Inside Conan: An Important Hollywood Podcast - Pete Holmes Revisits His Foray Into Late Night Television

Episode Date: May 31, 2023

Actor, comedian, and author Pete Holmes joins Mike and Jessie to discuss Conan plucking him from obscurity and donning him with a his own Late Night talk show, much like Lorne Michaels did for Conan i...n 1993 and how that opportunity led to his meeting of Judd Apatow and the eventual hit HBO series Crashing. Got a question for Inside Conan? Call our voicemail: (323) 209-1079 or e-mail us at insideconanpod@gmail.com. 

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Starting point is 00:00:00 And now, it's time for Inside Conan, an important Hollywood podcast. Hi, and welcome to Inside Conan, colon, an important Hollywood podcast. I'm one of your hosts. I'm Jesse Gaskell here with Mike Sweeney. I'm one of the other hosts. That's me. Yeah, that's you. Right.
Starting point is 00:00:30 And yeah, and we're co-hosts. Yes. Where two people do the work of one or half a person, a quarter person, but we do it, damn it.
Starting point is 00:00:42 Yes, we do it. We do it in style. Yeah, we sure do. I mean, if you could see how we're dressed right now, that style is the word. We're allowed to wear whatever we want because we are on strike. Right. But you're not allowed to point it out. That's. We are on strike. And what a segue into. Yes. Our current state of affairs yeah yeah yeah we're on strike yeah the writers guild that is have you been in unions prior to this prior to the wga no no no yeah in in your work history okay no i've been in unions but i never yeah you were in the mailman's
Starting point is 00:01:18 union i was in the mailman's union i was in the amalgamated Meat Cutters Union. Really? What is that? I was a deli worker at A&P. Oh, my God. There's a union? Of course. Amalgamated Meat. It's called the Amalgamated Meat Cutters Union, which I just love that name. Is the meat amalgamated or the union is amalgamated? Head cheese.
Starting point is 00:01:38 Okay. It qualifies. Yeah. And then when I was a stand-up comic, they tried to unionize. Oh, my God. In New York. And they formed. Oh, that's kind of hilarious.
Starting point is 00:01:50 And they had a meeting. I went to the meeting. It was just bad comics trying out their material. And that's when I learned. I literally was like, I will never go to another meeting. Yeah. A union meeting. So, yeah, we're hoping this strike gets wrapped up quickly
Starting point is 00:02:05 and in our favor of course yes whatever that whatever that means i i think wrapping it up would be in our favor yeah i think we'll get to that point sure pretty quickly yeah um do you write i don't write slogans on my signs oh god i. I don't. I did. I did end up writing one, but I really, I stressed about it because I, you know, it's, it's basically your calling card and people have been Instagramming all the funny signs. And I've seen a lot of funny ones that made me laugh. Yeah. So I just felt a lot of pressure to be hilarious. But then I thought there's nothing worse than trying to be funny and coming up short.
Starting point is 00:02:46 So I ended up not really going with a funny one. Yeah, yeah, yeah. More poignant one. Oh, very nice. Yeah. Good for you. If you see me out there,
Starting point is 00:02:54 you'll see my sign. Do you write up a new one every time? No. Do you take it with you? But I might have. Yeah, I took it with me. Is that true? I like it.
Starting point is 00:03:04 Okay. Yeah. Just to have it because otherwise you end up with you? But I might have. Yeah, I took it with me. Is that true? I like it. Okay. Yeah. Just to have it because otherwise you end up, you start the day and you have to look for a sign that someone else has written and you have to decide.
Starting point is 00:03:14 You could spend hours just looking through all the signs. That's what I did. I like, I'm going through. I feel like it's a bargain bin of like. Yeah. And they're there. Yeah.
Starting point is 00:03:22 Road records. Yeah. There's some bad ones. And yeah, and you don't want to, you don't want to hold a sign that's not you no no i i feel like a bad sign is only going to prolong the strike they're going to be like hey wait a minute oh this is the kind of writing you're doing exactly i know uh anyway this season yeah we if you're still with us we are covering conan on Road. And that means Conan,
Starting point is 00:03:45 that's outside Conan. Anytime Conan stepped away from the desk to go on a remote or do a travel show. Bathroom break, anything. Anything. We are discussing. We've got it. And today we're joined by the hilarious, this is extremely outside Conan, Pete Holmes. Pete Holmes is hilarious. And he had a really funny talk show. He did. On TBS. That was filmed in the Conan studio, but it was not Conan. So I feel like that counts.
Starting point is 00:04:16 Yeah, it was shot right next door. And it was produced by Conan and Jeff Ross. Yeah. So a lot of people from our show helped get that show up on its feet. Yeah. So here's Pete Holmes. Here's your cold open. Okay.
Starting point is 00:04:36 Okay. Thank God. For three seasons, we've been looking for one. I feel great about being Conan O'Brien. Good, good, good. Oh, no, that's not the podcaster. Oh, I'm so sorry.
Starting point is 00:04:49 I know Mike White. Did you think Conan was going to be here? I never heard that on a podcast. I know Mike White! I was on The Amazing Race with him. Who says that? I meant not Mike White. Who's in The White Stripes? Oh, Jack White. There's a Jack White, there's a Jack Black,
Starting point is 00:05:05 and there's a Mike White. You clearly don't know Jack. You don't even know Jack White's name. I don't know my whites. I don't know my whites. I don't see color. They have their time. Yes. They have their time.
Starting point is 00:05:13 It's over. And I'm into the... Say the three white people talking together. Talking about nothing and being recorded. We're like Hitler in his bunker.
Starting point is 00:05:24 It's the last days. It does feel true. For these three white people. Yes. Oh, we are recording. Yeah, like Hitler in his bunker at Celestis. It does feel true. For these three white people. Yes. Oh, we are recording. Yeah, yeah, yeah. Oh, yeah. We're not ashamed
Starting point is 00:05:31 of anything we're saying. I, I, I, I. Yeah. Here's a cold open. Yes. What's our podcast? You've never brought in Leon the Professional.
Starting point is 00:05:39 That's me. And you guys are Natalie Portman and you're 12. Is it appropriate that I'm a hitman and I took you under my wing? In the 90s, it was fine.
Starting point is 00:05:47 It was fine. Absolutely cool. It was fine. It's called mentoring. It's called older mentoring. Yeah. But look at her now. Nothing is okay.
Starting point is 00:05:55 That was okay in the 90s? Yeah. Yeah. Finished your sandwich. Right. When did we all start saying we finish each other's sandwiches and we're like, but now it's the new phrase. Oh, is it?
Starting point is 00:06:05 It was a joke. It was on Arrested Development, wasn't it? It was on Arrested Development. And so were a lot of things. You're saying it's not a new phrase. But it's bled into the vernac. Here's your cold open. My father, if you give him a gift, he takes it as an assault.
Starting point is 00:06:21 Like if you, because he will be like he doesn't. Even on his birthday? You give him, give me these lentils and I'll be my father. Pete, can I offer you? No, Pete's dad. Okay.
Starting point is 00:06:33 How do I know you're not Pete Jr.? I don't know your fucking dad's name. My name is Jay. Oh, Jay. Okay. All right.
Starting point is 00:06:39 All right. Jay, I went out on a limb and got you a bag of lentils. Half-eaten lentils. I just assumed you were Jay. got you a bag of lentils. Half-eaten lentils. I just assumed you were going to- Oh, just exactly what I wanted.
Starting point is 00:06:50 He has to immediately put it down and cut your legs out. Yeah. Because it's too vulnerable. He's so old school that if he was like- Thank you. Sweetie, I love pink Himalayan salt. Like, that would be too much vulnerability. It would.
Starting point is 00:07:08 Pretty gay. Also, he doesn't know me. He doesn't accept a gift. He knows you. Well, that's our cold open. He reads the credits. Are you mocking? No!
Starting point is 00:07:18 It was a fine cold open. Thank you. It's cold. Oh, a cold open. It's cold. Pete, just what I was hoping for. It's cold. Thanks, Pete. A great cold open. It's cold. Oh, a cold open. It's cold. Pete, just what I was hoping for. It's cold. Thanks, Pete.
Starting point is 00:07:26 A great cold open. It was a good, it was a, it wasn't. Roll that theme music. It was a good cold open. We should do cold opens from now on. Do you not do a cold open? You don't do like a little taste? Do you do a cold open on your podcast?
Starting point is 00:07:37 Yeah. We just started doing a little taste. Just a little taste. Yeah, what prompted that? Was that a note or you just. A note. I listen to other people's podcast, just like all of show business.
Starting point is 00:07:48 I just heard it on someone else's podcast and I was like, that gives a little taste of where it's going. A little teaser. I listen to someone else's podcast today to prep for that person being on my podcast. Sure. The whole world is just podcast, podcast, podcast.
Starting point is 00:08:03 It's a verb, it's a noun, it's a place, it's, podcast. It's a verb. It's a noun. It's a place. It's a job. It's a calling. It's a passion. Soon a building. A state of mind. And now it's a building.
Starting point is 00:08:11 Right, right, right. But I was listening to you on their cold open. Oh, I should tell you what show it was because that would be nice to them. Yeah, let's get them on. Let's get another podcast. Now we're plugging other podcasts. It was called the DOAC podcast, Diary of a CEO. Oh.
Starting point is 00:08:26 Oh. He does a cold open. This motherfucker. No wonder he's a CEO. He opens with four minutes of cold open. What? Just the best snippets of the entire episode. That you're about to hear.
Starting point is 00:08:40 Before any ad. There was no ad. Before any welcome to SiriusXM, nothing. Just pow, pow, pow, pow, pow, pow, pow, pow. And I was like, that was incredible. You know when you see someone else doing what you do but with like effort? Professionally.
Starting point is 00:08:57 And a plum. And you're like, oh, like you're embarrassed. Like you're suddenly, you widen at the buffet. I'm in a wet bathing suit at the buffet. You widen and there's chandeliers and white tuxedos
Starting point is 00:09:11 and everyone's like, I'm a woman with a monocle goes, he can't, you know? And I'm just like, what? I swam up. Or if you're like me, you just assume he's doing it to show me up.
Starting point is 00:09:22 It's like this motherfucker. Ah, you're like my dad. What are show me up. It's like this motherfucker. Ah, you like my dad. What are you thinking about? That's exactly what I wanted. Is that his name? Jay. John. John. John Holmes. John Holmes. John. In our family, we called him Shorty. Ah.
Starting point is 00:09:37 Sorry, John Holmes. See, you're too pure or young. Oh, I thought that was a John Holmes of porno actor. Oh, he's a porno actor. Oh. Does he have a short penis? No, I thought there was a John Holmes porno actor. Oh, he's a porno actor. Oh. Does he have a short penis? No, he has a huge, huge ding-dong.
Starting point is 00:09:50 Huge but short? No, no, no. We go, growing up in my family, so my dad's name is John Holmes. Yeah. My brother's name is John Holmes. We got a lot of crank calls.
Starting point is 00:09:59 Back in the day, you crank the call and you'd just go in the phone book looking for names of porn stars. Yeah, yeah. You'd call Mrs. Whitehead and she'd be like, yeah, when are you gonna pop? You crank the call and you just go in the phone book looking for names of porn stars. You call Mrs. Whitehead.
Starting point is 00:10:09 Yeah, when are you going to pop? We call Bruce Wayne and we go, Wayne, it's the Joker. And if you want to see Robin again, we've got him down at the warehouse. And they were like, yeah, yeah, yeah. Oh, boy. Let me put you on hold. I'm on another Bruce Wayne prank call. Thank you so much for this humorous prank call.
Starting point is 00:10:26 Well, we appreciate the attempt at levity. We also ask you to respect our residential... My mother has lupus. That's the whole thing. The phone frightens the dog. And while, yes, your take was unique
Starting point is 00:10:39 and refreshing. Now you have to text them, you know? It's not the same texting Bruce Wayans. No, you have to bet they're hard know? It's not the same texting Bruce Wayne. No, you have to bet they're hard to track down as well. What was I saying? John, you're growing up. Oh, so they're both
Starting point is 00:10:51 named this huge wiener porn star. Boogie Nights is based on John Holmes. So we would get these phone calls and they'd ask for John Holmes and they'd be snickering and laughing. So the family joke was that my father, who would sometimes take these calls,
Starting point is 00:11:08 would go like, in our family, we call him Shorty. So the joke that I grew up in from like six years old was like, we have bigger dicks than John Holmes. Yeah. Which I'm not complaining. No.
Starting point is 00:11:22 Like you'd think I'd be like, that's weird. I was like, my family to this day even though I grew up religious and a little bit uptight in certain areas like jokes were always okay here's an example my mom she's like
Starting point is 00:11:37 your father called me a bitch and I go were you being a bitch and she laughs so hard my dad morbid jokes. Like you can be like, well, I'll see you next time. And he'll be like, well, and I'm like, yeah, unless you die. And like, everybody's like,
Starting point is 00:11:51 I'm just like, I wouldn't say I talk shit about my family. I'm just, I'm one of those mopey. Like I like feelings. I like going into the dark corners of my psyche. I'm going to say something very positive about my family. We love jokes.
Starting point is 00:12:04 And like way before it was cool or like normal, I'm going to say something very positive about my family. We love jokes. And like way before it was cool or like normal, we had the like, if it's funny, it's okay. And even on crashing the show I did, I had them sign a release because the lawyers wanted me to sign, get them to sign a release. And they didn't care at all. They were honored to be mocked on our show.
Starting point is 00:12:22 I know, yeah. So you don't have, because I know a lot of comedians, especially that have a thing where they're like, I have to wait until my family's dead to be able to talk about certain things. A lot of people.
Starting point is 00:12:31 Yeah. I know a lot of people. I know a lot of, I feel like that's too dark, but there are a lot of people that are waiting for sexual revelations. Oh, yeah. And that's a tragedy.
Starting point is 00:12:40 That's a tragedy. But my family would, I don't know how that'd be if I was gay, but they would have to fucking deal with it. I'll tell you right now. Yeah. I would love to break their hearts. Not break their hearts,
Starting point is 00:12:50 but I'd love to just rock their boat. Just say anything. Yeah, you could do it. I know. You could do it. I know. I wonder how they would take it. Just for fun.
Starting point is 00:12:58 My dad would be like, come on, get out of here. Just exactly what I want. It's a bit, right? It's a bit? You call them bits? He knows the bits knows you're doing this just to spite me
Starting point is 00:13:07 he knows the bits so when you were six yeah big dick joke did you did they explain about who John Holmes was
Starting point is 00:13:15 and yeah I don't or you just understood it instinctively yeah you heard it he also died of HIV right
Starting point is 00:13:22 HIV oh so I knew that too. Wow. So when it was explained to me, there was a big ding-dong porno star who was very coked up and tried to break into the mainstream of movies.
Starting point is 00:13:34 And he was also one of the first, I think, notable or known people. Yes. He'd get HIV. And that sort of began the thing. But I also think that didn't help the, I don't know if it was part of the stigma. It probably ruined the prank calls.
Starting point is 00:13:48 It's helping the podcast. It's helping the podcast. HIV, AIDS, people want to hear about this. Sure, they do. On a college podcast. We usually always segue into 9-11. Yeah, we do. But it's kind of-
Starting point is 00:13:59 Hitler in the bunker. Yeah. Why was he in the bunker, sweetie? What had just happened? Oh, it's okay to skate on the thin ice, but I can't jump in the water? I think an army was invading his beloved Berlin. So he went under Berlin. Well, hey, Pete, I hate to lay tracks for this train.
Starting point is 00:14:20 Lay tracks. I'm so sorry. Because I honestly don't know. How did you come to be in the Conan cinematic universe? How did you get your... I don't know that either. Your talk show. You actually caught the UV blocking umbrella that he keeps his whole staff under. He goes, we'll be safe under here.
Starting point is 00:14:44 Okay. I was doing stand-up comedy and I wanted to be on Conan by the time I was 30. That was my goal. Oh, that was actually, you had kind of written that out. I had, what if I ruined the podcast? I manifested it.
Starting point is 00:14:59 Just everything sucks. The whole rest of this thing sucks. I believe in positive vibes and I believe in setting intentions. I like to say, you don't get everything you manifest, but you did manifest everything you get, if that makes sense.
Starting point is 00:15:11 Meaning, you do hit what you aim for. You don't always hit it, but if you hit it, good chance you were probably aiming for it on some level. Yeah. So I did set my sights on doing Conan. Cool.
Starting point is 00:15:22 I didn't really watch him very much until I moved to Chicago, which is when I started doing stand- Cool. I didn't really watch him very much until I moved to Chicago, which is when I started doing stand-up when I was 22. I had been doing it for a couple years, but I got serious
Starting point is 00:15:31 when I was 22. Okay. I'm just curious. What year is it? No, I don't care how old you are. It's your favorite year, 2001.
Starting point is 00:15:40 Any riffs on 2001? A clear Tuesday? Not a cloud in the sky? Are we getting warm? You knew exactly what I meant. Where were you doing stand-up for two years prior to moving to Chicago? Barely in Boston. Okay.
Starting point is 00:16:01 Barely. I imagine that's a hard time to break in. It was. And I just didn't know what I imagine that's a hard time to break in. It was. And I didn't know, I just didn't know what cocaine was. And you didn't talk fast enough. I'm not even kidding. I mean, it's just. Hilarious.
Starting point is 00:16:12 And I don't mean that in a bad way. No, I'm not saying like hilarious, like some tough guys are like, that's hilarious. But they want to fight you. I mean it like that's hilarious. I was just so, I was religious and I was sweet. It's like, just picture Jack McBrayer and I'm going into comedy clubs. I'd rather not. Me too.
Starting point is 00:16:28 That guy's a, he's a knife wielding savage. Also very tan though. Is he? I don't care for that. Okay. So you're in Boston. And so what made you move to Chicago? Did you have friends who were comics who were there
Starting point is 00:16:39 or did you feel like it was suited, would suit you better or something? Well, I'd never felt like Boston was going to let me be a grown-up inside of it. I'm one of those prophet in his hometown people. Like, I still feel like a child when I go to Boston. I don't like the feeling it gives me. If you're not from Boston and you're not from Boston, go to Boston. You will love it.
Starting point is 00:17:01 I go to Boston and my penis goes inside my body. I hate it. Like, I can't go back to my high school. It I go to Boston my penis goes inside my body I hate it like I can't go back to my high school it's terrifying to me even yeah so Chicago
Starting point is 00:17:10 but I got a sense but I wanted to be on SNL so I was like what did Chris Farley do and this is like very early internet pre-internet basically so I'd read books
Starting point is 00:17:19 about Second City and it basically sounded like truth and comedy all of that. Yes. And actually, Truth in Comedy was a big one
Starting point is 00:17:27 because that was like... In Truth in Comedy, it says, it's very... In fact, I call such hard bullshit on this, but Sharna Halpern is like, stand-up comedians are like
Starting point is 00:17:37 sad, lonely Arthur Miller salesmen. They go around and hawk their gags for pathetic laughs and then go cry in a holiday inn. Improvisers. Not like improv. They were like, behold the improv. They made it sound like, let's talk about good mental health.
Starting point is 00:17:52 They made it sound like Mormonism. They were like, it's a community. There's game night. There's free beverages and everyone's yes-anding and it's corporate and communal and beautiful. Nobody gets paid. But I totally, exactly. It's basically, it's a beer drinking group with an improv habit.
Starting point is 00:18:09 Yeah. I believe that was an Onion headline. But I was like, I just needed some guidance and that's all I had to go on. And what Farley did was he lived in Madison. He went to Chicago. Mike Myers was in Toronto, I believe. Went to Chicago.
Starting point is 00:18:26 Or maybe he did Second City in Toronto. It doesn't matter. Everybody was doing Second City. Yeah. I was like, I believe went to Chicago like or maybe he did Second City in Toronto it doesn't matter everybody was doing Second City yeah I was like I'm gonna do Second City
Starting point is 00:18:29 I'm gonna get an SNL because in college everybody was like you should be on SNL because nobody knows anything but you're the funny guy so you're like you should be on SNL
Starting point is 00:18:36 and I was the tall lumbering improv not celebrity but like the I'm gonna to own.
Starting point is 00:18:46 I was the standout of my college. Yeah. Yeah. Says the professional comedian of 22 years hesitantly. You know, I did sort of, I did well. I did well. Well, we looked up every member of your college improv team. They're here now.
Starting point is 00:19:02 That's why these screens are here. I wasn't the most beloved though. That's why these students are here. I wasn't the most beloved, though. That's why I hesitated. It wasn't that I wasn't liked, but some people were just like the favorites socially. And then the game would start and I'd be like, scoreboard! But nobody likes that guy. I wasn't cocky about it. They were better at being everybody's friend.
Starting point is 00:19:22 And I was very like hyper focused. Yes. I was very loud. And then I got to Chicago and I realized, like I'd go to a Second City audition or something and everybody looked like me. It was all six foot five. They're all six foot six.
Starting point is 00:19:36 Oh, you know what? There's a lot of giants. There are a lot of giants. Actually, now that you mention it. Yes. And we all like looked at each other. In your same plaid flannel. We just had different hats.
Starting point is 00:19:47 Like some were cowboy hats, some were trucker hats, some were fedoras, but we were all the same guy. And we're like, there's only one slot. So then I realized very quickly, I moved to an improv city to do improv and ended up doing standup.
Starting point is 00:20:01 I worked at Bennigan's on 150 South Michigan in San Juan Walgreens. But I would walk, my stop was Irving Park, Irving Park Brown Line. So I'd walk past a place called the Lion's Den every day on the way
Starting point is 00:20:14 to the train. And there was a sign, all it said was Monday comedy. And then Tuesday, other things. But you know, Monday comedy. The too much detail guy.
Starting point is 00:20:27 Taco Tuesday. Wine Wednesday. Totally unnecessary. I can't remember for the life of me what Wednesday was. Because all you cared about was that stand-up night on Monday. Tell us what happened. Yes, can we talk to him?
Starting point is 00:20:42 The guy that saw that side. So I was so, I was scared. I think I had a sense that it was a standup night, but I just went in the back just to see the room. Yeah. Not on a Monday, just to see where it was. And it was this little box. It was actually perfect, but I didn't know anything about comedy rooms, but I was like, it wasn't very big. I was like, okay. And I left. And then the smartest thing I did and sort of the best advice I have for people that want to do standup.
Starting point is 00:21:11 And then I die. There's your cold open. Cold closed. Cold open number three. I went and watched. And that's the best advice I can give is you're so scared. You think everyone's going to be so good.
Starting point is 00:21:28 And I was raised by an overloving mother and a withholding father. And that's a recipe for talent. That is a recipe. So I went in. I was ready to be a comedian, but I was still very scared. And I went in and I watched. And I'm not being cocky. I feel like a lot of people would feel this way.
Starting point is 00:21:44 I was like, I could smoke all of these fools. It was terrible. You said AA meeting. It is a little bit like a lot of these people are unstable or just in a rough spot. They're just kind of getting up.
Starting point is 00:22:00 And going back to my earlier point, stand-up wasn't like I'm not saying it was for dorks or anything but it was a fringe activity. And like going back to my earlier point, stand-up wasn't like, I'm not saying it was for dorks or anything, but it was a fringe activity. So like, we weren't, you wouldn't watch and go like, oh, he's doing Seinfeld,
Starting point is 00:22:13 or maybe Seinfeld, but he didn't have the lexicon that we have now. So it's just a bunch of people doing bullshit, some funny people. And that was the smartest thing I did because the next week I went and I signed up and I started doing it. And I had done it in Boston, but that really felt like my start. Oh, that's great.
Starting point is 00:22:30 Yeah. And, and so. And you were immediately good at it and that's the end. One week later, you had your own show. The trouble with social media and YouTube and all these things, there's that great line in Inside Llewyn Davis where they're like, Oscar Isaac goes, I never released the early stuff. It kills the mystique. And I really think there's a killing of the mystique that happens now. It's because you start and you start posting your clips immediately.
Starting point is 00:22:59 You don't have that whole learning curve. You need to be underground for a little bit. And that's what was awesome about Chicago. I'm not saying it's underground necessarily anymore. But before you moved either to New York or LA. Exactly. And it was just to be the best person in the scene. And not even necessarily to make it.
Starting point is 00:23:18 I definitely was like, I'm going to be a comedian. Full stop. No joke. That's what's happening. And plus there's less pressure probably being there. There was. Yeah. There's other details in the story.
Starting point is 00:23:29 I got very lucky when I was in Chicago. The few times I opened for somebody, it was Bill Burr and Jim Gaffigan. Oh, wow. Literally the two times my friend Dan Kaufman. So you really had a community already of people who either were already doing well. Yes.
Starting point is 00:23:42 And when I moved to New York, I got a phone call from Jim Gaffigan and he was calling to ask me to open for him in Indiana. And I was like And when I moved to New York, I got a phone call from Jim Gaffigan and he was calling to ask me to open for him in Indiana. And I was like, I just moved to New York. And he was like,
Starting point is 00:23:49 well, I can't fly you out. I was like, okay. So I was like, ah, fuck, but at least we were in touch. I have so many stories. But that was the other, the other thing I tell people
Starting point is 00:23:58 that are doing stand-up is I was like, don't try to be funnier than Kevin Hart. Try to be one of the funniest people just on the show. Right. Just try to shine on just that show.
Starting point is 00:24:10 Yeah. And that's your mark. And if you're doing an open mic, and those days at the Lions, and 50 people would sign up, it would take hours. Yeah. So, you know, if you could be in the top five of those people. Right.
Starting point is 00:24:22 And you know, what will really give you a leg up is if you have a coherent beginning, middle, and end. If you write your set. Yeah. You'll be... Cold open. Yeah, if you do a cold open
Starting point is 00:24:31 and a 9-11 and a Holocaust and an AIDS, you're in business. Smooth sailing. You got bingo. It's just mop up after that. If you're not drunk and if you're not just trying
Starting point is 00:24:42 to say things you're not allowed to say, you're way ahead. Yeah. And if you write a beginning and if you're not just trying to say things you're not allowed to say, you're way ahead. And if you write a beginning and if you study comedy, I don't mean to make it about this, but like even when I wasn't that funny and I wasn't, nobody is, I had a beginning and in what I thought might be around the four minute mark, I'd try to do a callback. You came back to something.
Starting point is 00:25:02 I'd try because I saw the pros doing that. And I remember my parents came and told me, this was actually in Boston. I can't believe I was okay with them coming to see me. I still get terrified of that. But they came in and they watched me and they still talk about this, that the host of the open mic at the Comedy Connection, I didn't do that well.
Starting point is 00:25:18 I did okay. I still remember the routine. It started talking about free samples at the food court in the mall. I remember this is a joke. I remember I go, food court? I was a big Seinfeld guy. What is this?
Starting point is 00:25:31 Where rebel foods go on trial? Wait for the tag. I go, you're going to fry for what you did, chicken. It's terrible. But I talked about the free samples. And it was this whole like- This is the reason you had to move to Chicago. Oh my God.
Starting point is 00:25:46 I had to run from my past. After that. The routine was, I don't think I've ever really talked about this. Not that it's hot take, but when you do your own podcast, you get excited when you're like, I think I found something.
Starting point is 00:25:58 Something I've never said out loud before. Something new. You guys know. You guys know the thrill I'm talking about. But I, it was talking about that you would take a free sample
Starting point is 00:26:09 it was always general in Boston you call it general gow's chicken general so's chicken I believe most of the world calls it one drunk guy at a Red Sox game
Starting point is 00:26:17 said gow's and you're like I think it's what the fuck you're saying to me and it was just gow's it's now gow's oh are you from China
Starting point is 00:26:24 yeah oh you're from China you you from China? Yeah. Oh, you're from China. You're from China. And you come right to Fenway. Like, where do you get the G in that word? It's TSO. Anyway, I got to go through gal pre-check.
Starting point is 00:26:38 Gal. That was a stretch. That was a stretch. I know what you were doing. And I love, that's all I need. In comedy, if you know what I was going for, still a B minus. I talked about how you would take a sample.
Starting point is 00:26:54 You just have nothing to talk about. I'm 20, 21 years old. You have nothing to talk about. You just need something. I haven't been in a bar yet. Exactly. You just need something. Maybe I was 20. And I was like, just talking about,
Starting point is 00:27:06 you'd eat some of the General Gals chicken. You don't want it, but it's so good. You buy a plate of the chicken. And I think I started, it's called a false premise. You go, how do they afford to give away the free chicken? That's a false premise. The chicken costs two cents. Like that's, I didn't know anything,
Starting point is 00:27:23 but I'm arguing circular logic to prove the stupid point. How do they afford the free chicken? Then I thought about it. This is so stupid. You eat the chicken, then you order the plate. You don't even want it. You leave it. You walk away. They come by, put in a couple of toothpicks, right? And like, that's the punchline is an ellipses. Yeah. They put in a couple of toothpicks. You're just hanging out. I threw that one over. You guys, I think I'll wait.
Starting point is 00:27:52 I'll leave this here. You can finish my sandwich on that one. That was my ellipses. That development is not a rest. I like the way you were kind of doing your early. You were kind of doing. Yeah. My Seinfeld-eld-esque back then.
Starting point is 00:28:06 You put it, well, you had to. See, what Seinfeld is a master of is he figured out that there's how you say it. Right. It's an attitude. Like, what's the deal is an attitude. And most people, the mistake they're making, and I'm sorry, I don't mean to turn this into a stand-up tutorial. No. Most new comedians, I want to pull them off stage and go, how do you feel about what you
Starting point is 00:28:25 are saying? Yeah. How do you feel? Because there's a lot of autism. There's a lot of like brilliance and there's a lot of heavy stuff. And someone needs to go like, where in your body is that joke? You know what I mean? I'm not saying you need to be doing this, but you need to be going. You said that is Seinfeld. Where in your body is that joke? Where are these jokes in your body? And people like Seinfeld that figure that out, that aren't naturally embodied and not, I wouldn't even say I can't prove this, but I have to think he taught himself to emote on command to get a better response. That was the only motivation to learn how to talk like a human was to get better laughs. Because I'm sure he's even more of a weirdo.
Starting point is 00:29:10 And some comedians amplify like their personality. Oh, yeah, of course. So I'll give you an example that you don't care about and you won't enjoy. I'm just kidding. When I was starting out, I wrote this joke where I go, unicorn, How about unicorn? It has no corn. Right. Then I did on my HBO special and I yell it. I go, I, it opens like
Starting point is 00:29:34 this. And first of all, the first joke of benign violation is a joke, right? The first joke is that out of nowhere, I go unicorn, unicorn, but I'm yelling right how about unicorn that's a joke yeah because the joke isn't just the word it's the joke is actually not to dissect the bird but the joke is that that's what you're getting upset about right and that can be canned and overused and fake and bad but it it went from something that's embarrassing, never say that again, to one of my most quoted jokes. And it's a stupid joke.
Starting point is 00:30:13 And by the way, my social person just posted that clip on social media. The other risk, the comments are full of people telling me about Latin. And I don't know why I looked at the comments. But I was like, you're never too old to learn. Yeah,
Starting point is 00:30:26 that's right. This is also the enemy of comedy. Some, some new comedian would post that. Somebody called the joke lazy. I don't, I really don't know why I looked at the comments. I never do.
Starting point is 00:30:37 Someone was like, look, I don't mean to, but I just got to call out this lazy joke. Like it's uni and a eunuch. And I was like, you fucking, like I'll burn down a whole,
Starting point is 00:30:48 like a reenactment village. And that's their livelihood. Just to spite this person. Like I'll burn Plymouth plantation to the ground. Do you do that digitally? Do you get into it with people online? Oh no, I'll never do that.
Starting point is 00:31:02 Yeah. I won't give the says. You have like a fake troll account. I will say it here and they'll never hear it, but I like that. No one will ever, no, I'll never do it. Yeah, yeah. I won't give this as a... You have like a fake troll account. I will say it here and they'll never hear it, but I like that. Yes, no one will ever hear it.
Starting point is 00:31:09 They'll never know. No, no, I don't mean that. Oh, that's our guarantee. Yeah, yeah. Cold open or no. So let me speed forward. I do stand up. Two weeks later.
Starting point is 00:31:18 I get good. I moved to Chicago. Yeah. Like after doing stand up for very short, I moved to Chicago. So like six after doing standup for very short, I moved to Chicago. So like six, maybe did it six times in Boston.
Starting point is 00:31:29 Moved to Chicago to do improv. Walked by the thing. Monday nights. Comedy Monday. Didn't get into anything I auditioned, except I got an improv team, but there wasn't enough action. I need,
Starting point is 00:31:42 you know, it's like late night. I like that. I want to turn and burn i want a new joke new monologue new laugh let's go let's go fucking improv look i love improv but this fucking get your 10 idiot friends together to rehearse once a week to perform once a month i'm like you guys are not snorting the same powder I am. I've never done cocaine. I'm just saying I'm in this. I want it.
Starting point is 00:32:07 I actually need it as an anxiety reduction. So I was like, look, we either need to rehearse every day and do a show four times a week or I need to start doing standup. I'm really glad I started doing standup because that is all the thrill and all the pain. It's all the risk and all the reward. And I preferred that.
Starting point is 00:32:28 I was like, I'll eat shit and want to like cry. You bombed so badly. If it means maybe in three weeks, I'll kill so hard. And also the bad ones are like pulling the bow string back. And then the next one's amazing because you're fighting. Like you're exactly like, it's no wonder we call it killing or dying. It's like, it really is like a little battle. And when you get your ass kicked, you train harder.
Starting point is 00:32:51 This is why I don't like, Swin, you're a writer. I know you see your things on their feet, but like writers that are just sitting around thinking about a novel, I'm like, how do you, how do you motivate that? Yeah. I write because if I don't write, I die. You don't write, you get to jerk off and eat some Oreos. Like, you win if you don't write. I'm on a treadmill.
Starting point is 00:33:14 You're going for a walk in Madison County. Like, I don't understand how they do it. And yet I envy them. I envy them as well. I love that. I wouldn't trade it for the world, but if you could just kind of like find your dad's critical voice in you
Starting point is 00:33:30 and be like, tickety-tickety, tickety-tickety. There's like, I have shows coming up. I have to, I have to get that joke right. Well, and that thing you're describing, I think you had to have that to be successful. I don't think that you, I mean, doing, performing once a month, you're not going to get the experience that you need. It just wasn't working for me. You need the reps.
Starting point is 00:33:52 But wait, so after three years, you looked elsewhere and where did you end up? Well, speaking of Seinfeld, I saw the movie Comedian. It's a very fond memory. I went and saw it with Kumail. You know, Kumail Nanjiani. The most Italian Pakistani. Nanjiani.
Starting point is 00:34:13 Kumail Nanjiani and I had a big bowl of pasta. He had a unibrow and smoked parliaments at the time. This was not... Pre-Marvel. Yeah, pre-Marvel. And we went to the movie theater like where... I wouldn't even call it the movie theater. We went to the movie theater, like where, I wouldn't even call it the movie theater. We went to a movie theater where a comedian was playing,
Starting point is 00:34:29 but it wasn't on a lot of screens. But we went to opening day matinee. And we sat down, the theater was already dark. We watched the movie. Of course, it changed my life. By the time the movie ended, I was like, I am moving to New York.
Starting point is 00:34:41 And when the lights came up, we looked around and it was every comedian. It was all stand-up comedy. But we didn't know. We didn't And when the lights came up, we looked around and it was every comedian. It was all stand-up comedy. But we didn't know. We didn't know until the lights came up. It looked like... Especially the matinee.
Starting point is 00:34:51 And you all immediately moved to New York together. Well, you know, it's an interesting... It's for the bus. To me, obviously, because what I did ended up working for me.
Starting point is 00:35:01 It was a really important moment. And I wonder how many of those guys were like, I should move to moment. And I wonder how many of those guys were like, I should move to New York. I wonder how many did. And the answer isn't a lot. Kumail did.
Starting point is 00:35:09 Yeah. And I did. And look, and a lot of brilliant ones stayed. But what I wanted to do was go to New York. And I did. And because of that movie,
Starting point is 00:35:20 almost single-handedly, I told my wife at the time, we're moving to New York, like just like that. Wow. And not like, like cutting a steak, black and white.
Starting point is 00:35:30 We're moving to New York. It wasn't like that. Pack up the kids. I was very sweet and very meek. I probably just was like, what do you think? Next thing I know, we're faxing.
Starting point is 00:35:38 She was a teacher, her resume to schools that we just found on a map. Wow. Having a wife where it's like, we're moving together, that's... Well, yeah. I mean, this is my ex-wife
Starting point is 00:35:48 and she ended up being the impetus for crashing. But again, to say something lovely about her, she was very supportive and believed in me. And when we broke up, actually, she was like, you know, she had an affair and she regretted the way that it happened. But she was like, the nicest thing she said was like, I believe in you. She's like, I think you're going to be.
Starting point is 00:36:08 Oh, that's great. She said, I think I could cry. I think you're going to be one of the greats. I'm not leaving you because I think you stink. I'm leaving you. I'm leaving because I'm jealous. I'm leaving. She said, I'm not attracted to you.
Starting point is 00:36:21 She said her truth, which was, I don't, I'm not interested in being a famous comedian. Yeah. And that was great. Before, like years before I was famous. Oh, she got out at the right time. That's not for me.
Starting point is 00:36:32 Yeah. I've also joked that she also left like the year I started making good money. I was making nothing. Like she might have liked it a little more. She's holding you back. How do you like it in a mink? Yeah. But yeah, so no, she was supportive
Starting point is 00:36:48 and she did move to New York. And she was working and I wasn't breaking in and I wasn't going to start doing enough $50 spots. I wasn't getting any $50 spots. I was making no money. But then Jessie Klein, you know, Jessie Klein, she hosted a show on Wednesday night at a place called Rafifi,
Starting point is 00:37:07 which we also rebuilt for Crashing. It was just on East 11th, between 1st and 2nd. And it was this alt haven. It was like really like… I almost always show up at things right when they're ending or falling apart. I happened to show up at this right when it was fucking sweet. Three Conan writers talked about it. Todd, Levin, Dan Cronin, and Andre Dubichet.
Starting point is 00:37:32 Oh, yeah. Andre Dubichet. I think they all became friends and met there. Yes. So many wonderful people. A.D. Miles, Eugene Merman, Bobby Tisdale. I mean, it was incredible. And they were all like one of a kind.
Starting point is 00:37:49 Nobody was doing the same thing as anyone else. Did you feel like you were somewhere special when you were there? I did. This time in my life, I met Demetri Martin, another Conan writer, and I made a fake newspaper. I came home and I was so adrenalized just from meeting Demetri. And I made a fake newspaper. I came home and I was so adrenalized just from meeting Dimitri that I made a fake newspaper in Microsoft Word and put a picture of him in it. This is truly embarrassing. And wrote, I think my wife called me Pums. Well, let's hear the whole story first.
Starting point is 00:38:16 I know. It said, anti-Semite crashes Boston Comedy Club. No, it said, Pums meets Dimitri Martin. And I wrote the story of how I met him because I left it out for my wife to read in the morning. Right. Called like the Peter,
Starting point is 00:38:31 the Peter Times or something. But this is how like single focus I was. I know you didn't mean it, but I looked at you and you were kind of like,
Starting point is 00:38:41 just like a slight like, are you sure you want to tell this story publicly? Indicating Joe, our engineer. No, no, no. Her name is Joy? Joe. Oh, that's more fitting.
Starting point is 00:38:52 I'm just kidding. JK, JK, JK. So let me, I'll try to speed it up. But Jesse Klein had that show Wednesday. She and Nick Kroll had a show called Welcome to Our Week. I read about it in the Village Voice. And the way they described it, it sounded like it was a talk show, which is a show in the back of a bar.
Starting point is 00:39:14 But I got there and it might as well have been a talk show. And she worked for Best Week Ever. She was on Best Week Ever. And I think she was a writer. But no, I don't know what she did. But she was an executive at Comedy Central. And she was on think she was a writer, but no, I don't know what she did, but she was an executive at comedy central and she was on best week ever. And I, again, set the intention. I had Conan by 30, but I was like, I want to do that show. I won't tell you all the, uh, other shows I did. Hopefully like literally like a training montage, trying to get people to notice me so I could finally meet Nick Kroll at UCB,
Starting point is 00:39:46 which I did, and finally ask him, can I do your show? And finally get booked on it. Nick's not there that night, but Jessie is. I do the show. I do well.
Starting point is 00:39:55 That's important. That's key. It's not just networking. It was like, I was ready for her to see me. Preparation needs luck. Yeah. I emailed her.
Starting point is 00:40:02 I don't even know how I got her email. I must've asked her. And I just said, I thank you so much for having me. I've always wanted to be on Best Week Ever. It's like a goal of mine. And I've always wanted to do Premium Blend because that was a Comedy Central show. She didn't reply. Instead, I got an email from Fred Graver, who is the executive producer of Best Week Ever saying, Jesse Klein told me that you'd like to do Best Week Ever. Just like that. One of the coolest moves.
Starting point is 00:40:27 That's pretty good. She didn't even reply. Yeah, yeah, yeah. She just forwarded it. She just did it. Right. And he reads out, next week I'm on. Now I'm making $400 a week doing Best Week Ever.
Starting point is 00:40:36 It was fucking incredible. It became a regular gig. Yeah. It was a regular thing. That's great. I learned so much doing Best Week Ever that everyone here takes for granted. It's like attitude, rephrase the question, that say, what was it about Chuck D's response
Starting point is 00:40:53 that made you laugh? And you'd go, the crazy thing about Chuck D's response is like you learn those things that when you interview like a college intern, you go like, oh, like you don't know what you're doing. You don't know how to talk showbiz talk don't know what you're doing. You don't know how to talk showbiz. You don't know how to talk in soundbites. So I did that show. Then again, I moved to LA. It's boring. I wrote a writing sample. I did Montreal. I got my agent,
Starting point is 00:41:17 Zach Drucker and Doug Luttrehan at WME. They still are my manager, blah, blah. I wrote a modern family spec yes I submitted it haven't we all haven't we all literally I think it was
Starting point is 00:41:30 I have one too the year before they started saying no more modern family scripts yeah yeah but I'm very proud of this story too because I had never
Starting point is 00:41:37 written the spec I just they sent me a sample of a script and I had never seen the show and they sent me DVDs. This is how long ago it was. I watched a couple episodes.
Starting point is 00:41:48 I looked at the scripts. I was like, the first scene is four pages. There's a second scene. Exact cold open. The second scene is, and that scene comes back here. And I swear, I just, a beautiful mind did that. I just went like, uh-huh.
Starting point is 00:42:03 Like it took a weekend. There's math involved, uh-huh. Like it took a weekend. There's math involved. It is. I wrote it in a weekend. Wow. Because I really only did that. Right. And there is math involved.
Starting point is 00:42:13 Yeah. It's like there's a musicality and there's a pattern. Sure. And then I was like, this guy is a corny dad. I'm like a corny dad. I still remember some of the jokes I had him say as Arnold Schwarzenegger. He was playing Mr. Freeze at the time I went
Starting point is 00:42:27 I used to see you so I put in parentheses as Schwarzenegger I used to see you and I was like I think I'm getting this job and I did
Starting point is 00:42:35 oh shit I got it first back first thing on Modern Family not on Modern Family I got a job on a show called Outsource
Starting point is 00:42:43 oh okay for NBC but that moved me to LA oh yeah now we're getting closer to Not on Water Family. I got a job on a show called Outsource. Oh, okay. For NBC. But that moved me to LA. Oh, yeah. Now we're getting closer to what we're supposed to talk about. Who cares? Who cares?
Starting point is 00:42:57 Now I'm doing more standup and I'm 31 years old now. So I'm a year off my cone. Oh, wow. Yeah. I'm a little- The clock is ticking. I didn't see this wrinkle coming. I assumed. I'm so used to- Yeah. It's like see this wrinkle coming. I assumed. I'm so used to, it's like when, you know, on my 30th birthday.
Starting point is 00:43:10 Yeah, yeah. But you're 31 now. Oh, my God. 31. And you're a fucking failure. And I had already done Fallon. I broke my seal doing Fallon, which was okay. I did okay on it.
Starting point is 00:43:23 But then I really was like, I'm going to get on Conan. So I really want to, at this point I had been submitting tapes or links probably by this point to JP Buck. Yeah. Wasn't working though. But I happened to be at the improv one night when JP was watching someone else run their set and I was closing out. So I did like 20 minutes at the end. I did the joke, the Google joke. I had just written the joke about, believe it or not, this was cutting edge at the time, was I have Google on my phone and it's ruining everything. It almost sounds like a chat GPT joke because I say it's like a calculator that you can cheat at every subject, which is what chat GPT is. But so is Google. ChatGPT is just like a very sexy Google. It's like, let me,
Starting point is 00:44:08 not only will I tell you, I'll write it for you. You can also be married to me. Yeah, exactly. Now you can marry pornography. I never leave the house. It's like pornography that also makes you a huge meal.
Starting point is 00:44:22 So he did the joke about Google. Yes. And JP, and this was great. He was like, I want that joke to premiere on Conan. Oh, cool.
Starting point is 00:44:31 I've never even heard of. We want that joke exclusively. Yes. And I just, how old are you? 31. Oh, sorry.
Starting point is 00:44:42 And I just taped it on. I don't know if it was John Oliver's New York standup show or some other show, but it wasn't going to air for a couple months. Yeah, yeah. But this is what you want. You want to manufacture urgency. So I had urgency.
Starting point is 00:45:00 Yes. And he saw me live. Huge synchronous. You could just say it's a mitzvah. It was like a gift. Yeah.. Or you could just say it. It's a mitzvah. It was like a gift. Now I'm going to do Conan. I'm 31.
Starting point is 00:45:09 I do it. Then I'm writing on the other show. I had a breakup. I lost 50 pounds and I did Conan a second time. I left my writing job. It was on the Warner Brothers lot. And I walked to Conan.
Starting point is 00:45:23 Oh, funny. Literally was in the writer's room. I was like, I'll be right back. I got to go do a set real fast. You know what? I hope you took a moment to enjoy that. Nobody gave it to me. What?
Starting point is 00:45:34 Nobody. They seemed to put it off. They were so jealous. They were kind of like, how was it? How was it? I'm like. Oh, how was your little taping? My makeup?
Starting point is 00:45:43 Yeah. Why am I wearing makeup? And my favorite shirt, you know, my favorite. So the second time, the first time I didn't, the first time I'm,
Starting point is 00:45:53 I'm two 85 and I'm wearing a smock. Oh, wow. Like, uh, like I had never won the shirt. You really lost. I lost 50 pounds in between my first corner and my second corner.
Starting point is 00:46:05 Bad, bad relationship. And I did a juice cleanse, and you can tell because my skin could cook bacon in the second one. Radiating kale juice the second one. And it was that one that I didn't know that they were looking for the follow-up to the Conan show.
Starting point is 00:46:22 Oh, wow. And so I didn't know, which I'm glad. Thank God. Yeah. Thank God. I mean, although you might be really good at that stuff. A little pressure,
Starting point is 00:46:29 I guess, but I was already swinging for the fences. It's nice not to know. But Conan was really effusive and I remember, I think it was Jeff Ross was like,
Starting point is 00:46:37 he never does that. Yeah. Like he came up and talked to me for like 10 minutes and I was like, that was nice. And they were like,
Starting point is 00:46:43 he doesn't normally do that. And I was like, really, Mr. Ross? It's true. Oh, really? It is true. You say that to all the girls. It was very sweet.
Starting point is 00:46:52 And we bonded about being from Boston. I was going to say, I feel like you have a lot in common. You're both really tall. Irish. Yeah. Exactly. Spent time in Chicago.
Starting point is 00:47:02 I went to Harvard. I've been to Harvard. Harvard Westlake. But this is where I think it gets pretty interesting is that I, I, I didn't, I knew they were looking for somebody and I missed this naivety, this sort of purity that I had because my manager day was like, they're,
Starting point is 00:47:22 they're looking for someone to host a half hour talk show after Conan. And I was like, great. And they were like, so Conan wants to meet. And I was just so happy that I got to meet Conan. Like I had a meeting in his old office. And I remember I sat down and I was nervous, but I was also like oddly confident. And I was like, can I sit here?
Starting point is 00:47:42 I don't want to fuck up your shit. And I don't know why I said that. Like it was one of those like, like the first thing I sit here? I don't want to fuck up your shit. And I don't know why I said that. Like it was one of those, like the first thing I'm saying is I don't want to. And he goes, you can sit there. You won't fuck up my shit. And I was like,
Starting point is 00:47:51 oh, okay. Game on. That's when I knew we were good. And we just talked. I didn't know any, I swear I was so green in show business. I was like, aren't we going to like talk about the show?
Starting point is 00:48:03 I didn't know. I wonder if I had a pitch or something. I didn't, but I was just kind of like, and we just chatted about our families and all that stuff. But that was the interview. Yeah, it was. This is very sweet.
Starting point is 00:48:17 This is so saccharine. But he said, I don't, this is the last thing he said. He goes, I don't know what it is about you, but when I'm with you, my funny tuning fork vibrates. It's a weird phrasing, I suppose. So I had my little Warner Brothers parking pass
Starting point is 00:48:31 and I framed it and I drew a tuning fork on it. It's still in my office, but I remember being like, that's what I got from that. I got a parking pass and a tuning fork. Next thing I know, we go back to the TBS, which probably means six months. But next thing I know, we get another call. You're going to meet with Jeff
Starting point is 00:48:54 Ross, not the roastmaster, Conan O'Brien at his office. And this is how it went down. I'm sitting in Jeff's office, which used to be much bigger. Yikes. And, uh,
Starting point is 00:49:08 You weren't supposed to go up there. And I'm sitting next to Conan and he's wearing his Indiana Jones light brown leather, which I was like, it was so weird to see Conan in the wild. I like,
Starting point is 00:49:22 that was so kind of, again, I still get excited when I see Conan, don't get me wrong, but it was really like, he wears leather? Like what? He doesn't seem like a leather guy. Like I didn't know he's leather.
Starting point is 00:49:35 This deal is off. I walk. I draw the line. And in the meeting he says, well, we're going to go to TBS, tell them we want to do a talk show and we're going to tell him that we found the host. And I swear to you, I thought, who is it? I did. I went, who is it? I didn't say it. I knew well enough to shut up. But I was like, and it slowly dawned on
Starting point is 00:50:01 me that he meant me. And it was like And it was like fireworks went off in my body. But I was just sitting there like. And he knew how to deliver that news to you too. Do you know what I mean? Like kind of. He did it. It's still that way. Because he's one of the few people who's been in those shoes.
Starting point is 00:50:20 I never thought about it, of getting that kind of news. He did say, look, I would say this if he was in the room. He's like, we're going to tell TBS you have to be on the air for a year. Oh, wow. We're going to tell them you pick us up. You have to be on for a year. Yeah. It didn't happen.
Starting point is 00:50:35 But that's not his fault. You did do a couple seasons, though, didn't you? Here's what happened. It's a little more spicy than that. And then I died. We shot the pilot on the Conan, yeah. On the Conan set, which was a thrill. And the guests were Nick Offerman for one,
Starting point is 00:50:53 Bill Burr for one. That's the one we used and TJ Miller for another. So these- That's good. How much time went into getting ready to do that pilot? What was great was for the monologue, I did my closer, which was one of my best closers of all time.
Starting point is 00:51:10 And it just so happened to be clean. Okay. And I just did the story. Great. And it was like some fake way in. So you had that done. I was like, I'm doing this new thing. I'm not always the most comfortable guy.
Starting point is 00:51:22 And then I tell a story. Oh, great. But we knew that was going to murder. And it did. And we did it again when we shot the proper pilot. And then we were most worried about the guests. And the moment that it's hindsight being like, I knew we were going to get picked up.
Starting point is 00:51:37 I knew I did a good job. Because Bill Burr was the guest. And this is sort of before Bill became like the most legendary Conan guest of all time. Right. Yeah. Who always comes on in 20 Slays. 12? I'm bad with time, but that sounds right.
Starting point is 00:51:53 Okay. And he was doing a bit. And it was perfect because it was just getting a little tense. Just a little tense. A little Burr tense. You know, you get a little Burr on your sock. Yeah, yeah. You get a little Burr on your sock. You went through the meadows, you got a burr on you. And he's, he's talking about Hitler, your favorite. And he's going, he's been going for
Starting point is 00:52:15 a while and I'm, I'm the host. I'm supposed to shine. He's doing great. He's doing what he's supposed to do, but I'm kind of going like, what, how do I score and help him score? And he's going to Hitler, giving these speeches. He goes, how did he, how did he convince all those people? I've seen the speeches. And he goes, well, what was he saying? What was he, I mean, what is he saying up there? And I go, and the joke came to me, sorry to, you know, my own war story, but I lean in and I go, probably a lot of hear me outs. And the crowd goes wild. And I had gotten the card to wrap. Oh my God.
Starting point is 00:52:50 And I closed it. Yeah. And I go, when we come back a little bit more with Bill, just like my dream, I'm throwing a commercial. And as everyone's clapping, Bill goes, that's very funny. And I was like, and this is the guy that I opened.
Starting point is 00:53:06 That's right. In Chicago. And he, and it's part of why he did it. He was like, oh, that guy that I opened for. I literally opened for him
Starting point is 00:53:13 in Peoria, which is where Richard Pryor's from. Oh, yeah. Where the birthplace of the expression, will it play in Peoria? Right. Meaning,
Starting point is 00:53:19 will regular people get it? And I ate shit most of the time, but Bill liked me and it all came back. What is this? The movie Big Fish? Like, what the fuck is happening in this tale? But it's so charmed
Starting point is 00:53:33 and it's such a pleasure to remember. So we shot it. Here's where it gets kind of interesting. TBS went ahead and told us they had no intention of picking it up. Here's why I know that. And then I die. I know because the deal that we wrote out, if this goes to series,
Starting point is 00:53:51 here's what Pete gets, here's what the writers get, money-wise, budget-wise. They were like, look, we want to pick it up. We can't honor that contract. That was, and Conan knows this,
Starting point is 00:54:04 that was to placate Conan. He's our guy. He wanted to do this. We said, yes. Oh, wow. We gave you like a fake contract. Like, like, uh, yeah, we'll give you, uh, it wasn't a ton of money, but it was like, I don't know. I don't even remember what I made for that show, but it wasn't, it wasn't a ton of money and I'm not complaining, but they, the contract was more generous and they're like, we want to do it. We didn't expect it to be this good. So good news, bad news. We want to do it, but we want to renegotiate this because we can't afford to do this. That's insane.
Starting point is 00:54:39 Isn't that wild? Yeah. This is like old showbiz. That's literally like a bait and switch. I know. Yeah. Good news, bad news. Good news, bad news. Yeah. And again, it wasn't necessarily framed like that.
Starting point is 00:54:52 Like I'm saying it very directly. Right. Yeah, yeah. That's my recollection of how that happened. Nobody was like, smoke a beer for a while. Man, I called Bob. Man, I called Bob.
Starting point is 00:55:00 Nobody was like that. They were just like, my manager was like, they want to make the show. That's all I heard. There's just one sticking point. I was so thrilled. No, I was on the toilet
Starting point is 00:55:12 when they got canceled. Anyway, I was doing Elvis when it got canceled. But the way that we justified the budget or whatever, because it was a very low budget,
Starting point is 00:55:22 was we would shoot six episodes a week. And it was non-topical. So there we are like shooting in the summer and I'm like, Valentine's Day is around the corner. Like literally.
Starting point is 00:55:32 That's a classic thing. And was that to air every night or to air once a week? Four times a week. Just like you guys. Monday, Tuesday, Wednesday, Thursday. And we would bank episodes. But here's,
Starting point is 00:55:42 it never would have worked. Not, I consider the show a great success. I actually, believe it or not, have a lot of fans. And because of, thank you, that means a lot from you.
Starting point is 00:55:52 And from Instagram and TikTok, for real. But Instagram and TikTok, no, but my compliment, I'm sincere, is giving it this whole second life. And YouTube gave it this whole second life. Is TBS in this weird pre,
Starting point is 00:56:06 for once the artists benefited from like a, we didn't know what to do with streaming stuff. They let us have it on my YouTube. Oh, that's great. That was like in the deal. Yeah. You can host it on your YouTube. This is before anyone knew what YouTube was
Starting point is 00:56:25 so before you know it they could monetize it yeah there's like we should have monetized it by the way yeah yeah like that would have been
Starting point is 00:56:31 incredible but I can't because I didn't pay for it but they could have that was kind of dumb sorry I'm just in my brain counting the money
Starting point is 00:56:41 I know I'm sorry I went to a taping once and you had on a new material. Was it new material Seinfeld? That made me laugh really hard.
Starting point is 00:56:50 Who did that voice? Joe DeRosa. Okay. My dear friend. Oh, yeah, yeah. New material Seinfeld was something I used to do just to make people laugh.
Starting point is 00:56:58 It is very funny. I was like, well, what's a cup? Glass bowl, but it's tall, tall bowl. Tall bowl. Hollywood bowl. Why is it a bowl? It's not a bowl. It's a shell. Shell gasoline. glass ball but it's tall tall ball tall ball Hollywood ball
Starting point is 00:57:05 why is it a ball it's not a ball it's a shell shell gasoline it's not gas it's a shell what's a dinosaur fossil
Starting point is 00:57:13 fossil jeans jeans you put on jeans diesel Vin Diesel does he wear diesel jeans and like you just work and do a thing
Starting point is 00:57:21 and then you go is that anything that's my favorite you have a pad and a pen. That's it. This is how I know. Do you feel he did it justice? He did do it justice.
Starting point is 00:57:31 He was great. What were you going to say in Tripped? I was going to compliment and say a true comedian, you, knows that the joke is, is that anything? Yeah, yeah. Like someone watching is like, I like the part. No, the audience, that would kill when he goes, is that anything? Is that anything?
Starting point is 00:57:48 That's the punchline. But Nate Fernald, one of our writers, I remember he wrote this joke. It was so Seinfeld. It was so good. It's really a testament to how clear Seinfeld's voice is.
Starting point is 00:57:58 I'm not saying that just to kiss his ass, but I'm kissing his ass a little bit. But he's like, he's like, macaroni. They always have the clear, he was like, uh, macaroni. They always have the, uh,
Starting point is 00:58:06 the clear window. Then you can see the macaroni in the box. Yeah. He goes, meanwhile, cereal's over here in the dark. Why is macaroni getting rid of you? I was like,
Starting point is 00:58:17 that is a great, that's a great joke. It's ready to go. That is a great joke. You could give it to Seinfeld. It's so ready to go. So cut to me You couldn't give it to Seinfeld I was like It's so ready to go Yeah So cut to me This is actually kind of a synchronicity
Starting point is 00:58:29 Because I went to the Palm restaurant For the first time yesterday First time since this happened The first time I went to the Palm restaurant Which is like a famous Yeah Hollywood restaurant Like very sceny
Starting point is 00:58:40 The faces of famous people On the wall Yeah, yeah And they bring you a prime rib and a martini at 11am on a Sunday so I went to the Palm and I was telling this story
Starting point is 00:58:50 that I was like the first time I was there was Jerry Judd Apatow my dear friend and I mean that like we're actually
Starting point is 00:58:57 very close I love him very much and we talk all the time and I don't know why I'm getting sweaty about that I just mean like
Starting point is 00:59:04 he's just a like he's just a comic. He's just like a new balance. He wears this shirt every day. I'm dressed like him. Regular guy. And I love that we can be pals. And he invited me to this thing that Jessica Seinfeld, so Jerry's wife, was having a fundraiser.
Starting point is 00:59:21 And I was laughing with Val, looking back that I was like, that had to be like a five, maybe $10,000 seat. And Judd, like classic rich guy thing, didn't have anyone to go with me. I'm sure Conan's been like, Sweeney, do you want to come to Mick Jagger?
Starting point is 00:59:35 He's never asked. No, Mick Jagger's having an Easter egg hunt. Yeah, yeah. To raise money. Gotta show my face. Anyway, but I don't really eat meat. Even though I ate steak yesterday, I still don't consider myself a red meat eater.
Starting point is 00:59:49 So they're bringing out these steaks, these incredible steaks. Jason Bateman is there. Judd is there. And then I'm like, I don't even, they bring me the saddest mushroom I've ever seen in my life. It was a $10,000 portobello.
Starting point is 01:00:02 And I was just thinking about Judd being like, uh-huh, I paid for this. I invited the wrong motherfucker. So that was to redeem that. Here's why I bring it up. Okay.
Starting point is 01:00:13 I'm counting it as a synchronicity. Jerry Seinfeld is there, of course. This is the man who changed my life. I saw his movie. Right. Yeah.
Starting point is 01:00:20 And I moved to New York and everything changed. He comes up to me. I have no stories like this. I'm in a dumb blazer like a Sunday school student. He looks amazing. He walks up to me and he goes, What's with the mushroom?
Starting point is 01:00:34 He goes, what's with the mushroom? I'm sorry. Why is it a mushroom cap? It's not a hat. It's like, it's a shade. It's not graduating. It's not graduating? Move the tassel?
Starting point is 01:00:45 Move the fungi? I'm a fungi. She it's a shade. It's not graduating? It's not graduating. Move the tassel. Move the fungi. I'm a fungi. Mitochondria. Psilocybin. He says, but I also blow it in this story, I think. He goes, I, he goes, I just want to say. He doesn't do it. He's a regular boy.
Starting point is 01:01:03 I just want to say. You can't help it. That's better. He's doing it doesn't do it he's a regular boy I just want to sign you can't help it that's better he's doing it as a puppet that's him regular he goes I saw that new material sign oh god
Starting point is 01:01:13 wow and I loved it oh that's and I this is where I think I blew it but it was honest I couldn't stop myself
Starting point is 01:01:19 if I tried to quote your friend Mick Jagger from the Easter egg thank you wild horses couldn't have stopped this I went like this. I went,
Starting point is 01:01:27 and I, and I immediately cut to him later. Pete just did a mind blowing mind blow with the two hands, like pans, labyrinth and my eye pop. And I just, you know, he,
Starting point is 01:01:42 he rolled with it, but I was like, that's exactly like an episode of Seinfeld where he cuts in a diner. He did the mind blow. You don't do the mind blow. A legend of comedy comes to your chair, you don't do mind blow.
Starting point is 01:01:56 Because it took up too much space. Yeah. Well, if your hand hits him in the eyes on its way out. My wingspan is just too great. It's like the conversation. I think I did manage to squeak out, thank you for making me do it. I'm sure you did.
Starting point is 01:02:10 Yeah. I think you're over. I think you're being, that seems like a totally normal. I appreciate it. Nice response. I mean, what are the chances? You're narrating the moment in the moment,
Starting point is 01:02:19 which is what's funny about it. How could he have seen it? Yeah. How could he have seen it? Somebody probably sent him the YouTube clip, to be honest. But like, it was a highlight for sure. That's so cool. So we did the show and we got two seasons
Starting point is 01:02:33 and there was like six months in between the seasons. But here's the, it even worked out, getting canceled when we did worked out because the way we were doing it was evergreen. It was never supposed to be that way. So we're not interviewing celebrities when we're, I'm talking to Adam Scott when he has nothing to say, which was so hard.
Starting point is 01:02:53 It was actually kind of pre podcast though. It was like, just what's up. Tell me about your family. That's true. Yeah. And then we did all of these sketches and Batman sketches and Doctor sketches. And we just had access to like Conan's toy box and your art department and your talent booker.
Starting point is 01:03:15 I was wondering, was it sort of... It was incredible. It was produced by some of the same people, but then you had your own writers. It was all the same people. We had our own writers, but we felt incredibly resourced. But we had Billy Balatino directed most of them.
Starting point is 01:03:31 A lot of the same camera people, Peter, I'm trying to remember the camera guys, but Peter's one of them. Same cue card guy. Right.
Starting point is 01:03:39 And it was just like, looking back, boy, I'm going to be in a good mood the rest of the week because I'm just like, I really was handed the keys and Conan really was like, do whatever you want. Here's how, and this is also what's great about it. That's nice to have someone like that behind you
Starting point is 01:03:54 too. And he was behind us and we felt that and TBS and I'm grateful to TBS. It's all different. Everybody at TBS isn't the same people. Oh yeah yeah, yeah. But here's how not watching us they were. In the pilot, the first episode, I said, fuck, and they didn't believe me. Oh, wow. That's how unwatched we were. And when we, there was like a real, almost like Lampoon-y revelation
Starting point is 01:04:22 where we realized there was like a moment of sadness where we're like, no one's watching. And then we were like, like a movie, it'd be like pushing in, no one's watching. And we started doing just like, you know, I flatter myself putting us up with like the Ben Stiller show and stuff, but we had our own smaller version of like,
Starting point is 01:04:43 we can do whatever we want. We swore so much. We were doing like, it was very dirty at times. I'm drawing dicks and stuff. It's not getting blurred. Just very adolescent. And it was this time in my life, I was single. And my brother actually loves the monologues because he's like, it's a, it's a snapshot of a single man figuring out how to be alone in the world. Not alone, bad alone. Yeah. But like we did a monologue like called have a morning and it was the most earnest, like, don't just set your alarm before you have to go get up early, read the paper, make some coffee. But it was like the most earnest. Like I had just figured that out. You're just becoming human.
Starting point is 01:05:28 Yes. And I would think of the monologues driving in. I lived in Los Feliz and I'd drive through Griffith Park and I'd have all of these monologues. We'd write a monologue. I saw a guy, yes, I saw a guy on a motorcycle, but like one of those fat motorcycles with like
Starting point is 01:05:43 compartments on the back. We just did a whole, the three wheelers. Saddle bags. A whole monologue about how not all motorcycles are cool. Yeah. And would put it on its feet that day.
Starting point is 01:05:54 That's amazing. And you get into that like white hot mania. It's not bad mania. Like Charlie Sheen, I'm not trying to make fundamental illness. I'm just saying,
Starting point is 01:06:03 wasn't bad. It was like, it was like drinking from a waterfall. You're like, think it, do it. And, and I'm really,
Starting point is 01:06:10 really proud of it. And, and, and Jamie Lee and Nate and Joe DeRosa was one of the writers as well. Adam, I'm forgetting. I'm always Nate from, I'm going to forget some of them,
Starting point is 01:06:21 but really incredible people. And of course, Oren Brimmer, who directed all the sketches and wrote. Oh, great. And we still work together. And Matt McCarthy. Oh, I love Matt.
Starting point is 01:06:30 Who was in everything. He's such a great performer. Our lives have been so long that Matt and I and Oren are working together again. I'm not promoting anything. We just started going like, you know, what are we doing? We have different projects. All of us have different projects from time to time, but we're like, let's just go back to the basics. Let's scrap together some money, get a space. This would be a great space, you fucking assholes. I think it might be available after this. Actually, I'm a hundred percent
Starting point is 01:07:04 getting when I call you assholes, I'm like, maybe available after this. Actually, I'm 100% getting when I call you assholes, I'm like, maybe you guys could let us use this room because it's those clicks away. We shot,
Starting point is 01:07:13 we're about to release Batman Fires the Justice League, which is me as Batman just letting everyone go. Yeah. We did that with X-Men for the Pete Holmes show. Yeah.
Starting point is 01:07:24 And now, you guys know, it's like when your career is long enough to have these phases where you're not together and you kind of miss each other and it's sad. And then you get back together. You know what was the best was when we were just making stuff. Yeah. You're just doing it for its own sake. And then it becomes like, because you can, I say this in a great way, not a slimy way. You can monetize it. You can hopefully get enough views that these guys can get work out of it now. And now everyone's like benefiting from a legacy that we created together. And then it'll, it'll branch out into this. So if, if you see those, please watch them. Yeah. That's great.
Starting point is 01:08:01 I love that you're going to be sketch comedy it's really yeah it's exciting I will say this is the last little so this is a sweet nug oh please yes I'll tell you two sweet nugs to close bring it home
Starting point is 01:08:12 two nugs we did one of the most popular videos in the hardest bit that killed the hardest we ever did on the Pete Holmes show was called Romano Duets I did a video called Romano Sings we just shot it in Oren Brimmer's apartment in New York.
Starting point is 01:08:27 And this is before you even said it went viral. It was popular. And it got back to us that Ray Romano had seen it and we were unbelievably thrilled. Cut to years later, I'm doing a talk show. A lot of the things we did on the Pete Holmes show were things that I had already done very low budget. So we did the X-Men series where someone's firing Vega because you can't.
Starting point is 01:08:51 Oh, the Street Fighter series. He's firing Vega because you can't bring a claw into a street fight. I mean, the joke is right there. But I didn't have any friends or cameras. So I just shot it in photo. I made Photoshop stills. Oh my God. And this is kind of before that was a thing,
Starting point is 01:09:08 like lo-fi, not animated, just cutting back and forth A and B. And I had Premiere. I stole Adobe Premiere off a Torrent site. And I just made it and I just voice acted it in my little room. And of course, I love this story. Then we later shot it with Thomas
Starting point is 01:09:25 Middleditch and it's one of our most popular videos. And we did Romano sings with a literally a felt green screen and it did well. And then we got to reshoot it for the Pete Holmes show. And now it's beautiful and it's looks a lot better. Then someone's like, do you think we could get Ray Romano to do it? And we'd do Romano duets? So we did do it and you can watch it. And I stand by it. It's very funny. But the best part was we're on the lot, stage nine, I believe. And I'm standing in the dark and, you know, there's a proper green screen.
Starting point is 01:09:56 And I'm just kind of doing my part before Ray gets there. So I'm at the mic and I'm like, hip hop hooray. Oh, hey, you know, doing that. And the door. It's a little Kermit-y. Oh, it's very Kermit-y. Yeah. We used to do it. It's like Ray Romano's like, yeah. Then like Kermit is like, hey, hey, hey. Oh yeah. And Ross Perot is, ah, and Aziz is, wow. It's like, they're all sort of like.
Starting point is 01:10:21 They're all on the same spectrum. They're all a blend. So I'm doing it and I'm really, I'm wearing, my hair is dyed black and I'm wearing his style of shirt. But it's like kind of like making fun of him a little bit. Having fun with him. Yes. But I hear a door open and it's dark
Starting point is 01:10:42 and I just hear in the distance, he goes, my poor wife. If that's what I sound like. And he walked in and he did it. Oh, that's great. One of my fans. Then we played it on the stage and it murdered.
Starting point is 01:10:57 Yeah. Like standup level, like rolling. I was like, this is the greatest thing we've ever done. I missed a good one with Jeff Ross. When Conan auditioned on 30 Rock, he was filming like a test pilot and he was very green and he didn't know what he was doing. And I told Conan how much it meant to me and Jeff that in the,
Starting point is 01:11:19 between acts one and like two and three, like before, after the desk bit, before the guest, Jeff handed very nervous green Conan a note that said, you're killing. And that's in The War for Late Night. And I just mentioned offhand
Starting point is 01:11:32 how much that meant to me. And before Bill Burr, before I interviewed him, he handed me a note that said, you're killing. Oh, that is nice. The other framed thing I have. Oh.
Starting point is 01:11:41 That's in my office. And I, it's a treasure. So, then the show gets canceled and this'll just lead into the next chapter, but, uh, we don't have to go into it. I mean, this'll be okay to close. I'm on the toilet. They call me Elvis style and they're like, the show is not getting picked up. You know, when all your reps are on the call, it's either bad news or good
Starting point is 01:12:02 news. And this was, this was bad news. But we had done 80 shows, 80 shows. And we had literally done as many shows as we could have done before it started getting bad. Like for real. I'm a good spin doctor, but I was like- You got out on top. How many St. Patrick's Day monologues can you do? Were you just- You've gone through-
Starting point is 01:12:23 29. Yeah. You've gone through a full year of holidays. Hilarious. But at least you also had what was going on. Yeah, yeah. 29. You've been waiting for someone to ask that question.
Starting point is 01:12:37 So we got out when the getting was good. And then just to tell you, again, out of gratitude, what it did was Judd was a fan of the show. He did a sketch on the show. On the show that this aired, the joke was that I would pitch. Everybody has this pitch for Judd, by the way. If you're doing a sketch with Judd, come up with another idea.
Starting point is 01:12:59 But we didn't know that, which is I'll pitch you bad movies. It's the stupidest idea. You know, we had a lot to learn. But I remember pitching him a movie called Beargician and Froggician. And but then Jed's a great improviser and he goes off script and he like completely deadpan is like, what's your real idea? Like, what's your real idea? And I'm like, that's actually terrifying.
Starting point is 01:13:24 Like now thinking about it, who cares? At that moment, I was like, Jesus. Like, it's almost like, it's almost not fair. Yeah. You know what I mean? It's like Bono is like, but if you did open for me, what would you play? Yeah. You know, and you're like, gotta go.
Starting point is 01:13:41 So in that moment, I go, well, uh, I was married when I was 22. My wife left me when I was 28. I was very religious and I got very sad, but I ended up falling really hard into the standup comedy scene. That was not pre-planned. But on the top of your head, that was your pitch.
Starting point is 01:14:00 Yeah. I was just like my life. And he goes, that just sounds really sad. And that was the joke. It made the sketch was that he was like, your life sounds better. That would just make people want to kill themselves. I was like, okay. So the show's canceled. I'm on the toilet. And I love sharing the story just because like, hopefully it can give people hope. So it's this low moment and you know, what are you going to do? Like, is that it? And I called Oren and we were in that rhythm.
Starting point is 01:14:28 We were making stuff. We were doing stuff. Yeah, you had momentum. And we believed in ourselves. There's nothing like when you, I don't know much about sports, but when a basketball player is in the pocket or on fire and they're just hitting shots, get the ball to him because he's in. It's unconscious. Yeah, you're in the flow. Right. And that's how I felt. So I was like,
Starting point is 01:14:49 okay, I'm lean. I don't mean physically. I just mean like I'm ready to go. Let's not mope while the show is still airing because it was going to air for like six more weeks after it was canceled. You had that many in the can. Maybe it was, I'm making that up. It might have been three weeks at least. That's amazing. That's a real hit of steam. Yeah, exactly. Totally.
Starting point is 01:15:11 I was like, let's go to Comedy Central and we'll pitch them a sketch show because our favorite part of the Pete Holmes show was the sketch show. So we go and Kent Alterman was the head of Comedy Central at the time. I like, he's a good guy. He's great.
Starting point is 01:15:24 I love Kent very much. And like, he's a good guy. He's great. I love Kent very much. And we were not in a Hollywood way. Like I just for a second caught myself sounding like a phony. Oh yeah, love him, love him. Yeah. We've had drinks and like opened up. It's been beautiful.
Starting point is 01:15:36 But we had this meeting and it's a warm room and they knew the show and they were fans. And before the pitch, they said, Kent said, well well one thing's for sure we don't want another fucking sketch oh my god and me and oran are sitting there like like wallflowers we're like oh god yeah oh god no neither do we i wish we had the i I bet we did like, oh, are you kidding me? Schumer, Key and Peele, get out of here.
Starting point is 01:16:16 So we just, we literally pivoted and acted like we were just there to touch base. Yeah, yeah. Okay. Yeah. But the frustration of that, again, I want action. I want to go. It's like the standup improv thing. I'm like, I've had a taste. I don't mean of fame and I don't mean of money.
Starting point is 01:16:27 Certainly not. I just mean like I've been making comedy. This is what I wanted to do since I was fucking six years old with the big dick jokes. Got to stay in the forbidden city like George. George Costanza. So I'm in my car outside of Comedy Central and in this moment of frustration, like kind of feeling down,
Starting point is 01:16:49 like, well, that was the plan. I asked that question, which I feel like people need to, this is the swelling YouTube violins, you know, when people appropriate your content and get millions of views and put ads on it. Pete Holmes blows me away with an inspirational speech. But I had the courage and the vulnerability to go, no, really, if you could
Starting point is 01:17:13 do anything, what would you do? And that's a vulnerable thing because if you really admit that to yourself and it doesn't happen, you're the guy in the wet bathing suit at the buffet, right? And I said, I would do a show like Girls with Judd Apatow on HBO. And I was like, okay, what would that show be? And I was like, well, it would be about me being married. Okay, that's, I'm slowly, believe it or not, at this time in my life, I'm almost 33. I'm finally putting together what's unique about me. Thanks to the talk show. Like, oh, I didn't know that was weird. Religious. I did. Married so early. Divorced. And then I was like, and then I thought of the engine of the show, which was, oh, every episode,
Starting point is 01:17:57 I'll stay on a different comedian's couch. And I was like, oh, and I'll call it crashing. So I literally, that was on a Tuesday, booked a flight. I asked Judd's office if I could pitch him something. Because he had been on the show, he said yes, but he was shooting train wreck. So I flew on that Wednesday to fly to New York, spent the night Thursday morning at like 6 a.m. on a couch. That was the pilot. We shot it on an iPhone. Pitched him the show and it just went from there. Thursday morning at like 6 a.m. on a couch. That was the pilot. We shot it on an iPhone.
Starting point is 01:18:26 Pitched in the show. And it just went from there. So the Pete Holmes show even bled into that. So how long after that Comedy Central non-meeting? That was Tuesday. I pitched to Judd that Thursday or Friday. Wow. You really were amazing. I have a Wow. I literally have like a Delta. I have a Delta.
Starting point is 01:18:47 I wish I still had it. Like cocktail napkin where I wrote out the show. Wow. Oh my God. And it fucking, and this is key because that could just be mania or momentum. He was like, write the pilot. And just like my modern family,
Starting point is 01:19:02 I wrote it in two days, turned it in. And I've seen Jed work with a lot of people and the number one thing that happens, and I can have this too, sometimes the whole table is set. Yeah. The meal is there, the fork is there,
Starting point is 01:19:15 and you can't eat it. I see this happen. Like it's imposter syndrome, it's fear. Yeah. Self-sabotage. Fear of success, self-sabotage,
Starting point is 01:19:24 unworthiness, all this sort of stuff. But because the Pete Holmes show had me at like an Olympic, like my body fat was zero. He said, write it. I wrote it. Yeah. Because you're doing six shows a week. But it was, this is helping me realize again, how grateful I am to the Pete Holmes show and to Conan and to Jeff and to everybody and to TBS, even though I shit on them. It's okay. All those people. You pled ignorance about TBS.
Starting point is 01:19:52 That's right. Which is different. That's true. It was like running with weights or like running underwater. Yes, absolutely. And then he said, write it. And I wrote it.
Starting point is 01:19:58 And he said, rewrite it. And I rewrote it. And he said, rewrite it. And I rewrote it. I was like, and Judd, like minds like that, minds like Conan and Judd, they want that. That's their dream too, is to find someone who's like young and hungry and ready to go. And this is stupid to be like, and the rest is history. And that, it was like swinging from a vine to another vine. And it was incredible. No, that's right. It's so cool. And that, it was like swinging from a vine to another vine.
Starting point is 01:20:25 And it was incredible. No, that's right. It's so cool to look back at it in that way and have those things that at the time probably just felt to you like, this is, I'm partly running on just instinct and following these leads and kind of like trusting my gut on things.
Starting point is 01:20:39 But then you look back and you're like, no, this path makes sense when you look at it in this way. Yeah, yeah, yeah. I have fantasized about winning an award later in my career. Okay. So I was wondering what your next manifestation was going to be. Yeah, yeah. Here it is. And by what birthday? I say one behind me. Yeah, yeah. 40. So there are these gratitudes, but here's the one that I can't wait for. And it's not for
Starting point is 01:21:04 the award. It's for the speech. In the speech, I've laid awake many nights being like, how fucking great. Let's say I'm on some show. I win an award and I go up and I accept it. And I go, I'd like to thank Conan, Jeff Ross, and JP Buck, and Nick Bernstein. And thank, it's absurd.
Starting point is 01:21:26 It's not, it's like somebody with a cigar go, it's not done. You know what I mean? But like, and then take that to Judd and Judah Miller and Oren Brimmer and Matt McCarthy and then lead up to the show that I'm on. But like, I'd love specifically, even more than crashing,
Starting point is 01:21:46 to give that, that first break, the thanks. And so that's been my fantasy. Not to thumb my nose at Hollywood or the future, you know, hypothetical show,
Starting point is 01:21:57 but just to like, how long did it take me to say, I want to thank Conan O'Brien, Jeff Ross, and J.P. Buck for giving me my first break on the P-Dome show. Because it clearly was this incredible push down the mountain.
Starting point is 01:22:10 But that is a better look. I mean, every award is really almost more of a lifetime. I mean, you know, occasionally an actor will win something at 22 or something, but usually this is a culmination. Which also reminds me, this isn't to... I guess there is a certain defensiveness where you want to be like, it wasn't just, I didn't win in like a lottery.
Starting point is 01:22:31 Yeah. It was a show where you do monologues, interviews, and sketches. I was doing standup monologues. I was doing podcasting early on. So I was doing interviews. That's how they knew I could interview. Yeah.
Starting point is 01:22:44 And I was doing sketches. That's how they knew I could interview. Yeah. And I was doing sketches. That's how they knew. Right. But that's, again, swell the violins and the YouTube misappropriated clip. That, it was like I was doing the Pete Holmes show
Starting point is 01:22:53 and then they gave me the Pete Holmes show. Yes, exactly. It was the easiest yes in the world. Yeah. So, you know, it was my version of dress for the job you want. We were doing these sketches in,
Starting point is 01:23:04 if we could find a corner, we would go, that kind of looks like a doctor's office. And we'd film 10 sketches. And you do a podcast way before you were like, and this will pay my mortgage. You were like, this will be something I upload. Like, I think people will listen to it. So there was a purity to that too. I just don't want anyone hearing this and being like, oh, all I need to do is be tapped.
Starting point is 01:23:29 I get the job and then I start doing the work. No, you do the work and then you get the job. And there is obviously luck and timing and all of these things that are completely out of my control. And, you know, they say like enlightenment is a gift. This is a weird parable to say, but somebody goes to a Zen master and they're like, if enlightenment is grace,
Starting point is 01:23:49 meaning it happens to you like an accident, you know, like it's just given to you by the universe. Why do we do all this practice? And the master says to be as accident prone as possible. And that's how I feel. It's like making it, making it, getting tapped, getting this, getting that,
Starting point is 01:24:06 is grace, is an accident, is luck, or whatever you want to say. You can put yourself, stand in the hallway where people keep getting lucky or whatever,
Starting point is 01:24:17 you know, it might help. You should, I'm fascinated by all the bits you did before that you got to redo with a bigger budget on the Pete Holmes show. Might be fun to do like a little behind the scenes. Side by side.
Starting point is 01:24:33 And show the original and then how you did it. That's cool. Yeah, and you talking about it. That's a fun idea. I think that would be cool to watch. Yeah, with a little director's commentary. Yeah, yeah, yeah. I think we could do that.
Starting point is 01:24:44 Yeah, yeah, yeah. That's a great idea. But anyway, I think that would be fun. I'm going to write a little director's commentary. Yeah, yeah, yeah. Yeah, I think we could do that. Yeah, yeah, yeah. That's a great idea. But anyway, I think that'd be fun. I'm going to write it down. Executive producer Mike Sweeney. I'd like to see it. Yeah.
Starting point is 01:24:51 And I'd like you to thank me when you win that award. And for the guy who had me do the behind the scenes videos. Well, this is great. Yeah, this is so great. Thank you, Pete, so much.
Starting point is 01:25:01 Thank you, Pete. Here's the longest Inside Conan. It is. In our family, we call it shorty. Fucking circle. Thank you to Pete Holmes. Yeah.
Starting point is 01:25:19 And guess what? Pete has his own podcast. What? I knew you thought he was a little too comfortable in front of a microphone. He did seem like he didn't seem to be in a rush to leave. Very comfortable. And his podcast is called You Made It Weird. Right.
Starting point is 01:25:35 It's a great podcast. It is. Be sure to check it out. And we have a listener question. Ooh. I don't know if Pete does that. I don't know if he's got the guts. He doesn't have time. But we take our listeners head on. We have plenty of time. We have time to fill.
Starting point is 01:25:51 Here's our question. It's from someone named Tara. Hi, Jesse and Mike. I was just listening to your recent podcast intro where Jesse stated that since she was born in Panama, the country, she cannot be president of the United States. This is actually false. If you are born to two parents with US citizenship, you are considered a natural born US citizen and are in fact eligible to run for president. And she quotes the law. Wow. Yeah, so there you go. And so this, I don't think really is a question.
Starting point is 01:26:29 It's more of a correction, I guess. It's a correction. Which I appreciate. Maybe we'll segue into just have corrections every week. That would really fill up. That would fill a lot of time. So, Jesse, you can do it.
Starting point is 01:26:43 Jesse for president. Yes. Oh, boy. I would love it. Jesse for president. Yes. Oh, boy. I would love it if you were president of our country. Oh, God. I would hate to do it. I would absolutely hate it. My favorite part of it would be you still
Starting point is 01:26:57 carving out time to co-host Inside Conan, an important Hollywood podcast. You got to do it. Sorry, under contract. You gotta do it. Sorry, security counsel. I'm actually disappointed because my whole life I've been using this excuse of not being allowed to run for president.
Starting point is 01:27:13 Right. And I thought, okay, I'm off the hook. Yeah, no, yeah. She's absolutely right. You can run. Too bad you're not old enough. You have to be 35. Do I know how to butter up the ladies?
Starting point is 01:27:26 I still got it. I would never want to run for president. And we've talked about this before, that I feel like running for president should disqualify you from being president. Oh, yes, yes, yes, yes. Even just the desire to be president tells me you have no business being president. You have a serious mental defect. Yeah. Anyone, yes, you'd really truly want to lead. There should be like a bucket of names of people who want to be president. And then you immediately just put a red flag by all those people's names.
Starting point is 01:28:02 Burn. Never allowed. Pour gasoline in the bucket and set it on fire. And then the rest of the people, there's a lottery and each of those people have to serve for one year. They have to do it. Yeah. I think that's a great plan.
Starting point is 01:28:14 You can winnow down that group, like get people who everyone actually is like, wow, they're really. Yeah. Yeah. They're good at their job. And then. And then force them. Make them do it.
Starting point is 01:28:24 And they don't have to run. You just get selected. Right. And I think- And then force them. Make them do it. And they don't have to run. You just get selected. Right. And I think you could, how do you make them do it? You could kidnap their family and hold them at gunpoint for a year. Yeah. And then they have to do it. Right.
Starting point is 01:28:37 Or threaten them, say that your family has to be president if you don't do it. Your brother, your brother who you hate or your sister. Well, how do we get this into law? I don't know. I think I have to run for president. There you go. Just, we've come full circle on this one.
Starting point is 01:28:56 Well, thank you, Tara. Well, thanks for your correction, Tara. Yeah, Tara. I'm not too big to admit when I'm wrong. Yeah. If anyone else has a correction for us, please. Or a question. Or a question.
Starting point is 01:29:09 We'd love to hear from you. You can give us a call and leave a voicemail at 323-209-1079 or email us at insidecodempod at gmail.com. Yes. Yes. Please do that. And if you like the show, even with all its errors and grave mistakes, you can support us by rating Inside Conan, an important Hollywood podcast on iTunes and leaving us a review. You know what?
Starting point is 01:29:36 I'm not wrong about. What's that, Jessie? Loving you. Oh, my God. It's the right thing to do. Inside Conan, an important Hollywood podcast is hosted by Mike Sweeney and me, Jesse Gaskell. Our producer is Lisa Burr. Team Coco's executive producers are Adam Sachs, Jeff Ross, and Nick Liao. Engineered and mixed by Joanna Samuel. Our talent bookers are Gina Batista and Paula Davis
Starting point is 01:30:05 with assistance from Maddie Ogden. Thanks to Jimmy Vivino for our theme music and interstitials. You can rate and review the show on Apple Podcasts. And of course, please subscribe and tell a friend to listen to Inside Conan or an enemy on Apple Podcasts, Stitcher, Google Podcasts, or whatever platform you like best. I'm not going to tell you what to do.
Starting point is 01:30:30 Put on your hat, it's the Conan Show. Try on some spats, you're going to have a laugh. Give birth to a calf, it's Conan. This has been a Team Coco production.

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