Fresh Air - Judd Apatow Unpacks His Comedy Memorabilia

Episode Date: October 28, 2025

Long before Judd Apatow was directing box office hits or launching the careers of comedy superstars, he was a fan. As a kid he wrote letters to his heroes, collected autographs, and obsessively documented everything. He’s now opened up his personal archive: decades of photographs, letters, scripts, and journals for a new book that reveals how his childhood inspirations led to the creation of works like '40-Year-Old Virgin,' 'Knocked Up,' and 'Trainwreck.' It’s called 'Comedy Nerd: A Lifelong Obsession in Stories and Pictures.'Also, John Powers reviews the new museum heist film 'The Mastermind,' starring Josh O’Connor. Follow Fresh Air on instagram @nprfreshair, and subscribe to our weekly newsletter for gems from the Fresh Air archive, staff recommendations, and a peek behind the scenes. Learn more about sponsor message choices: podcastchoices.com/adchoicesNPR Privacy Policy

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I'm Tanya Mosley. If you've laughed at a comedy in the past 30 years, there's a good chance my guest had something to do with it. Judd Apatow directed the 40-year-old virgin, knocked up and train wreck. He produced Superbad, Bridesmaids, and Anchorman. He executive produced the cult classic Freaks and Geeks, which launched the careers of Seth Rogan and Jason Siegel. And he's written for comedy legends like Gary Shanling and Roseanne Barr. And he's mentored a young Lena Dunham, executive producing all six seasons of girls. But here's the thing about Judd Appet He's also a collector. Since he was 10 years old, autographs from his idols sealed in plastic, letters he wrote as a teen to and from his favorite comedians, photographs from every movie and TV show, scripts covered in notes and journals, documenting every high and devastating low.

Now at 57, he's letting us get a glimpse of his collection, which he compiled in a new book called Comedy Nerd, a lifelong obsession in stories and pictures. It's really unlike any Hollywood memoir I've ever read. It's part scrapbook, part confessional, part love letter to the art form of movie making, and a glimpse into maybe the psyche of a man who's been making people laugh for more than three decades. Jud Appetal, welcome back to fresh air. You've been here four times. Happy to be here. I feel like I'm Norman Mailer. I know. Putting those numbers on the board. Yes. Okay. This memoir, it's unlike any memoir I've ever seen, as I said,

almost 600 pages. And you write in the introduction that this isn't even everything that you've collected. Yeah. What made you want to put all of this stuff in a book? I don't know. I was always a fan of these books like the Marks Brothers scrapbook, and there was a Saturday Night Live scrapbook that came out in the 70s where they would have pictures and scripts and little notes. And I just thought, oh, I think I have enough stuff to do that. My family's always yelling at me to throw out all my hoarding, like, why do we have all this stuff? Where do you keep it? There's seven storage spaces around town and in my office, and they're like, why do you

save all this stuff? So I think I needed to prove that there was a reason to be a pack rat. Wait, you have seven storage units. At one time, was it all in your house, though? Well, there was a lot in the house. We have a new house now, and none of it is in the new house. But also, it's not like normal hoarding. It's not like there's a big mound with, like, you know, catchers' mitts and kitty litter

and magazines from the 70s. It's, you know, it's all, it's a well-maintained horde. Organized. Yes, it's an organized horde. It's what organized as it can be. Did any revelations come to you going through some of that stuff? Like things that in the moment you hadn't thought about, but you're looking through these old scripts or these old bits of paper that have notes from freaks and geeks, for instance, you know?

Well, all of it, I think, is. is working something out. So if I look at my career, I think, well, I did something about having a baby. I did something about going to high school, something about going to college, something about your first job, something about getting married, you know, trying to make relationships work over the long haul, getting sick, your mortality. So you could feel like, oh, I'm just thinking through, you know, my point of view about the big things that happened to all of us. Yeah. I'm stuck on this word obsession because there's a story in the book. where you collected Billy Jean King's autograph 13 times?

Yes. I went to a tennis tournament at Hilton Head Island, and we would go every year, and I was 10 years old. And all the tennis players were hanging around. This must have been like 1978, 77, something like that. And there would be Tracy Austin, and there's Pam Schreiber, and there's Billy Jing King and Martina Navratilova, and Dr. Renee Richards. Everybody was there.

And I would just run around on a bike. they'd have a match. I would sometimes watch the match and wait for them to come out, and then I'd get their autograph, and then the next day, I would just do it again. And if it was the same people, I would just get all their autographs again. And I remember Billy Jean King saying to me, I think you have my autograph already. I know. After a certain point, did you start to have conversations with them?

They're like, this kid is, you know. A little bit, a little bit. But it was just so fun. I mean, it was just, it was like a weird hobby to go, can I get to Yvon Gulagong today? I mean, it's a weird hobby, but it also, why do you think you were doing it? I think on some level, especially like with trying to meet comedians, I was trying to figure out, is there a way to penetrate that bubble? Like, can that become real? You know, you see them on TV and people are so funny or they're great actors or actresses, but can I meet them?

And if I can meet them, then maybe it's a real enough world for me to enter at some point. When did that come to mind for you? Not necessarily that you could do it and you could enter it, but that, like, that spark of, oh, these people are interesting. I'm kind of fascinated by them. Well, my grandmother was friends with this comedian named Tody Fields, and she was, you know, in that world of Joan Rivers type of self-deprecating female comedian. And she was so funny. And my grandparents talked about her like she was the coolest person in the world. And I knew her since I was born.

And occasionally, we would go see her. And I think on some level, I saw her and thought, wow, she's a different kind of person and she's getting standing ovations and people love her. It must have planned to see at a time that I don't even remember. Like, that would be a cool thing to be able to do. Seeing the reaction to her action. Yeah. Yeah, that was a thing. And someone who could talk about what was weird about themselves and how they saw the world and be rewarded for it, to be embraced for discussing your imperfections.

Okay, you have to tell this story of you threatening Steve Martin over an autograph. Well, you know, I was a little kid, and I used to always ask my grandmother to drive by his house because we knew which house he lived in. And I couldn't believe he lived there. This is in 1980. So it's 45 years ago. And, you know, I'm 12 years old. And one day he was outside, and I asked him for his autograph. And like a normal human being would, he said, I don't sign autographs at my house.

Like, for me, if someone knocked on my door, I mean, there's a chance that I'd have a drone police officer get involved. You know, there would definitely be a different reaction than Steve Martin had, which was, I'm sorry, I don't sign it at my house. And so I wrote him a funny letter asking for an apology. It was more than a funny letter. I basically said, you know, you're the funniest man in the world, but you treat your fans like garbage. And you wouldn't live in that house if I didn't go to all your movies. and buy all your albums. And so if you don't send me an apology,

I'm going to send your address to Homes of the Stars, and you'll have tour buses passing by 24 hours a day. And then, like, six months later, in the mail, I got a book of cruel shoes, this amazing short story collection he had written. And in it, he wrote, to Judd, I'm sorry, I didn't realize I was speaking to the Judd Apatow. And I was 12 years old.

And I thought, oh, I must have made him laugh. And then now he's trying to make me laugh. And I look back on it now, like it was very, very impactful on my psyche that he sent that to me, you know, almost an invitation. And I'm sure he just is funny and probably did that to tons of people because he's a great person. But to me, it was like the person, I think is the funniest person in the world thought it was worth his time to do that. And so it probably gave me a lot of the confidence that I had to be insane to go interview. you 50 comedians from my high school radio station and work as a dishwasher and a comedy club, it only, like, set the fire more for me to try hard to figure out how to get into it.

I think of you as a 12-year-old to kind of threaten him to say, like, I'm going to give your address out to everybody. I think that was just my Long Island rat attitude. That part of it, you know, people ask about it sometimes, and I think I was just so obnoxious. I just was like a, I didn't quite know where you. humor was, and being from Long Island, there was so much insult humor. And we all gave each other such a hard time. And so in a real annoying Long Island boy way, I thought that was funny. Was it like that in your home where you guys would be with each other? Absolutely. And with my friends. I mean, it was certainly a world of insults with love. Yeah. Did you ever get to talk to

Steve Martin about that? I did. Once we were in a meeting together and someone asked me to tell the story, Then afterwards, they said, Steve, is that how you remember it? And he said, how I remember it, I knocked on Judd's door. Okay, so it started with these autographs and then it extended to letters. Like, you had a whole process. This was almost like an assembly line where you'd write letters to people. Yes. I realized at some point that if you wrote a letter to someone who was on television, a lot of them would send you a signed autograph.

I think I probably had a friend who got an autograph back in the mail. I remember one of my friends got an autograph from Bob Hope. I think it was my friend, Josh Rosenthal, showed me as Bob Hope. And I'm like, I'm going to write to Bob Hope. And then I did get an autograph from Bob Hope. And then I did, you know, I wrote a letter to Paul Lind. And I got an autograph back. So I wrote Paul Lind again.

He sent me another one. I kept writing Paul Lind to see how many times when he keeps sending me the photo. So I have three Paul Lind autographs. And I would just sit in my room at night with this. Homes of the Stars book, and on the back page it had the address of every movie studio. Wait, there was a real book. It was a book that had, so you could go see where Lucille Ball lived, or, and probably half of it was inaccurate, and it was their addresses from a decade before, but the back of it was the addresses of all the movie studios and TV networks, and so I would write Carol Burnett and, you know, the Saturday Night Live people. I got an autograph from Andy Kaufman, and he signed it on both sides. That was what was so unique. it said, you know, to Judd, thank you very much, Andy Kaufman. But on the other side, he wrote a letter that kind of said the same thing.

It just said, Dear Judd, thank you for writing that letter, you know, Andy Kaufman. So even that was in Andy Kaufman mode. I have this letter that you have a copy of. First off, the book, you have a lot of letters that you wrote to people at certain time periods. How did you get them? Well, the letter in the book that's my letter to the talk show host, Mike Douglas, must have been one that I didn't send. And I found it in some stack of papers. It says, dear Mike.

So I was very familiar with Mike Douglas. You know, who was like a day. And tell people who Mike Douglas is. He was like a daytime Johnny Carson. Yeah, yeah. So there was Mike Douglas, there was Merv Griffin and Dinah Shore, and they had shows earlier in the day. Yeah. And it was out of Philadelphia.

And, you know, it was an amazing show because everyone would go through Philadelphia. He, you know, he would have on Richard Pryor and Sly and the Family Stone. But Kiss would be on there. And then Bob Hope and that group of people. And he was kind of a, you know, kind of a creamy, conservative-looking guy. And it was really, for me, like a place I would escape to this Mike Douglas show world. And everyone was so happy in talking about their projects. And so the letter says,

Dear Mike, my name is Judd Apatow and I am 10 years old. I always watch the Mike Douglas show. It's great. I learn a lot from it. Now you have the best guests. I'm glad your show moved to Hollywood. Now you get better guests. Yours truly, Judd Apatow.

And the funny thing about that is when I found this letter on top of it was a letter to Merv Griffin. And it said almost the exact same thing. Well, I also think what you wrote there was so adult for being 10 years old. So, I mean, you've got this little assembly line where you're writing letters to folks. You are getting autographs. I mean, were you also going outside and just hanging out and playing with friends and stuff? Yeah, I was. But I wasn't good at sport.

So there was always a lot of time where friends would be on the football team or the baseball team. And I was left alone because my friends were the athletes. I was the goofy guy with the athletes. And so I would just go home and. Watch Live at Five with Sue Simmons and write letters. Like any normal kid would do. You know, you'd go home and you watch Mike Douglas and the people's court. I mean, I can remember, like, the things I would watch.

And I would also watch all in the family, Mary Talbot, Morshow, Bash, Bob Newhart, like every single day, odd couple. Yep. And those people, like Norman Lear and Larry Gelbart and James Brooks, programmed my mind of what was funny and what was moral because I spent so much time hearing those stories. What a time, too, though, because that's when syndication was, like, really making its way. And we were receiving all of those old shows.

So you got a chance to really know the greats who weren't even part of your, like, the generation before you. They were from several different generations. Yeah, you'd watch the honeymooners, but every day for years and years. And you had this very deep relationship with the characters on the show. I mean, now, you know, TV shows are six episodes or eight episodes. and then he disappeared for two years. And, you know, after five years, there's 30 episodes.

But back then, there was always a new episode, and you would watch a show for seven years or ten years. And by the end of it, you know, that's why 100 million people watched the last mash. Yep. You know, here's what fascinates me about your obsessions as a child, because it's not that you were just a fan. It was also that you were seeking something.

And maybe, like, it was almost, a telegraph to your future self. I mean, now we can see that so clearly. But were you thinking those things? Were you daydreaming about that stuff when you were writing these letters and thinking about these people? I thought that life wasn't so easy now, but I think as a result of this interest, it will get easier later. So I had this sense of one day you're going to get to be a part of this. And right now, no one cares about it at all. You don't have any friends to talk about it with in the way you would like to. But somewhere there's a world where people care about Bob Hope's monologue or whatever, like, show business thing it was. And then I did move to

California to go to USC cinema school in 1985. And I met all those people. It turned out I was right, all the comedians, all the filmmakers, that there was a place where all the judds of their high school congregated. Met up. Right. You guys all met up. It was a nerd. Convention. Right. It was the nerd convention, the comedy nerd convention. But you mentioned, like, things weren't so great when you were a kid. Yeah. There's also a pretty, you describe it as a nasty divorce. Yeah. With your parents. Yeah. Well, it's a, you know, very 1970s, early 80s thing. I mean, now everybody consciously uncouples. And people understand the effect it has on your kids when you're in conflict. But back then, no one knew. And it was, it was like a bare knuckle brawl. And so things didn't get resolved. And no one knew to check in on their kids to see how it was affecting them. You know, no one said to me, how are you feeling? And so as a result, I internalized everything.

And I just thought, oh, I need to take care of myself. And, you know, my parents, you know, are great. My dad, like once my dad, you know, I said to him, like a few years ago, like you never talked to me about any of it. and he said, yeah, I did. And I said, no, you didn't. You never, like, said, how are you doing? And, in fact, the only thing that really helped me was, like, there was a book in the house called Growing Up Divorced,

and I looked at a couple of pages of it once, and it, like, explained some of the dynamics of what this conflict was about in a way I could understand. And my dad goes, yeah, I left that book out for you. And I went, what? He's like, yeah, I left it on the coffee table. I said, you left the book on, that's how you communicated with me. And I said,

What are you talking about? He's like, it worked. And I went, but you never asked me if I read it. You didn't know I read it. And so that was the 70s in a nutshell, in terms of communication, that even very nice people with the best of intentions, they didn't know from their families, you know, how to tune into each other. And so as a little kid, it just made me confused most of all. And I think part of that led to being fascinated by people like George Carlin or Mel Brooks. who broke down society and broke down how families work and religion works and

poked holes in things and challenged things. And so I think that was part of the obsession. Did you ever talk to your parents about your dreams? What did they think about your obsessions? They were so helpful and so supportive. And they were the reason why I was into it because my dad had a big interest in comedy. And so the house was filled with Lenny Bruce records and Bill Cosby records and Woody Allen records. And so they treasure.

that stuff. And they also thought comedians were the coolest people. And when I said I wanted to be a comedian, you know, they were, they're like great. And so if I wanted to go to an open mic at a comedy club at 17, my dad would drive me to chuckles and then come back two hours later the middle of the night to pick me up. Like, they thought I would make it. And so I think somewhere in me that gave me a lot of confidence because when I talked to them about it, it was like there was no chance that I wouldn't make it. Tell me a little bit about your granddad, Bobby Shad. You say he's basically one of the founders of the music industry as we know it.

He was a man from the Bronx, and after World War II, he would take the money from his job and hire jazz players to record songs. He would get them printed up himself and then go to the record stores and sell them by. hand and then at some point got hired by labels to run their jazz and blues departments. So he was, you know, one of those people who figured out, how do you record jazz? Where do the microphones go? You know, like he was, you know, a real innovator. And he did Charlie Parker and Dizzy Gillespie. Dina Washington. Dina Washington. Cannonball Adderly. He produced the first Janice Joplin album. And he was a real inspiration because he was a hustler in and made me think, oh, you have to create your own path, and he just

did it. And so it was always interesting to have someone in your family that there was this feeling about, like, oh, this is a really special person doing something really fun and important. And I think I became obsessed with comedy and the way he was obsessed with jazz and I felt there was a connection because a lot of the comedians like Lenny Bruce started by performing into the jazz clubs. And so it all all felt very much part of the same world. Our guest today is filmmaker Judd Apatow. We'll be right back after a short break.

I'm Tanya Mosley, and this is Fresh Air. What was it? WKWZ. Yes, it's still there. In Sajasid, a Long Island. And it was run by this teacher, Jack DeMacy, who was very, very inspirational. He was our Dead Poet Society guy, and he basically pushed all of us to use the radio station to do whatever you wanted to do.

If you were into sports, use it to talk to professional athletes and learn how to report and do play-by-play. If you're into music, you know, a lot of people would go to concerts and write reviews and interview artists. So my friend Josh Rosenthal, he would go interview people like REM in the early 80s. And he said, oh, maybe you should try to interview comedians. And so I created a show called Club Comedy, and I got a tape recorder, and I would go off and kind of trick comedians. into doing interviews with me, which was the easier... How would you trick them? I just wouldn't tell them it was a high school radio station,

and I would just call a publicist and say, I work for WKWZ. Does Mr. Leno have any time while he's doing rascals in New Jersey to speak with me? And I would show up with some huge tape recorder from the school, the AV squad, and they would all tolerate me. This wasn't just like a few people, though. I mean, you interviewed, as you said, like 50, 50 folks. Did anyone ever turn you down?

These are big names. Well, there were people I couldn't get to. I couldn't get to Dangerfield. I couldn't figure out how to get to Andy Kaufman, who was down south wrestling at the time. Oh, he was doing that. So I would call the management office, and they were like, we don't know where he is. We haven't talked to him in months. But people like Howard Stern and Sandra Bernhardt and John Candy talked to me and Harold Ramos, and they had good advice.

I mean, I was asking them, how do you write a joke? How do you get on stage? How do you write a movie? And they would answer. And I look back now and go, what a head start I had. And a lot of it was just about work ethic, them just explaining what it takes to make it. Like, it's going to take a long time and you have to find your voice, things that I had never heard about before. Was there ever a moment that you remember that they gave you advice or anything that you were thinking, yes, that has come back to you in real measure?

I mean, a lot of it did. And just hearing about their failures and knowing that it was hard made me realize that the only way to make it is to be able to withstand an enormous amount of rejection and to be willing to work hard to get better. And that that would not be a short process. So a lot of people said, oh, it takes like seven years to find your voice as a comedian. Well, to hear that as a 16-year-old is good because you don't think, oh, it's what's happened now. So it's like becoming a doctor. It's going to take a really long time. So I think it set my timer in a good way.

And then they all talked about bombing. So when I bombed, I didn't feel like I should quit the business. I thought, oh, this is part of it. I'm in it now. And even Jerry Seinfeld told me about the first time he did stand up and he said, he got so scared that he just said the names of his jokes. You know, just like school. Yeah.

Your parents. Because he panicked. But knowing that someone that I looked up to, panicked like that, you know, gave me a lot of a fortitude when I was bombing and when I was panicking. Like, oh, this is part of it. Tell me about that first time you got on stage. The first time I went on stage, I was, I mean, I'm sure it was so terrible. It was at Chuckles Comedy Club and Mineola. Which is a fun name. Exactly, which was a great comedy club. And there was a very vibrant comedy scene at that time. I had just been a dishwasher

and a busboy at a club called Eastside, and I would work there and spend all the money I made there on the cab home. But I just wanted to be in a club, and Rosie O'Donnell was just starting out. Then Eddie Murphy was still coming in. He was 21 years old back then. And so the first time I did it,

I had a joke where I said to the crowd, I don't know how to handle hecklers because this is my first time doing it, So I thought maybe we could practice that you could heckle me and I can learn how to respond. And so if you all could heckle me right now, let's get this started. And then people just started cursing and screaming and they wouldn't stop for like a really long time. And my friends were with me and they started yelling at people and it just became like almost a riot where I couldn't get them to be quiet again. Because the joke was supposed to be that they would just scream out, you know, screw you or whatever.

And I was going to take a pause and go, see, Yeah, I don't know what to say. I don't know what to say. I haven't figured it out yet. But that was the first time. How did it feel? It was really fun. It was like, oh, this is possible. So it did make me want to go do it. But I was so scared. I mean, I would just be falling apart before every spot for the first few months. You only did stand up for a short time. I mean, you did it for a moment in high school. And then you graduated high school. You went to U.S. You dropped out of USC, and you did stand up for just a short period of time. Well, I did it for about seven years. That's, okay. That's a significant amount of time.

And then I stopped for a few decades, and then I started again in 2014. Seven years is pretty significant. That's exactly the amount of time that it takes to really get good, right? I stopped right when I was beginning to figure it out. But my writing was taking off, and I co-created the Banciller show with Ben and Sudden you know, I had a job and it was a job that was all-consuming. So I thought, oh, this is the universe saying you should be doing this. How did you know that you could write?

I did some writing at USC Cinema School. I studied screenwriting. And when I lived with Adam Sandler, after college, we wrote some sketches together. And there was one sketch we did on the Fritz Coleman variety show, which was like a local show on NBC after Saturday Night Live. and then I got a job writing for Tom Arnold and he had a few specials where they were like kind of reality comedy but we had written sketches to set them up like film pieces

and people like Martin Mull and Jim Carrey and young Ben Stiller and Frank Zappa did these like intro sketches that we all would write and with Stephen Leo with other writers he's great comedy writers and so I saw some of that come alive. And then when I met Ben, I really learned how to write by working with Ben. Really? How to write sketches, because he had had had an MTV show, which was really

brilliant and groundbreaking. Similar to the Larry Sanders show, before the Larry Sanders show, where he was the host of a sketch show on MTV, and you saw the behind the scenes of it. And it was really special. All those people, though, are so different. They're so different in their comedy and their approach. How did you come to understand the approach to take for everybody? Like, what were you looking for? What are you looking for when you're working with someone who's, like, you're just meeting them and you're trying to understand the thing? Well, I think when you're young, you know, you're in some ways able to get in other people's heads because you haven't figured out your own yet. So I didn't really know what my point of view was as Judd, but I could sit

with Roseanne and write jokes with her and imagine I was her. And that was just a, a skill I had as a young person trying to break in, and I could do that with a lot of different people. And it took a long time for me to figure out how to do, you know, to tell stories that were based on my own point of view. That took like another 10 years to really understand what that meant. And that's what I learned from Gary when Gary Scheng was doing the Larry Sanders show. It was so personal. And I watched him write and pitch all the stories for these episodes, and I saw the process he went through of how he mined his inner world for the show. Gary Shanling was like a father to you.

He was like a really older brother or father figure in the sense that he, I mean, he really was so nice to me. And so I was, you know, in California, trying to get my career going. I wrote jokes for him for the Grammys one year. And then he really took me under his wing to help. you know, write things. He was on the pilot of the Ben Stiller show. That's part of what helped us get picked up,

was that his involvement made us look like we were... Legitimate. Yeah. But then when the show got canceled, he hired me as a writer on the Larry Sanders show. And that gave me all the direction because I didn't know how to really write stories yet. And when he hired me, he didn't say,

oh, this is going to be helpful for me. He said, you're going to learn a lot. And so in ways I didn't quite understand, he was being really, really giving to me. Then he asked me to co-run the show one season, like five years later. And then he asked me to direct the show. And only later did I realize, oh, every step of the way Gary was the bridge to the next step. And he never had kids.

And after he passed, I thought, oh, in a way, he was so kind to me because I played that part in his life. And I always thought he wanted to treat me the way he wished his parents had treated him. Like, almost like he wanted to show that that was possible. And so it was a really important relationship. I mean, he's still, you know, in my head all the time to this day. One of the things that, well, the Larry Sanders show was so brilliant. And one of the things about it is that it satirized, you know, Hollywood and stardom and this need for that type of, like, attention. And did you guys ever talk about that need?

Like, because there's, like, that need for attention that can never quite be satiated. Well, Gary understood this issue that I think has taken over the world, which was, do I exist if I'm not on TV? I saw that written in one of his, like, journals or joke journals. He was on Letterman once, and I think he might have said, where are you been? He's like, I've been living my life. I just haven't been on TV. And I think now the whole world feels that way. Back then, it was just, you know, celebrities or performance.

Now everyone is on Instagram or TikTok, and so you have an entire, not just country world, where everyone is checking how many views they're getting and how many likes they're getting. And they had the same anxiety. How many people care about me? And is my self-esteem just based on outsiders approving of me? And that's what the Larry Sanders show was about. But it's like the whole world became Larry Sanders and that neurotic. Let's take a short break.

If you're just joining us, my guest is filmmaker Judd Appetack. We're talking about his new visual memoir, comedy nerd, a lifelong obsession in stories and pictures. We'll continue our conversation after a short break. This is fresh air. Documentary filmmaking, the last few years, you have really been on a role going back and revisiting all these folks that you really admire. What was the turning point for you to say, I want to document these things? I always loved documentaries. I didn't know how to get into it.

it or what, you know, what that path was. I met this man who I direct with a lot of the time, Michael Bonfiglio. I was doing a show called Iconiclasts. And Lena Dunham and I were the subjects. And Mike was the director. And I just thought, this guy is so good. And we became friends and someone asked me to do a 30 for 30 documentary for ESPN. And I had this idea to do one about Dwight Good and Darrell Strawberry.

And I asked Mike to do it with me. And that's the first one we did. And, you know, we've since did a bunch together, like the Gary Shandling one and George Carlin. There was one on Don Rickles, one on the Avet brothers. And we just finished up Mel Brooks and have a Norm MacDonald documentary coming out later in the year. What do you think you're searching for when you excavate so deep? Because, I mean, this is work you've been doing since you were 10. You've just been digging and digging and digging.

I mean, it's probably just as simple. What is the meaning of life? Like, why are we here? What are we doing? What is the purpose of this? Some of the movies have been about that, like funny people, but I like tracking someone's entire life and looking at it and seeing what they did with their work life, but also what they did with their personal life and what lessons did they learn along the way?

And what strategies are you using to get through this? What is this about? How do you give it meaning? I want to ask you about something I know that you've had to have thought about. because of your Carlin documentary, because of your own politics. There's this tension now between comedy as a business and comedy as truth-telling. And we saw that with this Saudi Arabia festival where a bunch of comics went. And they got a lot of money for it. But Human Rights Watch called it an attempt to whitewash Saudi repression because they had to sign something saying that they

wouldn't kind of like make fun of the Saudi government. As someone who thinks deeply about comedy and comics and the role. I mean, what goes through your mind when you see that kind of thing? I just feel bad for the world in general with all of it, right? So you have a regime that is terrible to its own people. And suddenly they're like, we're going to buy golf and we're going to buy all these sports and we're going to try to buy comedy so that you don't question what we're doing here. We're going to make it seem like we're okay. But really, if you say something bad about us, you might go to jail and never get out. And I think it puts a lot of people in a terrible position. People are trying to make money and support their families. And now they have to

figure out the ethics of, all right, I won't play for them, but I kind of play for these people. And I've kind of done a show at this stadium, which is owned by this person who's a terrible person. And so I have compassion to both sides. I do understand why people say, don't take money from people who are doing mass executions and sometimes of people who are just speaking out for their own civil rights, that makes sense.

And other people, they have a very strong point of view that if you don't infiltrate the culture of that country, they're never going to know what they're missing and they're never going to want to fight to expand that.

Oh, that's an interesting perspective. And so, and I've talked to people on both sides of the issue and everyone is very, very passionate. And it's sad that it makes comedians fight with each other because it's kind of not what we're all supposed to be doing. Did you kind of get embroiled in that when that whole thing was happening,

like having conversations with folks? I didn't get embroiled in any of it. I mean, I talk to friends about it. I more feel sympathy for everyone because we're not the people running the repressive government. You know, we're trying to make people laugh. We're trying to connect with people. And so it creates these ethical dilemmas that, you know, each person has to decide for themselves, where, you know, where do they stand?

I wasn't asked to go. I, you know, I didn't have to make that decision. I didn't have to find out what my price was. But so I just wish everyone, you know, got along better and that we don't get pulled into the polarity that we see in the rest of the country. We don't want the comedy community to be at each other's throats the way the rest of the country is. The comedy world that you write about in this book that you have really showcased for us all these years, it does seem like such a close-knit community, even though it's comprised of so many people. Is it still that way today? I think so because there's only a few hundred people doing it. So there's, you know, how many comics are there? There's, you know, a few hundred, you know, say there's 500 in the whole country. And I think we all have a lot of empathy for each other. because we know how hard it is to do well.

It's not the easiest life. There's a lot of traveling, and it's certainly not consistent. It's not a stable career. And some people go to the stratosphere, but most people are just working really hard to be good at what they do and to be able to support themselves. So I think that, you know, whenever you meet a community, you feel close to them because, like, you both understand something that other people don't understand. Jud Appetal, thank you so much for this conversation. Thank you. Judd Apatow's new memoir is comedy nerd, a lifelong obsession and stories and pictures.

Coming up, our critic at large John Powers reviews The New Film, The Mastermind, starring Josh O'Connor. This is Fresh Air. In the new movie The Mastermind, Josh O'Connor, plays a suburban husband and dad who sets up a robbery at a local art museum. The movie, now in theaters, was written and directed by Kelly Reichard, who's known, for putting unusual spins on traditional genre stories. Our critic at large, John Powers, says that the mastermind may be her most enjoyable film because it goes places you just don't expect. Ever since the asphalt jungle, John Houston's 1950 film about a jewel robbery,

audiences and filmmakers have loved heist movies. You get the precise laying out of the plan, the robbery itself, the roaring getaway, and the moment that things go wrong. There's always a snafoo. A good heist movie offers the exacting pleasures of both the crime and the plot unfolding like clockwork. The clock comes unsprung in The Mastermind, the latest film from Kelly Reichert, whose devoutly un-Hollywood movies are as admired by critics as they are underseen by the public. Working with a deliberate approach all her own, she here takes the classic heist story,

gives it a few tugs and shrugs, and winds up with a funny, sad movie that gets stronger and more original as it goes along. Set in 1970s, Massachusetts, and inspired by an art theft back then, the mastermind centers on James Blaine Mooney, called J.B., a suburban family guy played by Josh O'Connor, who you'll know is the young, awkward, not very likable Prince Charles on the crown. Quiet and hard to read behind his scruffy beard, J.B. is an unemployed cabinet maker, hook Zud's an air of unearned superiority. He's distant with his wife, played by Elana Hyam, wheedles money from his indulgent mother, that's the Great Hope Davis, and feels disdain

for his Philistine father, played by Bill Camp, a judge who hectares his son for not getting ahead. Pleased with his own cleverness, the movie's title is scoffing, J.B. enlists some dumb pals to help him rob the local museum, and make off with four paintings by abstract artist Arthur Dove. Though his plan is simple and rather silly, put on your panty-hose masks, fellas, it's doable in the era before 24-7 high-tech surveillance.

Here, after the cocky J.B. tells his two buddies how they'll grab the paintings, they express some doubts, and he tries to reassure them. I don't know, J.B., I can't carry four paintings alone. You won't be alone.

Ronnie Gibson will be with you. Wait. Little Ronnie Gibson. Gibson? He's not a kid anymore, and he's through selling weed. He's doing other things now. Trust me. Giving it a lot of thought.

Gibson's perfect. He's got a lot of nerve. He's nervy, I'll give him that. Not that this requires a lot of nerve. So you keep telling us, this place is just giving away paintings. I do it myself. I'm in there too often. I'm too recognizable.

As you can tell, these aren't exactly the, prose who just stole the crown jewels from the Louvre. Still, they do get away with the paintings. But once J.B. has the art in hand, this spoiled manchild finds himself plunged into a real world of cops and gangsters and life on the run. That includes a visit to his friends, a hippie couple marvelously played by John Magarro and Gabby Hoffman. That's like a desolately amusing snapshot of an entire era. Serenated by Rob Mazzurik's jazz score, they both heightened and mox his situation, J.B.'s' whole life has become a snafoo. Now, as she's shown in movies as diverse as Old Joy, about two friends going camping,

or first cow, about milk thieves in the Old West, Rikert's granular approach is far calmer and more oblique than her peers. Seeking to catch moments that flicker with the rising sparks of life, her camera is curious about things that may seem off the point, like a garrulous child yacking happily in the museum, or accentuates something we may not have fully noticed before. As J.B. waits for his cronies in the getaway car, we register not just his anxiety, but his boredom.

O'Connor is a compellingly ambiguous actor. He doesn't insist that we love him, and he commands the screen just thinking. His gloomy-eyed J.B. never tells us what he's after, but we sense that he's one of those quiet men who feel trapped in middle-class life and are prepared to chew off their paw to escape it. Where many male directors might find this heroic, Reikert finds it deluded and often comical.

She can spot a narcissist at a hundred yards. Unlike so many crime movies, the mastermind sets the action in a very specific time and place. Not only does Reikrit give us a small Massachusetts city in all its 70s sleepy pseudo-innocence. She keeps J.B. and us, bumping into the story's precise historical moment, with its Vietnam War on TV, street protests, and pundits talking about millions of people feeling, quote,

powerlessness, cynicism, and apathy. Words that could all apply to J.B. As it happens, the anti-war demonstrations turn out to have a bearing on J.B.'s fate. And in the moral logic that undergris' words Reichert's work, they serve as a measure of his self-absorption. The guy's so busy being a mastermind that he can't see what's going on around him. John Powers reviewed The Mastermind, now playing in theaters. Tomorrow on Fresh Air, director Nia DeCosta, who brought us the Candyman reboot and Marvel's Miss Marvel is back with an adaptation of Henrik Ipsen's

an 1891 play Hedda, about a woman trapped in a life she never wanted. DeCosta's version is set in the 1950s, a period that she describes as the great pretending. I hope you can join us. To keep up with what's on the show and get highlights of our interviews, follow us on Instagram at NPR Fresh Air. Fresh Air's executive producer is Danny Miller. Our technical director and engineer is Audrey Bentham. Our managing producer is Sam Brigger.

Our interviews and reviews are produced and edited by Phyllis Myers, Anne-Marie Boldenado, Lauren Crenzel, Teresa Madden, Monique Nazareth, Thea Challoner, Susan Nacundi, and Anna Bauman. Our digital media producer is Molly C.B. Nesper. Our consulting visual producer is Hope Wilson. Roberta Shorak directs the show. With Terry Gross, I'm Tanya Mosley.