giving you back is really important. It's not that easy, I don't think.

[Scott 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. I mean, totally, totally.

[Ben Stiller]

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.

[Scott 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?

[Ben Stiller]

Well, it's a lot of it is, I think, compromise. And if you really care about this person, you have to figure out, again, how to meet them, where they're at. Also, if you have a career or something that you're really focused on or revolves around the things you want to do, you have to communicate and really talk about what's important to both of you. And that's the thing. I guess I just said it before, but the gift of getting back together is that you realize that just because you're married or just because you say you have a commitment to each other, it doesn't mean that it's going to work. 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. If you're in a good relationship, that's going to 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 are a good couple and you're meant to be together, you have to give each other the freedom and have the trust.

[Scott Galloway]

So I affectionately say we're the exact same age. 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.

[Ben Stiller]

Literally, I had the prostate cancer already.

[Scott Galloway]

Oh, that's right. Oh, my God. That was so. That was so. That was so uncouth. I mean. That's right. You actually had prostate cancer. Yeah. Yeah. Talk a little bit about that experience and how it. How if and how it changed you.

[Ben Stiller]

Well, it's scary. Scary.

[Scott Galloway]

That makes sense.

[Ben Stiller]

That was so awful.

[Scott Galloway]

I make a. I make an irreverent reference to ass cancer. And you raised your hand and said, well, I did have ASC cancer. I have prostate cancer, Scott.

[Ben Stiller]

I've spent a little bit of Time with you. And as much as I talk about my kids and my parents, you talk about ass cancer. Look, are obsessed with.

[Scott Galloway]

I think we have the beginnings of a Madagascar 6 prostate cancer. I think it's coming.

[Ben Stiller]

There it is. And didn't I tell you that if you get a colonoscopy. I think I told you this at the wedding. You get a colonoscopy, you go to the right doctor, he explains to you why colonoscopy is a good thing. Because it's. If there's stuff in there, they can get it before it gets bad. So anyway, 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, it's like, stop. You don't know if you're going to be alive in six months. If you don't, you know, if this doesn't get dealt with, it's like your worst fear. And I had a bad diagnosis in terms like the doctor wasn't great. When he told me, you know, he's like, 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 45 and up.

[Scott Galloway]

Even that's kind of unreliable, though.

[Ben Stiller]

Yeah. But you have to watch it. And my doctor started testing me early. It was supposed to be 50, but he started testing me around 45, and he saw it growing. And then you do a biopsy when they see something that's spiking up there, which is scary. And they stick a needle in your butt and it's not good. And then all of a sudden you're in a room with a guy saying like, yeah, yeah, it's cancer. So.

[Scott Galloway]

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

[Ben Stiller]

He's like, yeah, so it's cancer. And I got a different doctor because I wanted a better.

[Scott Galloway]

Hoping for a different diagnosis.

[Ben Stiller]

Yeah, no, I just wanted a guy who was going to actually, like, just, you know, I felt like, yeah, empathetic. But then I went to this amazing guy, Ted Schaefer. Dr. Edward Schaefer, who's now chief of oncology at Northwestern. He was at John Hopkins at the time, Johns Hopkins at the time. And he, you know, met with me and he's. And he. 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.

[Scott Galloway]

That was 10 years ago.

[Ben Stiller]

Yeah.

[Scott Galloway]

So cancer free. 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?

[Ben Stiller]

Well, the great thing about human nature is that when you get further away from an event that's painful, you kind of. You know, how you forget it a little bit. My first PSA test that came back zero after operation, whatever, when it was like, yeah, you're officially cancer free, that was. I cannot tell you what a great feeling that was. So whenever anybody I know or even somebody I see on Twitter or something says, hey, just got my cancer free diagnosed, that's. To me, I know what that feeling is. And I tried to hold onto it. But if I'm being honest, as the years go by, you do put it in the rearview mirror, but you walk around with a sense of, at any moment, something could happen. And obviously, just because you had cancer once doesn't mean you can't get cancer again 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 yet it's like, in three months, I got to get that scan, you know, and see if I'm. And I've had so. I mean, so many people. Why can't we. Scott, why can't we cure cancer?

[Scott Galloway]

That's a very good question.

[Ben Stiller]

These, like, moonshots and money and, like, could, you know, one of these billionaires just put, you know, all the money.

[Scott Galloway]

In the world, 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 that we can treat it really well.

[Ben Stiller]

But it's also. It takes such a toll on people, even when they're being. It's just off. I mean, but look, it's also.

[Scott Galloway]

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

[Ben Stiller]

Yeah. I was incredibly lucky that 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, you know, on a daily basis when, when they do get these diagnosis and also, like, access to good doctors and, you know, people who care because, 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.

[Scott 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've gotten pretty cynical. We're just going to figure out, what do you think?

[Ben Stiller]

So you think AI is.

[Scott Galloway]

We're just going to figure out new applications that depress our daughters. I've become very cynical about it. I hope there's a. 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 ambulance. So AI has obviously tremendous opportunity to speed the cycle time of testing and discovery. But yeah, so let's cross our fingers, but 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 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 you've had. You occasionally get lucky, occasionally with the buckshot of your career, hit something.

[Ben Stiller]

You.

[Scott Galloway]

Know, you really have from all dimensions. You've had a pretty storied career. Like what? Trying to literally just if you can, lowering your guard. What do you want to accomplish in 10 years? What are you hoping to accomplish that you haven't yet? Or is it just more of the same?

[Ben Stiller]

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 what the Runway is, right. And time goes by so quickly. I feel like I want to make some more movies that are closer. This documentary is probably the most personal thing I worked on. And I realized, oh, for me, 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, I guess, just explore filmmaking in a way for me that will allow me to get closer to expressing myself 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, I just hope in 10 years, 20 years, I still have my faculties 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 connect with people in some way through the creativity, you know, I love comedy, too, because I find it really challenging. But when it's done well, it can really, you know, it really can unlock a lot for people. But 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.

[Scott Galloway]

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

[Ben Stiller]

The Fockers sounds like fuckers.

[Scott Galloway]

I mean, just. There's, like Tropic Thunder. It's staggering. The Book of Work here. And most recently, the hit TV series, which is just kind of at least rocking. The Galloway household. Jesus Christ. I'm sick of hearing about it. Severance, which is 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 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. 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. It's just nice to meet someone who kind of is exactly as you would imagine and hope they would be. Congratulations on all your success man.

[Ben Stiller]

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

[Scott Galloway]

Thanks brother.

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