The Three Questions with Andy Richter - Nick Kroll (Re-Release)

Episode Date: March 3, 2026

As Andy travels the nation on the "Dancing With the Stars" tour, we're re-visiting his 2021 conversation with Nick Kroll. The star of "Big Mouth," "Kroll Show," and "The League" joined Andy Richter to discuss birth order, his journey through comedy, doing roasts, and more. Do you want to talk to Andy and friends live on SiriusXM’s Conan O’Brien Radio? Tell us your favorite dinner party story (about anything!) or ask a question - leave a voicemail at 855-266-2604 or fill out our Google Form at BIT.LY/CALLANDYRICHTER. Listen to "The Andy Richter Call-In Show" every Wednesday at 1pm Pacific on SiriusXM's Conan O'Brien Channel. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Hey everyone. I'm Andy Richter. This is the three questions. And I am very happy to be talking to Nick Kroll today. Hi, Andy. Thanks for having me. Sure. Thank you for being here. You're coming to me from an undisclosed location out in the desert. You're working. You are just a tag-along spouse, I understand. I am. I am truly, my wife is here doing some work in the desert. And I am a plus one. ordering room service throughout the day, breakfast and lunch so far. I think might go out for dinner, but man, there's nothing like a turkey club from room service. How long are you guys out there? Oh, just a couple days.

Yeah, yeah. A few days. It's fun, though, to be just along for the ride. Like, it's fun when your partner is. It is. It is the work. And you just get to kind of hang out. Yeah.

It really is. It's been, it really is. And I find my wife's work interesting and, cool. So it's a nice thing to be, to be a tagging along on. Yeah, she's like a, like a landscape designer, botanical artist,

botanical installation artist. She does all types of things. Some of them temporary, some of them permanent. And so she's, yeah, she's working on a permanent installation right now. So I'm she's out here scouting and I'm just hanging out in the desert,

which is beautiful. Yeah. You forgot how gorgeous, like this Palm Springs, Palm Desert area is. It's like, it's so cinematic. Yeah, when it's not 9,000 degrees, it's nice. Yeah. Yes, absolutely. I was there once for like the two or three weeks that things bloom and it was magical. Uh, but every other time I'm there, it's just seems like a purgatory. I love a, I love like a July 31st, uh, just a hundred and 115 degrees. At eight a.m. Yeah, just like watching. watching the Botox ooze out of some elderly people and getting a getting a couple hot hot pancakes

a heavy hot pancake breakfast now I you know they sent me research on you and I glanced at it I mean you know come on I want to keep it spontaneous but I saw that you and your wife met on Raya yeah I think that I think that you're like the one successful couple that they can boast of. I know. I didn't, it's one of, the unfortunate thing is like, it's not like you can get then a free membership. You know what I mean? There's nothing good. Right. Yeah, we met on a dating app. And I, and I, um, for those, for the, in your audience who might not know riot, it's for, um, it's for like, I mean, there's all types. I mean, it's like, it's supposed to be like, quote unquote, the, for creative types and, and what that meant,

at least when I joined, it was for like beautiful women, some of whom were quite talented and accomplished, and some of them are just beautiful and like successful men or like hot guys in front of like a Ford Bronco with like wide brim hats and like, you know, like a picture of them with their dog. Yeah. A rented puppy. Yeah, yeah. A vintage. Puppie and, you know, like a lot of bracelets. So, no, we met on there. And I find it actually kind of romantic. It serviced exactly what it was, which was like I was trying to find, I was trying to meet someone outside of my circle because I feel like I knew most of the people that I was in the

world that I was living in, and let's say in the comedy world, I knew many of those people. And it was trying to figure out a way to meet someone outside of my circle. And I did it. And now we're married and have a child. Nice. Yeah. Yeah, because I was, I've been single for a couple years now. And I attempt, Rye is the only attempt I've made at a dating app. And I, I scurried away as quickly as I could. It felt so, I've told this before, but the thing that did it was seeing a woman whose, her job was listed as denim architect. And I just was like, I don't think this is my crowd.

Yeah. I don't want to, you know. And then just, and also too, just everyone seemed impossibly young and impossibly hot. And I just felt like, get out of here, you leering old creep. Yeah. Yeah. No, I think it was the place that I felt like safe to be on an app because I was like, I was scared of being on like Tinder or something like that and people being like,

wait, that guy and like. Yeah. And also fans. You don't want, I mean, I don't know. I don't want to date. I mean, I like it if people like me, but like, I certainly don't want somebody to go, like, oh, I want to go on a date with that guy from the Conan show or with Mort from Madagascar. You know, it's like.

Yeah. Yeah. I mean, I would have been like, oh, I want to date the guy from quintuplets. Well, of course you would. But no, I think, I mean, ironically, my wife told me that she was like, she was a big sports fan and she and her brother used to watch the league together. And then my face came up and she was like, oh my God, fucking Ruxon. She's like, I hated your character.

Like he's the worst. And I just assumed that you would be like that. but I was like, and I may as well like swipe right or whatever, approved just like at the very least I might have like a laugh, you know? And so I'm glad she chose to and didn't judge me. But it made me realize like, oh, people do think you are possibly who your character is. You know, like if you only watch the league, my character on the league was, sorry, my F-18 is flying.

That's all right. Um, if you only watch the league, you'd think my, I mean, Ruxin was like a truly deplorable human human beings. Yeah, he's an asshole. Yeah. The worst. Yeah. And I'm only, and I'm just the, I'm just the pain in the ass.

I'm just right. Right, right. You aspire to those levels. Yes, exactly. Yeah. Yeah. Yeah, well, that is, I mean, sometimes though, I always feel like that's not a bad bet to think that someone is a lot like characters they play.

because people are frequently cast in things that they are that are you know that's appropriate to them like it's kind of like they've worn a natural groove in their personality to play this kind of person so I mean but also too you've also you play you know you play some charming people too occasionally I seem I seem to get cast I've gotten I have been very I've been very fortunate to get cast or to do different things but I definitely for a long time at least my sweet spot was like douchebag assholes yeah which are which are always fun to play it's you know it's like it's a fun and trust me i don't i i'm not complaining about it but but at some point specifically there's something about the league where and like manzukas jason who is was played my brother-in-law raffan league who's a on the show a stone-cold maniac like pure id yeah which which is a character that Jason plays somewhat often and plays unbelievably well. Yeah. And what people don't realize in real life,

and I'm sure you've spent time with Jason. Like he's actually a very thoughtful, pretty, a very emotional guy and also a massive OCD germaphobe. Yeah, yeah, quite reserved because he's, you know, in a prison of his own making. Yes. And so, but people before the world, like before COVID, you know, before the collective trauma of COVID that we've all gone through. We would be out and about and like every real life, Raffy, his character from the league, would come up to him and be like, you Raffy, I'm Raffy.

And he'd be like, please. Yeah. I can't, like, you touching me scares me so much. But I kind of enjoyed it because I am like, you've, you know, you've chosen this. Right, right. So, this, you know, this podcast is sort of, you know, it's, as John Gabris called it, the origin story, which makes it sound like I'm only interviewing villains. So you grew up on the East Coast, New York.

Yes, where many villains come from. Where many villains come from. And it's, I mean, it's not a secret. Your dad owns a pretty big, big. business, like a pretty big company that's, like, well known out in the world. Uh-huh. And so, you know, you had kind of an East Coast. I had an privileged East Coast upbringing.

Yeah, yeah. And how'd you end up so nice? That's the crazy thing. You know, it's so funny. It's this weird. It's a very, I mean, it's, I mean, it's, I mean, it's, I mean, it's, I mean, it's, I mean, it's, I I feel incredibly blessed growing up in my family because my dad did well. I will say for whatever it's worth and it's worth nothing, my dad did very well.

He has done not nearly as well as the internet would have you believe he did, which is not to say anything about like the incredible privilege that I grew up with. Right. But no, no, if you, on the internet it says that, like I have $10 million. I don't, I do not have 10 million. I don't have anywhere near $10 million. Shit.

Well, if you don't have 10 million, why am I doing this podcast? I thought I was making a million to do the podcast. So I grew up with insane privilege, not, but not the, but I will say just not the level of privilege with which or the amount of money. And also my dad has built that business over the years. Yeah. We grew up very comfortably growing up, but it's, it was something. that he built over many over 40 years or so.

So, but I grew up with a ton of, I grew up, yeah, I grew up very comfortably. And, but also, my parents just did, were, are nice people and, and would, it, it would never even have crossed my mind to not be nice to people because that's how, I think, because that's kind of how my parents were with, people with everybody so yeah yeah the modeling was like who cares if you have money or not like everyone has a name and everyone is a person and everyone has a family and you treat them accordingly um and i have found life to be easier being nice to people um like from a purely pure pragmatic way as an i i've always said that like if you just want if you're just like a crass motherfucker that wants to get the most work out of people, be nice to them.

Like, be concerned with them. Yeah. Even if you're evil and all you care about is productivity and that people are machines, be nice to them. Yeah. And I think,

you know, it's, look, there might be a part of that that's like, it's easy as like, you know, like straight white man to be like, it's so easy.

Just be nice to people and they'll be nice. Like there isn't it, there is a slight, Like the world, if you are nice, the world is there to work with you, which might not be as easy for other groups. But I can only speak from my own experience, which has been like, you know, if you're running late for a flight or your room, you're not getting the room you thought you were going to get at a hotel or like you're like your, the package that was supposed to be delivered hasn't come. like I don't I have found for the most part that being like nice and reasonable gets has gotten me what I've wanted as much or better than people who are like you like I will threaten you like I just think people I just watch people shut down when you threaten them

now you're also the youngest in your family would you say that you are the baby like for you by how much like who's what's the age it's a seven year spread from oldest to youngest so So it's my brother, Jeremy, then my sister, Dana, then my sister Vanessa, and then me. And it's Jeremy's seven years older than me. And then Dana and Vanessa are two years younger than him. And then there's a three years split. So we're pretty tight. Pretty close.

Yeah. Pretty close. You're one of how many? I am one of four. My mom is married twice. I have an older brother who's three years older than me. And then I have a younger brother. from my mom's second marriage. So we have a different dad's, and they are twins. And they are

nine years younger than me. So, okay. So you were kind of the youngest. I was, I was, I got to be the youngest for a little while. And then I was like the middle. Right. You know, because when there's two at the same age, that's functionally the same person, and you don't have to treat them. You can't separate. You treat them as one entity. Right. It's a time saver. I, I, I believe, very much in birth order. Yeah. I'm a big. Conan always did too.

He always believed in that. Really? Yeah. I really do believe birth order is massively important in who you are. Like other people are like, what's your sign? I'm like, I don't care if you're a fucking, you know, a Gemini or a Sagittarius. I'm like, where do you fall in your birth order? Yeah.

I think that that has a massive impact on, on who you are. Yeah. And what's Lily? Uh, she's also a Gemini. She, no, no, I mean, I mean, uh, birth order was. Oh, she's, she's the old older of two. Oh, okay. Um, and she there's not a, I don't, I'm trying to think amongst my various serious relationships. There's not a huge amount of continuity, but, um, but actually a couple of them were

older siblings, older girls to younger boys. And so I sort of make sense on some level. where it's like, oh, you're the older, like, you know, because it was my brother than my sister, then my sister than me. And I definitely felt like there was always like a kinship with a, that like sister was a little older than me, like where you sort of relate to, like that relationship was an important one,

I think for me of like how, you know, she taught me like, how do you talk to women? How do you, how, whatever that relationship was, I think became a central one for me. And I think as the youngest, I think of the youngest oftentimes as performers, as the ones who end up becoming performers, because I think they have been, like,

I think they're verbal younger because you're catching up to your older sibling. You're like, you want to do everything. And also your older sibling is oftentimes, like, showing you things, showing you movies, showing you like introducing you to a lot of stuff. And yeah, I have, I've got a whole sort of chunk in my stand-up about birth order that I, I just can't give it to you.

I just can't. I know, you can't give that shit out for free. You can't give that away, baby. But I, yeah, I don't know. Do you feel like a youngest or, and do you feel like a middle? Like, where do you? I do feel like, yeah, I mean, for the, longest time I was the youngest in lots of different things. Like I, like I was young in my school

class, you know, how like there's just a range of age over about a year and a half. Like I was always one of the youngest in whatever class I was in, you know, whether it's third grade or what, when is your birthday? What, when was, October 28th. Okay, wow. And this is before they had like, this is before they had like cut off dates where it's like, if you're born after March 1st, year. I don't even. You're the next year. Like I have no idea how it worked. I think that it was just, you know, and especially too, it was like it was Yorkville, Illinois, you know, grade school. Right. Like York, Illinois in the 70s. They're like, you're born and you're born in the year. That's the year. Right. Exactly. You say, hey, my kid was born October 28th, 1966. Oh, he's going to

school next year. Okay. You know, and then you just do it. Yeah. Similarly, I mean, I'm a June birthday, which was always on the later end of even, even that. And I was a little guy. I was a late bloomer and so so i think even that made me feel like you know and especially in those critical like seventh eighth ninth grade when that half a year meant a lot physically for you um that it was and then being on the second half of the year birthwise like i definitely think i i felt younger throughout you know yeah well and then when i started like i like i have my brother's three years older and I ended up hanging out with his friends a lot. Like I just ended up hanging out with older kids.

I mean, I had friends my age and all different ages, but I always kind of was around a lot of older people. And then when I started doing improv, I was one of the youngest of, you know, when I went to film school, I was one of the youngest. And it was kind of like halfway through my first stint on the Conan show, that there started to be, writer's younger than me and I started to feel like, hey, wait a minute. I'm supposed to be the

youngest. I'm a little wonderkin. I'm a little baby special man. I'm the one who's out, you know, who's pushing his potential as far as he can. Yeah. No, I'm just meeting expectations. I have similar, I have similar things in that, especially when I started doing improv and I was like, you know, I came to New York and started doing UCB. And I was, My brother went to college with Owen Burke. And so Owen was an improviser producer and UCB. Yeah. Yeah, it was my intro into UCB.

And through him, I met, you know, Shear and Hubell and. And then through just all of those relationships, it was like Manzoukis and Brian Husky and Seth Morris and that whole crew of folks. And I was friends with them. and then, and I was like, I'm used to that. I was used to being friends with the older guys. And then as I've gotten older now and created my own stuff, I've collected, I've started, you know, I work with younger people.

And now I'm like, it's very weird to be like, oh, I'm, not only am I not the young guy, but I'm now like the older guy. Yes, yes. I hate that feeling because it creeps up on me because I'm sure that as most people, you know, most people they say they feel about like whatever, you know, 16 or 17 or whatever, you get to a certain age. And I don't know if it's that young that I feel. But all it takes, and I kind of almost avoid doing it, like UCB shows, I would go do UCB

shows that somebody would say, hey, you know, this person that you know is going to do this show, will you come do this show? And I'd say, okay, and then it would turn out the person that I know wasn't doing the show and it will all be people I don't know. and it would be me and then what felt like just a room full of people that are 20 years younger than me. So I just was. Yeah. No, I know it well.

I'm like, oh, fuck. I feel so old. Yeah. Well, go get on a kid's dating app and then you'll feel much better. Oh, no. I couldn't do that. Not a kid's dating up. I take that back.

Right. I know what you mean. There also is the internet rumor that I'm, uh, because of, of my show about kids sexuality, that I'm also a pedophile. So I want to, you know, dissuade.

You're one of two favorites. I wouldn't mind putting that one to rest. Can't you tell my loves are growing? When you were saying like, you know, that you had a sister to teach you how to talk to women, that was, I didn't have it, you know, an older sister. I was, but yeah, I just knew how to like, you know, like that game that you play with a balloon

where if it touches the floor, the world ends. It's like that, but the balloon is the woman's mood. That's what I learned, you know. Don't let it touch the ground. So anyway, hopefully my mom won't listen to this one. She's a big fan of the pot. She's a big fan of the pot. It's unfortunate that she does know about it.

things now. There was like a little brief window where she didn't know about anything. Right, right. And then it's like, well, we were listening to Andrew's podcast. Yeah, yeah. And we heard. Yeah, I wish we should say nice things about the family sometimes. Yeah. I'm like, well, maybe you should have thought about that. You should have been years ago. Yeah. When you were being just a, I'll never mind. Here's your ventilator back. Now, I want to back up a little bit from, from you. starting in New York because like, you know, are, is it a funny family? Like, are you fine, are your mom and dad funny, funny, funny siblings? You know, yeah, sorry, I finished a question.

No, no, that's, I mean, are you funny? I mean, in the family. Like, are you like, is it like, oh, Nick's so funny? Yeah. I mean, I feel like you probably talk to people who were like, no, it's like, I mean, you always heard like that thing of like Mike Myers being like, my brother is the funny one, you know? And like, and then, you know, I mean, you know, I always, my family's got to, I think has a very good sense of humor. I think my dad and my dad is, is funny. My brother's got a very, like, really dry sense of humor. And I see it in myself too, where it's like when you meet people and he like,

people don't know him, don't know if he's joking or not. You know, that thing where it's like, oh, you're too sarcastic, too early. People don't know. Like, I remember the first time I met Matt Walsh. I was at a founder of UCB. I was like, Sonor Owen brought me to his, a party at Walsh's and you might have been there. It was like, you know, 1999 or something at weather. And I walked in and Matt was like, hey, you can put your coat in the bedroom.

And I was like, you know, I probably said to me like, no, I'm going to wear a coat and I'll probably put one another coat on, like trying to be like, hey, I'm funny. Like, look, I'm funny already. I remember Matt looking at Owen and being like, is he, is he serious? And I was like, oh, right. Like, he doesn't know me. Like, he doesn't, you know. But no, my brother's funny.

My sisters have good. Yes, I think we're a funny family. I think I was always, quote, unquote, the funny one because I think I was the youngest, like, I was always performing for them. Yeah. But I would, I've always said that, like, I think amongst my family and definitely my, like, my friends growing up, if you'd been like, like, will Nick become a successful professional comedian?

They'd be like, oh, I doubt that. Like, he's pretty funny. He's like, but Stevenson, Stevenson's funny. And I'm like, I agree. Stevenson's hilarious. Like, I have no problem. I think Stevenson's funny as hell. But like, but I definitely had the feeling, especially as I succeeded,

that people were like, oh, wow. Holy cow, look at that. Yeah, yeah. ended up being successful. I just talked to Bill Hader and, like, what's amazing about his is that, like, he was a PA. And just because he wanted to direct movies, he decided to start taking improv classes to just, and also to meet actors in case he wanted, you know, do short films, because he was all about being a director.

And Megan Balali saw him on stage, recommended him to, to, to, to, Lauren Michaels and like he said he had a friend that went to Europe for a month and left and it was Bill the PA working in the film business and then came back. He's like, oh, I'm moving to New York and I'm going to be on Saturday night live. Which that's so nuts. That's such a, you know. Yeah. I think my trajectory was much, has been much more gradual. I mean, I've been very privileged to work at each stage.

but mine was like, start a UCB, like, do open mics, do, you know, whatever, get on a, I didn't even, I never made a Herald team, started booking like little radio voiceover commercials, then like full, like, you know, on-camera commercials, then like best week ever and like VH1 awesomely bad metal songs and then slowly, you know. But that's pretty prolific. It was all very prolific, but it wasn't like, boom, one day, I'm on Saturday Night Live. Yeah, yeah. It was like, boom, one day I could go to an S&L after party.

And then four years later was like, boom, a friend was on S&L. Yeah. Like four years later, it was like, boom. Yeah. I was allowed to sit in Lauren's office and watch Saturday Night Live. Oh, man. Yeah, now, I mean, in high school coming up, are you thinking about doing this for a living? I mean.

No. No. in high school, I was sort of like, my high school was not terribly supportive of the arts. It was just not a place where, you know, it was like a, it was a private high school in Westchester. It was like grooming people to, I guess, like be like financey kind of folks. Right. Is it a boarding school or is it? No, it was a, it was a school where my friends would get kicked out of boarding school and end up back at a, it was a Rye Country Day. I was like, okay, no. Totally, you know, for many people, a very good school. It ended up not being a school that was like, I had a nice teacher, Mr. Fuller, who like was a cubby on the original Mousketeers.

Wow. Who like put me in a play. But I didn't love it. I went to this place called the Mountain School in Vermont for one semester on a farm and a lot of weirdos there in the best way that encouraged me to like kind of let my freak. flag fly and oh that's great like i felt and i was like oh this is what i want to i want to be more like this person you know what year was that it was junior year it was one semester my junior year is that just because you wanted to go somewhere green and away from yeah yeah my sister again it's the advantage of being the youngest my sisters had gone there was one semester you live on this like organic farm fully self-sustaining uh 45 kids uh know uh everybody worked the farm and work the school there was no like, you know, staff.

I mean, there was teaching staff, but it was all just like you do everything yourself. And is that a big, is that a striking difference from the Westchester private school? Yeah. Just in terms of the kids and they're like. Yeah, the kind of kids like I got there. Less spoiled. Is that? Yeah.

Well, the kids like the kids of the mound school were just like they were all kind of like interesting. They were comfortably being weird. They were just comfortably like, you know, my friend Josh was like in the like blues guitar. and introduced me to like Charlie Parker and my other friends were like, you know, like we're wearing like dress guys. We're like, this was well before it was like binary, non-binary. It was just like, oh, I'm going to wear a dress today

because like it's comfortable. Like, you know, it was there was like, there was no partying really, but like we'd all get together and have like coffee houses. And I remember doing like a lip lip sync to like James Brown in like a weird orange jumpsuit and wearing a kitchen clogs and was like, oh, this feels fun. Yeah. But even still, I then went to college and went to Georgetown and did improv there and met Barbiglia and Malaney and everybody else.

Even there, I started doing improv and I was, I remember the first time I did improv. We did a mini, like a little sketch show my freshman year. We had a read through of a bunch of sketches. And I walked out of the apartment we were doing it at. I was like, oh, this is what I want. This is it. Like, and I don't think I'd ever realize. But even when I graduated, I still was like, I wasn't like, well, of course I'm

going to go become a professional comedian. Like, it didn't, I don't know why it didn't cross my mind that like, I was like, I knew. I was like, I grew up watching Saturday Live. I grew up watching everything. And, but I still was like, oh, but that's something that other people do. Do you know what I mean? Absolutely. I know what you mean.

Yeah. I always, I always liken to you, like, if I was a kid and I thought, it was similar to like thinking, like, I'm going to be an astronaut. Like the rough, like the, like I don't even know how you do, how you get there. But I do know it's complicated and takes a lot of specialized training. And I don't have a fucking clue as to get there. It felt like that. And it also felt, and I don't know if this is just a Midwestern. thing, but like so, you know, the Midwestern phrase, tooting your own horn. Like, so, like, like, you must think you're hot shit, don't you buddy, you know?

Yeah, I think you're going to get, but I mean, but it is like, well, you do. The idea is you have to think you're hot shit. Yeah, you're getting on stage. Yeah. In front of a room full of people. And the idea is they're quiet and they listen to you. And they all look at you like, yeah, there's some ego there.

There has to be. There has to be. I had less of because it's not Midwestern. It's like New York Jews. So there is a little bit of like, of course. To celebrate oneself is a mitzvah. But it was sort of more like you don't like, no, like you go get. And it wasn't really my parents.

I mean, my parents have been incredibly supportive. So I recently heard it's very funny. I recent, I haven't heard it, but second hand, I heard that just a little podcast. gossip. I mean, it was on that Marin had Dave Chang on his podcast. And he was like, your friends of Kroll. And he's like, and again, not to tube my heart. He's like, I like, I like, I like, but I had to stop following him. I saw too many pictures of him like as a young kid smiling. Like he had a normal childhood. Maron said this or David. Yeah. Yeah. Marin said that. I'm paraphrasing. But I was like, I was like, oh, I get, I get that. That's fair of him. Like,

who wants to like, who wants to, who wants to, who wants to, who wants to, who wants to, who wants. wants to watch the guy, you know, who seemingly had a, had a well, uh, you know, well adjusted. Yeah. Yeah. So, but I, but I do think it was not like, so I had a supportive family and, and all that stuff, but, but it was, it just wasn't assumed like, I don't know if you felt this, but like, if you ever told people you were going to, you were going to do comedy or

something and people kind of like, were like, oh, how's it going? Like, or like, like, when we were dating, when Lily and I were dating and she was like, oh, I'm dating a comedian. And they're like, people are like, how's it, how's he doing? You know, like, because it, the assumption is it's not going well. Right, right. And so. And that's a, that's a safe bet.

You know what I mean? Like, it's not like, like, I bet he's very successful. And they're like, no, no, odds are, you know. Yeah, odds are. He's also, he's also doing DoorDash and Uber. So no, it's been it, I didn't assume I never, it was not assumed that it would, it would work or succeed. Yeah. But and I, and I don't think until I graduated was I like, yes, I want to go.

I think I'm going to really give this a shot. And then I was like, yeah, I want to try. I want to try. I want to see what I can do here. Yeah. Yeah. Do you have you ever, have you looked at your Wikipedia page lately? I have not looked at it in, you know, because, you know, why?

It's just there's a fun, like one thing made me laugh because it mentions you go into Rye Day, country, or country day or whatever the fuck is. And then, and then he went for one year to this school in Vermont. It was here that he developed his love of hiking. Like somebody, somebody felt the need to like, you know, point, like, as if people are out there wondering, like, where did he get this love of hiking? What's the origin story of hiking? What did he?

I mean, you don't just go walk in the wilderness and enjoy it. You have to learn that. It is, it's a very, I mean, it is funny, like what gets into Wikipedia and what photo, no matter how hard you try to remove as your Wikipedia photo. Yeah. I cannot, I cannot get that photo removed. I gave up years ago of just caring about not necessarily how. I look, but like about how how you look to other.

In pictures, yeah, in photos. And every time I've ever been in something, because for people that don't know, they'll, you know, you'll do press photos and then they'll give you a proof sheet. Like, yeah, like, so where you can look over all the photos and the I, I think, a kill list or something. And then you X out the ones that you don't want distributed. And I'm always like, I give it to, I'll give it to like, you know, a bus boy and say, hey, pick which ones I look best in

because I have no frame of reference and it's all turd polishing in my mind. So I just... I am the same way. I make some... I have someone else to it because I have no. It's like because if it was up to me, none of these would be...

None of these would be approved. I did a movie with Ashton Cutcher and he... It was like... It was... We had... We had, we all had to, there was cast had to come to set on Saturday. And a bunch of people were really hung over, including him.

And he was like apparently very, very much a stickler about how he looked in the photos. And he said, to me, he said, I look like an idiot on the dude. Where's my car poster? And that's going to live forever. And I just thought, yeah, but in that movie, you're an idiot. You know, like the name. The movie is, dude, where's my car? And you're eating up our Saturday by being a stickler about this.

Because my thing with those kind of photo shoots is always just like, if it feels bad and like too much, it's what they want. And if you give them what they want, you can go home. You know what I mean? Yes. It's a, that is a very, it's a very logical, very reasonable take on it. Yeah. And it is. And it's also like, if they'll make.

You're like, you're a bags under your eyes. They'll like get rid of the, now they'll just like get rid of the bags. Right. Right. And also like, they'll weirdly Photoshop your head onto someone else's body. Yeah. Like every, you know, you look at like 80% of independent films. You look at the movie poster and you're like, they, why did they put their heads?

You can tell that those are photo. Yeah. Always. Always. You're like, how did we, how does this impossible? Can't you tell my love's. growing. So what makes you, you just head out to New York after college? You went to college and, I went to college in D.C. and then moved to New York and was like, I'm going to give it a shot.

And again, a couple of my Georgetown buddies from my improv group had already come to New York and were taking classes at UCB. And I knew Owen and had already been going to like, I mean, I remember going to see in college, we would do weekend workshops. We'd do like one workshop during the year with, you know, with UCC. people like, you know, Walsh did one, Andy Secunda did another. You would go to New York or they would come down to. Yeah, we would like as a group would go to New York and go do a workshop, a full day workshop with like, you know, yeah, one of the senior level people's. And then we'd see an ask cat. And I remember seeing you at an ass cat at the 22nd Street Theater and be there.

I can't. And I was like, I cannot fucking believe I'm in the same room as Andy Richter. Like I couldn't, I couldn't believe it. Like it was, you know, that little, that was like, I don't know, maybe 100, 150 seat, 100, maybe 100 seat theater. Yeah, yeah. And like we, I remember very clearly sitting on the floor on the side of the stage seeing you and, you know, Tina and Amy and just being like, I cannot believe this. You know, like, it was and it was so, it was so unbelievably exciting to watch, to watch you guys perform. and inspiring. And we just went back and was like, you know, trying to then forced college audience.

Watch us do long form improv poorly. Yeah, yeah. And it was terrible. But it made me be like, I want to go to New York and I started taking class of UCB and then started doing sketch and, and started doing characters and then was sort of like realized like at first I was doing stand-up, but I was so much more enjoyed doing, honestly, doing the characters on stage than I enjoyed doing improv or stand-up because it was like, it felt like the best of both worlds where I was like, I'm going to prepare something, I'm going to be able to interact with the audience, and I'm going to play a character that I feel like has a more interesting point of view than I have and, and like start to build my stuff that way. And that became sort of my more of my entree to stuff than either straight improv or straight stand-up. Yeah. At first. And I just was like, went to, you know, I was just like at a open mic or a practice group or going to see a show like every night.

You know, I graduated in 2001. 9-11 happened. And then so I waited until the new year and moved into the city and like, my New Year's resolution 2002 was to do an open mic and then it went from there. Wow. And did you just then end up doing mostly just the character work? Like did you do, you know? I kind of like, would you mix it up?

That was really kind of where I kind of, I did like a, you know, I started doing more characters. Like I had like, you know, like you've probably now seen every version of every character I did at some point. like I did an Argentine stand-up, Nico Pajamas, and he was, all of his jokes were kind of like making fun of Bolivians, you know, it was like, it was like the bad, like every, I'm like you've seen a hundred times like the bad stand-up character. Yeah, yeah. And I did a character named Fabrice Fabrice, who was the craft services coordinator for that So Raven. Yeah. I think that's the first time I saw you doing character work. And it was at, uh, a roast that Paul Tompkins had for himself.

Yes. Yes. Which I was, I was like, in that, I was like, I'm not falling for this trick where I say mean things about Paul Tompkins, and he remembers them till the end of time. So I made the decision to sort of like butter him up, but in sort of like a satirary kind of way. And he wasn't prepared for it because he said some things to me that still sting.

That's still haunt you. Yes, he said, the one I remember most was he said that I look as if the, the Michelin man just smelled shit. And it's really, that's pretty fucking good. But still, come on. Come on. But it sticks me. That's the thing with roast is like, and I think that's why I'm doing this in character.

Yeah. Because I don't, because I don't want to, I can say whatever I want. That was the beauty of being in character. It's like, you can say whatever you want and kind of. get away with it. Because they're like, oh, well, Nick, Nick would never say that. Fabrice, that's Fabrice. Yeah, yeah, that's nice. I did one roast.

I did the roast of James Franco. And it was like me and Rogan and Sandberg and Aziz and Hater and Natasha Lagerro and Sarah Silverman, Jeff Ross, Jonah, Hill. It was like a really great, like, very current group. And it was the one of the, one of the. I mean, like, I'm glad I did it because I think it was a good one, but it was one of the most unpleasant performing experience I've ever had because you are, you're up there making fun of your friends, which is kind of fun, but then you're like waiting that they're going to make fun of

you and then, or they're not going to make fun of you and you're like ignored and you're irrelevant inside of it somehow. And it was like, all of it felt terrible. Why didn't I get insulted? Yeah, kind of. Yeah, yeah. I just, to me, it's just like, I mean, you know, comedy, comedy always has like a little pinch to it, or, you know, it almost always does, and you are. And like you say, making fun of something is like,

it's a nice phrase, you're making fun of something. But I do find it's like they're very formulaic, and it's like, do this list of algebra problems that will make someone feel bad. Yes. Because you go like, okay, you know, that guy's got a double chin. Let's see. What can we do with double chin?

You know, and then it's just, and then you're just trying to fill in the blanks of some, you start, you start at the end of it, which is, you know, horse face. And then you work backward from horse face to think of a way to make, you know, some sort of artful construction that gets you to horse face. that gets you to horse face. And it's just trafficking and meanness. I don't. Yeah.

I have a tremendous amount of skill for the math of it. Because it is math. Yeah, yeah. And but I simultaneously am like, I think I'm done. I've done my roast. I've done my roast. Yeah. Because you are up there either with people you don't know and either love or not.

And if if you don't love them and they're just like sad, you know, like formerly important people, then you're like, oh, you're just kicking this person while they're down. Or they're your friends and they're like, hey, that really, um, yeah, it really hurt my feelings. Went out of your way with that one. Yeah, and you're like, that's what I'm supposed to do. So tell me, um, because, you know, you're performing and it's kind of got to build to it. And, you know, and you, that has got to feel good, especially because, you know, you are, you are,

are, it's a relatively short amount of time, you know, to go to New York City and start actually get paid to perform, yeah? Yeah. Yeah. I mean, I think it was 2002. I started really. 2007, I booked, I'd come out to L.A. that year for pilot season. And I booked cavemen, the hit show Cavemen. Based on the Geico Caveman. Based on the Geico Caveman, the beloved Geico Caveman commercials. So, and, you know, say whatever you will about that show, it was to get cast on a network TV show especially.

That was nearing the end of the beginning of the end of network television. Yeah. As we knew it, like, to be like the epicenter of everything. And the cash cow, you know, like. You know, your phase is sealed. If you can get on a hit show, you're kind of made for life. That show did not. Thank God it didn't go because the makeup was four hours of makeup every morning.

And my skin, I don't think, ever quite recovered from it. But I learned a ton. And I actually think there was funny stuff in there. But I really learned so much about performing and about being on set. And how do you show up at a table read? and how do you advocate with wardrobe and how do you deal with the, you know, the sound person and how do you, you know, do you take orders from the writer or from the director who's really running, you know, all that stuff that you just have to, you just have to do everything

for the first time at some point. And nobody can teach you that at school either. No. And then, and so I did that and I, the show got canceled them the first, the right? writer strike happened. This is 2007. And then I put on a writer strike show that during that period of time to, like, raise money for the American motion picture television fund, like,

blow the line worker folks. And just kept me busy. And then, and then from there started booking, you know, stuff. Yeah. And have been, been able, luckily, worked ever since basically, So that was, so it was about five years until I got like a, a movie or TV show of sorts. And, and then the side's not that fast.

You know, I mean, no, it's, it was pretty, it was like pretty. And I don't, I don't mean to belittle it or anything. You know what I mean? I mean, it's just like it's like, because, A, you're talented. So it's like, it's like, I'm not trying to say like, well, lucky you. No, you're, you're fucking hilarious and really good at what you do. And so that was recognized fairly early on. Yeah, no, as I really do believe, like, I don't now looking back, I think like when I started and for many years, I was sort of like jealous of the meteoric rise of like, how come, and it was many of my friends.

I'm like, how come that guy is already in movies or why is, why does she get to like go out and like open for him and like, you know, and it wasn't, I wasn't like ever, but I was, you know, that's natural. It's natural to feel that. way and it's the first thing you feel and then you put it aside yeah and it was always and it was it was less dis it was less like unhappiness for them as it was for for myself yeah because i think it's sort of that that competitive ambitious quality inside of you and again i attributed honestly a lot of it to being the youngest where just like your your brother's three years older and he's he's already riding his bike so you want to learn how to ride your bike quickly too so that you can keep up up with him go off with his friends, but he's going to be a better bike rider than you for a while,

because he's three years older than you. So you were like, I got to keep up. So it made you ride bikes faster than the kids in your grade, but you were still slower than his friends. And so you felt, you might have felt like shitty or like, and I kind of look at some of my career stuff that way of like, well, I was doing this faster than some of my peers, but I was always comparing myself to the guys a couple years older than me and the women a couple years older than maybe and like, why aren't I doing that or why can't, you know, and so, but no, I've been very,

now I feel incredibly grateful that I've had such a consistent, like, it's been a nice upward trajectory, but it's, and it's been, so at every stage I feel like I've been pretty ready for whatever happened because none of it came so quickly that I was like, whoa, I'm in a, I was just doing open mics yet last week and now I'm on set with, you know, you know, the great, you know, Maggie Smith. Great game Maggie Smith. Yeah. Which is.

Which is. Which of course, how James Cameron started. He was an improviser and then he immediately got Titanic. And then there he is. I don't know. I don't think Maggie Smith's in Titian. I don't know. She might be.

I know Billy Zane and his eyebrows are. Oh, yeah. Great head of eyebrows. Kroll Show was so fucking funny. It was so good. Croll Show started. I had done a special. My first stand-up special was sort of like a stand-up character hybrid,

going back to like the character, so I was doing Fabrice and his character Bobby Bottles service. Me and John Daly. You guys, Rich Hicks or something was? Yeah, we, so we did, we did, I did, um, uh,

on the special I did stand up and then I did Fabrice, Bobby Bottle Service. I did an oh hello bit with Malaney. And, um, and I don't think we did it. I don't know if there was one more or not. And then stand up. And,

and then, and then Daley and I with John Kreisle did a, like a pilot presentation. of Rich Dicks, uh, these characters that we did and for Comedy Central. And Comedy Central was kind of like, we love,

we love rich sticks, but we really love, we want to do this, like, we want to do your characters, like what your, what your stand-up special was, basically function as like a backdoor pilot,

like a proof concept of all these characters. And so they, so we then, yeah, out of that came Kroll Show, um, you know, the pitch was sketch, but kind of recurring character sketch. I think we didn't quite know from the beginning that what we were going to do was ultimately kind of this hybrid of

more narrative-driven stuff alongside these characters, but that it was going to be like, Seth Myers, I think at one point jokingly coined it, but I actually think it was not a bad version of it was called, as he called it, like, scatuational comedy. It was kind of like somewhere between sketch and more long-form narrative because all of the characters recurred and by season three all of the world started to collide almost like a herald you know it's like yeah the third the third beat where all of your stories are hopefully now coming together and yeah we did three seasons of it and another internet thing people are always like why did they cancel kroll show and i was like they didn't cancel it i mean like it was not a it was not

wild success. Yeah. But they, but I was like, I was, I was creatively, um, exhausted,

creatively, exhausted. You know, sketches, sketch is a fucking beast. Yeah. And also too, I did,

just the things that, some things are, you know, movies can't go on forever. Books can't go on forever. And TV shows. That's like, like,

like, you know, the strength of some of these English shows, like faulty towers. like, you know, how, what a strong, funny show that is. I mean, you know, there's some racism and cruelty and, you know, whatever. Nothing, nothing as well. Yeah.

Yeah. But, but there were only like 10 of them. Yeah. You know, and because that's all they're supposed to be. And yeah, it was like, we did 30 episodes of that show. And I'm like, yeah, that feels about right. Like, I was like, that feels like we did what we set out to do. and and I agree.

I think it's, I think it's, I think some stories don't require much. I mean, I think it depends on the subject matter. But I think, I think so. I think it's like certain things are like, yeah, okay, we got it. Yeah. Well, you can see, you know, some dramas that were imported from somewhere else. And I can't, I think it's called The Killing. Like, watch it, you know, there was an American version of it.

And you can tell because it did kind of well. they got to the end and they're like, well, we can't solve the murder. You know, like, the whole thing is like, who did the murder? And then you get to the end and it's like, we don't know. And because we're coming back next year and all these people, you know. Yeah, you've got to keep them all hooked in. I think that's the weird thing now with all the streamers is sometimes they're like, nope, three and out's good.

Like, we're good. We're good. Yeah. We need more. But they also want it. Serial. It's just a different. It's, and yet.

You watch like a show like the office or Parks and Rec or those shows like become massively successful on streaming in a way that they weren't on air. You know, like it's this weird thing. Well, the streaming, you know, the three seasons and they, they dump things after three seasons. I don't know, you know, and people will be puzzled by it. But it's because usually the way it's structured is after the third season, all the principals get a big, raise or it's like it's time to renegotion it's not economically feasible it doesn't they don't benefit from keeping something on the air after a certain point and all they care about most of them is new subscribers so having a show that most of your viewers that are watching already watch and like that doesn't

do anything for them they have to constantly like you know Netflix constantly has to be getting new people new people new people it's like a drug to them it's like a yeah I mean And it's like, and it's like how I do heroin. Right. Like a, like a vacuum cleaner, like a Dyson, sucking up dirt. Well, what's next? Where are you going now? I'm not tonight, you know.

Tonight I'm going to dinner with my wife and some of her business folks. I am. Don't get too drunk and say stuff. Oh, my God. What a nightmare if I did. I'm doing, let's see, we're doing big mouth. which are is actually now made it through those the three seasons and out they've they've held on to us and season so funny it's just and now that's one where holy shit the legs that you're getting out of puberty you know what i mean yeah much better legs that on the show that i'm getting into puberty than i did in real life um but yeah that we're still doing that um we're doing a spin off of that called human resources that is in the workplace of the monster and creatures, the shame wizard and the hormone monsters and the love bugs and the ambition

gremlins and the depression kitties and stuff. So that will come out next year sometime, you know, springish. And then we've just started ironically talking about how sketch is exhausting. We've just started writing History of the World Part 2 as a show for Hulu. Oh, right. I read about that. That's fun. Yeah, that's, I mean, it's like Mel Brooks. I mean, it's insane. You know, he's kind of my number one. Yeah.

And I watched that movie hundreds of times as a kid. And he came to me and we put together, you know, to be like, do you want to do this? And I was like, yeah, yeah. And so we put together a great team. It's, you know, Wanda Sykes. and Ike, Baron Holtz and Dave Stassen, who I'm sure you know,

Chicago Days and beyond. And we've got a great group of writers and we just started writing that. So we're writing that and we'll, you know, we'll shoot it, you know, once we're done writing it. And so I don't know when that'll come out, but those are the, and then I've got a,

I'm trying to produce for other people. So I'm helping people get their, hopefully get their shows and movies made with a sort of just helping to produce. So I'm doing a bunch of stuff and I'm, I really like doing all of it. It's incredibly lucky. I really enjoy doing it.

Are you going to stay in L.A.? Like, just having a child make any difference to you now geographically? You know, I'm from the East Coast and I miss my family. And we just spent a lot of time this past year in the last couple of months on upstate. on a lake. I love being like, you know, I think that's the thing about COVID is you're like, oh, I could, I can't kind of go anywhere, you know. Yeah. I mean, I like L.A. I have so many friends in my community there and obviously work. But I also really like, I really do like being in,

you know, as Wikipedia says, I love hiking. You learn to love at the mountain school. Right. And you can hike in L.A., but it's, it's, it's crispy. It's dusty. L.A. is dusty. I don't like it. You're done? Where would you go?

I would very possibly move back to Chicago. Chicago is a very comfortable kind of town. But, I mean, you know, it's all, it's all depending on, you know, my kids are old enough and it's kind of, you know, I'll probably always stay close to them. Yeah. wherever they are. Yeah. Which they don't have a choice about. No, no.

Yeah, in fact, there's, they have contact. There are like actual restraining orders. It's, you know, that they've sought out just to keep me away from them. No. Good luck. Good luck. Oh. Yeah.

Well, what is, like, what do you think is the thing you've learned, like the biggest thing you've learned about yourself? And then the thing, the biggest thing you've learned about. life, you know, what's your, what your path is taught. Ooh. So it's a huge question. Yeah, I know. What I don't have to answer it. I mean, what I have been learning, what I have been learning, I think is like, you know,

we were talking about, you know, like when you're a performer, you clearly have to, like, like, like yourself enough to be willing to perform. But you also kind of, while I am incredibly, you know, as a weird joke, like, I feel like I'm generally pretty well adjusted. You know, I think we also have like a, I think performers do oftentimes have like a real revulsion for ourselves, as we mentioned also like looking at pictures of ourselves. And I think, I think it's like really trying to figure out self-love. Like once you can love yourself in a healthy way and not in like a weird narcissistic way,

but like embrace yourself and all of your perceived shortcomings, the more, the more you will have a capacity to love others and be loved. Yeah. You can love yourself with in the same way that you have a healthy love with another person. Like you kind of have boundaries. Like, you know, I love me, but I'll only tolerate this much of me. Like, you know,

a bad tendency that I have or, you know, taking advantage with the people. Like being hard enough on yourself to not excuse the bullshit, to not excuse the bullshit, but also enough love to yourself to forgive yourself for whatever your shortcomings are, you know? And that I think for all of us is like a lifelong journey. But I am,

I'm working on that, I think. I think I'm working on like, I'm working on like trying to really, you know, look in the, mirror literally and metaphorically and and and and and really give that give that fell a hug you know oh geez I wish we were I'd hug you right now I'd hug you too buddy well thank you so much for taking the time to do this I appreciate it I know you got a lot going on you got babies and

dinners and you know yeah I mean the night the the desert night life well and let's not forget the horse track where I spend 85% of my time. Oh, that's nice. Yeah. I'm very dinted to horse racing. You got to have a job. You got to fill the day. Yeah. You got to fill your heart with paramutual gambling. But I thank you for having me again. As I said, seeing you on stage at UCB like over 20 years ago was like insane, like insane highlight for me and the idea that like here we are talking on a podcast, which I knew was coming 20 years ago. I knew it was going to be a thing. But the idea of talking to you now is like a friend is like tickles me to no end. So I'm privileged. I'm lucky to be here. That I mean, I it's very flattering to hear you say that. It's weird to hear,

you know, like somebody like to matter that much to somebody when you were strangers. Yeah. But it's, but it's, it's nice, you know, but it is like I just just, I just, I can. can't because, you know, I mean, it's like you said, you can't walk around in the space of thinking that, I bet young comedy kids, minds are blown when they jump into me at Ralph's. You know, it's like, and it's, it's good not to think that way, but also somehow allow yourself to be like, no, that is like I have had an effect on people in a real way. And I'm, what I've done matters. And, and I have been a super impactful person on, on, on. people, which is real.

It's good. And you're doing it. You're doing it now. Thanks, sir. Well, thank you. And thank you all out there for listening. We'll be back next week with more three questions. I've got a big, big love for you. The Three Questions with Andy Richter is a team Coco and your role of production. It is produced by Lane Gerbig, engineered by Marina Pice, and talent produced by Galitza Hayek. The associate producer is Jen Samples, Supervising Producer Aaron Blair and executive producers Adam Sacks

and Jeff Ross at Team Coco and Colin Anderson and Cody Fisher at Earwolf. Make sure to rate and review the three questions at Andy Richter on Apple Podcasts. Can't you tell my loves it growing?