On with Kara Swisher - Judd Apatow on Meme Politics, Being Funny in 2025 & the Comedy Biz

Episode Date: October 27, 2025

From an early age, writer, director, and producer Judd Apatow has been obsessed with comedy. What started as a quest to interview comedians for his high school radio station ultimately evolved into one of the most prolific careers in Hollywood today, with hits like “The 40 Year Old Virgin,” “Knocked Up,” and “Anchorman.” Now, Apatow is looking backwards. His new book, “Comedy Nerd,” is a visual memoir of his decades in the business, working with a who's who of the biggest names in comedy.  Kara and Judd talk about how he reimagined the genre of raunchy, R-rated comedies about stunted adolescence; what he got right about American masculinity in the mid-and-late 2000s; and his recent pivot to making documentaries about some of the greatest comedians of the modern era. They also discuss whether AI can be funny and the ways politics is shaping comedy right now.  Questions? Comments? Email us at [e-mail] or find us on YouTube, Instagram, TikTok, Threads, and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

I would just like to say it really clearly. I'm more mature than Scott Galloway. I don't know how much more mature. So this next phase of my career, I call 15% healthier than Scott. Hi, everyone, from New York Magazine and the Box Media Podcast Network. This is on with Kara Swisher, and I'm Kara Swisher. Today I'm speaking with comedian, writer, director, and producer Judd Apatow. He's been one of the most prolific filmmakers in Hollywood and comedy over the last few decades.

His hits include films like The 40-year-old Virgin, Anchorman, Knocked Up, Bridesmaids, and Train Rock. He pioneered the genre of raunchy awkward R-rated films about growing up that drew big crowds to the theaters in the mid and late 2000s. Apatow has a new visual memoir about his decades in the business called The Comedy Nerd. He writes about how as a kid he developed an obsession with comedy and started collecting autographs and memorabilia from some of the comedians he idolized. As he got older, he kept up the habit. So the book is really a behind-the-scenes peak

into the making of his movies and TV shows. In the last few years, Apatau has also turned to documentary filmmaking. His subjects are some of the comedy grades of the modern era. He won primetime Emmys for his films on George Carlin and his former mentor, Gary Shandling, and his upcoming documentary about Mel Brooks, is set to be released next year. All right, let's get to my conversation with Judd Apatow.

Our expert question comes from comedian Jane Lynch, who has appeared in a few of Apatow's films, including The 40-year-old Virgin. This is a fun one, so stick around. Rinse takes your laundry and hand delivers it to your door, expertly cleaned and folded, so you could take the time once spent folding and sorting and waiting

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They were truly rented from Google or from Facebook. That's Brian Morrissey, the Super Sharp Media Observer and Media Operator. And this week on channels with Peter Kafka, I talked to Morrissey about how to run a media business without getting big. What happens to the industry next? That's this week on Channel. channels, wherever you listen to your favorite podcasts. This week on Virgin History, the Verge's new chat show about old technology, we're talking

in Guitar Hero. You know, the game that we all spent countless hours standing in our living rooms, hammering away on a plastic guitar, just trying to be rock stars. And you know what? We were rock stars. On this episode, we go through the whole history of the game, from its origins in arcades in Japan, to its incredible ascent in the music industry, all the way to a somewhat surprising place you can still see remnants of guitar hero. All that on version history, on YouTube, or wherever you get podcasts. It is all. Judd, thanks for coming on on.

Happy to be here. Let me ask you a question. Is it a funny time we're in right now? Is it funny? Yeah. No, it's not funny. I don't think. I'm not laughing at most any of it. It's a weird time to create comedy because you feel like we should. to just be talking about what's happening and not like, oh, it's hard to get a date. You know, whatever your movie stories are, it feels like there's more pressing things happening.

But we still need that. That's the tricky part. You know, we still need joy and distraction and entertainment and creativity. But it's hard to focus, you know, when you see things happening that are troubling. The reason I'm asking us to party this weekend, and it was a fun party. It was for an anniversary, friends of buying 20th wedding anniversary. And they started with, it feels like we shouldn't be having a party or fun right now. You know what I mean?

Or nothing is funny. And so it's really hard to deal with that impulse of kind of sillier things or things that were part of comedy before, that you don't have to immediately deal with only tearing down the White House or whatever manner of horror is happening at any given day. Well, I think there's always been terrible things happening all through history. And now a lot of them are revealed and illuminated, and a lot of this type of thing has always been happening.

And so it makes us all feel like, how are we supposed to behave? What are we supposed to do? And part of what we do is live our lives and be happy and be kind to our friends and our families and ourselves and look for opportunities to get involved and try to move things in a direction that aligns with our values.

So that's what we all have to do. We have no choice. It's a long day. There's 24 hours in a day. So, you know, we can't just be troubled every second of it. No, and definitely. The Middle Ages sucked. So let's dive right into it.

In your book, Comedy Nerd, you say that almost all stories are about obstacles to love. Now, most comedy fans probably wouldn't come up with obstacles to love if they had to describe Judd-Apital movies. But some of the movies are directed, like the 40-year-old version, Knocked Up, This Is 40, Train Rock. The through line is obvious. Talk about that a little bit. And how is your understanding of what love means changed over the years making these movies? Well, I never thought about any of this when I started.

I was just trying to write jokes. And so, you know, the beginning of any comedy person's career is just how do you make that crowd laugh? You know, I was doing stand-up. And I didn't really think very deeply. I didn't think emotionally. I was just trying to survive up there and not get booed off the stage. And then, you know, when I worked for Gary Shanling, we were doing the Larry Sanders show, which was a satire of talk shows.

Great show. And he said, this is just show about people who love each other, but work and ego get in the way. And I had never heard anyone talk about stories in that way. You know, the idea that your career and how you feel about yourself is so important that you'll do all these terrible things to support your brokenness

and your need for approval, and that that was the comedy of the show. But underneath, you knew they loved each other, and they were just all kind of blocked by this. And slowly I realized that that's true of almost every situation, right? We have conflicting impulses to either help people or try to do something selfish for ourselves. That's why this period is very troubling for people,

because it's really driven by a lot of people on all sides on all sides with endless need and narcissism and gluttony. And not a lot of it feels like they're really looking out for other people. Right, absolutely. But talk a little more about this obstacle to love. That's sort of in the broad sense, which it's not just work. It's all kinds of obstacles to love, correct? Yeah, I mean, an obstacle to love can just be like your fear of being loved,

your fear of making a mistake, your fear of having your career not work. I mean, it's endless. It's very hard to stay open and connected and to be there for somebody else. So, you know, in any of the movies, a lot of them are about like two people trying to decide if it's going to work. So, you know, knocked up is about, you know, a man and a woman and they accidentally get pregnant. And could we be a couple? Like, could we raise this baby together? I guess we should find out and hang out a little bit before we go our separate ways as they assess each other.

Like, is this dangerous or could it be positive? Right. So let's talk a little bit about the book itself in your start in comedy, because this is sort of your journey, essentially. And you write in the book, even from an early age, you had an obsession with comedy.

You would collect autographs and memorabilia. You would go to the library to look of articles about comedians on microfiche and kids. Microfiche was so cool. Both of us are of the age that we use. Kids love microfiche. I mean, what is the internet except a giant microfeesh system?

It is, but it didn't have that sound. of getting it wrong and mangling it. I just explained, I was teaching a course at University of Mission. I was explaining card catalogs to the kids. Like, what? I was like, oh, it was hard to even explain. Anyway, you wrote a 30-page research paper

on the Marks Brothers, and this is when you were in sixth grade. Your parents went through a messy divorce when you were young and you write that they didn't ask you how you were doing. So you looked at comedy, you explained the world in the way that it was. But it was also a way to code,

Talk a little bit about this earlier history that you were just enmeshed in it, eating and breathing it. It gave you comfort, right? I mean, just like, you know, some people, you know, when they're young and they're feeling disaffected, they might get into a band, you know, or a songwriter, and become obsessed with it.

For me, you know, growing up, you know, starting in the mid-70s, it was the beginning of Saturday Night Live and Monty Python and SETV and Steve Martin and Richard Pryor and Carlin And so I think I always looked for the answers of what was going on in the world through comedic voices. You know, listening to George Carlin, he was breaking everything down. And also making you question the system, questioning how society works.

And I think as a little kid, I was just fascinated to hear, you know, this person explain something to me, which I knew absolutely nothing about. And then that grew into like, who was this Lenny Bruce guy in reading that book, ladies and gentlemen, Lenny Bruce, which talked about that era, and then I just couldn't get enough of it. I mean, and so maybe as a result of, you know, going through a rough divorce as a kid, I just, I needed something to be my own, and it also was like safety. You know, oh, maybe I can get a job doing this. Like, there's a way to take care of myself in the world. And also, no one was into it.

So there weren't other people who loved comedy like I did. So I think in my head, I thought, I think I can get a job doing this because there's no competition. At least in my head. Yeah, no one cares about this at all. Were you a funny kid? I mean, you wrote a 30-page research reward on Marks Brothers. I mean, that's kind of a choice. That is a nerdy thing.

And I look back on that, and it's really, you know, strange to me. Having raised two children, you know, if my kids in their room writing a 30-page biography of the Marx Brothers that no one requested. But I just wanted to know because, you know, I love the anarchy of the Marx Brothers, and they were so funny. And I knew I didn't quite understand what all the jokes meant. but that it felt like, oh, this is the best stuff. I didn't know it was the greatest writers in the world

writing these silly movies. And so the book that I made, it is a little bit of a tribute to the Marks Brothers scrapbook. Because when I was a kid, that was the book that had all the articles and the photos and the memorabilia. And I thought, what if I took all the memorabilia and the femur and the notes from the studio

and all these weird things and created a book that would be like an autobiography, but with these visuals. Yeah. And so I spent a... like two years putting that together, which in a way is the Marx Brothers' biography. I just, I finally did it on myself. Yeah, you remember the S&L book?

Yes, the S&L book. I love that book. Yeah, because you thought, how did they make this show? Who are these people? Then they put out a book. And it was the scripts with coffee on it, coffee stains. I read that over and over again. And they would have all the notes from, like, you got a call from, you know,

Gerald Ford administration and little jokes. And I wanted to know those people. So I think also in my head, I thought, oh, there's like a group of people somewhere that are really funny and cool. And I couldn't get enough of just trying to crack the code of like, how does this actually work? Uh-huh. So as writer, director, and producer, you've created some of the most successful comedies, obviously, so well-known. And you've collaborated with some of the most talented comedic actors and writers in the country. The first show, a lot of people associate you with, obviously, the one that kind of launched your career was freaks and geeks.

NBC canceled it partway through the first season. But it's found a huge following since. There's a lot of shows like that. But you said in 2014, everything I've done in a way is a revenge for the people who canceled freaks and geeks. What is it about the show that's given such a staying power after 25 years? And what held it back at the time? I mean, I think that Paul Feig, who created the show, had a very clear vision inspired by growing up in Michigan about the kids who we didn't see on TV, which was,

nerds and potheads. And I remember he gave me the script. And he didn't tell me anything about it. One day he just, like, handed it to me. And I saw the cover and just had freaks and geeks. And I was just so in the second that I saw the title. And it's so brutally truthful that I do think it just like gets in your craw and doesn't come out. Because a lot of it was about failure and how we lean on our families and our friends

to survive things. And obviously, it was a magical cast, and the directors and writers did remarkable work. But I think some of those stories are so real. There was an episode that our friend Jeff Judah wrote about his childhood with his partner, Gabe Sachs, about a kid who was watching, based on a true story, was watching Donny You,

and it was all about how to know if your husband's cheating, and the kid realized that the dad was cheating. And so he found a garage clicker in the car that wasn't theirs. And so he would ride around on his bike, clicking it at houses, seeing if he could figure out who his dad was cheating with. And that came from a very personal place. And we made that episode. And as a result, it's really powerful.

And a lot of the episodes were built that way. Even the funny ones like John Daly in the Parisian night suit that he thinks is going to look cool walking down the hall. But it's the most embarrassing outfit ever. That's something that happened to Paul Fieg. And so it really was about a different type of feeling. It was almost independent film on television. It was pre-streaming.

So it was a vibe that you didn't get. And so it didn't last very long, but it touched people. Right, absolutely. Cowanex was my issue many years ago. But there's a contrast. It was airing around the time of Dawson's Creek in the wake of 902 and O, right before the O.C. And it was sort of a counterweight to those kind of shows about high school. Yeah, it was meant to.

to say like it usually doesn't work out like that. And that's okay. You know, at one point in the studio kept asking us to give them more wins. They need more wins. And we said this show is about losing. What did you say? When you got that note, what did you say?

Well, this kind of tells you like how I would handle those notes because I was very young and I didn't know how to have these debates without getting aggressive or just managing it in the wrong way. So we wrote an episode where Martin Starr's character, Bill, is playing baseball, and he's always picked last. So it's about being pick last, and the daily humiliation of that. Yes, the Janus Ian of all, but go ahead.

And so the ball flies to him in right field, and no ball ever comes to him in right field, and he catches it. And everyone goes crazy. But he doesn't know that there's only one out so far, and the person on third, you know, tags up and runs home. home and scores because he's celebrating and he actually doesn't understand the rules of the game. So that was not the win. And we love the fact that we had tricked the studio into having the fake win. But when we were canceled, it was funny, we get canceled. And then years later, you know, they do a documentary about the show.

And they interviewed the guy who canceled us. And he was happy that he canceled us. He stood by it. He didn't go, you know, look it back. I shouldn't have done that. He literally was like, yeah, that was. a good decision. He said, you know, I was watching this show where the nerdy kid breaks up with the cheerleader, and I said, yeah, that's enough of that. But to us, that was the ultimate

triumph, was that there was an episode where Sam Weir, he is dating the cheerleader Cindy Sanders, and he takes her to see the Steve Martin movie The Jerk, and she thinks it's not funny. And so he breaks up with her because he realizes that she's not actually right for him, which is the appropriate good thing to do. But, you know, to a network wanting those wins, they thought that's the craziest thing anyone's ever done on TV. Yeah. Should you have given your characters even little wins, more wins? Do you, was that note ever good? Well, I think the win really was their great friendships with each other. Just how much they cared about each other. And a big win also was that Sam and Lindsay loved their parents. It wasn't a show about, you know, rebelling against

your parents. It was just the normal things that happened as you as you grow up. Right, the kindnesses. And a lot of laughter, a lot of like nerds laughing and, you know, really like enjoying each other's company and feeling like, you know, we're the oppressed. And also what made us laugh is that the nerds always knew that they were cooler than the jocks. They just, like, it just wasn't their time. Right, right, right, exactly.

It's funny because I bet that guy who canceled you probably didn't want to relive his experiences from high school and therefore canceled you. Every episode, we get a question from an outside expert, here is yours. Well, hello, Judd. It is I, Jane Lynch, your old panel. Question for you. After freaks and geeks and undeclared, both of them, which are now called classics and were critical successes, but they were canceled after one season each. How did you navigate that emotionally? And what did it do to your self-confidence and your view of yourself? in this business, because you went on to take a really big swing right after that and direct your first feature film, The 40-year-old Virgin. So that's my question, sending you lots of love. Jane is great.

Jane was in the 40-year-old version. Oh, Jane's the best. The best. Yeah, so we did it, you know, Talladega Nights with her and walk hard. She's so, so funny. So how did I handle that? Well, it really was painful. You know, when we were doing freaks and geeks,

I always had a sense that this is special, like, this is our group. And I've made it, right? Because there's so much rejection. Yeah. So, you know, so on one level, it's like this is the great group. I love all these people. And we haven't finished telling this story. So that's such a terrible feeling when someone could just walk in the room and go,

okay, stop doing this thing that's working and never talk to each other ever again. And it just felt so wrong to me. Also, as a child of divorce, I projected all those abandonment issues onto that relationship with the network and the studios. And I thought, wait, magic's happening here. This is like going into a recording studio and just unplugging Led Zeppelin in the middle of recording a great song. And then we did a show called Undeclared About College with a lot of the same people. And the same exact thing happened. We were canceled after 17 episodes.

And I mean, I got so stressed. My back went out. I had to have, like, surgery on my back just from the stress. And I was probably not at my best in my communication skills. So what I did was suffer. I mainly just suffered. And you know how they talk about Michael Jordan that he needed to be mad to be great?

And so he would find someone on the court to be really pissed at and then he would play better. and it was very manufactured a lot of the time. I think on some level that's what I did. I just thought the best revenge for this is to prove that each of these people here deserves a really big opportunity and career. And I love them and believed in them

and wanted to stay connected. And then they did it. Then you know, all those people went on to amazing careers as writers and directors and actors and actresses. but it was almost like a manic state. Like, it's only something you would do when you're, like, young and just full of it to, you know, make that attempt and to have so much energy to do it. But also, they were also talented.

Right, but what did you do, as she asked, how did you navigate it emotionally? And where did the self-confidence come to move along? I knew the work was good. I just, as a fan of comedy, and I think I do come to it as a fan first. I knew how good freaks and geeks was, and I knew how good everyone was. I had no doubt that a lot of these people were better actors and comedy stars than were around for the most part. So I have a lot of confidence in that. And I also think I had a little bit of the rebellion of someone who loves a band that no one listens to in massive numbers.

I would love all those alternative bands that didn't sell a crazy amount of. records. You know, I was an Elvis Costello fan, and he had a big crowd, but he wasn't Whitney Houston at that time. And I just thought, it's okay to be Elvis Costello. It's okay to be the replacements. And there was almost a badge of honor in making something great that isn't big the way like John Cassavetti's movies didn't make $100 million. That's how I rationalized my multiple failures. So like Jane mentioned, you then went on to make huge hits and take this swing. You wrote, direct and produced movies like 40-O-O-Virgin and knocked up and you produced girls. Anchorman, Anchorman, too, which is my son's favorite movie, train wreck, bridesmaids,

stepbrothers, all these kind of fit in a mold that became your calling card, raunchy, mainly R-rated comedies about extended adolescence and growing up. And if you take a step back, what do you think you got right about them in that mid-to-late 2000s era, and especially about men in particular, because they often centered on men developing themselves, good men, developing themselves, essentially. Yeah, I mean, I think a lot of it as we grew up on these Ivan Reitman, John Landis, Harold Ramos movies,

and that usually was the core of why they worked. It was a reluctant hero story. So we definitely had an awareness that men are really immature and need a little bit of a beating to get it, to grow up. And so some of those movies are about, you know, the challenges

of real life intruding. Like, I just want to be a pot-head and have a porn website, but I just got someone pregnant, and now I have to become a man. Yeah. And read these books. And read the baby books.

And I think that, as I look at it now, I remember I used to talk to Norman Lear about his history and his childhood, and his dad went to prison when he was a kid for this stock fraud. And he was still talking about it at 100. like his emotional problems that resulted from dealing with his dad. So I realized, yeah, these movies are coming of age movies in a way, but also we're always coming of age.

I don't think it ever ends. So if I do this as 40, it's just another phase of how hard it is to learn the lessons of life and how much has to happen to you for you to begin to get it at all. And the through line for you there was... I mean, the through line for me is, you know, life is suffering and we soldier on. You know, that it's like there's a lot of challenges, and it works best when we're kind to each other, and we figure out how to be there for each other, and you take a lot of hits. The hits are funny.

That's what we like in these movies. But for me, you know, when I'm working with a writer on their script, I always say to them, Okay, what's the problem and what would have to happen to this character for them to learn the lesson? Like, what bottom would they have to hit to wake up? We'll be back in a minute. Support for On with Carous Swisher comes from LinkedIn. As a small business owner, you don't have the luxury of clocking out early. Your business is on your mind 24-6.

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I mean, you had a series of movies and sort of the system worked really well for you. One of the, obviously, the biggest changes has been the move to streaming away from big theater releases. It's been especially true in comedy. and since the pandemic comedies don't pull in the same kind of box office revenue they used to. And you told Variety a few years ago, quote, we have a system now that does not reward success for a lot of these projects. If you make something in a billion people watch, you don't make more money than if it was a disaster, that's not good for creativity.

Talk a little bit about the shifts. You know, here you are sort of running from movie to movie to movie and in a system that then shifted dramatically for you. Yeah. Well, I mean, I think the first change of the system was, that the DVD disappeared. And a lot of the economics of comedy were very simple, which is you could make a movie for $20 million. And if it made $40 million in the box office,

it would usually make $40 million on DVD. So suddenly that investment would pay off. Now we don't have the DVD money, and it wasn't really replaced significantly by streaming and digital downloads. That only covered a part of it. covered a part of it when that changed. So as a result, the bet is different. And with comedy, there's usually the discussion about whether or not it will work overseas in non-English-speaking

country. So an action movie might work great in Bulgaria, but we, you know, often, you know, because of language issues or cultural issues, it's not as consistent that comedies will work overseas. I remember being in Germany watching Wayne's World and you know, monkeys fly out of my butt. It's translated into German. I was sitting and I was laughing hysterically when he said that and the Germans were like,

bus, monkeys, what, what? In German. And I was like, oh, I can't explain it to you. They're not actually flying out of it. And then it was lost. Then it was done. I remember they weren't going to release bridesmaids overseas because they said they don't have bridesmaids in most of these countries.

And then they did, and it made, you know, a hundred and something million dollars overseas. So there's tons of exceptions to this where, you know, there are giant breakthrough movies. But that changed the bet because then it became easier to make a $5 million horror movie, which would work in Bulgaria, than a comedy. And then when you start making less comedies, then people lose the habit of going. And at the same time, there's a lot of comedy on streaming that you don't have to, to leave the house for. And on your phone, you're basically watching gags all day long. Right. The snackable moments, right? Yeah.

Only the best jokes, right? And they're great. They're great. I can watch a montage of like cats scaring their owners for hours. And so it's not like on the weekend, you're like, oh, God, I need some comedy. I mean, literally, you were probably in Starbucks looking at TikTok videos for 15 minutes. Right, right. Please, by all means, search cats and and tinfoil. Yes. Oh, yeah, exactly. Pickles.

I mean, you know, so then you go, what's the need? On the weekend, you might go, oh, I want to see a horror movie because I haven't seen anyone get killed this week. I want a thriller and, you know, it changes habits. But also those habits change back. If somebody made the hangover or something as good as a hangover, I still think it would make a billion dollars. I don't feel like there's been gigantic great comedies that have failed because people don't

want to go to the theater. I think we're not making them. And as a result, young people go, wait, there's no money in this. And then they write for YouTube or TikTok or get a job as a staff writer on it. Yeah, I think it changes the career aspirations of people. And then you get a little bit of a doom loop going. But, you know, I remember when that movie came out, it was like a maybe Roman Polanski movie called Pirates. And it was just such a gigantic bomb.

It was with Alter Mathout. And for decades, people said, the worst thing you ever could do is a pirate movie. And then, you know, decades later, Pirates of the Caribbean was, like, the biggest thing forever. And I think that's how show business works. You know, you need something to be a hit, and then they chase it for a while. And it kind of cycles. Right, right. They always do that.

That's always a thing. But streaming in particular, and you were just noting a lot of looking at TikTok and the pulling apart and the snackable moments. Is comedy just by nature very vulnerable in that regard? when it becomes, everything becomes little bits. I'm thinking of late-night television. It does really well online, but the ratings don't work. Well, I think, you know, another issue is that in some ways, horror movies are comedies.

They usually have an enormous amount of humor. Weapons, you know, in the theater, it gets gigantic laughs. And movies like Barbie, they are just comedies. The Marvel movies are comedies. They're also action movies, but they definitely are going for the comedy. So it's not like comedy has disappeared. It's just kind of morphed in with other genres where they all use comedy.

So I do think people want it. It's just mutated. And then you do need breakthroughs. You know, you need people to do something very original to show how a comedy should work in 2025. It doesn't have to feel like, you know, the reluctant astronaut with Don Nott. You know, you do have to take risks. And you also need a new general.

of comedy people, because if you don't make a lot of comedy movies, then the next generation never gets their break. And then suddenly people go, we need a comedy star. And everyone goes, wait, but we haven't broken one in 10 years because we haven't given anyone an opportunity to show that they're a comedy star. Or they break somewhere else. I did a great interview with Josh Johnson, who got his star. Yeah. You know, a lot of them are getting their starts elsewhere, right? And in different genres that they seem to be very native in some fashion. Josh is doing something that's really spectacular, which is... Oh, it has to be excellent to start.

You know, he's so funny, but he's putting up basically full-length comedy specials every few weeks that feel like he's been working on the set for years, but they're about things that are happening currently in politics, and it's really remarkable. So, yeah, some people are inventing new ways to be funny and do it. And, you know, the one thing that is bad about podcasting is it's allowing people not to be funny in a way that someone like Conan O'Brien or Letterman was funny in terms of being inventive and sketches and grinding for all of these new ideas because two people talking is fun. But we're not getting a lot of people going, I'm going to use this format to come up with something completely new that requires writing, that requires shooting things. And so it's easier. It's way easier, and we need some lunatics to do it the harder way.

Speaking of that, you're talking about the next generation of stars. In a forward your book, Lena Dunham wrote about the creative freedom you gave her to do risky things, which was making girls, which you executive produced and how rare that was. Talk about who's helping people take what you're just talking about, this kind of risk, because your longtime collaborator, Seth Rogen, just won a whole bunch of Emmys for a show, the studio at its core. It's about how the industry has come so averse to taking all kinds of risks needed to make art. And it's funny, but it's also, there's something deeply sad about the show, too.

Like, oh, look at this. Look at these people sort of pretzling themselves to be not excellent, essentially. Talk about that. Who's helping people take those kind of risks and what you did with Lena? Well, certainly Seth is, you know, with his show and the people and the writers that he's working with and the people who perform on it. And he is exploring what this challenge is, which is in a world where everything, It needs to be gigantic.

There's all this pressure. A lot of the movies we like best that were the biggest movies all time were little movies, and they were little risks. And as a result, you know, you would get whatever, the last detail or a midnight cowboy. And now people want everything to be able to make an insane amount of money. And that's why that show is so funny because it is about people who want to make good movies, and they're trying to figure out how to work in a system that has, so many demands that are very difficult to figure out.

You know, in the old days, it always felt simpler to me. I always thought it was like a studio would have, say they had nine movies. Three they were going for like the mega movie. Three were like these kind of dramas, mid-level costs. And three were like horror and comedy. And it kind of made sense as the ratio of things. Like, okay, they have a couple of slots for high-end, a couple of slots for popcorn. in a couple of slots for the comedies and the horror things.

And now it's like, as soon as you know a movie could make a billion dollars, then in a lot of ways that's like, for the majority of it, it's the hope that things could just, you know, be a big hit, become a toy, work in every country in the world, have sequels. And so a lot of the intellectual energy, the bandwidth, goes to that, which makes sense. Right. But you need more bandwidth on, let's just make new things. Let's take chances.

Let's figure out the next stage of this. And so hopefully that will change. And things do sneak through all the time. There are a lot of amazing movies came out this year, you know. They did. You know, but they, of course, they were more successful as they felt original. One of the things I'm just recalling is interviewed with Ted Serendos. And he said there will be no middle movies anymore.

He said there'll be the small movies and the big movies and everything in the middle will be hollowed out, which is what you're talking about. And he was talking about comedies. he was talking about sort of the middle of the range because of the way the system was setting itself up. But how do you then mentor people or give people freedom? You don't really have freedom if you're in a formula, correct? I mean, for me, you know, in terms of mentorship, I, you know, I was mentored by people like

Gary and David Milch and Eric Roth and people like that. And, you know, so I look for opportunities to help people with their projects. Sometimes I'm part of the project. Sometimes it's just as a friend. And I think that that's essential to getting better is to find people that have some wisdom that you don't have. I mean, I wouldn't have been able to do anything without it. And even now, sometimes I write a script

and I just wish Gary Shandling was still alive because just the fact that he liked something I was working on, gave me the confidence to not give up on it. Like, oh, Gary thinks this is worth pursuing. And so I would keep grinding because of it. We'll be back in a minute. Scott, we're hitting the road, bringing Pivot Live to the People. Seven Cities, Toronto, Boston, New York, D.C., Chicago, San Francisco, and L.A., of course.

You went to Oasis, you went to Beyoncé, you saw the remake of Wizard of Oz in the sphere. All those suck compared to the Pivot Tour. This is the biggest tour. Same people that are organizing our tour that organize Taylor Swift's tour. They are much more excited about our tour. All right. That's enough, Grandpa. It's going to be so good.

And we're bringing our brand of whatever we do to the people. And we're excited to meet our fans. We love our fans. For tickets, head to PivotTor.com. See you there. Hollywood is also grappling with the arrival of AI. It's something I write and talk about a lot. And it was a massive issue in the 2023 writer strike.

You told Variety studios and streamers weren't treating writers as essential and that there was a, quote, existential problem. Screenwriters did win a bunch of protections against AI in the fight, but AI isn't going anywhere. And obviously it's even going further with tech billionaires spending billions on energy and compute. And Sora, too, just came out. and it will keep being an issue of future contract negotiations.

Talk a little bit at how you're looking at as a creator, because I had a lot of discussions with Hollywood people during these things, and I said, you don't understand who your real enemy is. It's not Disney. It's Google or Open AI or whoever it happens to be. How do you think about it right now? I mean, I look at it like any other factory, right? So if Tesla is opening up a factory, then they're just trying to figure out

How few human beings can I use to have it function? And there's all sorts of entities that are thinking that right now about everything to do with film and television production. You know, can I do this without people? Can it get written without people? Can they get directed without people? Do we need the development people? I mean, to every end of it, I mean, there were great black mirrors about this

where they were creating content specifically for people, in real time. And so that's scary, and the only thing that makes it less scary is that it's soulless. Right, it's not funny. It's not good. I mean, there are definitely ways that technology can help people. If you can go on a computer and make it look like deep space and it doesn't cost $3 million, it costs $40,000, well, clearly, in some ways that will help people.

It will decimate the people that made space, but it seems like we're not going to be able to stop that when it gets cheaper. But the writing and the directing will always wind up generic because it's scraped and it's just copying other things. And I think even when Zora was released, we instantly thought, wow, I'm bored of this in like a day and a half. I can't watch any more of dead celebrities doing weird things. So can AI be funny? I mean, it would be wrong to say it can't be funny at all. But there's no point of view so it doesn't ever fully work.

You know how, like, when you watch these things, and it feels like this bizarre dreamlike space, and it feels like hell, a lot of the AI stuff. Yeah. You know, at some point, if you know how to use it, I assume it'll become like a Pixar movie where people are, it's basically animation. Yeah, the back end is where the real winds are right now. Yeah, and so, you know, there'll be some fusion, and then there will be people who are like, you know what, I like it when the real people do it. and it'll become a mix at some point. But, you know, no one's going to make the movie that Paul Thomas Anderson just made on Sora.

No one's going to do what Nicole Hollisenter does or Quentin Tarantino. So it's going to be a lot. I can just slop and garbage, and it's scarier for the next generation that doesn't know what, you know, good movies that are authentic, made from people's hearts, what that is.

Like, if you were raised on the slop, At some point, do people not care about what's better? They're used to slop. Yeah. I think probably they will, but that's what's scary if you don't know the difference, and you just go, no, this seems fine. So on top of all these changes, there's also been a broader cultural shift towards more censorship.

You have folks like Dave Chappelle, Bill Maher and Ricky Vervais, who said cancel culture is hurting comedy and breeds censorship. On the other hand, there's people like Sarah Silverman and Seth Rogen who say these fears are over-blown, comedy changes stop whining. And knocked up the lead characters working on a site that tells people where all the nude scenes are in popular movies. And you write that, quote, looking back at it is 100 types of wrong, both morally and technologically, but it still makes me laugh. Talk about that and how you're looking at the risks as people grapple with what's offensive and what's not. I mean, I think that when we would do jokes like the one you're talking about in the movie, the point was, you know, this is wrong and ridiculous.

This is something you should grow out of. So we would always show bad behavior as a path to showing how you would realize that you shouldn't have the porn site that just tells you where the nude scenes are. Although the technology that is funny, like, that movie is so old now that even the technology of it tells you like where it is, where now it would just show you. But I do think that in terms of cancel culture, there are not many people whose careers were affected negatively by cancel culture. In fact, you would say that most people got really famous as a result of being seen as edgy and got bigger crowds. There were some people that had things happen to them. But it's pretty small compared to like how much money it actually generated to be seen as someone, you know, saying things that you're not supposed to say. So that always felt false to me.

And I'm in comedy clubs. People are, you know, they're basically saying most anything they want to say. And I think that some guardrails are good. It forces you to be creative. And I always quote Colin Quinn, who said, you know, you can say anything you want as long as you're willing to stand behind it. Right. So if you want to be thoughtless and dumb, someone's going to criticize you. And comics are, I think, pretty thin-skinned about taking criticism.

Very much so. You know, they'll criticize everyone and pretty brutally, and they'll name names. But if you come at them at all, they literally throw a fit and lose their minds in a kind of almost comical way. Yeah, yeah. You're 100% right about that. And obviously our whole country is based on that you should be allowed to say anything you want to say as long as it doesn't create some sort of dangerous situation. We need South Park.

You know, we need, you know, voices that are, you know, fighting power. And, you know, some of those voices are going to be terrible and have bad opinions. You know, that's part of it, too. If you want to have all the comedy out there, you're going to have the bad stuff also. Well, the political climate is tough, though. How do you think about sort of right-wing meme comedy, maga humor? I mean, you joke in 2016, the funnier of presidential candidate always wins after Trump won. You even told the New York Times that, well, Trump has a demented sense of humor.

He was way funnier than Hillary Clinton. Although I would argue the private Hillary Clinton is very funny. And now she's funny again. She's funny publicly now. I just had Bernie Sanders on. We were talking about this. one of the things Trump is really good at as he normalizes racism by delivering it

as entertainment. His humor can make all the horrific things his administration seem less scary and dangerous. The pooping slot video that he did, the AI video, was a version of that. Do you think that's effective still? Is it funny or what is it? And that's what their excuses all the time. It's oh, it's just funny.

I mean, I think the reason why people like Hillary Clinton, you know, weren't funny is that they are afraid to say certain things. They're afraid to take the comedic risk. that it'll be taken the wrong way. So as a result, they seem like they're covering, like they're controlling their expression.

And Trump is just pure expression. And so you look even more full of it when people can see your eyes thinking, I don't want to get in trouble, I don't want to get in trouble, I don't want to get in trouble. And then you get a real muted version of yourself. Yeah. And people feel like there's something to not be trusted

in that self-censorship. Now, some people would call that trying to be thoughtful or dignity. But I think that's what they're sensing, where Trump's like, nah, I'm going on 10, 24 hours a day. And then it all loses its power. And so then he can say the worst things, or put up the dumbest memes, and everyone's like, well, that doesn't mean anything.

But it means something if your health care disappears. It means something if you're at work and you're from Mexico and you're a legal immigrant and they put you in a camp. So is changing it to entertainment? effective? Is that worrisome to you? My feeling is that it's always more complicated than we know. I don't think this memeification is based on someone's instinct. I think there's think tanks and psychological studies and everything that's being done is

being done because it has been proven to work as propaganda. And we take it like, oh, he's being crazy. And I can't believe he said that or I can't believe he posed to that. It's totally planned. But I think there's literally like psychiatrists figuring out how do you make people lose hope. How do you make people think that they can't win a fight? Right. And then tell them it's just a joke.

Yeah. Yeah. I mean, it all started with the Cambridge Analytica. Like when we realize, oh, they know what we think before we even think it based on our behaviors online. And yeah, they're flooding the zone. and everyone's brain is melting. And then even though there's millions of people on the street, Trump poops on them, and it's supposed to make everyone feel sad, like, well, no one listened.

So that's why it's important for everybody to just continue to fight, to speak up, to find ways to support candidates and organizations you believe in, in spite of the fact that people want to humiliate you and make you feel hopeless. So I want to finish up by talking about what you're working on and what's next for you personally. You've made multiple documentaries in the past few years to take a deeper look at some of the great comedians in the last few generations.

You've made films about your longtime mentor, Gary Shanling, George Carlin, friendships between Bob Newhart and Don Rickles. You've said you find it more enjoyable and less stressful than making comedy. I love to know what you think of it, and you've done, you have multiple projects in the work. You said you're working on a film about the late Norm MacDonald. You're putting finishing touches on a documentary about Mel Brooks.

You're working on a comedy about country, Western music. I happen to love country western music. Talk about this shift to documentary work. Well, you know, documentaries are just really fun, and I think it is also an extension of, you know, me writing a paper about the Marx Brothers and no one requested. I love the history of it, and I think it's really fun to look at someone's life and their work

and try to create a documentary that really captures who they are, what their personal journey was, and how it related to the art that they put into the world. So I just finished up with my friend Michael Bonfiglio, a documentary about Mel Brooks called The 99-year-old man that'll be on HBO in January. And it was a great opportunity to talk to Mel Brooks in a deep way about what he's seen over the last century.

I mean, he lived through the Depression, and he fought in World War II, and he fought the Nazis, and then he mocked the Nazis, and he fought racism and, you know, change comedy forever. but he also is a brilliant man. And just to ask him, how did it feel? You know, what did you go through in your journey? And I find that to be just as fulfilling as scripted fare

and less stressful because whenever you make a movie, you never know if the jokes will work. So the whole time you make it, you're like, man, I hope I'm not crazy and people will laugh at this. But when you make a documentary, you're not in constant terror of humiliation. And you get to talk to Mel Brooks, who's such a legend. Yeah, yeah. So I really love the form.

And as someone who loves comedy, I love like going through every interview Mel Brooks ever did and looking for these hilarious things that no one has seen in 30, 40 years. Well, that one where he's singing with which I call it, Anne Bancroft. Yes, yeah. That is a wonderful thing. Yeah, and to be or not to be. Yeah.

So toward the end of the book, you write that your career, quote, was a desperate cry for help from a person that never feels whole whose pain and trauma never eases and who needs to numb himself with busyness and accomplishment. Ow, you seem to have a lovely family, by the way, but you also write underneath all the healthy and unhealthy reasons

for working and expressing myself as a love for comedy, the people who make it. What does that mean about you and the next iteration for your characters? What are the characters, and this is 50 look like, I guess? Yeah. I mean, I always think about, you know, there's a healthy reason to work. There's a healthy reason to want to make movies and TV, to connect with people, to reveal yourself, to explore, or how you think about life.

And then there's the unhealthy part that's just needy and broken and wanting approval. And unfortunately, the broken part is the engine a lot of the time. And I think as you get older and hopefully saner, that part of the engine starts going away. and you start making the primary motivation to express yourself and to connect with people and to find something to say. So hopefully there's always new subjects to write about and deeper places to dig to find comedy.

I mean, life is so weird. It couldn't be weirder now. And everybody needs someone to help process all we're going through. So it's just a search for, a story that can illuminate some of this. Is it still out of pain for you as we started, or has it shifted into something else? I mean, again, you have a wonderful family, it seems.

It's definitely not what it was when I was young. And I also think when you're young, you're just nuts. I think you're a genetically crazy... It's something probably Scott Galloway talks about all the time. You just have this need to prove yourself and to figure out your place in the world and to survive. And that goes away. But he's an open wound, let's be clear.

Yeah, exactly. So, what do you find funny now, then? What is, you know, if you're looking about your long history as a comedy nerd, what are you nerd out on right now? What am I nerding out on? There's a great show on Hulu called Such Brave Girls, which is just this gem comedy I recommend people watch. I do love what Josh Johnson is doing.

I love what South Park did this year. They really don't want to talk politics that directly, And the fact that they made the choice to do it because they felt it was necessary was incredible. It's really funny. And it's about how the world is changing and everything that's terrifying about it. I thought that, you know, to see the two of them, you know, do, you know, work that's as great as their greatest work is remarkable. I thought that was really inspiring, just how strong that season was. So there's always things to nerd out on.

Are you going to make a Marks Brothers movie? You know, I don't think I will. I think that's sacred ground. It's sacred ground. That would be great. They were geniuses. They were fucking geniuses. Anyway, thank you so much, Judd.

I really enjoyed the book. It's a really wonderful book. And it did remind me of that S&L book that we talked about before. Yeah, thank you so much. Today's show is produced by Christian Castor Roussel, Carrie Yocum, Michelle Eloy, Megan Bernie, and Kaelin Lynch. Nishat Kirwa is Vox Media's executive producer of podcast. Special thanks to Onika Robbins.

Our engineers are Fernando Aruta and Rick Kwan, and our theme music is by trackademics. If you're already following the show, you are Harpo Marx. But if not, monkeys are flying out of your butt. Go wherever you listen to podcast, search for On with Caro Swisher and hit follow. Thanks for listening to On With Caro Swisher from Podium Media, New York Magazine,

Network and us will be back on Thursday with more.