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

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2:14Welcome 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 scoff-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 discuss 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?

2:49I 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. Anyways, with that, here's our conversation with the immensely talented Ben Stiller.

3:24Ben, where does this podcast find you? I am at my house. Well, we need a little more detail than that. At my house. 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, 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. So people don't know this. Ben and I started at UCLA the exact same year and Ben dropped out.

4:05And, you know, things really haven't worked out for Ben. But Ben, can you, this is a bridge to. And things didn't really work out for you, Scott, either. 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. Yeah. Well, I mean, I'm a Nepo baby. I grew up around show business. My parents were a comedy team, Stiller and Mira, 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 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 nightclub act and commercials and sitcoms and uh but i knew movies were what i really wanted to do.

5:16Then 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, you know, New York in the 70s was much more, I think, rougher around the edges. So like, 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, 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, you know, segregated really.

6:01And 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 how did you end up at ucla 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 kind of sort of like put it you know It was sort of this wonderful world of, I love the history of the movies and the idea of going out there and becoming a director.

6:47So UCLA, USC, Boston University, and NYU were the four places I applied to. And I got into those four places except for USC. 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. It's shocking you got into UCLA and not into USC. 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 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.

7:27and 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 of weeks, his freshman year of like embracing it and loving it.

8:07And I never really opened myself up to that experience. And what was sort of your first gig? So you dropped out of UCLA. What did you do? 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 six o 'clock in the morning and, you know, got back to New York and sitting on 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 uh i got um i got a job working as a bus boy 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 uh started to get callbacks uh you know which is where they have to call you back for another audition to get closer and closer to get the part uh but it took 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 you know started to get better at at that process and then i got a job in this play uh off broadway called the house of blue leaves by john guare and it was at lincoln center theater and that production uh was there's 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 steven spielberg was directing and then i got another small part in another movie empire of the sun i forgot about that yeah yeah what was your i I remember Christian Bale, but I don't remember Ben Stiller.

9:50Yeah. Ben Stiller is one of the prisoners of war in that prison camp with John Malkovich. And I had maybe two lines. And what was your quote unquote big break? Like what sort of took you, what was a step change in your career? 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.

10:32And so I did these little parts 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, you know, doing being in comedy, which I sort of really kind of not wanted to do for a long time but then started to find um a sense of humor i guess that i connected with and shows like sctv and and saturday night live too and um and so i auditioned and got a a job as a i made a short film actually for them that i i sold to them that was a 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 88 season and i knew very quickly that i wasn't going to do well there because i i wasn't great at live performing i didn't love it you weren't at us now very long no no i was there like six weeks and i um 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 had a show right the ben stiller show the ben stiller show that was on 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 they and um there's a guy named chris albrecht who ran hbo comedy and he produced basically this show uh that we worked on for a couple of years that we sold to fox and then that got canceled after about 12 episodes um 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 um david cross and like all these people were just sort of starting out and that got canceled but then somebody saw that the some of those sketches and in 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.

12:55And they put us together, and we started to work on that movie together. And Winona Ryder signed on to 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 on to it. ethan hawke was in that right exactly yeah ethan was in it and um and then 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 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 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 you know got along and so this was a you know a point where Jim was just, you know, every movie he was doing was, you know, bigger and bigger.

14:08And 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, you know, we did it and it came out and was not super well received. 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? 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, motivation to go towards something.

14:50I wasn't self-aware back then to understand what was pushing me towards it, but I did definitely deal with 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 make something. I think you're being unfair. You've had a lot of negative reviews in movies. I mean, along came Pauly. like i mean there's definitely oh my god yeah um there's well i didn't get to those yet this was i think you're being really hard on the cable guy 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 movie the heartbreak kid starsky and hutch which i enjoyed sarah i mean come on this is we're gonna need a bigger boat I mean, this is not your press tour, Ben.

15:49I'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. That's right. Oh, yeah. Night at the Museum, Battle of the Smithsonian. Yeah, I'm sure that wasn't for the money. Hold on. Yeah, and Madagascar 3, too. Fresh Horses? I don't even know what that is. If Lucy fell, the watch. I could tell you about all of these because each one has an amazing story to it. Oh, my God. If you type in Ben Stiller's worst movies, there's three pages.

16:29Oh, 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 going to work. Something's going to work. You have taken so many shots here. like i i this i'm a i'm similarly one out of seven businesses work so i've started nine oh right okay right let's yeah it's a law of averages anyway sorry sorry 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 uh 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's like you didn't mention duplex to duplex envy i was i was holding that but you know that 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.

17:40And 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? 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?

18:12And what other pieces of work you thought, this is good, but it ended up being a huge commercial hit? You know, I don't know. 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 98 when movies were, you know, in comedies and theaters. And that movie might have 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.

18:50And 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 1993, 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, you know, 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 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 i've 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 going to be the one you know what i mean except for maybe fresh horses because fresh horses was i was it was that was 1987 and i was just uh you know just starting out and it was these movies.

19:57And it was like, this was the Brat Pack. And I was like, oh man, I'm going to be in the Brat Pack. I'm going to be in the movie. This is it. This is my moment. The movie just tanked. And, but it was literally to this day, my favorite experience ever making a movie. Really? Yeah. Cause it was, you know, it was like six 20 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. So I know you're dying to know what my favorite works are of yours.

20:35First off, my, my partner is literally obsessed with severance for me or two favorites, probably the Royal Tenenbaums. 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. What and don't say Robert De Niro.

21:16You'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 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? well i mean i would start with saying that you know in tropic thunder you know 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 um 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 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 in taking the chances so i think uh with him in that movie and i think everybody in that movie like jack black everyone's 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 i think uh you know working with greta gerwig and greenberg with noah bomback um which was like her first sort of role that people sort of you know discovered her in uh and and watching you know the simplicity of what she was doing was um 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 we'll be right back after a quick break these days every business leader is under pressure to save money, but you can't crush the competition just by cutting costs.

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25:05From Pushkin Industries, I'm Jonathan Goldstein, and Heavyweight is back. The new season is bigger than ever. Bigger hopes. I keep waiting for this moment when he says, Mom, I get it. I'm sorry. Bigger dreams. Tom Hanks wants to meet with you. This is a real chance. And bigger heartbreaks. I thought it would be my movie moment. And maybe he would even whisper in my ear, I've always been in love with you. Check out new episodes of Heavyweight on Apple Podcasts.

25:50Let's talk about Failures? More failures? Literally everyone's glomming all over you on severance. I heard they talk about failure. Let's talk about Madagascar 3. Come on. Dude, we only have an hour and a half here. Okay. All right. You know, when you talk about business, you do learn. You really do learn more from the things that don't go well, as we all know. It's very true. I don't know if you've heard this, but my pivot co-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 apologizing and saying that, no, night at the museum, the Smithsonian meets the Fokers meets whatever.

26:30Anyways, 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, 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.

27:09And 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 Chitura, 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.

27:48That 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 got to do this? 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 I really loved, like Office Space or The Office.

28:42And 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 they were saying like okay you know go ahead develop these scripts we like it um 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 um 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 different than what apple saw but i think i have to give them credit for saying yeah like 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 um 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 um 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 about.

30:10There'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.

30:50What 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. 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'd make a movie and then you'd, you know you'd release it in theaters you make money there and then you go to dvd and vhs right and that that was the the dvd streaming um 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 i don't know like eight nine years ago saying like it's all going to change it's all changing.

31:50And 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.

32:24But 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 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 some star attached or some IP that it's based on or something that is going to basically 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.

33:09So people are not taking as many chances and it's really tough out there. 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 lives. lives. I believe your mom died in 15, your dad in 2020. Talk a little bit about your parents, their approach to raising you.

33:48And, you know, I don't want to say the impact they had on you, but I don't think I've ever been with you. And within an hour, you don't reference your parents. 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 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.

34:27I 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 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 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.