Sunday Sitdown with Willie Geist - Judd Apatow on Comedy Legends, Cult Classics, and the Secret Sauce Behind His Movies

Episode Date: November 2, 2025

From a Long Island teen interviewing his comedy heroes on a high school radio station to the producer, director, and writer behind The 40-Year-Old Virgin, Anchorman, Trainwreck, and more, Judd Apatow is a modern-day comedy icon. He sits down with Willie Geist at New York’s Gotham Comedy Club to trace his rise to fame, from the tough early years and the mentorship of Garry Shandling to how the cancellation of Freaks and Geeks ultimately helped launch a generation of stars. Apatow also talks about his new scrapbook-style book Comedy Nerd, his love of stand-up, and his deep dive into documentaries, including new films on Mel Brooks and Norm Macdonald. Along the way, he reflects on how setbacks shaped his success, and the persistence that’s kept him creating for more than two decades. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey guys, Willie Geist here with another episode of the Sunday Sit Down podcast. My thanks as always for clicking and listening along. Very excited to bring you my conversation this week with the hilarious Judd Apatow. The man needs no introduction. Going back to the Ben Stiller Show. Back to the Larry Sanders show with Gary Shandling. Back to Freaks and Geeks. You know the resume.

Jud has been either the writer, producer, or director of so many of our favorite comedies of the last several decades. The list is long. The first film he directed was the 40-year-old virgin. He'd go through to Knocked Up, super bad, forgetting Sarah Marshall, funny people, bridesmaids,

Anchorman, the list is long. I bet you've got a favorite among those. He grew up on Long Island, obsessed with comedy from a very young age, and he's written a book now called Comedy Nerd. It's really a scrapbook. It takes from his childhood up to current day and just documents

every interaction he had with comedy. As a kid, he would write letters to famous comedians and get their autographs on headshots. Those are all in the book. He'd tell the story about why they loved them. He famously, in high school, growing up on New York's Long Island, had a radio show where it's 16 years old. He audaciously approached the biggest stars in comedy and would go interview them. They said yes, and they'd be on this teenager's radio show. He was obsessed with what was funny and how you made people laugh and made a career about it. So this book, Comedy Nerd, gets to all of it. And it's really, when you think about it,

a walk-through comedy of the last 40 years because he's been involved in so much of it. Such a funny guy, so much to stay about comedy back then and comedy now and advice for people coming up in the business now. Jud and I got together at the Gotham Comedy Club in New York City, a place where he has performed many times as a stand-up, has fond memories being in that room. he did his first stand-up gig when he was 17 years old on Long Island and still gets out there today.

So sit back, relax, and enjoy Judd Apatow right now on the Sunday Sit Down podcast. Judd, thanks for doing this. It's good to be. It's good to be back. You're back. We did this once before. You remember. In another era, I probably had dark hair.

You did have dark hair. I actually watched it this morning. It was 2017. We're in a comedy seller where you also perform stand-up many times. This time, we're here at Gotham, a place where you perform. when you're young and performed now. I do perform. What is this place conjure for you when you walk in here?

This is a great club. This is really one of the great clubs. So before I did my special for Netflix, I came here and practiced the hour. And yeah, I love this place. When COVID was the ending, I saw Jerry Seinfeld here do his first set after not being on stage for a long time.

Wow. What was that like? It was great. It was great to see him rusty. Yeah, yeah. Because he's just the best of all time. And just to go, yeah, He's got to work to get back in rhythm. And it was really fun.

It was fun. People were so happy to, you know, just to be back in the club. Let alone to see Jerry Seinfeld. Yeah, yeah. So how young were you? Do you remember when you first started performing here? Like, what era was this? Well, I started performing here in 2014.

Okay, so recently. Yeah. I did stand up when, from the time I was 17 to 24, and then I started up again 11 years ago. And it's really fun. I don't think I was very good at the beginning. I think when I was a kid, I was just kind of an idiot.

I mean, I would get on the TV shows and I had an okay career, but I look back now and I think, you had literally nothing to say. I mean, all my jokes were like, you know, is it weird when one of your nostrils is clogged and then suddenly it switches to the other? That was as deep as it got. Do you get a reaction from that one? They loved it. They loved talking about congestion.

It's a great comedy topic. On Long Island. Yeah. But I had nothing to say. So it's more fun now because I have some life experience. So you were 17 years old when you did your first stand-up comedy senior at Syoss at high school on Long Island. I believe it was Chuckles and Mineola. That's right.

Do you have that right? Joe Bolster was the host of my first open mic nights. What gave you the courage as a high school kid to get up on a stage and do stand-up? I mean, it's wild that I worked up the courage to do it because there's nothing scarier than like talking to a group of adult strangers. Because also you're a child. So it's not just like you're performing for people. you were performing for adult people. Right.

And I thought about doing it, you know, almost my entire childhood. And just, I mean, the jokes were so bad. And I would bomb, and it was painful. But I had interviewed all these comedians from my high school radio station. They all said, you're going to bomb. And so when I bombed, I thought, this is great. I'm in it. And I had this joke I would do at the end of my act, and I would say,

you know, the great Jerry Lewis said, you learn nothing about how to be funny by getting laughs. You only learn by not getting laughs. So thank you for giving me a college education tonight. That's a good line. Then I'd get a big laugh and I'd get off. And I'd go, I think that set went well, but it was the only laugh that I got. But that's part of the process, right?

You're literally building it like line by line. And I get two jokes at work. Yeah. Three jokes at work. So that and so much more going back even further is in this incredible scrapbook, yearbook, it's a collection of all the things you've gathered over a life in comedy called Comedy Nerd. And it goes back to the beginning of your passion as a kid. It seems to me reading this, there was almost nothing else for you in terms of like looking at the future anyway of like,

I'm going to be in comedy. It's just a question of how I get there. Do you remember when or how that was sparked in you as a kid? I mean, some of it was my grandfather was a jazz producer who worked with like Disney Gillespie and Charlie Parker. And he all also was friends with Tody Fields, the comedian, who was like a Joan Rivers type comedian. And then I would hear like, oh, he was at a party with Bob Newhart. And so there was something exotic happening. And he was kind of a hustler and a cool guy. And so show business seemed interesting to me.

And Tody Fields was so funny. But she was, you know, a self-deprecating female comedian. And people, like, adored her. So on some level, I thought, oh, what a cool. job. And then also comedians broke down like what's fair, what's unfair in a way that no one

else did. So I would listen to George Carlin or Richard Pryor records or Lenny Bruce Records even. And it was like religion. Like it was, oh, here's a way of looking and analyzing the world. And I love like

the Marx brothers because I just love that they like attacked the bullies. They attacked the socialites. and they were funnier than everyone, but they'd have to run away. It was running away after saying the funniest thing. And there must have been something about

the rebellion or the anger of it that I was connecting to. The way you tell it in the book, you kind of get home from school at 3 o'clock, get yourself in front of the TV, and basically watch comedy through Letterman, which I think...

So at 1.30 in the morning. Yeah, right? In those years, you were on 1230. Like a lot of days. Yeah. And also watching the news, So I would watch Mike Douglas, I'd watch Dinah Shore, and then I would watch Sue Simmons and Jack Cafferty on Live at Five, and then I would watch the national news,

and then I would watch all the sitcoms, and then Carson, and then Letterman. And what did your parents think as they were watching this, their child getting home from school and watching 12 hours of television? Well, they were concerned enough that they bought me a motorcycle, right? So they basically bought me a death machine to get me out of the house. You know, they got me a KX80, a Kalasaki. Wow. Because some of my friends, you know, were into dirt bikes.

And they bought me one just so I would leave the house. And then we'd be, like, running from the police and, you know, riding our dirt bikes. You know, they'd be building, you know, a new building, and there'd be dirt everywhere. And we would go there and get chased. It was so dangerous. Then one day I flipped over the handlebars. And I hit my head, and I was like, yeah, I'm not going to do this anymore. I'm going to get back to the Mike Douglas show.

where I belong. This is my people here. I'm curious though, like I was a huge fan too, SNL, I'm sure we shared a lot of things we grew up on together. When the idea of fandom becomes an idea of, I'm going to do this with my life. I'm going to someday step through the TV and be a part of whatever that world is.

When did you start thinking that way? I don't know. I started like recording Saturday Night Live with a tape record. This is before VHS. Oh, just the audio? Just the audio, and I would transcribe it and try to understand how it worked. And then there was a book.

It was like a Saturday Night Live scrapbook that was like this. And it had all the sketches and you could read them and see the people working behind the scenes. And I thought, I could maybe be in that world somewhere because it seemed fun, right? Like they were like a group and they were friends. Like, how do I have a group of friends like that? And I didn't know what I would do. I love to stand up. I'm trying to the back of my head, I'm like,

how can you become Bill Murray? You know, like, but I would never admit it to anybody. But like, how would be, like, the best life if you could be like the guy in stripes. Right. Or something like that. And then I was just trying to figure out

how to get near it. Like, how could I talk to any of these people? And my parents got divorced, and my mom got a job at a comedy club seating people. and I always thought that she only took the job because she thought I would like it because I was like, how much is she getting paid

to seat people in a comedy club for a couple hours on the weekends in 1984 that it must have been something that she, on some level, consciously or unconsciously, thought Judd's supposed to see this. And so one summer, I just went to every show all summer and got to meet some of the comics And then decided to really get more serious. So then I got a job as a busboy and a dishwasher at Eastside Comedy Club.

And Rosie O'Donnell was just starting. And Eddie Murphy was still coming in. He was 21. Wow. And I would watch the shows and dream of doing it. Still never tell anyone. And then I started interviewing comedians from my high school radio station. And then I could finally go, how do you do it?

And I could just sit for an hour and go, how do you write a joke? and people would tell me. And they were helpful. Like, they were all really helpful. And it was like Shandling and Seinfeld and Leno and Sandra Bernhardt and people like that. No, that's the amazing thing. I mean, that radio show is legendary at this point. 88-5, WK, WZ.

Yes. That's right. So I said high school you say in the book that the signal didn't quite make it out of the parking lot. I know. Like, you would never hear of anyone who heard any of it. But the idea that you as a 16-year-old kid could write to Steve Allen or just. Jerry Seinfeld, and they would come and do the interview. It seems like preposterous to most of us.

So what was your pitch to them? Why would they come to see you? Well, usually I had to go see them. Right. And I wouldn't say it was a high school radio station. I would just say it was a radio station. There you go. And then I would just show up looking like a child.

And then they would tolerate having to sit with me. But I was so passionate about it that I'm sure it was fun for them. But in the years before the internet and before podcasts, I don't think people wanted to talk to comedians that often in that way. There weren't a lot of places where a comedian would talk for an hour seriously about their craft, especially comedians who were working clubs. So I think it was fun for people to kick it around because it just wasn't something that they did often. You were kind of a podcast 30 years before it's time.

I literally was like I was trying to invent the podcast. I was like, where can I get an hour and a half interview with Jay Leno? It does not exist. I must do it myself. It felt like a small audience for that, but you found it. You got it. Exactly. This book is so full of just like gems.

And you go read through this. And you just can't believe, first of all, you kept it all. You knew where it was to organize it into a book. Yeah. So you've said you're sort of a, there was a mania to the way you treated comedy and kept things. So what made you think this was the time to sort of go up in the attic, get it all, and put it into a book? I guess I must have thought, like the world is changing so fast with streaming and, how we're processing entertainment

that in some ways it's an end of an era comedy continues, I continue to make things, but it does feel like there was a movement that could be discussed. We could take this moment to go, look what happened. Isn't it crazy? We got to do all this stuff, and people really liked it, and we did it for a long time.

And then people go on and do all sorts of other things, but this felt like of a piece. Did you have to go clean out a storage facility or something like that? Seven storage facilities. Yeah. I mean, when I was a kid, I would get like an autograph back from Dave Kingman from the Mets and I would like wrap it in a towel and treat it like the Holy Grail. You know, by Phil Collins' autograph poster would just be locked up.

Right. And you're not going to throw that away. It's got to go somewhere. I still have my Al Jeroe autographed record. I've got my Patrick Simmons signing my Doobie Brothers. this. And I'm so glad I haven't. Even as a kid, I'm like, these are the most important items on of the earth. Of course. Yeah. And so it's funny making the book because it proved the hoarding was worth it. It was. It paid off. She had to convince Leslie, trust me on this. Right. Someday. I'm not being crazy.

Someday this will raise money for fire aid. Because we give all the money to, you know, people who were affected by the fires in Altadena and the Pacific Palisades and to 826 as a tutoring and literacy center that Dave Eggers started and they're around the country. So yeah, it was worth it. I love that you're doing that. There's a really moving photograph right in the front of the house where you raise the girls where you don't live now, but a very significant place to you and then the after the fires and it's really just the brick steps going up. That must have been Tough to see. Yeah.

Oh, yeah. I mean, it took me half a year to go even look at it. And it's not just the house. It's just the entire community. So my dentist office burned down. My doctor's office burned down. Where the kids at dance classes burned down. The Starbucks burned down.

The pizza place burned up. Like, there's just nothing from that period of their lives, their childhood that exists. Good for you for donating all the proceeds here. The autographs you mentioned, there's a bunch of them in here. And I was saying earlier when we talked, it's kind of from a different era of our era where I would write to the Yankees and say, could I have Dave Winfield's autograph, please? And then he'd send back a picture of himself.

But you have an amazing collection. Was that a thing you did? You would just write to people? I would just sit there all night. Because there were these books that had, like, the address for NBC and ABC, and you could just write Carol Burnett and Mel Brooks and Johnny Carson, and you'd see, you know, who's, you know, who's sends things back. And some people clearly signed it. Other people auto-pend it. Sometimes you get a letter saying, Mr. Carson

does not have time to respond. They took the time to write a letter, but he couldn't respond. Yeah, yeah. And, you know, some of them were clearly just like photocopies. Yeah. But some of them were kind of incredible. Like Andy Kaufman sent me a signed photo, and it said, you know, to Judd, thank you very much. Here is an autograph. Andy Kaufman. And then I turned it over. And on the back of the 8 by 10, he wrote the same thing, but just longer. Oh, wow. Like, I'm so glad that you asked with the autograph, and here is the autograph.

And I just thought it was just so bizarre. You signed both sides of the photo. And when things like that would happen, I was just in heaven as a kid. Kind of what you would hope for when you write to Andy Kauf on something a little offbeat that he sent back to you. I got a postcard from Gilda Radner. Oh, no way. And it was clearly like she probably would sit there and sign that. Like something you could tell as a secretary.

Right. You know, you got a Bob Hope. I don't know if Bob Hope's doing it or not, but you got a Gilder Radner, you thought, yeah, that looks like what you would probably do in her office and be excited to do that. Yeah, Bob Hope's secretary says a stamp. Exactly. Yeah, yeah. The Steve Martin story in the book about trying to track down his autograph.

You kind of went with a more hands-on approach there. Yeah. Well, I knew where he lived, so I always was trying to drive by his house. So I was like 11 years old, 11 or 12. And anywhere we went when I would visit my grandmother in California, I would go, just make sure you take Bedford. And then just one day he was there. And I asked him for his autograph.

And like a normal person, he said, no, because, you know, if someone knocked out of my door asking for an autograph, I would, you know, security would be involved. You know? And so he said, no, I can't sign autographs in my house. And I said, well, will you sign it in the streets? And he said, no, I'm so sorry. And then I wrote him this, like, letter.

Trying to be funny, but like a mean letter. Yeah. Yeah, it's a little confrontational. I mean, I wish I had it because it's probably different than I remember it. But, you know, it said something like, you're the funniest man in the world, but you treat your fans like garbage. And if you don't send me an apology,

I will send your address to Homes of the Stars and you'll have tour buses passing by 24 hours a day. And then I put the letter in his mailbox, no stamp, which is extra. stalkery. Because I was like a little Long Island rat. I was like an obnoxious like a Bowery boy at that time. And then six months later, I got this book.

It was Cruel Shoes, this amazing collection of funny short stories he had written. And he wrote in it, you know, to Judd, I'm sorry. I didn't realize I was speaking to the Judd Apatow. And he underlined Thee. And I thought, I made. him laugh. Yeah. Like, he wouldn't have done that.

Like, we traded a joke. Yeah. And maybe he did that 50 times a day to all sorts of people, just being funny, writing things. But to me, on Long Island, who never really met anybody, and he was the person I looked up to more than anyone in the world, it almost felt like, oh, you could enter this world. Right. Like, he gave me, like, you're okay.

And it probably gave me some confidence. to believe I should keep my obsession going. Yeah, that's so cool. Like an acknowledgement you can play on the field with us. Yeah. I saw what you wrote. It was pretty good. Yeah.

I took the time to send you back. Even though I was the biggest a bit, though. It was a bit. It was a bit. There may have been other jokes in there that, like, those are the only jokes I remember from that. Like, in my mind, I can see the letter, and it was like a page and a half.

But I only really remember, like, three sentences of it. Yeah, it might have been a little darker than we were relaying. You go to school at USC. We talked earlier about the dating game, which is the reason you effectively dropped out of college because of success on the dating game. Well, I ran out of money. I couldn't afford tuition.

And I was kind of getting depressed because everyone at school was so much more talented than me. And I was 18 years old, a sophomore. I'm in class with people who were kind of geniuses. Like Matt Reeves, the director was in my class, and his movies were incredible. And my movies were, like, so terrible. And I was just really depressed.

And so I went on the dating game and won. And the trip was to Acapulco. And it was during finals. And I thought, you know, I'm not going to keep going to this school. I'm going to Acapulco. So I quit college to go to Acapulco. Did you go with the woman? I went with her in the chaperone.

Oh, there's a chaperon. And it wasn't romantic at all. The first day I sat outside with like no sunblock and I got like really burned to the point where like I couldn't go outside the next day. It was the ultimate nerd date. I'm sure she was like, who is this? So no follow-up to that trip. No follow-up. I've looked up her Instagram.

Her life is very good. Like, everything really did work out for her. She's skiing. She's having a great time. I love how you gave up everything. They go to Acapulco and get sunburned and just wipe it all the way. Yeah, yeah.

Hey, guys, thanks for listening to the Sunday Sit Down podcast. Stick around to hear more from Judd Apatow right after the break. Welcome back now more of my conversation with Judd Apatow. So what was your first taste of success? That's what I'm curious about when you're out in L.A. and you're kind of poking around. Was it the Ben Stiller show? Or was it Larry Sanders?

Or when did you feel like I'm starting to get my foothold here? The first thing was that I wrote jokes for the Grammys for Gary Shanling. And I looked up to him as one of the great comedians and comedy writers of all time. So the fact that he would want me to be part of his joke writing process as a really young kid was a bit mind-blowing at like 22 or something like that. Just that he thought I was funny enough to be in the space with him. And that probably changed everything. And then he was a mentor to me. And just being with him, he would learn how to write.

And then we did the Ben Stiller pilot for a sketch show. And Gary agreed to be on the first episode. And he did another episode when we got picked up. And then when we got canceled, he said, why don't you work on my show now? And hired me at the Larry Sanders show. And then he said, do you want to run it? And so the last season, I co-ran it with Adam Resnick. And then he said, you want to direct one?

Wow. And so it's like at every stage, you know, he would bring me to the next level. In a way, when, you know, you look back, it's just remarkable. He was just the kindest guy, just, you know, a really good, person to me. And it was, you know, like, I don't know if it was like a brotherly relationship or, you know, parental type thing. But he really couldn't have come through for me more. And that gives you confidence, doesn't? If he thinks I can do it, I can. Maybe you didn't even think you could do all these things. He was asking you to do, right? Oh, yeah. Absolutely.

Because I knew how high his standards were. And so if he thought, oh, I can write at all at any level there with him. But we always got along with the jokes. I don't know if we had similar moms or something, but I always felt like when I pitched him an idea or a joke, I was always in the neighborhood. He could always fix it and make it better. But like I think we thought the same way we were neurotic in a similar way. And so it just worked and made him comfortable. There were certainly writers who were way better than me at crafting the show. But there's something about my understanding of his personality and what he was going through in his head that made him comfortable to riff, you know, on the show.

He's so funny. You go back and watch the Larry Sanders show. I mean, it's an all-timer. It's just so funny. You read a lot in the book about sort of the Freaks and Geeks era, and you show the launch of that. You're often credited with starting careers, you know, Jonah and Seth and James Franco. The list is long.

Freaks and Geeks, again, a little bit like the Ben Stiller show, only people don't realize lasted one year? Yeah. Less than a season. Less than a season. 18 episodes. And now is looked back on as this classic, this cult classic. So is there any point when you're working on these shows that you believe are good

and later will become viewed that way, that you're like, what the heck? I'm making these good shows. I think you're good and the network's just not getting it. Was that frustrating at all? I was completely out of my mind. I was out of my mind. Because I knew what was happening. It felt like someone was, I mean, not to exaggerate, but I will.

It's like if the Beatles were making Sergeant Pepper and then someone just kept coming in, giving them terrible notes, you know, lose the trumpets. You got to, you have to play it backwards? And then finally like, nah, we don't like this. Stop making it. And to me, as a child of divorce, it was just so brutal because I really felt like,

oh, this is a family. we're all in perfect sync and it's just getting better and better and then there's this entity that's like stop like we don't get it, we don't want it. I just couldn't believe that it could even happen and my back went out

I'm like on Vicodin. I'm editing all the shows. We're not even on the air. I'm like finishing the shows and I don't even know if they're going to air ever be seen again. And then I'd have a back surgery. I'd be like half crying on the phone

with the executives. I mean, It's not when they canceled the show. They canceled it on speakerphone, and they're all just laughing. There's like a whole group of executives laughing while I'm crying. I wrote a long article about it from the L.A. Times. I mean, I'm obsessed about it.

Yes. Because it just seems so wrong. And I also thought, God, everyone here is so talented. And they have so much in them. We have to find a way to keep doing it together. And so we did undeclared afterwards, and a lot of the cast was involved in the crew. and made all these movies together

because it was, I don't know, I mean, it might have been mental illness, is the truth. You know, like, I do look back and go, like, that is just a crazy thing to be so mad that you just go, we will prove them wrong. But I believed in everybody, and I loved everybody, and it was fun to go, oh, you don't think that person could be the lead of the movie?

Watch what they do. Right. And then they all would come through. They were brilliant, and they would write their own movies and then direct their own movies. And so, you know, there's some like, you know, Michael Jordan-esque rage. You know, how Michael Jordan would look for someone to be pissed at to play better. It might have been some elements of, like, needing that anger to get the energy to make stuff.

But I totally get that, which is I understand comedy. These people are funny. This show is good. And you don't know comedy and you're telling me it's not good. Like, you know, that needs. Yeah, which is always hard because comedy is to be. So anytime you talk about it, it sucks anyway. Any conversation about what's funny is the worst conversation of your life.

Because you just don't know, right? You have no idea. Why is it funny? Cameron Diaz's hair is up and something about it. I don't know. You want to write a term paper about it? It's all instinct. And even when you're good at it, sometimes you are completely wrong.

So you will tell people like, this is funny. And then every once in a while, you are proven to be completely wrong. But you've been telling them it's going to be funny. for two years. Yes, right, right. Because no one, you know, that's a thousand. Yeah. But you have to be passionate and you have to make your case.

And how gratifying to see all these people in those shows and those movies go on to become massive stars and carry their own films and series. And how versatile they are. Like, you were right about them in the end. Yeah. I mean, I see Seth, you know, make this incredible show, the studio. And him and Evan, you know, winning all these Emmys and my friend, Pete Hike and Alex Gregory, who worked at the Larry Sanders show when I was there,

and they wrote the episode, which was the first one I ever directed. You know, they created the show with them. And, you know, it's remarkable. It's just fun to see, you know, how it all spreads out. Yes. It's really amazing. And I remember seeing Seth on a tape when he was 16 years old and going, that kid seems interesting.

What's going on there? Yeah. And you never would imagine the depth of what he could do. Right. And that was true of a lot of people. You know, Jason Siegel creates his own TV shows. And, you know, everyone has had these careers where they also have been written and directed. And it hasn't even been limited to just acting.

You have a way of doing that, you know, whether it's like Pete Davidson, King of Staten Island or Amy with train wreck. What is it you think you see or you're. looking for in someone that maybe other people didn't quite see that like, no, that person can carry a movie and do something different than what you know them for, whether it's SNL in Pete's case or stand up in Amy's case. What do you see in people like that? Certain people have, you know, a story. You know, Pete and Amy, you know, had really interesting stories. Kamal Nangiani and Emily had an amazing story. I look at it like, it is a comedy nerthing. I look at like a fan. When I was a kid, I was very aware of Andy Kaufman.

And Andy Kaufman would be on Saturday Night Live and talk shows. And then one day I heard like he's going to be on taxi, this TV show taxi. And I would then I'd watch taxi. So I was tracking them like someone might track athletes. And so when I meet people, it's really as simple as, you know, I heard Amy on Howard Stern. Yeah. She was just talking about her life and her dad. And there's their struggles, you know, because he had to MS. And she just told these really hilarious but also heartbreaking stories. And I thought, oh, these are movies. This is something I wish existed.

Like, I wish there was an Amy Schumer movie about this. And that's when I try to get involved. Because as a fan, I just want to see it. Like, oh, I want to see the Camel and Emily movie. Right, right. And I think if I'm not involved, I don't know if it'll happen. Right. So the only way I'll get to see it is if I, like, try to figure out how to support them.

And you're doing it with Nikki Glazer now, I saw it too. Like, this is kind of a similar idea, right? And it's really fun to work with people on their first movie or their first screenplay because they care so much. Right. And, you know, when people are writing their 40th screenplay, I mean, I wish I can say it's the same, but it's not. Right. And you really work harder than you'll ever work in your entire life when you're trying to kick down the door. So if you can identify the Judd Appetatat,

secret sauce, if you'll forgive the expression of when I see a movie, I know it's your movie, I know it's going to be good and funny and smart. What is that sauce, if you can describe it? What's different about what you do than other people do? I don't think it's so much different. I'm just trying to do it well in my own version of how other people have done it well. So, you know, the people I look up to are like James Brooks and Nicole Hollifson, and, you know, Cameron Crow and Barry Levinson, and Elaine May. And so, Albert Brooks, you know, there are certain people that have done things really well. And I think, oh, there's a way to do this, like, human comedy about just life is just hard.

You don't even need a big villain or a crazy thing to happen. Sometimes just like getting someone pregnant is enough. Sometimes just trying to get along with someone is enough. Because a lot of times life is the villain. You don't need a villain. Just like getting through the day, trying to figure out how to not be crazy, how to connect with people.

And to do that in a funny, compassionate way, I try to make it hopeful. Sometimes when I sit with a new writer, we'll try to figure out, like, what is their problem and what would have to happen to you for you to get over this? You know, so if you're stuck in a rut, usually you hit bottom.

And what would that bottom be that would make you have to adjust and learn the lesson? Like Adam Sandler and funny people, you know, he gets a comedian who gets sick and gets all this wisdom when he thinks he's going to die, but then he gets better and all the wisdom disappears and he's a jerk again. You know, those types of stories.

You know, how do you get to, a sater place. One of the most fun parts of this book is seeing famous movies, how different they were before they became famous movies, thinking about some of the scripts that you included here, and one of them is Anchorman. Yes, yes. And part of the script that's in here does not resemble the movie that we all love.

What was the original idea? Will Ferrell and Adam McKay wrote an Anchorman script that was about a group of anchor people, and they're all going to an anchorman convention. And they're all on the same plane. And while in mid-air, their wing hits the wing of another plane, which is like a FedEx plane

filled with chimpanzees and Chinese throwing stars. And so they crash into a mountain, like a snowy mountain, and it's like the movie, Alive. And it becomes about them trying to survive. And slowly they wonder if they need to eat each other. and every once while they're getting attacked by monkeys with throwing stars.

And it was so funny, and they hadn't been able to get anyone to make it. And they brought me in at some point. And they wrote a new script, which was what became Anchorman. And those characters were really funny in almost any situation. And finally, after years, because it was hard to get people to believe that would work, they let them make the movie. Because even the new version that you helped them with was a hard sell.

But then Spielberg stepped in? You write in the book? Yeah, because for all these comedic actors, there were moments where people didn't know if they could be the lead. You know, can go for it'll be the lead? I remember being in a meeting at Fox, and Jim Carrey was on in Living Color,

and we said, you know, we should make movies with Jim Carrey. And they were like, yeah, no, we don't think he's a lead. You know, so there would be these like gatekeepers who were just. just wrong. Right. And I'd have been proven really wrong. And then Will was in this movie,

Todd Phillips, maybe, old school. It was hysterical. Yes. But DreamWorks had just put us in turnaround, which means they weren't going to make it. And then Universal was saying, I think we would make Anchorman. And then one day in a meeting,

Steven Spielberg said, old school is a big hit. What else do we have with Will Ferrell? We should do something else with him. And they're like, well, we just put it in turn around. And he's like, well, get it back. And he was able to get Universal to get it back to them. And so he was the reason why Adam and Will were allowed to make Anchorman.

So without Spielberg, there's no Anchorman? Well, or a different Anchorman. A very different Anchorman. So when you're producing a movie like that or you're directing and writing, a scene like the Anchor Fight. Yeah. You sit down, somebody's written that. Is the room like, yes.

Yeah. This is going to be so great. and how can we like build it up and make it even more absurd, just to get at the comedy process, how you guys come up with stuff like that? Well, I mean, Will and Adam were magic together. Nobody has ever been funnier writing together. They had a real vision for these types of movies.

And, you know, I was certainly just on the side trying to like fill logicals maybe, you know? Like, how can we make this make some kind of sense or have some emotion in it? because it was always insanely funny. So something like that, like there's a lot of talk of an anchorman fight and that they get in a little fight.

Like, just as a producer, I'm just like, what if it, like, really, like, just went, like, crazy. And it was, like, a really big fight. That's all producing is. You say, like, one sentence and every once in a while someone, you know, like, listens and then they come up with this, like, magical thing.

Bringing NPR. Yeah. Sometimes, as a producer, all I do is, I think that could be longer, you know. Like I did a punch up on Happy Gilmore. And Tim Hurley and Adam, who wrote it, had a scene where he gets in a fist fight at a pro, like a celebrity golf match where he's with Ed McMahon is how it was written. And it was just like one sentence in the script. You know, and so as a producer, you know, I was just like, I think that could be really long.

Like, maybe you want to show the whole fight. And that's it. Like, you don't think of anything. But like, if that was in the movie, maybe it could be. expanded. Right. And that became the Bob Barker. Fancy. They got Bob Barker. Iconic. To do it. Yeah. Stick around for more of my conversation with Judd Apatow right after a quick break. Welcome back now to the rest of my conversation with Judd Apatow.

So when you actually went through all this and you sat down to write this book, is it amazing to you? Do you allow yourself this everything you've accomplished since you were the little kid washing the dishes at the comments? Club on Long Island that you're now this guy who's one of the most influential voices ever in comedy. Do you reflect on that? How far you've come? I try to. I mean, both the healthy and unhealthy part of it is it never ever, I never feel that good, which is the fuel to continue to go. Right. So even with a book like that where I can turn the pages and go, oh, look at all these things we did, my insecurity always wins out. You know, you always feel like a fraud and a jerk.

which is completely necessary. Because I think if I did appreciate it, I would just take a nap and just go fishing for the rest of my life. Right, I did it. It's over. I always feel the need to have something to prove, you know. So, like these days, like, people aren't going to comedies. Well, I'm going to try to figure out how to get them to go to comedies.

Right. I'm not going to give up. Right. You know, even if people aren't going to the theaters. And I'm going to figure out the one that will make you go to the theater. And that's fun. You always want to feel like an underdog. Right.

But I also look at it and go, it also feels like a manic episode. Like a really damaged young man. who worked way too hard to prove something to somebody, and he really needs professional help. But look where it got you. It worked out. And that's the thing. You do have to be a little crazy,

especially when you're young to believe that anything will happen. Because when we were young, we thought we would do well. We didn't know how, but we thought it, and now I look back and just go, we were just so delusional. But I think that's like in your DNA, just as like a hundred gatherer to believe in yourself.

Because we should not have believed in. ourselves. Right. We were not good. Right. You know, like, it took a long time to figure it out. But you do have to have that energy. That unearned swagger that you had as a kid. You got to be a cocky nerd. You got to be a cocky nerd to do any of this. One of the things that keeps you humble, I understand, is your daughters who are in the business. Don't really watch your stuff or give you really any feedback. Not religiously. Not religiously. Like, I'll do a whole series. I'm like, you ever see that show? I saw a couple. Like, nothing you do ever really impresses your kids.

That's true. The best you could do is, like, my kids, you know, would show no interest in anything I ever did, even the stuff they're in. Right. And then they'll have, like, a sleepover with a couple of friends. They're, like, 14, and I'll just go in and say good night. And they're just, like, watching the 40-year-old virgin.

I'm like, what are you doing? Watching 40-year-old virgin? How's it? Do you like it? It's funny. That's, like, the most... Yeah, that's a grand sam homerad. That's the biggest compliment you'll ever get.

And you were saying you don't stop and watch your stuff either. Is that true for the most part? Not really on purpose. I just, I don't know. I know people who are like, I'd never want to watch my stuff. Right. It's not conscious. It makes me uncomfortable.

Even things I know are great. I'm just like, okay, let's watch. And then usually I will like it. Like, I just saw The 40 Old Virgin with an audience of a thousand people. and I hadn't seen it in 20 years. Wow. And I got to watch it like I had not been a part of it. Because I forgot all of it.

I forgot like literally 80% of the jokes. So I was like really having real laughs at it. And it was very fun. And that was the first movie you directed. Yeah. So that was a special one. Yes. Yes.

And we all, you know, we improvised so much. We overshot every scene. Like, we can't fail. So if there's like the poker game scene where they're, they figure out. he's a virgin. Like, we're just shooting it for like 10 hours of improv. Just so when I get to editing, I don't go, oh, no, I don't have anything strong enough. Right.

So we were all, like, in a panic. Steve, you know, this was a huge break for Steve. He had never been the lead in a movie. And he would say, I'm just going to be nice to our casting director. So if the movie bombs, she'll still use me. You know, like, that's what it felt like. This is like our shot. That was another example of you spotting in Anchorman,

noticing, boy, Steve Carell's really funny. You kind of had your eye on him. Will was the guy and saying, hey, let's do something together. And it became the 40-year-old virgin. You have those instincts, it seems. Well, just as a fan, I mean, if you were on the set of Anchorman

and you were just watching the shoot, there was no one there who wasn't like, Steve Carrell is the funniest guy ever. I mean, he was destroying, and the whole cast was like, what Steve is doing as a brick tamlin, was making everyone laugh so hard. So just one day I'm like,

do you have any ideas for yourself as a lead? And then one day he told me about this sketch. He worked on once about a guy who is at a poker game and they're all talking dirty about sex. And it's clear he's lying and hasn't had sex. And I thought, sadly, I understand. I know how to develop that. Relatable, relatable.

More recent years, you've done a lot of, lot of really good documentary work all over the place, too. Comedy, but sports, politics a little bit. What do you love about making those films? I'm just such a fan of documentaries, and I connected with this amazing director, Michael Bonfiglio. He was directing an episode of Iconiclass about me and Lena Dunham. And I just noticed that he was an amazing director.

And so we connected and did one for 30 for 30 about Dwight Gooden and Darry. Doc and Darrell. And then did one about the Avet Brothers. And so then, you know, in recent you have some comedy ones about Chalding and Don Rickles and Bob Newhart and Carlin. And we just finished Mel Brooks, which will be on HBO in January. It's called Mel Brooks the 99-year-old man. And it's amazing because I got to spend 10 hours interviewing Mel. He's, you know, he's 99.

And so, you know, he can talk about World War II and the Depression and how the world has changed. And it's a very intimate look at his life in addition to, you know, he's a very intimate look at his life. in addition to his amazing work. And I love that you pull someone like him into modern popular culture with your film because there's a whole generation that doesn't fully appreciate how funny and irreverent and groundbreaking,

someone like Mel Brooks is. And some of his stuff, people say, couldn't you do it today? Because he was so bold that people are more scared now. I mean, he did movies about racism. He was attacking power. He was attacking fascism and Nazis. And so in a lot of ways,

his voice is more important than ever. Blazing Saddles was the first comedy my dad showed me. Yeah, yeah. And I've watched it a million times, and today you watch it like, hmm, I don't know. Could you pull that off today? He would try that, would be. Oh, yeah. I mean, you could do anything if your heart's in the right place.

And how about Norm, our beloved Norm MacDonald? That's right. Yeah, I used to write jokes with Norm McDonald for Roseanne for her act. So before he got Saturday Night Live, she hired us, and we would go to her house on Sunday. days and sit at her breakfast table and write rosanne jokes. Wow. So we've been working on a documentary about him. That is influenced by the idea that people go online and they watch all the clips of him. They go down the rabbit hole of Norm.

Yeah, I do that a lot with Norm. What is it about him for you? Is it the fearlessness? Is it the delivery? What made him so great? I mean, he just honestly was so funny and had such a unique approach. and he was daring. If a joke didn't work, he would slow down. Like, everyone else speeds up and tries to get to the next one, and he would just, like, sit in it. Someone said to me that he had said that he wasn't having a relationship with the audience.

He was having a relationship with the joke. So he's loving the joke. And you can jump on or not jump on. But he's getting a kick out of doing it. And wasn't bothered by the fact that no one was laughing. almost like reveling in it in some strange way. I mean, I'm sure it wasn't fun a lot of the time, but it was a provocation if a crowd wasn't getting things

because that's what it's like to be a comedian. Some nights the whole thing just works, and other nights the crowd's a little weird. And some comedians just work hard in that moment, like, how do I get them? And then other comedians are like, oh, now I'm going to take you on a different kind of ride if you're going to be like that.

It wasn't afraid to go on a late-night show. You watched those clips on Conan until like a, a six-minute joke with kind of a corny payoff. But the journey was the joke. Absolutely. It's just like so funny. I love him. I can't wait. When's the norm one? In the spring. Spring. Okay. Before I let you go, I'm thinking about the 16-year-old kid, you on Long Island, and now that you were the guy that a 16-year-old kid would want to talk to about comedy, right? All this accomplishment you've had, all these movies you've made, these classics. So what do you have? So what? What? You're is your advice to young people getting into comedy? People who come to you in L.A. or up in a club

in New York and say, how do I do the thing you did the way you were asking Jerry Seinfeld? What do you say to them? Well, I mean, part of what I would say is part of how I built the book, which is I put all the failures in there also. So all the pilots that weren't picked up, everything that was a bomb. And I talk about how that happened. How did things fall apart? What's it like when they work? what's it like when they don't work, because you just have to love it so much that you have thick skin, especially in this era.

You have to really experiment and put yourself out there and be willing to take all the slings and arrows as you're learning your craft. Because it's much worse now. When we were young, no one was paying attention to us. So we could go to comedy clubs for years and no one would talk about what we were doing.

So you'd have to really be strong and find your voice and not give up. I always say, you know, if you give up, it's not going to work. So, you know, the key is not quitting. Just hang in there. Hang in there. It's good advice. And the last real question is,

did you ever get around to listening to the New Testament as voiced by Johnny Cash? I listened to a little of it, a little of it. Scared me a little bit. It scared me a little bit. I'm going to finish it. John, thanks, man. Thank you. Love the book.

Great talking to you. Thanks. My big thanks to Judd for a great conversation. His new book, Comedy Nerd, a lifelong obsession in stories and pictures available now wherever you get your books. And we should point out proceeds from this book, go to organizations benefiting people still recovering from those terrible wildfires of earlier this year.

My thanks to all of you for listening again this week. If you want to hear our conversations with my guests every week, be sure to click follow so you never miss an episode. And don't forget to tune in to Sunday today every weekend on NBC to see these interviews with your own two eyes. I'm Willie Geist. We'll see you right back here next week on the Sunday Sit Down podcast.