Conan O’Brien Needs A Friend - Judd Apatow

Episode Date: February 17, 2020

Writer/director/producer Judd Apatow does not feel hopeful about being Conan O’Brien’s friend. Judd sits down with Conan to talk about using silence in their work, lifting up comedy stars like Seth Rogen and Pete Davidson, fashion tips from Jon Lovitz, reminiscing about eating, and comic rhythm. Plus, Conan and Sona dish on producer Matt Gourley in his absence.

Hi, my name is Judd Apatow, and I don't feel hopeful about being Conan O'Brien's friend. Hello there, and welcome to Conan O'Brien Needs a Friend, a little engine that could, just truckin' along. Yeah, we were the underdogs. They said it couldn't be done. They said after 26 years in television, there's no way. And I said, I'll show you. Yeah. And then they said, why are you yelling at your father? I'm joined as always by my loyal assistant. You are loyal, Sona. Yeah, I need to be. I just bought a house.

That's right. Sona just bought a house with her husband, Tak. Yes. And this is your first house that you've owned? Yes. Well, you're an adult now. Yeah. So I gotta, you know, you have to just keep going for another 30 years. Who, me? Yeah, till I pay it off, because I can't work anywhere else.

Well, that would put me way past my life expectancy. So I'm just telling you, I'm just being honest. And I also live, I sort of, one of those guys that lives on the edge, so I might not go the distance. No, you do not. You're talking about it. You're one of the most cautious people I've ever met. What are you talking about? I'm a mad man. You've been a center. I'm a daredevil.

No, I'm not. You know you're not. It's okay. No, I like to think that I'm a, you know, edgy guy. Matt Gorley is also here. You're the producer and engineer. I'm just saying you're the engineer. I don't think, are you really the engineer? I'm not at all the engineer. Yeah, but I don't know what Will does. He's the engineer. Is he though?

He is. Will's always in the background and I've never seen him adjust a dial. He doesn't have a microphone. He's always adjusting dials. Do you have a microphone available, Will, that you can talk into? Let me explain what Will looks like. Will looks like a back woodsman with a trim beard, but he does look like someone who just participated in a barn raising. Oh, boy.

And now I'm told you're an engineer. I swear to God, I thought you were back there doing like a Civil War sketch for posterity. We've been doing this since like 2018, I think. He's right. Well, my heart is with you right now. He's right. Well, Will, thank you. I didn't realize you were the engineer. I thought you were here as a fan, kind of a creepy fan who showed up every week and just stared at me through the booth. But I'm realizing now occasionally I do see you adjust a dial or something.

From an engineer's point of view, Will, and again, I'll picture it, he is wearing a denim shirt, trim beard, very late 19th century haircut. Looks like someone who may have tried to assassinate Garfield in a train station. Will Bekdon, if I may use your last name. You may. As an assassin, you'll need a middle name. Do you have a middle name? McEwen. Okay, Will McEwen Bekdon. Oh, that does sound assassinating.

Yeah, when you add that, yeah. Will McEwen Bekdon attempted to assassinate President Garfield, but failed when the derringer he was holding melted in his hand. Because it was made of chocolate. He's not even a good assassin. Not even a good assassin. Will, from an engineer's standpoint, how do you think the show is going? Not creatively, but from the engineering standpoint, how are the levels? The levels are fine. Okay, just a prick. He just does.

Is my voice tough on the dials? Do you ever have to kind of ride me down a little bit because of my irritating, reedy voice? There's some dynamic range. Alright, want to talk about that? There's some lows and some highs. Yeah, as all great singers have. I can go low, I can go low, I can go high, high, high. I mean, that's a dynamic range. Treat me like a fool, treat me mean and cruel, but love me. You know, that's a song we can't clear, so good luck getting that in there.

Will, will you pay the Elvis Presley estate, whatever it costs, to play that song? I forgot that you can't pay for it because you only have Confederate money. It's not your fault, Will. But I'm glad that you think from an engineering standpoint of you, this is going well. From that point of view, this is going fine. He's stressing it. God damn. Talk to me after, Will. I have some coping.

I'm curious, how do you, Matt Gorely, the producer, how do you interact with the engineer, Will Bekdon? Well, after a session, Will sends me the files. He sends me the files. My precious files. Can't you make it sound a little cooler? He sends me the show. He sends me the episode. We're doing a podcast. There's no way to make this cooler. They're files.

See, that's the problem with podcasts. You guys have all accepted that it's nerdy. We could make it cooler than it is. Say, after we've wrapped an episode, I get the episode and I manipulate it. Will drives it to me on a motorcycle. Cool. Much better. Is it like a Royal Enfield motorcycle, the one that killed Lawrence of Arabia? It's exactly that one. It has a little side car. And just a little World War I German soldiers in the side car.

Yeah, and Will is wearing goggles and he speeds it to you and he takes it to your house. Well, it's not a house. It's a bunker. Yeah, a bunker. And he gets it to you and he has to dodge shells. It's like 1917 in the way. It's all in one shot and he gets you the episode and you take it out of the lead canister and then you put it on the old reel-to-reel and send it out to the Americas. I send it pneumatic tube like at Home Depot. Very good. That's what I want to think about the show.

Well, that's what happens. Next time I ask you, don't go, hmm, he sends me the files. I don't think I did that. It's what you did in Dropbox. Dropbox, yeah. Dropbox, yeah. Dropbox. The show business I grew up in, and I know I'm an older gentleman,

but the show business I grew up in was like, you could smell the popcorn. Everyone had the face paint on, you know? What? Grease paint? Grease paint, yeah. Face paint like from a child's party. What are you talking about? Back then, I grew up, when I grew up, you could feel the tap shoes

going up the wooden stairs as people ascended, getting ready to do the big review. That's the kind of show business I always wanted to be in. And now I find myself in this sterile environment with a guy who's like, hmm, files, and a late 19th century dust bowl farmer is twiddling some dials. I mean, the joy is gone. Let's get show business back into podcasts.

Don't you think? Yeah, I'm all for that. Wow. Let's do it. Okay, that's better. Yeah. There you go. Thank you.

Oh, okay. How was that? Hey, man, you asked for it. They never said that in a Mickey Rooney movie. Go screw it. Let's do a show. Yeah, we could do it. Yeah, says Judy Garwin.

Fuck yeah, says Mickey Rooney. We're going to fucking do this shit. Mitt, Cods. Mickey, come here. What happened? Anyway, I just want to make sure that show business, let's bring real old fashioned show business. Is there any way that we could get the sound of like

popping corn and crowds milling around in an audience? Right now, lay it under here. We'll do that. Yeah, something like that would be nice. Like an old film projector. Yes, the crowd's coming. They're taking off their hats and putting them in their laps and setting down and they're getting ready to watch the show.

Okay, well, that will happen and has happened. Okay, I like it. I like that we're in show business now. And Will, thank you for being such a good engineer. You clearly do a great job. Thanks for the things. You have to understand, Will's a little stunned. He doesn't get to the big city often.

This is a huge deal for him. See all these blinking lights. Well, I want to jump in front of this bullet somehow, like pull out a handkerchief or show expose later. I'm sure you have a handkerchief on you. I know, we've talked about it. I know, yes, I'm sure you do. Well, you know, enough dilly-dallying

and enough shilly-shallying. There's no time to waste. We must get on with the show and what a show it is. That's right, gang. My guest today is a writer, director and producer of some of the most well-known comedies of the last two decades. His movies include Knocked Up, Superbad, The 40-Year-Old Virgin, and The Big Sick.

He also worked on The Larry Sanders Show and now has a book. It's Gary Shandling's book, honoring legendary comedian and his mentor, Gary Shandling. I'm very excited to talk to this gentleman. Judd Apatow is here. Hey, Judd. I have to say, I walked in and I saw you today

and sometimes you seem miserable. I do today. I do. I am today. And today I am, yeah. Are you really miserable? You just seem miserable. Oh, no, no, it's happening. It's happening right now.

Okay. Is there anything you want to talk about that I could help you with? Well, you know, sometimes, I don't know if you've been through this. You're working through creative problems and you have a day where you realize that maybe you're wrong about everything

and deserve nothing in your life and you're a fraud and you're about to have epic worldwide humiliation. And then you walk in and there's Conan and you can't hide it. You try to hide it. No, I saw it right away.

First of all, cannot relate to what you're talking about. I've never made a comedic error or a creative error in my life. I was thinking about this the other day. For me, a string of, I mean, day to day, just massive successes. So what you say falls on deaf ears as far as I'm concerned.

Understand, you've been here a million times, not here in the studio, but you've been in this place mentally a million times. And it still doesn't go away. That is the beauty of making anything is that no matter how many times you've succeeded, you do not feel that it increases your chances

of succeeding again. And all the success gives you no self-esteem. That's the surprise, the lack of self-esteem off of success. I remember I was at a restaurant. We bumped into somebody. I mean, it was literally like Steven Spielberg, but it wasn't, but someone like that.

And they said the nicest things to me that a person could say to me, the things as a child you would dream that an idol would say to you. Right. And when they walked away, I said to Leslie, I should never be insecure ever again

because that just happened. And five minutes later, I sunk back down and I realized it doesn't hold. It doesn't hold. No, the best way I can describe it is that if someone walked up to you and they had a vape pen

that dispensed self-esteem, and they took a big pull and then blew that bubblegum-flavored self-esteem into your face, and for like, I would say, as long as you can smell that bubblegum for, that's how long you feel it, and then it dissolves or it goes away.

A writer can get in my face about, even jokingly, about one of their pieces that just did well, and I can instantly access one from 25 years ago that missed the mark. And they'll just, they'll laugh,

but they're also just stunned that I can remember Yoda Plumber. But now you're still going to do baby Yoda Plumber. Yeah, yeah, now we'll have to be baby Yoda Plumber, but it's just absolutely... They don't know how sick we are, really. I'm just going to cover the sound of your straw

going into your very rich, chocolatey drink that you're about to have. I call it the fuel, the ice-blended mocha fuel. Yeah, yeah, that's 8,000 calories of just pure sugar. I'm going to be so focused and then get home and then it's just two hours of diarrhea,

but it's worth it. A sweet, creamy diarrhea. An attractive diarrhea. Yeah, oh my God. It doesn't change its shape. As diaries go, it is a fantastic diarrhea. And Starbucks, we thank you. You started to cheer up a bit

when we were talking about other comedians. And I thought we should just, you know, we were talking about Sandler. And Sandler's a really good example. Adam Sandler's a really good example of a guy who's just had, he has never rested on a laurel for like a half a second and just always looks like a man who,

I think they're on to me. You know, I think they gotta go. And I think you're another guy is the same thing. It's hard not to be that way because I feel like most people don't realize that in their jobs, when they fail,

it isn't a massive public humiliation. You could screw up, you know, change in an oil filter at work and you're like, okay, I'm going to redo that. You don't have the entire world calling you an asshole. And so it's just very different to states. I don't, there was never a time in your career

where everybody called you an asshole. I think you have a prism in the front of your brain. It would probably show up in a CAT scan. There's a prism large in the front of your brain and when input comes in, it gets refracted nine different ways and you get this crazy rainbow of misery that's not accurate.

I totally. The whole world has never called you an asshole. Because I think when you're young, you think, God, if I could get everyone to like me and appreciate me, I won't feel bad about myself. And then when it happens, you feel just as bad about yourself. It's like, damn it, it didn't work at all.

And that's the strange part. But I think what's good about it is, it's like why Sandler's great in uncut gems. It's because there's no part of him that feels comfortable with anything that's happened. So his level of effort on uncut gems is the same as how obsessed he was doing his third set at the comic strip.

Because he can't feel it, and most of us can't feel it, or we would, you know, stop. You have a unique understanding of this because as a young, young guy, you were hanging around with Sandler, Shandling, Jim Carrey. You were around all these people,

some of them before they were famous, like you were around Sandler before anybody knew who he was. And so you've seen them from the very beginning all through the process. And you know that fame and getting recognized and having a lot of money

doesn't change a fucking thing. Well, also you have your friends from school who are not in show business. And sometimes you just go, I think they seem way happier than us. They're like, hey, I'm going to Fire Island this weekend. Then we're going to go to the Yankee Game and then I'm going to go visit the kids at school.

And you feel the lack of stress and tension. And you know they have worked stress and the things they need to do to keep their lives going. You don't feel the filter. Because I think when you're in the creative arts in any way, every second of the day you feel like I could be working fixing something. And that's a weird feeling

that I think a lot of people, they check out. If you're a chef, you check out and then you go do what you're going to do. You're not like going, there's probably a joke in there somewhere if I could figure out how to punch that scene up. And as a writer, every second of the day you could be writing.

So you either feel like you're writing or you're neglecting writing. And it's just a strange thing and you try to shake it off and you focus and you learn to meditate and you go to hot yoga or whatever you think is going to change it. But ultimately in the middle of hot yoga

you're like, I don't know, I think I probably could bring them in for 80 yards. Well, I can add a joke in the back of his head. And it's just a strange life. I had someone recommend during a particularly difficult time in my life that I try meditation. And I tried so hard.

And I failed consistently because my head is, imagine one of those baskets that just spins around with ping pong balls in it at a lottery where they're going to pick one out. It's just constantly spinning around and all those ping pongs, some of them are joyous and have good ideas

but a lot of them are also incredibly negative and it's all rattling around. I could not sit still. I think Gary Schelling documentary where they show him talking to Ricky Gervais. And Gary says, you should use silence. He's trying to get him to be quiet.

He was irritated at Ricky Gervais because Ricky Gervais sort of surprised him in his kitchen for something he was shooting. And you can see that Gary's really rattled by it. And Ricky, it's very awkward. Ricky's trying to have fun in the moment with it and Gary's very upset. He keeps saying to him,

you should use silence to Ricky Gervais. You should try using silence. And what he's basically saying is, shut the fuck up. But you should try silence. There's such a nice way of saying it and also a very, you know, Gary way of saying it. Yeah, and it's a fascinating moment because Gary was, by the way,

I have a book, it's Gary Schelling's book if you're interested in such things. But Gary said, I'll do an interview with you for your TV show where you interview famous comedy people. But I want to interview you for the DVD extras for the Larry Sander show. And I guess the agreement was that they would do

Gary's interview first and then he would do whatever Ricky wanted. And also don't come in the house until I get home. And he gets home and they're all set up. And that's not necessarily Ricky's fault. He may not even know any of this. But Gary instantly gets all

negative and worked up. And he feels betrayed and hijacked. And it's way out of proportion with what's happening. But in the moment, Gary decides to out awkward Ricky Gervais. Yeah. It was almost like he was saying,

oh, you think you're the office awkward guy? Let me show you how awkward works. And he creates a scenario that is maybe the most awkward thing you've ever witnessed. And then I found a camera that was one of Gary's camera men had some video of this moment, which wasn't in the DVD extras

or in Ricky's show, which is Gary telling him you should use silence in your work trying to get Ricky to not talk. And then Ricky kept saying, I can't. I don't understand. He was having the experience that you are talking about,

which I have had every day for the last 27 years. I read through a bunch of my old journals the other day. I swear every entry is me going, you really should meditate. You should meditate. You'd feel better if you'd meditated. Your inner voice is so annoying.

You should try meditating. That's why I don't meditate. Now you're doing it. You're getting to a very Zen place. Edwin is my inner voice. Or the waiter from the Isle of Lusie. Lucille. Yeah, that's your problem.

We just identified it. It's your inner voice. If you could get Samuel L. Jackson to dub your inner voice, I think you'd be in a better place. I hate my essence. That's what I've learned. When I get to pure quiet, and it's only me and no one is there,

I'm like, fuck that guy. Shut the fuck up. That's your true self. That's my true self. Just a piece of shit. It's so funny you bring that up because I have all these journals that I've found and they're all

so annoyingly self-help-y. I hate nothing. And you'll run on a machine for six hours and you'll get it's just white. And it's like, that's 1995. Wait, 1998.

Here's an entry from 2014. Here's one from 2019. And it's just a litany and then I come to work and Sona will back me up on this. There's this guy that sits right near Sona. And he's just happy.

And he's really happy. And every time I come in, I'm just like, David, what's up? And he's like, I went to Disneyland. It was really fun. I'm with some friends. Then we went and saw a movie. The next day we went to this room.

Then we went back to Disneyland. And I'm like, oh, you went to Disneyland, did you? You have a good time riding in the tea cups. I'm so mad at him. For loving life. I always wonder where that comes from. Because I think it's a form of hyper-vigilance.

I think that when you come from certain backgrounds or family strife, it clicks on some part of your brain that's like, you better fucking pay attention or shit is going down. It's like watching the door of the restaurant to see if like gunmen are going to come in.

Like you're just hyper-vigilant. So it's not even like, it's not happy. It's just like, giggly talking about my Disney day. I'm going to miss the thing that's going to chop my head off. And so you're just fucking focused every fucking second.

And that's the thing I'm always trying to get rid of and it is very hard. Only watching 90 Day Fiancé helps. Does that really help you? Does that bring you to a... Maybe it does. Maybe 90 Day Fiancé is your happy place.

At least I don't have to convince this woman to marry me in the country. Do you find this though? I mean, you might be joking. I don't know. That might actually be your show. But you know, the show that you love. But I am so happy watching things that don't have anything to do

with comedy. I like things where I don't have to like, oh, I see the seam in the workmanship or I see, oh, they're doing that. Okay. I like to be transported and if it's comedy I might not be transported.

It doesn't mean all comedy, obviously, but I just I could get triggered. So the thing that's not going to trigger me is an absurd reality show or a documentary about a terrible murderer in the 1950s.

A great documentary about Hitler on meth. Yeah. Right? They were all on meth. They were all on meth. That's what we know. Yeah, and then you can't admit to your friends like that show you've had for seven years. I've never seen one second of it because I rather watch Hitler on meth. Yeah.

Well, you know, we're surrounded by all these people that make comedy and they're they all are churning out comedy and they're doing comedy specials and there's this sense that we're all supposed to be watching all of it. But if you look at my cue it's always like you may also like

and then it's just swastikas. Like just and I don't mean in a please take that the right way ladies and gentlemen but it's all like Hitler carpentry. Hitler when he went on vacation like anything about Hitler or Stalin

or any of those people and it makes me I look at that and I think what kind of monster am I? I love it too. I'll watch I'll get like Showa and then I'll go oh I'll read something like oh the guy who made Showa made all these other documentaries because he had so much stuff that he then made a whole bunch of other

documentaries with the extra footage and then there's there's a documentary about the guy who made Showa showing him how he made Showa which actually has an incredible scene where he would pretend he was like from some magazine and interview some Nazi

and hiding in Argentina and then they figured it out that he was fake and they beat him almost to death that's like in this documentary about and I think it's good because it makes us root for the good guys. We like to know what the bad guys do so that we can fight them

so I think it's part of our preparation for future wars. Thank you for making me feel better about my really dark viewing habits. You just reminded me I just I always remember moments of humiliation and shame and when you mentioned Showa

I remember when I was in college going to the movie theater and the movie's done and it's a multiplex and I come out and I see a bunch of my friends coming out and they're all weeping from their movie and I said

what did you guys just see and they said we just saw Showa and they're just like Claude Lanzmann's Showa 10 hours and they're like weeping and you were walking out of no and here it is they said what did you see and I said

Rambo too I just I still think that occasionally whenever someone brings up Showa I remember that I was watching the least good of the Rambo movies not even the original I was watching the one where they're like

can we get a little more out of this can we get a little extra mileage and literally the wall my cinema shared on the other side Showa was going on and I'm watching Sylvester Stallone just blow people up you did a beautiful thing every time

many times I've run into you I've said when Gary Shanling passed away you did such a lovely thing which is you put together this incredible memorial for him which we all attended and it was just great and then you made this fantastic documentary about Gary

and now you've got this book which is entitled it's Gary Shanling's book which is out right now and it's fantastic I think the reason this sort of relates to our overarching conversation is that you were mentored by Gary who was very generous

to you and then you've turned around and paid it forward with all these people that you found whether it's Lena Dunham or Amy Schumer or Seth Rogen James Franco you find these people and you say hey they're not there yet but I'm going to put a light on them

which I think is a mitzvah to use my people's term you really are into all aspects of Jewish life from the Holocaust documentaries to using the word mitzvah yeah well mitzvah was used that word came up a lot in Rambo too

people keep thanking Rambo for things he goes like it's a mitzvah I mean I always look at it like I'm just a comedy fan and as a kid I would obsessively watch like the Mike Douglas show and every once in a while there'd be a new comic and I would track them the way a kid would track an athlete

like oh my god who's that Michael Keaton guy I need to be doing stand up and then I'd hear oh he's got a TV show with Jim Belushi and then suddenly I'd be watching Working Stiffs and then it gets canceled immediately I'm like oh he's got this movie night shift and I would track them

so I always think of it more like like that and now I see people and I think oh I like them I wish they were in a movie I don't know if people will give them one maybe I can try to help make it happen but it's more like I want to see the movie

it's funny because I was going through my diaries just the other day it hadn't in like years and like in 2002 it just said connected to nothing maybe I should make a movie with Seth Rogen as the lead which you know coming off of undeclared being canceled and it wasn't like

I thought like wait I think he should be the star of a major motion picture but in my head as a fan I just thought I think Seth's the funniest of everybody right now I wonder what that would be and that just continues I just finished a movie with Pete Davidson

and we met him five years ago when he was a kid and I thought well that's clearly a guy that could carry these movies even as a 19 year old it was pretty obvious I was talking to John Mulaney Pete Davidson came up and I was saying what is it about Pete Davidson

because he does have this aura and I can't quite identify what it is and he was saying John Mulaney was saying he really feels like he's like a young Sinatra like if you see footage of Sinatra

in 1944 Sinatra has this kind of it's slightly twitchy but menacing but also vulnerable like it's this whole package that you just go like who's that guy who is that guy I don't know who that guy is but and

I don't really know Pete Davidson's stand up you know I'm always reading about something that happened after he did his stand up or this incredibly beautiful woman he was seen with before the stand up or after the stand up but I don't really know his work well he's one of those people

he doesn't know how to not be completely raw and honest and tell you exactly what's in his head at any moment there's just no censor whatsoever it's just a live feed from his brain that sounds terrifying I don't think I want to

meet him now I mean it makes like you know his acting and his comedy like really immediate and funny and I actually think of him more in a way as like an expression of a lot of the way kids feel today of anxiety and pressure and depression

and they're struggling in a way that's different than we did as kids and it's hard to know exactly what the source of it is but he feels that you know probably more than most people because he's gone through more than most people but I think people relate to this vibration he puts off

which is I'm struggling I'm trying to laugh and have fun and be a good guy but it's hard like life's hard and I'm really trying to figure it out and I think that's where a lot of kids feel that's why there's this connection

he represents in some way what's happening in the zeitgeist which is a word I throw around but I never really understand what it means you know one of my favorite things I forgot to mention in the documentary but it's also in the book is you talking specifically about Gary being

on your show bombing and what it felt like to watch it and be a part of it and be in it I was in it Gary was in a bad place in his life and I think in his health although I don't even think he knew it yet

and he came on my show and he had all of these as you know he always had notes always had notes and papers and he's backstage and I remembered reading basically what we were going to talk about in a rough

outline form and it was just going to all be hilarious and then he had thrown all of it out on the way to the show and he had all these papers and he was flipping through them and I could see just wild scratchings and scrawlings on them and he was saying yeah maybe

maybe instead of that I'm not going to do that but what if you just but also and I put my hands on his shoulders and I just said Gary it's just me it's just me and it's just like this is not going on Johnny Carson for the first time

and it's make or break I was trying to say this really doesn't matter in your life but he came out and he was so in his head and he kept looking at himself in the monitor and commenting on how he looked and how he wasn't what will people say about how I look and

it just the whole thing and I was trying to help him but I couldn't and I was right there and I'm the host and I felt like it's my job as the host to make everybody look great and I couldn't do it and it was really painful and

uh so you brought that up well it is you've now brought me into a miserable pit I remember Steve Carell was on Jimmy Kimmel and he did his first talk show appearance right I don't know if it was for the Forty Old Virgin or maybe it was for

the office which aired just before the Forty Old Virgin came out and he was nervous and he just started sweating but sweating like Albert Brooks level broadcast news in life but not even like an exaggeration like it was like a level of sweat

you've never ever seen before and we're watching it and we're like is Kimmel gonna mention the sweat like is he gonna acknowledge it and the audience is tightening up and it's just it's way too much sweat and then Steve finally like commented

like I'm sweating a lot and Jimmy Kimmel was like oh my god thank you for saying it like it popped the moment but it was like one of those where you're like oh no I've seen that happen up close yeah we're always that guy no matter what like I saw Love It's I may have told you the story uh on your show

once but I told I saw Love It's at this party and he looked great I'm like John you look great he's like yeah I'm using this new shampoo Control GX shampoo your hand it makes it a little darker and then if you want a darker you just shampoo it again and then when you like it stop using it and so

of course I got the shampoo and I use way too much of it my hair went jet black I look like Paul Manafort I literally look like Paul Manafort and then I was like why am I taking fashion advice from John Love It's

but I've always embraced like I am not cool I cannot I don't I still dress like I'm 13 years old I don't like you know sometimes people they pick a look like suddenly like Wes Anderson looks like Tom Wolfe

or something and it works and then you have friends like that Paul Feig suddenly is wearing three-piece suits in a top hat and I'm always like what would that be what would I become Euro trash or what what is my look and I'd give it up and like nope it's eighth grade at Psyoset High School

that's all it is I can't be cool I it's not gonna happen I'm just always amazed at like there's people like Jeff Goldblum who he'll just decide that he's gonna dress like a crooner in the 1920s and and wear glasses that were made

in Germany in 1850 and do it and it's all like of course yes hurrah Jeff Goldblum and it works he pulls it off we can't do that no it looks so and it sucks though that if we did that it would look so crazy

like I have friends who are actors who have completely gray hair and then I'll see them like a month later and they have just like black hair and then you see them next year they have like red hair and no one blinks like I guess like I'm a chameleon I can change I can be anything and I'm like

I'm slowly turning into Santa Claus but if I suddenly went black hair I look nuts like I look completely crazy so I have to like accept my decay I can't be like Dick Clark like with black hair at 85 years old right and I'm kind of fascinated

with what would happen if I had a let's say I had a two-month hiatus for my show for whatever reason and I went and got a lot of stuff done to my face would people say stuff to me that's a tough thing I don't know that you would say that

people don't say it to Simon Cowell and America's got talent you know he did that and his face is completely different and it's not like a contestants like you don't like what I did your face looks fucking nuts man who you can judge creative choices your eyes

have been pulled to either side of your hand Cowell no but I just would dare I want to do it almost to just then see who's going to have the courage to come up to me and go like I what did you do? would do it but I don't know if they would do it on air

but I respect people trying like you know for me like I like that Simon Cowell does it I'm kind of jealous that the ease to take those risks and you know I feel bad for people who get plastic surgery because sometimes it doesn't work like some people it must be

terrifying to go under the knife knowing like there is a chance for the rest of my life I look nuts right here we go I just always think whoever if you're in comedy you can't do it I don't I mean I think that's my feeling is that if you're

in comedy you can't but no one's ever looked at me like hmmm he's a drill treat for the eyes gotta check out my Conan O'Brien you're like that's not and so if I'm cutting into muscles that I use

to try and make Deepa laugh and then suddenly I look a little better but I'm frozen I don't know it may be helpful to us to look weirder I'll do it I'll do it we like old Phil Silver's more than young it's like as we decay we get

that weird you know like Lou Jacobi face and maybe it's better for us I like that you say decay because it's true as opposed to as we age I'm going to start saying to older people you're further in your decay

you're more advanced in your decay yes and just see how they take it yeah no I always see the decay because you feel it like okay we're on the other side it's we're slowly going down I'm not sure how slow I can make this but clearly we're in falling apart mode right yes

yeah but again that's just my very specific Jewish perspective of reality although I have been going to the gym a lot lately I could tell which I hate and I found a way to be as strong as I've ever been while remaining equally as fat

so I'm like I'm like I have muscles but I'm equally as out of control with eating and fat so you just do you eat your feelings when you're nervous about a project or a movie what is your go to would you eat a whole Bundt cake would you would you drink molasses black strap

molasses out of a jug well like sometimes in the office there's some place they make little Bundt cakes and so someone will send them to the office and just every time I pass a refrigerator I will eat one so by the end of the day I've had 11 mini Bundt cakes but yesterday I was I was

feeling down and while just talking to the editor I did three quarters of a pint of fish food Ben and Jerry's ice cream but so fast it was so fast that I had to say to the editor while you said that I ate three quarters

of a pint of ice cream and then I didn't eat like the last inch I was so proud so proud that I put it back with an inch what do you eat quickly so fast my wife and I go to war about this because she's like I'm sitting here

in the restaurant eating staring at your empty plate for way too long so I've had to what I do now is I'll eat really fast and then leave like three things on the plate to create the illusion for my wife that I'm not done but really I'm done so now tell Judd how I eat um it's shockingly

fast I mean it within seconds enjoy your sandwich will be and joyless so no no joy at all no joy in their hating it when you eat yeah it's uh you're not a food guy no and I've I have to admit my wife

when we go someplace she's like looking online and she's seeing which is the really good food and I'm thinking it doesn't matter I'm gonna put stuff in the hole in my head and I'm gonna shove it in as fast as I can and then

we're going to go back home and I'm going to look for Hitler on Netflix you know that's all what is you know that's the difference that's how we know you're not a Jew this food part of this conversation uh because for me and me and Sandra have these talks all the time

like when we talk about eating we'll reminisce about eating like oh god you remember when we lived together we would go to Red Lobster oh that was so good we had no money and we spent it all on Red Lobster and we thought it was fancy

and now we've eaten everywhere in the world and it was better than everything in the world but we love it so much because it's like it's a great way to shame yourself because you know you're hurting yourself you can numb yourself you're rewarding yourself it's very hard to like unravel

the food issues if you have them you know as like a kid of divorce I used to go home and make hamburgers we had like a little kitchen island that had a grill on it so I'd be like 13 at home and these burgers for myself watching the Merv Griffin show

turning it into like the most fun event ever watching like Michael Winslow do sound effects on the Merv Griffin shows but so to me that was like a like a joyous escape so now when I see a hamburger I'm hardwired that this is like the best moment of my life

how old were you when your parents got divorced? cause that was a seminal and that was like the atom bomb blast of oh yeah cause they never got along again like they broke up but they never worked it out they fought until they both had no money and they

really never said like yeah we took that too far like it just went on it through college after college and so it wasn't something that was like a year or two event it was like you know a lifetime event right so that's

clearly the okay comedy will fix this I'll go into comedy I'll go into comedy I'm gonna get a job I mean it made me feel like I gotta get out of here I gotta get a job I gotta get like create my own safer space which was weird you know you're not supposed

to be worrying about getting a job when you're 14 and you're like plotting your your attack on Hollywood but like when you're just nervous you're like I mean you could either like become a pot head or go hunt down Howie Mandel to interview him for your high school radio show you know like that's what it's your choice is

you interviewed some for your high school radio show you interviewed some big names yeah I was crazy I mean I well one of the best ones was John Candy I went to the new show yeah so I have to learn Michael's left Saturday night live for a few years he did the new show I remember and John Candy was a cast member and

and I did like you know I'm not gonna brag but I did do Willie Tyler and Lester at the same time at the same time at the same time yeah I did George Kirby you know I went deep I went George Kirby I went Guido Sarducci I was you know I was going one by one well I got to spend

in 1985 I got to spend a day with John Candy because I was in college and I hoodwinked into him into coming in and visiting our human magazine in college and I spent the entire day with him

and to the it's one of the greatest experiences in my life he was everything I wanted him to be he was funny like as if he were in a sketch he was funny and took me around and I was supposed to be showing him around and he's like

kid kid come here you're with me kid and it was just like oh my god he's Johnny LaRue it was the greatest experience I'll always have that but that's a great scam of college yes you give awards to people to get them to hang out with you yes and the awards are meaningless as much as they are in this

town like National Lampoon in the Harvard Lampoon you do hasty puddings every year who else came when you were there let's see we got oh Cosby I've talked about this a lot but we got this was back when the Cosby show was just

taking off and we got Cosby to come and so I picked him up at the airport and my dad's really fucked up station wagon that my dad bought from a motel so it's yeah and it said

Pine Lodge Inn on the side and had a painting of a pine tree and it was a crappy fucked up Ford station wagon that had just been it was a real beater and I didn't know about getting a limo so I picked up Bill Cosby who was wearing a tuxedo

and flew in on a private jet and he landed at Butler Aviation at Logan Airport which I'll never forget because I was it was burned into my mind Aviation and I picked him up and he couldn't believe he had to get in that car and for years in a nice way like a funny way or like he's

actually furious I think he was actually way put off and I used to tell this story with great shame and now that he's in prison for these horrendous crimes suddenly I look like I was way ahead of the curve I look like you know I knew he was

up to something so he had to pay did he go backseat or front seat he went backseat and found and found a big Mac Styrofoam wrapper in the back and held it up and said and what would this be and I'm like don't worry about that

my brother Neil went to McDonald's he actually works there so he gets the big Macs for free we'll be there in about 40 minutes I wouldn't touch the door if I were you Mr. Cosby it just flies open sometimes

what was the conversation though let's really dig down into this I don't remember I remember being so it was so wrong on so many levels and I think we literally did go buy a bowling trophy and saw off the bowling ball

so it looked like a man was presenting you with comedy but it was really a guy bowling and we had saw it off the bowling ball and what would he do would he have to do a speech or something and it was then that I realized what a rhythm comic he is because I was standing behind him and I think

I was like 18 or something and I was realizing and I'm standing behind him nothing he's saying is making sense but he's killing so he went out there and it was just that he's such a great rhythm performer you know he had

he could change his pitch and so it was so musical so he went out there and he's a huge star so if you have great rhythm and you're a massive star you can go out there and literally it was just like Dazzam Deezam Slous Boo and people were just going crazy and he'd go remember don't be a Junebug

be a Biggle Boo and people were going nuts and going he's right he's right and I was the whole time standing behind him going I see well the weird thing is he discovered Sandler I didn't know that Cosby discovered Sandler Sandler goes to a dinner

and he's told this story before with Anthony Quinn's family because he was friends with Anthony Quinn's son and Cosby was there and then Cosby got a kick out of him and put him on the Cosby show I mean he was on five episodes of the Cosby show. That's right that was before MTV

and me and Sandler noticed that it was all rhythm comedy when we were kids and we lived together and it was one of the things that we used to do around the apartment all the time was like impressions of Cosby for very long periods of time because we realized that it was just the rhythm

so he'd just be like you know I tell this joke where I use the word asshole I only say it once I only use the word once in the act and he gets such a big laugh that I go home I make myself a sandwich I watch a TV show and I come back

and they still be laughing and we would just do that all the time just talk and then she's making the cake and the kids are looking at me and they're like oh no dad made us eat the cake and it's so weird to have so much love for somebody

yes and then have him be the devil it's a very strange experience because it's like you don't even want to say it like I got into comedy because of him and then you find out oh no and what does it mean that I loved him so much my mom because there was a lot of kids

there's six kids and we all had to kind of go to bed around the same time all in bed on the same we were all on the same floor on the same level of the house and she would just put us all in these different rooms and then she would put a Cosby record on and also a New Heart

but Cosby it is very strange every now and then I stop myself and go he's in prison for one of the worst things anybody can ever do that's stunning to me you just think about it

like the world is scary and so we go to this world with comedians and they're all nice and they're our friends and we love making people happy so it's weird to think that the place that's our escape actually has dangerous people in it like that's the mind fuck of it

oh no my little island you know has bad stuff also and it's not rational to think that the world of comedy wouldn't also have that because every profession has bad people well also in a way comedy might have more bad people in it than other professions

you and I have both had the experience without naming names of just working with people who are very talented and absolutely miserable and I'm gonna name the names Paul Linge because you know I go to this therapist and one of his theories which is

not his theory but the thing which is that the brain wants to remember bad stuff to keep you safe so I have that story I tell this under my stand up special about having to do a toast to Mel Brooks all these people are going up before me

like Sarah Silverman, Billy Crystal he sings like 11 songs from Mel Brooks movies and TV shows and Martin Short and comes out and I had a panic attack and I left I literally left, I turned to my daughter I'm really nervous and she goes

let's get out of here that's so funny because the person you're with is supposed to go no no no you're great but to have the person with you go let's get out of here she's like dad you look white as a ghost are you having a heart attack

and I literally found the first AD of like I think you have enough content I'm going and I left and I completely got taken over by the panic of bombing in front of like Mel Brooks and Sasha Brancoin just everyone was there

it was like thousands of people and since then I've prepared much differently I just wasn't that prepared for what I was going to do but Mel Brooks is also like sewn into your brain from birth like this is the guy right it's one of those

you look up funny in the dictionary and well his picture just won't be there because it'll just be the definition it'll just be the definition of funny I mean I don't want anyone looking in the dictionary because it's just going to be the definition I went with Bill Hader to visit him

you know every once in a while I'll go visit him just to bug him I don't know him that well but I'll just show up anyway out of worship and I brought Bill Hader and he couldn't be nicer and funnier and then we're leaving and as he walks us out he goes come again

but not for a while for four to six months and as we walked to the car he waited outside to watch us walk for a long time and he's so funny he's just watching us walk and he's just still there you turn around he's still there and then we turn around and he just goes

get the fuck out of here alright well I've kept you here way too long and I do apologize but I love talking to you this is great this is really great and it will never it'll never be heard I'm having this destroyed as it should be

keep it pure hey man it's just for now man it's just for this moment don't monetize this shit Conan oh trust me we have not I'm driving a Kia on the way home thank you so much for doing this this was really cool thank you

okay let me explain what's happening right now we are actually at my house we're in the basement of my house where it's nice and quiet and it's Sona and I and we had to tape some ads they needed to go out and then I realized

hey we're here without our producer Matt Gorely this is our chance to dish on Matt Gorely while he's not here now don't get me wrong I love GORLS that's what I call them GORLS some of your nicknames

they're not great GORLS with a Z it's GORLS anyway he's not here so this is our chance to talk about him dish sip a little tea is that what the kids saying what do they say I don't know honestly

I've heard my daughter say it is it sip a little tea you know what isn't it spill the tea well that's because you're dishing you're dishing some hot goss if you've got something to add here he doesn't have a microphone you can just lean in and say

what is it Blay or you say something and you say and that's the tea I like saying let's brew the tea let's brew the tea or let's let the tea steep then we'll use some sort of mash

to keep all little detritus out of the cup and then we'll pour the tea into the cup and enjoy the tea hence gossip do you like my way of saying it it's so long well it's a process

doesn't it take so long can't you just say spill the tea that's not what the way I like to say it let us brew the tea let it steep so the nutrients and flavors from within the leaf can become part of the broth

then strain aforementioned tea extracting with mesh all detritus and then sip the tea as it goes from warm to you know you're laughing

and then you're always putting the microphone away denying me of the one thing I really need which is laughter you need it so badly yes I do a drug addict and that's the drug oh I was going to say like tinkerbell but I remember you made that analogy in the documentary

you shot ten years ago where you're like tinkerbell like you need applause or else you die yeah yeah without laughter and applause I die I'm sorry I moved the microphone away from me if someone's not laughing at me then I don't exist well not only did you I'm laughing but you needed to make sure people knew

also if I haven't made someone laugh within a 24 hour period it means I never did exist all my past history is erased it's a weird thing it's sort of like what's that movie with Leonardo DiCaprio where buildings fold into themselves the revenant

yeah yeah the revenant remember in the revenant how skyscrapers fold in on themselves yeah yeah I'm sorry come on gorley inception

be nice to me gorley's not here okay let's talk let's spill the tea on girls yeah let's brew remove detritus drink said tea and then spill said tea if there's any left over after we drink it

on girls now listen I love the guy and he does an amazing job you know he's like considered a god in the podcast world I know hell we're in my house because someone's ringing the bell who is it it's probably gorley gorley probably knows we met without him

and he's he has a sensor they're talking so he probably got into his vintage sob and anyway but he's not here and I just want to say I do love the guy he's a maestro yeah do you think that it's wrong

that we're talking about him when he's not here to stick up for himself no no no that's the best time to talk about people behind their back yes yes I grew up Irish Catholic as you all know and I grew up in a family where you never confronted anybody at all you just don't what you do

is you wait till they're out of the room don't you think that that's wrong and that you should talk to someone yes directly it's terribly wrong but you want to continue doing it there are a lot of things that are wrong that we keep doing right right I still eat pizza

I'm not supposed to eat pizza pizza's amazing no it's terrible and it's wrong but this is the best time to talk about gorley because he can't stand up for himself because when people defend themselves it's just a waste of time it's a time what does that even mean

it means that when someone says wait a minute you just said that I like to defend myself that's all time wasted right so in your perfect world you just go after someone they don't stick up for themselves they can't they're not there you're awful

that's awful so anyway gorley yeah he's does it upset you that he's so popular in the podcast world and you just started off in this business it doesn't really bother me I'm very good at reverting to my own

narcissism my narcissism saves me it's like Iron Man's you know shell it's good you're a narcissist well yeah have you looked at the news lately narcissists are killing it narcissists are killing it out there

but anyway so no gorley let's list his positives quickly and then move on to the good stuff he's really nice he's very friendly he's got a lovely funny beautiful wife he seems to be

good at a lot of things he made these beautiful craftsmen style lamps that looked like they were made by a professional he's handy and then I just think that he you know

he sometimes gets in my grill you've seen him do that for someone who's known you for not that long it's actually impressive that he does that he fights back I think in the early episodes of this show gorley didn't know he was like oh my god this guy's coming after me

you know and let's face it I am a known figure in the world sort of like whatever I don't know a dandy or oh my god I'm just listing people that are also known that's not right

or Betty Crocker didn't eat enough and won oh there's gorley trying to get in again to stop me from relating gorley now wants in can you hear that? gorley wants in because he knows I'm about to list Betty Crocker and Gandhi

in the same sentence my point is what is the point really I wanted to you want to make fun of gorley when he's not here you know what I'm realizing right now it's not as fun when he's not here there you go isn't that nice

because I can't see his face contorting it's not like he looks like he's enraged but he gets this constipated look when I'm going after him he does and he's not here and that makes it less fun so I'm not going to stop because of moral reasons

I'm stopping because I like to see my victim as I attack so we learned a valuable lesson here which was you usually like to talk about someone behind their back but if you do that you can't see them feel pain

oh my god this worked out you've really matured I think I took a big step here so thank you I'm glad see there is some value to meeting in my basement

and talking a little bit about gorley and learning how to say drink the tea your version of spill the tea is probably not going to catch on you'll see it's going to be everywhere 16 year old girls everywhere

are going to be saying oh my god brew the tea and then remove the detritus with mesh then let it cool and then sip alright okay we should get out of the basement

I want to go home you want to go home Conan O'Brien needs a friend with Sonamov Sessian and Conan O'Brien as himself produced by me, Matt Gorley executive produced by Adam Sacks and Jeff Ross at Team Coco

and Colin Anderson and Chris Bannon at Earwolf theme song by the White Stripes incidental music by Jimmy Vivino our supervising producer is Aaron Blair and our associate talent producer is Jennifer Samples the show is engineered by Will Beckton you can rate and review this show

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