Mike Birbiglia's Working It Out - 70. Judd Apatow Returns (Again): He Has Fettuccine in His Heart

Episode Date: April 18, 2022

Judd Apatow returns for a record third appearance in support of his latest New York Times-bestselling book Sicker in the Head. He turns the tables and puts Mike in the hot seat for an interview tracing Mike's journey from "funniest person on campus" in college, to doorman at the DC Improv, and beyond. The two friends reminisce about about being paid in fettuccine, and co-workers embezzling money from comedy clubs. Plus, questions from a special livestream audience about self-esteem and Judd's creative writing philosophy, which he calls “getting it down, then fixing it up.” Please consider donating to:826 National

You were interviewing comedians when you were in high school, much like Cameron Crowe was interviewing rock stars. Yes. And then made a movie about a kid interviewing rock stars. You were literally the almost famous character, but with comedians. The difference between me and him is he wanted to interview his hero, so he went on the road with Led Zeppelin, and I took a train to Poughkeepsie to see Weird Al Yankovic.

Hey, everybody, it's Mike Birbiglia. We are back with a new episode of Working It Out. That, of course, is the voice of Judd Apatow, the great Judd Apatow, who has a new book out. Before we begin our conversation today, I want to mention a few upcoming shows. Couldn't be more excited about my run of shows in Chicago at the Steppenwolf Theater for the month of May. I'll be performing The Old Man and the Pool. I'm doing a show at the Ace Hotel in Los Angeles

on May 4th as part of the Netflix Festival. And then I'm doing a whole run of shows. I'm at the Mark Taper Forum in Los Angeles for the month of August doing the full old man in the pool with the set design and the lighting design. And it's going to be so cool. It's like an incredible theater. Today on the show, we have Judd Apatow. Judd is a three-time returning champion Today on the show, we have Judd Apatow. Judd is a three-time returning champion to working it out. He is a good friend. He's given me notes on The Old Man in the Pool.

And he has a new book out. It's called Sicker in the Head. It is a sequel to the hit book, Sick in the Head, conversations about life and comedy. I couldn't recommend it more highly. All of the author's net proceeds are donated to 826 National, which is a nonprofit organization dedicated to providing free tutoring and literacy programs. We've donated to them here on the show in the past.

Judd needs no introduction. He has directed, he directed me in the movie Trainwreck. He directed 40-Year-Old Virgin. He directed This Is 40. He's produced Superbad, Bridesmaids, you know, just on and on, freaks and geeks. It's such a great conversation. He sort of turns the tables on me and asks me a lot of questions, which may end up in the paperback version of this very book, Sicker in the Head. Get the book. It's on the bestseller list, and enjoy my conversation with the great Judd Apatow.

Of all of the casts you've worked with over the years, I was in one of them. I was in Trainwreck. Freaks and Geeks and Bridesmaids and 40-year-old virgin, all these movies and television shows. I mean, undeclared. I mean, like, who's the cast who you'd love to hang with again? Like, who's the reunion cast you want to get together?

The reunion cast. I mean, I have to say, it was really fun making a movie with Sandler. Oh my gosh, yes. I always wanted I have to say, it was really fun making a movie with Sandler. Oh my gosh, yes. I always wanted to have that experience of directing Adam. Yes, because you were friends, you were roommates in your 20s. We were roommates, and we did a lot of stand-up together, and I tried to help him with some sketches.

I was never an official writer on Saturday Night Live, but I would work on things with him. And then I did some just punch-ups on some of his movies. But I never had that full experience. And I was nervous about it because I thought, does Adam listen to you? I mean, he's very successful. Can he just say no?

Can halfway through the shoot, can he go, I've decided to change everything in the movie. I just didn't know how he would handle being in the hands of someone else, even though I knew he had done that and he really enjoys doing something with James Brooks or Paul Thomas Anderson. Sure, Punch Drunk Love. And then he was just amazing, just so fun and hilarious and very prepared. There were some emotional scenes where he got very upset about being sick,

and he would just show up, and he was just there. Like, I didn't have to direct him. I would mold the scene a little bit, but he was always, the acting was fantastic. He's a tremendous actor. I mean, obviously, he got a lot of awards attention for Uncut Gems, but meanwhile, he's been making great movies for like a million years. Well, I remember when we lived together,

he had just graduated from NYU where he studied drama. Yeah. I mean, he took acting and I didn't know what that even was. So I'm 20 years old and I'm like, what happens in an acting class? I didn't do any of that. No kidding.

I was young. Right, you were straight from the comedy club universe because your mom worked at a comedy club. And this goes back to the roots of Sticker in the Head. You were interviewing comedians when you were in high school, much like Cameron Crowe was interviewing rock stars. Yes. And then made a movie about a kid interviewing rock stars.

You were literally the almost famous character, but with comedians. The difference between me and him is he wanted to interview his hero, so he went on the road with Led Zeppelin, and I took a train to Poughkeepsie to see Weird Al Yankovic, which I don't regret.

It was one of the great nights of my life, and he's a great man. But his was a little cooler. He did Leonard Skinner and all of that. And we talk about it in the book, me and Cameron Crowe, this idea of loving something so much you want to get closer to it. Oh, my gosh, yes. And now with this new book, really,

it's about wanting to talk to people who do what you do and say to them, how are you doing? How are you holding up? How are you keeping your career going? Are you crazy? Do you feel sane? Are you gaining any wisdom? What is your journey about? And especially doing interviews during the pandemic

people were very open to sharing that. And that's why for this we thought well we always do a soft cover and we add four more for the soft cover that this could be a conversation with you that would go in the soft cover version. I just made it under the wire for the soft cover. Well, I was just on Seth Meyers and I said, I didn't interview you for the book.

He pretended to be insulted. And I said, I could do it right now. We could start getting that ready. And then I said, what trauma made you want to go into comedy? And he went, I don't want to be in the book. Oh, that's really funny. That was the joke. That's very funny.

And then we didn't talk about it anymore. Yeah, I mean, comedians are, interviewing comedians is pretty interesting because there's inevitably, if it's not trauma, it's definitely something extreme. Something is happening. Something's going on. There's no natural route to comedy. No.

I mean, there's smart people. Like Seth Meyers seems like a genuinely smart person. And one of my favorite things in the Gary Shandling documentary is this moment where they're sitting on a park bench and he says, I don't understand this thing about, I'm paraphrasing, Jerry's saying about how you have to be messed up to be funny. What about talent? Can't you just be talented? Yeah. And then Gary goes, why are you so angry? Yeah.

And so it has something. Even Jerry, I produced one of his stand-up specials. Yeah. And then Gary goes, why are you so angry? Yeah. And so everyone has something. Even Jerry, I produced one of his stand-up specials. Yeah. There were some documentary pieces in there. And he says when he was young that his parents really left him to his own devices. Devices, yeah. They trusted him and treated him in a very adult way at a young age. And he became super self-sufficient.

And if you see Jerry or talk to jerry he's very confident yes he believes in all his opinions very strongly yeah and maybe that's a type of parenting that led to a way of observing the world that's right and what do you think and and what is what do you think it is for you what was the break that led you where you are which by the way is you we were joking about it before we started but like you're so productive it's almost dangerous yeah there's something wrong there's something wrong you're there's a broke there's a brokenness if during the pandemic i make a documentary a book and a movie yes in an 18 month period in everyone's break yeah i mean i thought i was on a break.

That's the weirdest part. Because I didn't even see it as a period where I was busy. Yes. Which is just me being crazy. The good thing is, because I think I have a similar thing. I mean, in the pandemic, I did virtual shows and I created a podcast. I mean, I did everything you could do comedy on. I interviewed 87 people.

Yeah, exactly. But like, yeah, no, I think a lot of it, a lot of the thing that you and I have in common is we just need to have a pen handy to write it all down and discipline ourselves to do it a few hours a day. And what was the moment when you were a kid where you thought comedy seems interesting and maybe a job when i was a kid i would make plays at school like this is how audacious i was as a kid and this i think came from my mom

encouraging me which is a very positive sort of anti-trauma thing very positive thing she gave me the confidence to be like i would write a play and i'd go to the teacher and say i'd like to perform this play i'm in third grade i'd like to perform this play about hamburgers that's a rushmore yeah it's a straight out of rushmore yeah and uh and then at a certain point you know when i was in high school my brother joe took me to see stephen wright live at theod Melody Tent. His first live comedy show. And for me, it was explosive. It was probably similar to when your mom took you to see stand-up comedians in Long Island for the first time.

I couldn't believe it. I couldn't believe that this person was saying these things that were so mind-expanding. I remember the moment he did The Tonight Show. Because they had him on, I think, a week or two later. Yes, that's right. Which seemed insane. Yes. He was that good?

Yeah. He was that good. And so then, of course, I feel like the illusion of stand-up comedy, of course, is that you see someone who's a stand-up comedian who's great, and you go, that's exactly what I think. And you don't realize that actually it's hours and hours of the person writing and revising and writing and revising and cutting stuff to get to a point where they're making you feel that way.

But before you realized it was stand-up, so you were young and precocious. Yeah, I was just a precococious artist creator kind of thing and smart was your dad a doctor dad's a doctor mom's a nurse yeah what what neurologist yeah yeah and so you come from smart i would assume reasonably nice parents smart smart folks my mom is my mom is salt of the earth like one of the kindest people one of these like gives christianity a good name kind of people where you go like well gives Christianity a good name kind of people where you go like, well, she is a Christian.

They must be doing something right. She doesn't beat the shit out of anybody. Yes, exactly. What does it feel like when your dad is doing procedures on brains? He doesn't do the procedures though. Brain surgeons and neurologists work hand in hand. Brain surgeons get in the head. They open up the head and they make the big bucks.

The neurologist consults. He's the one who's figuring out what they saw in the head. Parkinson's, MS, all these really, really hard, hard diseases. And did you understand as a kid what that what he was doing at all what did he what did he bring home and explain to you at like 13 of what his days were like zero the because he thought you couldn't handle it maybe probably yeah i mean my dad would come home i would say very late at night i mean he would come home eight nine o'clock at night for sure. And like, and so, I feel like

most of my childhood was spent with my mom and the thing that I remember that was really, I recently started doing crossword puzzles and I think it's because,

the New York Times crossword puzzle and the reason I do it is my dad used to do it every day. So that's all, you'd just see him at the thing. He'd read war novels and he'd do the crossword puzzle and the reason i do it is um my dad used to do it every day so that that's all you you just see him in this thing he'd read war novels and he'd do the crossword puzzle it'll make you happy and he would just do it start to finish and it was clearly some kind of therapeutic activity for him and now that i do the crossword puzzle i totally get it because you have something

like that does it come yeah yeah but did you ever? Yeah, yeah. But did you ever, like say high school, 16, 17, were you ever aware of what he was treating and what he was dealing with? So one time we had a thing in grade school called Science Club. And every Friday night, what nerds we were, Science Club. Yeah. And every Friday night. And then one night, he was the designated speaker. And he brought his tools.

He got the medical toolkit, took out all the instruments, showed what they did. He brought like a brain, not a skull, but like a plastic brain and showed the different parts the cerebellum and all the cortexes and things and i just thought like wow my dad does all this stuff like he never mentioned this yeah i just thought he was like cortex yeah he's really mad about stuff all the time uh he's stressed he's stressed but then and then so then that was a positive thing science club and then the other positive thing was every now and then someone would come up to

me a group in shrewsbury mass outside of worcester and uh a patient would come up and go your dad is one is is one of the best doctors or if not the best doctor i've ever seen in my entire life and and it was very they were very moved by him. It was like, okay, well, he must be doing good work. I don't know. Yeah. And when you went to college, where were you at? You were at?

Georgetown. At Georgetown. Yeah. Did you enter Georgetown knowing you were going to go into something creative or writing or performing? I went into Georgetown looking for sketch comedy. Yeah. Because I loved SNL Georgetown looking for sketch comedy. Yeah. Because I loved SNL.

I made a movie about SNL. Maybe love is not a strong enough word. Obsessed. Obsessed. Has Lorne Michaels ever acknowledged the movie? No, but he's always very nice. I've never run into him. He's always very friendly.

He was just nice. I have a great deal of respect for him and the institution. What's funny about it is it was like I wanted to be a sketch comedian, and in college I did improv and stand-up and realized, oh, no, I'm a stand-up comedian. That's a weird thing. But it's a ballsy thing to say, I'm going to go to one of the finest universities in our country and use it to become a sketch player.

It's absurd. And especially at that time, I don't think people thought there was a lot of job opportunities. So if you didn't get on Saturday Night Live, what do you even think the sketch job is? No, as a matter of fact, I was studying screenwriting in college. And I thought, I'm'm gonna be a screenwriter and then i got towards the end of college and i realized uh you can't go on monster.com and type in screenwriter nobody wants them i mean you you dealt with this i'm sure where you're just going like well how do you make movies and like you know uh gary shandling or you know gave you a shot to direct

if I'm not mistaken it was his idea for you to direct. Yeah I would have never asked and I didn't even want to write movies I don't think I just thought there's no stand up major so I studied screenwriting but the opposite of you I didn't think I was going to do it I just thought I'll learn something

that'll teach me something but I was more into stand up and I loved Harold Ram, but I was born to stand up. And I loved Harold Ramis. So I was aware that there was some sort of writing performing job that might exist. And I loved Woody Allen and Barry Levinson. So I don't know, I guess it wouldn't hurt to know this, but I didn't take it very seriously. Yeah. And so I was studying screenwriting and then at a certain point I got a job working the door at the Washington, D.C. Improv Comedy Club, which is one of the best clubs in the country,

which is, by the way, pure luck. I mean, the same way that your mom worked at a comedy club, and so you got to see all these comics young, I worked at the door of a comedy club. It just so happened to be one of the best comedy clubs in America. It's just lucky. But were you thinking you were going to do stand-up when you got that job, or you were still a sketch guy,

and this was a good way to make some money while working? I wanted to see comedy. I couldn't afford it. I mean, I remember, like, first few weeks of college, I was like, I'm going to see some live comedy in Washington, D.C. Let's see when Burl gets to town. So I went to see, I don't think i've ever told the story i went to see flip orly comic hypnotist at the washington dc comic it was brilliant it was brilliant i i laughed so hard it was so funny

and and it's of course it's this great club, Washington, D.C. Improv. And I got the bill with all the drinks and everything. I'm like, it's like $95? You know what I mean? Like, I don't know what it was. It was so much money. I was like, this is all the money I have for the semester. I was like, okay, I'm never going to go to a comedy club again.

So I didn't go to that comedy club for another year. And then there was the funniest person on campus contest. And I entered. Nick Kroll entered, who I didn't know at the time. A bunch of, eight other, ten other people entered. I won. I'd never done stand-up. So one of the prizes was this big, giant check for $250.

Huge check, like this big. And then the chance to perform and open for someone at the Washington, D.C. Improv. So they said, we have this person coming, we have this person coming, we have Dave Chappelle coming. I was like, oh, Dave Chappelle. I love his stand-up. This is, of course, way before Chappelle's show. This is before the superstar. Chappelle's probably in his 20s.

Yeah, he was 24. Weeks before Half-Baked came out, actually. so he's 24 years old and you're 18 or 19 and i'm open for dave and uh which was a master class even when he was 24 you're going oh my god this guy's like this is genius for some people the height yeah because he had young crazy hilarious brilliant guy energy as a young man like sandler when when they're young like sandler and before they've seen and done so much sometimes there's a silly hilarious aspect to it that you don't get to hold on to no no and it was it was beyond brilliant and i just said to the club i I just begged them, like, please let me perform here again. How did you do, though?

I did okay. So it's your second time doing stand-up? Yeah, second time doing stand-up ever. And I was still doing characters? Yeah. So you're doing sketch as stand-up. Give me one of the characters. Oh, my God.

This is so painful. Give me one of the characters. Oh, my God. This is so painful. So the character that I was this guy from Boston. It was Marty. Like, my name's Marty Beckman, and I love partying. I love this.

He's just leaning into the Boston accent. It was very similar to Fallon and Dratch doing those Boston accent characters. I would just do that character for like 10 minutes, and it would kill. It would do really well. And then I started doing, I did like a seventh grade science teacher. Paul Feeney used to do that. He used to do the shop teacher. Oh, is that right? With the missing finger.

Mine was based on this eighth or ninth grade science teacher I had named Mr. Rutan, who people were so mean to, who was such a nice guy. And people used to throw pennies at his head and stuff like that. It was awful. And I always thought, that's an interesting character to play. He'd be like, hello, welcome to class. Please stop throwing pennies at my head. It was ridiculous. And so I'd play these multiple characters.

throwing pennies at my head. Like, it was, like, ridiculous. And so I played these multiple characters. And then at a certain point, I was like, I'm not, I literally had this feeling of, like, I'm not that good at these characters. Like, I know when people are good at characters. I do improv. I was in the improv group at that point.

And that's not me. But me talking in between the characters, that was pretty good. It's funny how that happens for people, because there's a lot of singers that become comedians because their patter is funny. Yes. Or a magician who drops the tricks. That's right.

Right? The magician drops the tricks. I mean, Toadie Fields was a singer. Yeah. And at some point, the patter was entertaining people more than the song. Yeah, so I used to do characters. And then I started doing regular stand-up. And the big big thing was and this is similar to your experience in long island is like getting to watch george lopez and margaret cho and jake johansson and brian regan and jim gaffigan

and mitch hedberg and david tell there's nothing that you could compare to that just getting to see them and also watching them do six, seven shows over a weekend and seeing really how they're doing it and watching the different performances and the way they change it up and where they're improvising and where they're not you don't even know what you're learning your brain is just a super computer

picking something up I always say this to aspiring comedians is work at a comedy club. Get a job at a comedy club just so you can watch so many comedians. You know, there's so many clubs. There's like 20, 25 clubs. Like Denver Comedy Works or like get a job.

Just watch all those comics. You know, watch, you know, you know, I'm trying to think of who's coming through town. Watch Beth Stelling. Well, that's why. Watch Atsuko Akatsuka. All these people. Phenomenal.

I mean, that's why it's what's so funny about our stories being similar is I did that, but I was a dishwasher at a comic club when I was 15 and realized I couldn't see the show because I was in the kitchen. Oh, that's interesting. And so I switched to Busboy after like four months. Yeah. Because I was like, this plan isn't show because I was in the kitchen. Oh, that's interesting. And so I switched to Busboy after like four months. Yeah. Because I was like, this plan isn't working because I'm in the kitchen. I was a door person. And I'll tell you something funny about the door person. I've never told this story.

There was another door person. I forget the guy's name. But what I realized at a certain point is that he was embezzling money from the club. He had a scam. Everyone's got a scam in a restaurant. Holy cow. I never, I've never, other than like, I think I stole something from the pharmacy on my corner when I was like 10 years old

and I got caught and I went back and apologized and my mom caught me. Other than that, I've never stolen anything. I'm like very like focused. I have a certain, you know, I see things a certain way. And this guy one day goes, if they show up late and they don't have tickets, you just get their money in cash and you put them at a table. So this guy was pocketing like three, $400.

And I was like, I'm not doing that. Are you fucking crazy? Like, it's inconceivable that you'd be embezzling money from a club. Yeah, well, we had a friend who did that at a restaurant where he would toss the checks in the garbage when people paid in cash. Because people used to pay in cash. No way. And then just, it was called check kiting, I think was the name. I've never even heard of that.

Yeah. And so they would, maybe like once or twice a night, just keep the money from a table and toss the bill. Before it was credit cards and there's so many ways to steal. We'll go over those later. And so you basically are doing stand-up. You graduate from school. You do a lot of improv at school with Kroll eventually.

Yep, yep. Gaffigan also? Gaffigan's a different era. He's the 80s, from the 80s. And so you're doing a stand-up group, and then school ends, right? School ends. And now it's like, I need to get a job. This has to pay now. Did it pay ever during college?

During college, yeah. So I would make about 50 bucks a set or 40 bucks, 50 bucks a set. But I wasn't doing that many sets. I mean, if I was lucky, I'd get like 10, 15 sets a semester. And you went where when school ended to go, I'm going to be a comedian? I'm going to New York City. I lived on my sister Gina's couch for a period of time. I lived with a roommate in Queens for a period of time.

Then I lived with my girlfriend at the time. Day job? Day job was just temping at one of the places was Pfizer. They've done some good work. They've done some good work. I did not do any of that work. Their work lives in me. That's right.

It lives in me too. It's extraordinary. That company is amazing. The amount of dead wood at the bottom, which is what I was, is extraordinary. I mean, they have such deep pockets. They don't even know, I feel like, who they're paying after a while. Salespeople. I was making like 14, 15 bucks an hour in the early 2000s doing like nothing. But supposedly doing what?

Supposedly being an assistant to someone. Who's doing something. Who does something. Like literally, I can't even tell you to this day. And so you're doing spots in New York. Yep. Till late at night. It was in the comic strip. The first club worker who gave me a shot was this guy lucian hole yeah uh who passed

away a bunch of years ago from a from autoimmune disease and he um gave a lot of people their first sandler rock rock um well maybe eddie murphy although eddie murphy i think was successful Rock. Rock. Maybe Eddie Murphy, although Eddie Murphy, I think, was successful by the time he got there. But I think Seinfeld, actually, he was – oh, no. So Seinfeld was so successful that actually Seinfeld would, at the comic strip on the Upper East Side where I was passed with Lucien, would decide whether comedians were passed and could work at the club.

Did you ever hear that? He would just say his opinion and that would be powerful? He would audition them, apparently. That's what Lucian told me. Like a period of time in the 80s where Jerry's time football would audition the comedians. Like what? I'm sure he was tough.

He was tough and fair. I mean, I remember one of the biggest moments in my young career was I was bringing on Jerry at the improv, and I just talked for a while before I brought him on. I just wanted him to see a couple of my jokes like you do. And he got up on stage and went, that was funny. Oh, that's nice. And during really a time where I wasn't getting much done,

that was a fuel. That's huge. Because I knew he meant it and I knew he wouldn't say it. Like he seemed genuinely tickled by a couple of things. He's impeccable with his word. And so you started going on the road a little bit? Live by the four agreements. So then I started going on the road, yeah.

You're middling, you're hosting. I was hosting and middling. I was essentially taking any work that would pay me $200 a week, essentially. And I was keeping a very meticulous calendar of how many hundreds of dollars I was making each week. Because I knew that I needed to make about $1,100 in a month to continue living in my that's that's in my apartment in queens yeah for me too my rent was 425 and so if i can make 800 bucks yeah i had food yep i could pay for gas yep and that was it and that's kind of the fun part of a young comedian's life is if you have a couple of places that will throw you a little cash

and you're willing to live very cheaply, you can have fun. Yeah. If the clubs will occasionally throw you a hamburger. That's really funny. Yeah, I mean, that's – yeah, so I was at the comic strip and then eventually Gotham Comedy Club, Caroline's. Caroline's was a big break because they have a kitchen.

So to speak to your thing about food, like you'd go like, oh my God, they give you a chicken sandwich. Fettuccine Alfredo. Forget about it. This is like luxury. I remember the improv. They throw me a Fettuccine Alfredo at the end of the night. Oh my gosh. Every night I'd eat me a fettuccine alfredo at the end of the night. Oh, my gosh. Every night I'd eat an entire fettuccine alfredo.

Sometimes I'd ask for double pasta in it. Double pasta. I'd go right to sleep. That fettuccine is still in my heart. And so when you were starting and you were doing jokes, and at some point you realized that you were a storyteller. Yeah, yeah. When did that happen where you found

what is your style because your style you know how you know you're like one of the greats is because people can do an impression of you know like like a like a smart person can do your cadence and you know you have almost and dare i say like a cosby-esque. Oh, no. And I say that as if. As though nothing happened in the last 40 years. But if we could just talk. Yeah, yeah. In rhythms and that you've created your own way of doing it. And that's really impossible to do.

There's very few people, I think, who have found something where, like music, you go, oh, that's what that band sounds like. Well, I think, so part of it is that I was asked to tell a story for The Moth when I was about 24 years old. And The Moth is this, of course, great storytelling series that now is like a popular public radio show and podcast. They have a book, et cetera, multiple books. But at the time, it was a storytelling series in New York. And they asked me to tell a story.

And Catherine Burns coached me through this story that was very embarrassing. That ended up in my girlfriend's boyfriend special about how when I was in high school, I had my first girlfriend and she told me not to tell anyone that I was her boyfriend. It's embarrassing telling it now still, because she had another boyfriend, but he didn't.

It's kind of sexy. Oh, God. It's terrible. And then it gets embarrassing because she invites me to meet her parents, and I'm so excited, and I meet her parents, and then this other guy's there, and I realize it's her boyfriend. And then he invites all of us to go to his house. I meet his parents and then the punchline of the whole thing is it's very nerve-wracking

meeting your girlfriend's boyfriend's parents for the first time because part of you is angry and then part of you still wants to make a good impression. How old is this? It's like high school senior? So that was, yeah. High school senior, yeah.

I don't know if you're allowed to say this anymore, but that is like a very dirty young woman who liked to live a life of treachery. She had a double life. She was turned on by having it be insidious and semi-criminal, her sex life. Her fake name in the story is Amanda. Her real name I will not say.

But it starts with an A. I know it does. I know you didn't go that far from it. Oh, gosh. It's Andrea. We know it's Andrea. No, I will not cast a judgment on her except to say. I'm saying I'm in awe.

Yeah, yeah. To be running two guys in senior year of high school. Running two guys. Didn't Charles high school. Running two guys? Didn't Charles Kuralt have two families? You know, that's what she was doing. Oh, my God. She was prepping for that. She had double family.

So I tell that story. It was at Aspen Comedy Festival in, I want to say, 2003 for The Moth. And she's at the show. No, I've never spoken to her since. Never? Very odd. No, and I've never, very rarely as an adult have I gone down the Facebook rabbit hole of like,

where are these people? But one time I was like, why don't I look her up, see if she's around? Nothing. I Google it, nothing. I'm like, oh, okay. She's, I think she's gone from the universe for me. No, she has a new last name.

She's married. Yeah, certainly. She has a second family somewhere else. Third or fourth family. She somehow found a way to have children with both families and not get caught. She has a fifth and sixth family. She's like that Inventing Anna character. Yeah.

But they were those kids like in high school. There were certain people that they really loved to cheat. Yeah, no, it was pretty wild. Like the degree to which high school kids develop at a different rate is very funny. Yeah. Well, that was what Paul Feig's whole thing about – Freaks and Geeks. With Freaks and Geeks was some kids wanted to grow up fast.

Some kids didn't want to grow up and were like hanging on by their nails to stay children. Oh, that's interesting. And that's what he wrote. I found his original notes. No kidding. And I put some of it in the book in the photos page. Oh, my gosh. But that's what he said.

It was the difference between wanting to grow up faster or slower. Oh my gosh, yes. And the geeks loved being kids. Yes. And everyone else was trying to get in the world. Oh my gosh. And so you realize after the moth

that you wrote a story really well. It's like having a teacher show you something. Yeah. And then you think, I got all sorts of stories. Did that hit you? That's what it is. I did the story and then I go, okay, so this connection with this audience is deeper.

Yeah. Than what I'm doing normally. And what I'm doing normally is pretty good. I did Letterman. Like I was doing pretty well. And so I was doing normally is pretty good. I did Letterman, like I was doing pretty well. And so I was like, let me go down this rabbit hole. And then sort of the breakout story for me was the sleepwalking through a second story window story because it was so Ira Glass,

who eventually put it on This American Life, and that sort of broke me and that universe. He always says like, it's the story that you can't follow in your own life. Well, we only have so many great personal stories that happen to us. Yes. And so that's just a... Well, it's so on the nose as a metaphor, sleepwalking through our lives and our lives are out of our own control, and all these different things about it that speak to a larger truth about things.

So I started telling that story, and that was back when, at this point I was doing a college tour for Comedy Central. I had just opened for, one of my first big breaks was I opened for Mitch Hedberg, Louis Black, and Dave Attell on the first ever Comedy

Central live tour. And you were the host. I was the host for like Philadelphia, DC, New York Beacon Theater, which is wild, wild. So like I just called the promoter and I just go like, I'll do it for free.

And he's like, well, we can give you 75 bucks. They probably would have paid someone $1,000 to do it. I'm like, I'll do it for free. And he's like, well, we can give you 75 bucks. They probably would have paid someone $1,000 to do it. I'm like, I'll do it for nothing. I just love these comics. I'll do anything to work with these comics. I still do that. I mean, it doesn't mean as much.

Yes. I don't need the $50 as much. But when I was young, I was always in a car driving three hours to see something or perform on something. Yeah. Never really cared about that

as long as I could eat a little bit. Yeah, the eating is key. But to get in those situations where you think it's all about the experience. It's all about, oh, I'm going to get to watch

Mitch Hedberg every night. Yeah, I've never, because I'm such a fan of comedy, I've never driven a hard bargain when it comes to getting to be around comedy I love. And what, at that point, what was Hedberg like? I mean, Hedberg was definitely on drugs. Yeah, there was stuff going on with Mitch,

and I sort of knew there was some drugs, and I would sort of just try to do my thing, which is I'd be like, hey, let's play tennis. Let's go bowling. And we would always sort of make plans, and I've had other addict friends over the years, and he would sort of inevitably break a lot of plans, which was always very sad to me. Oh, sure. Terrible.

And so when he passed, it was devastating. Like everybody with addict friends it's it's you know it's always devastating you try and figure out what could i have done and well i think we're a part of a breed of corny people yeah we're corny comics like we're afraid of some of that stuff yeah i've never done i've never used coke i've never used coke yeah yeah i'm way too afraid of it. I'm on stimulants. I'm on Vyvanse. Clearly. Get Vyvanse. Can I be the Vyvanse guy?

Do you write your commercials for Vyvanse? Is that outrageous? I've never felt clearer with Vyvanse. Oh, my gosh. And I'm able to fall asleep after an eight-hour lay down. Oh, my gosh. So you realized that there were more stories to tell. And you were on the road when you had the incident.

Yeah, I was on the road when I had the incident of jumping through the window. So when that happened, a few months later, by opening for Mitch Hedberg and Louis Black and Dave Attell, Comedy Central gave me my own college tour. It was called the Medium Man on Campus Tour. Actually, Mulaney opened for man on campus tour actually millennia opened for me on the tour we got a tour bus it was so strange we got this big tour bus and uh on that tour i literally still have the footage somewhere i started telling the sleepwalking story

and immediately it did pretty well yeah like it was like oh this is even though this story is crazy and really far out this definitely works yeah and that was like gosh 2004 2005 and then i developed sleepwalk with me this show for about four years uh literally years of working with seth barish my director and then we and then along the way like n Nathan Lane came to a show of mine at Caroline's one night, and I was doing the material from what became Sleepwalk With Me. And he and I became friends, and I said, I want to do this as a theater show.

And he said he would consider presenting it, you know, putting his name on it. Did you ever have anybody from the theater helping you know how to write a piece like that? Only pretty much my screenwriting and playwriting professor, John Glavin, who suggested I write a solo show, by the way. So he was my screenwriting professor, and I would talk to him maybe once a year,

once every two years after college. And at one point he just goes, I think you just have to write a solo play because there's no budget. It's basically free if you can get a stage. You know how to write a play. And so I wrote Sleepwalk With Me. I brought it to Seth Barish,

and Seth Barish helped me kind of hone it into what became Sleepwalk With Me. And then Nathan Lane presented it, which completely, in hindsight, changed my career entirely. Someone credible anointed you. Yes. So you need the professor to say, this is the road you go down,

because if not, you're just going to turn it into your new stand-up set. That's right. And then you need a professional actor legend to say this is worth paying attention to and then you do the work but also i've always found that uh most people don't do that work i mean there were people who did one person shows but you're you're really putting years the way uh you know someone writes a play into these literally years yeah and it requires you know uh an ability to stay focused and not lose your sense of what you're doing over many years it's like writing hamilton you know you you have to not lose touch with what interested you about it and because you craft it line by line you're every night it's like you're testing yeah every bit of it and i think that is why there really aren't

that many people i mean other than you and colin quinn there's not a lot of people really busting out these types yeah it's like performances Hasan Minhaj. Yes, yeah. Hannah Gadsby. There's only like a few people who are working in the space of like, and right now Alex Edelman, who I'm presenting his show, are working in this space of what some people call like an Edinburgh show.

And what can you accomplish in that format that you can't when you're just doing a comedy club or a theater as a comedian. I ask myself every day. It's lonelier in a way. It is lonelier because it's a longer track. It takes so long. I'm in the middle of writing The Old Man and the Pool

right now. I was just at Berklee Rep. I'm at Steppenwolf in May. I'm at Mark Taper Forum in the month of August and I was just at Berkeley Rep. I'm at Steppenwolf in May. I'm at Mark Taper Forum in the month of August. And then hopefully it'll go to Broadway. Hopefully. And it takes years and years and years. And like you said, like you have to stay focused on, in this case, this is a show about life, death, mortality. And, you know, the idea that we're, life, death, mortality. And the idea that we're,

I'm 43 now and the phrase for middle age is over the hill. And I never understood the phrase till I got on the hill. And I'm looking around, I'm going, oh, there's natural causes, there's diabetes. And it's like, it's wild. And I'm trying to, as best as possible in the show, bring people into my shoes, regardless of what age they are. Yeah, and make it enjoyable to think about the big stuff. Yeah.

Not a depressing night. It's not depressing at all. Yeah. Yeah. But that's the trick of it, which is let's go to the place that we're not always comfortable going. Yes. And we'll connect and we'll laugh and we'll exchange our feelings about this. Not only that, and part of this, by the way, part of it, look, there's a lot of people I work with.

I work with my brother Joe. I work with Seth. I work with my wife Jen. I work with Peter. But a lot of it is who you, they say it's like, it's who you know, but it's also like who you insist on knowing. I feel like you and I are friends for over the years. And it's like, it's like,

it's like you've given notes on this show that are directly in the show. And a lot of it. It better be. But I ask, like, I ask, I mean, I think you do too. It's like, I ask my smartest friends, smartest people I know, what their honest feelings are about my work,

and I'm ready to take it. And there's nothing more fun than helping someone, or at least saying, well, here's what I may give it, or here's what I might do. Because when you see someone else's show, you get inspired, but then you don't have to be responsible yes for anything you say yeah like someone said that that's what they thought chandling loved about mentoring people or giving advice because you don't have that pressure of

i'm gonna bomb with it yes but you so sometimes those people can crack it because they don't have that stress or that inner critic and they can just see it. There was someone who relayed a thing that Alan Zweibel said recently, which I thought was great. I love Alan. How can people become jerks in comedy sometimes? Because they lose their sense of wonder. Yes, that's true.

I have that always because I do feel like I never know if anything will work. Yeah. You just don't know. Nobody knows. And you don't know. How do you judge it? It's like the bubble comes out, and there certainly was some critics that were rough on it, and the crowd seems to really be loving it.

And you go, what does that mean? And I went back and I read the Cable Guy reviews. Oh, yeah, yeah. I love the Cable Guy so much. I don't meet anyone on earth who doesn't like The Cable Guy. That's so funny. In 2022. I read the review.

I mean, it literally was like we were mean-spirited. Oh, my gosh, really? And Jim is menacing. Oh, my gosh. And they're talking about each scene that's like the classic scene, like him doing karaoke, as if it's an example of the worst scene ever. Oh, my gosh, no. And as a person now, I have to go, I've been through this so many times. him doing karaoke as if it's an example of the worst scene ever. Oh my gosh, no.

And as a person now, I have to go, I've been through this so many times. There's so many things that I've liked. Some of them were loved by the critics and made no money, and then the crowd found them later. Some of the critics hated, and the crowd found it instantly. And then slowly you get this bounce back of, oh, looking back, we like that one. Yeah. Like heavyweights.

Everyone shit on heavyweights. Oh, my God. That's hilarious. I only hear from people like, I watched that 40 times as a kid. And sometimes maybe I'm wrong. Like I'll never know. I never watched the movie Clean. Right. I've been thinking about it for years.

So I'll never watch it with the way a person sees a movie no they've never seen so i'm just guessing it's good All right. So we have a question from Alon first. So Alon, if you could come on stage. Hi, Mike. Hi, John. My question is, when you're having a rough day of writing, how do you get through it without depleting your self-esteem? Oh, wow. How do you get through a rough day of writing? How do you?

That's a great question. I mean, it's nearly impossible for me to separate the two things. I would say, because I think it's just tactics, right? Like I think you and I both have a similar tactic, which is go for a walk, try to go out and try to grab some sunshine. Or stop. Or stop, stop writing. Give it up, give it up.

Didn't happen today. Leave some ink in the pen, as Hemingway says. Sometimes what I'll do when the day is terrible, if I'm not stopping, I'll just open up a document and I will just babble, just babble anything that comes to my head. Because I always think that things just bubble up and you don't know why, but there's a reason why, but you don't know. And I'll just start writing, free writing. And you could do a

thing where you just say, I'm not going to stop typing for 10 minutes. Yep. And there's always something good in it. And that could end the session. And maybe there's one thing. Some people call that timed writing. Yes. A timed writing. 10 minutes, 20 minutes, you set a timer, you put your stuff on airplane mode, and you just write whatever is in your brain and i do the same thing and i find it to be wildly therapeutic and actually i've written some of my best lines over the years from those timed writings because sometimes it's like you write out you accidentally uh spill your guts on the page yeah you just You just let, wherever it will go. Yes.

Sometimes in the morning I do that. The second I wake up, I start writing. Like this morning, I was like, okay, I'm on Seth Meyers. Hey, Judd, how are you doing? I'm doing great. Oh, what have you been up to? And I just start answering the questions I think he's going to ask me.

As if we're there. And I was like, oh, I have this new book. He's the king of comedy. Sicker in the head. And then he's like, well, I'm not in it. I remembered he wasn't in it. And I felt bad because he's a genius. Why shouldn't he be in it?

And then I said, can I interview you now? And then I just wrote down that his answer would be, sure. And then I would say, what's your trauma? And then his response was, and he didn't do this joke. I wanted him to say, actually, I had no trauma as a child. And I was supposed to respond, well, that's why I don't want you in the book because you're so damn boring. Oh, my gosh.

But he said on the show when I said, what's your trauma? Yes. He said, I don't want to be in your book. I don't want to be in your book. So just for the podcast listeners, if you're interested in getting sicker in the head and you need one more sales pitch to put you over the top, it includes interviews with Amber Ruffin,

Bowen Yang, Cameron Crowe, David Letterman, Ed Templeton, Gary Galtman, Gail King, George Shapiro, Hannah Gadsby, Hasan Minhaj, Jeff Tweedy, Jimmy Kimmel, John Candy, John Cleese, John Mulaney, Kevin Hart, Lin-Manuel Miranda, John Candy from 1984. Yes, Margaret Cho,

Mindy Kaling, Mort Sahl, Nathan Fielder, Pete Davidson, Rami Youssef, Roger Daltrey, Sacha Baron Cohen, Samantha B. Tignitaro, Whitney Cummings, Whoopi Goldberg, and Will Ferrell. And if that doesn't sell you on a book, I don't know what does. There's a great John Cleese

interview there where he just talks about how to be creative. Like, how do you get your brain going? So that would be the best answer is in the book, read the John Cleese chapter because he explains it. But I always have very simple theories of writing. Down-up theory, get it down, then fix it up. So you'll give yourself

permission to suck. Anything, just get something down. And then in a different session on another day, go into fix-up mode. That's the main thing. Who's next? Do we got someone else? Yeah, let's go to the next question.

So coming up next, we have Julian. So if Julian could join us on stage. Hey, guys. This is kind of a depressing question, but was there ever a moment where you didn't think it was going to work out in comedy? And if so, when was like the first moment maybe that fear went away and you kind of felt safe and comfortable where you were at? That's a great question, Julian. It's, I, gosh, I never thought there was any way to fail because my bar for success was so low. So when I worked at the Washington, D.C. Improv at the door and I was watching free comedy shows, I was like, I've made it.

Yeah, I think that's helpful. I never had a mega success dream. My dream was that the other comedians would think I belonged, which I think is still how I generally feel. Oh, that's interesting. If I could hang out at a comic club and be respected and do my thing in the same world that they did their thing, that was mainly the goal, to just be in it.

To be in the game with people. And I think that's probably a lot of what always drives me. If I'm doing any stand-up, I want it to be that if someone watches me in the back of the room, they would feel like I was doing something respectable. Yes. And so when people say, oh, I liked your set, that's very meaningful to me because that's most of the dream right there.

Yes. And then with movies, it's a similar thing. If you make a movie and then another filmmaker says, I like it, that's kind of almost more than my own self-esteem which is bad because you do have to have your own internal compass for if you think you're doing good work or bad work but as a young fanboy comedy nerd yeah that's was always a a driver and i think that there's always a moment where you think you're not good enough. I mean, I've had that over and over again, certainly in early days where you're aware that the people around you are so much better than you. But I always thought this takes a long time.

And so I gave myself a long timeline. I thought, oh, it takes like seven years to figure this out yeah so even when i was bad year three or right it's not that good i just thought well got four more years to get there that's interesting that was usually what was in my head yeah yeah i was talking to atako akatsuka on the podcast about this exact thing which is we're talking about how long does it take to become yourself on stage essentially and like the best theories I've heard are 10 years. Otsuka was saying she's at year 11. She thinks it was about year 10-ish too. I can even feel it now. I started doing stand-up again after a 20-year break seven years ago.

And I feel like I'm probably just now on the verge of figuring it out, I'm probably just now on the verge of figuring it out. Which means I feel bad for everyone who's paid to see me the last bunch of years. Part of it too, to answer the question too, is part of it's about creating your own community. When I was in college, I hung out with my improv group all the time. I got out of college. Nick and I and our friends Brian and Ed and Conrad

had this group called Little Man, and we performed all the time. We weren't very successful, but we had a nice time. We had a great time together. We had a lot of laughs. I will say the laughs I had then, the laughs I have now, it's the same thing that you're striving for, which is like a community. It could be a community of five people, ten people who you like to hang out with and do comedy with. Next question. Norman will be next.

So, Norman, if you could join us. Hey, Judd, Mike. Hello. Thanks again for doing this, guys. Appreciate it. Norman if you could join us hey Mike thanks again for doing this guys appreciate it um just kind of wanted to touch on this because I know you guys are kind of masters of observational comedy and for me that's kind of what's driven my whole storytelling sensibilities and what got me into comedy writing obviously but I just want to know like you know what's what would you say is the key

to preserving that almost observational eye that you guys have held across all your projects that makes your work stay this untouchable for this long? How do you keep your observational eye? Well, I try to think of it in these terms, and it usually simplifies it for me. simplifies it for me. I think a lot about Buddhism, that life is suffering, yet we soldier on. Yeah. And everyone is trying to make their life work. And the thing that makes us laugh is talking to each other about how it's going. What are you doing to make it work? And all the ways it's not working kind of makes us laugh because it's so human and funny the way we stumble as we're figuring stuff out.

We're all in the process of evolving and learning. And the lessons are funny. The beatings we take that give us a lesson make us laugh as long as it's not cruel or you make no progress. Right. Our high school girlfriend having another boyfriend is funny because we've all had something like it. Jumping out the window.

Jumping through a second drawer window is funny. It is. It's funny because you're trying to handle it. How do I make my world work in spite of it? What does it mean? How do I interpret this? How will I live? How will I have a girlfriend?

How will I have a family? You root for that person just the way you root for anyone just trying to make their life work. And so for me, at some point, I thought, no matter, if you get more specific, it becomes more universal. Even if the specific isn't the same thing other people have, on some level, they do feel like the person jumping out the window they have their version yeah certainly of it and that's what i'm generally observing so if i'm making this is 40 and paul red is hiding in the bathroom on his ipad just avoiding the family trying to get a break yeah i'm observing that of myself and then the the thing that people relate to because that's like a weird thing that everyone related to because it was earlier in technology,

of the way we make our little escapes to get a second because we're all trying so hard to do right by everybody, but we feel like we're taking a beating and failing so much that we're all hiding in the bathroom in some respect. Yeah, like Ira Glass is one of the best observationalists I know personally. And I think it's partly because he interviews so many people for his show. He's constantly carrying a shotgun microphone around the country and going, hey, how do you feel about this or whatever?

And he's just a big listener. He asks a lot of questions. People who ask more questions than they answer generally are pretty good observationalists. And people are weird. People are weird. If you pay any attention to anyone, it's all there. It's all there.

What Gary Shanning always talked about was that people wear a mask and they have the way they want to be seen, which is very different than who they are inside. Yes. And so we're all saying, oh, I'm comedy guy. I'm doing well. And then if you follow me out of the room, you see what it really is. Yes. And that's where the comedy comes from.

And if you observe anyone, you notice there's truth and then there's the comedy comes from and if you observe anyone you notice there's the truth and then there's the mask yeah and write it all down write it up, that's what I always say to people write it up, yeah write it up most people don't write it up

well you've had a really interesting experience over the years with like Amy Schumer for example she wrote it up. Yeah, she wrote it up. So like, so you heard her on Stern and she's talking about some of these really interesting stories about her life. And you sort of called her and were like, this is a movie. Let's make this as a movie. And she wrote it up.

I mean, that's it. There was a moment where we talked about what the movie could be. And we talked about, you talked about some of the beats. And then she just sent me 20 pages. Yeah. And they were good. Yeah. I mean, a lot of it's in the movie.

Yeah. And I just went, oh, she can really do this. Yeah. Because you don't know. So you read something with tons of people. You're waiting to see, can they translate these thoughts and feelings onto the page? Yes.

So how do you know when your show is done, the one you're working on now? Yeah. Because the themes are very deep. Yeah. How do you know when you are getting close to having it? Or at least maybe the main ideas have landed. It's funny because with every show it's different.

When I know it's done is like I tour, you know, I'm in the middle of touring 50 cities right now. And when I start to get to a point where when we cut to black and the lights come up, I can just see in the audience's face that there's an experience that's happened. And I go, okay, we're close. I can keep refining this and I can keep making this punchline better and blah, blah, blah.

But fundamentally, this story, that's what this is. Yeah. But do you ever get bored of doing the show? Do you ever think to yourself, I don't know if I could keep saying this for another year or two? I don't get bored of the show,

although you know what's funny is like, you know, I do some performances for my audience like the other night in Dallas and, you know,'s funny is I do some performances for my audience, like the other night in Dallas. And I've done shows in Denver and Seattle and everything. And those are for my audience. And then every now and then, I'll get booked at a college or a corporate event or something that's not my audience. And it's just sort of general, everybody who got invited to that event.

And then I really see what the show is. Because I'm like, how does this hold up under the stress test of these people do not know who you are. They do not care. And those shows teach me the most about what the show is. Because I go, okay, when it's not the audience that, you know, when people buy a ticket, they're invested in the show being pretty good.

Yeah. But when they didn't buy a ticket, that's when you know if you have something or not. All right. So we're going to wrap up. But thanks for joining us on Celebration of sicker in the head. It's all for charity for 826, for free tutoring and literacy programs for kids in different programs around the country that 826 runs that Dave Eggers started, that organization. My grammar was so bad in explaining the literacy program there.

I said everything backwards. That's, I think, the only proper way to describe a literacy program there. I said everything backwards. I think that the only proper way to describe a literacy program is with really bad grammar. But anyway, all the money goes to them. But thank you for doing this, Mike. Thanks for having me. I could do it for five hours more. I feel I'm just scratching

the surface. I was frustrated 40 minutes in with my time restraint. Working it out because it's not done. Working it out 40 minutes in with my time restraint. That's going to do it for another episode of Working It Out with Judd Apatow. He is phenomenal. His book is phenomenal. It's called Sicker in the Head. We want to thank Penguin Random House for setting this whole thing up.

You can follow Judd at Judd Apatow. You could follow him on Instagram at Judd Apatow. You can follow him on Twitter at Judd Apatow. You can watch his movies wherever there are movies. You can watch his television shows wherever there are television shows. Our producers of Working It Out are myself, along with Peter Salamone and Joseph Birbiglia, consulting producer Seth Barish, sound mix by Kate Balinski, associate producer Mabel Lewis, special thanks to my consigliere Mike Berkowitz,

as well as Marissa Hurwitz and Josh Upfall. As always, a very special thanks to my wife, the poet J. Hope Stein. Great news about our book. Our book is called The New One, and it is a finalist for the Thurber Prize for American Humor. We couldn't be more honored. It is a big labor of love.

We appreciate you reading it and listening to the audiobook. The Thurber House is in Columbus, Ohio. It's a phenomenal museum. It's just, I couldn't recommend it more highly. As always, a special thanks to Jack Antonoff and Bleachers for their music.

They are on tour now. They're going everywhere. They're going to London right around when I'm going to London. So you could, you know, go one night to Bleachers, one night to Berbiglia. As always, a special thanks to my daughter Una, who helped create a radio fort made of pillows thanks most of all to you who are listening tell your friends

and thank you for also telling your enemies they need to know we're working it out we'll see you next time everybody