The Three Questions with Andy Richter - Nick Kroll

Episode Date: November 9, 2021

Actor, Writer and Comedian Nick Kroll joins Andy Richter to talk about birth order, his journey through comedy, doing roasts, and more.

hey everyone i'm andy richter uh 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 I 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 of 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 the work and you just get to kind of hang out. Yeah, it really is. It's, it's been, uh, it really is. And,

and I find my wife's work interesting and cool. So it's, uh, it's a nice thing to be, uh, to be a tag along on. So yeah, she's like a, a landscape designer, botanical artist, botanical installation artist. She does all types of things. Um, some of them uh temporary some of them permanent and uh so she's yeah she's working on a permanent installation right now so i'm uh she's out here scouting and i'm just uh hanging out in the desert which is beautiful yeah you forget how gorgeous like this palm springs palm desert area is it's like it's so

cinematic yeah when it's not 9 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. But every other time I'm there, it's just seems like a purgatory. I love like a July 31st, just a 100 and 115 degrees at 8 a.m yeah just like watching watching the botox ooze out of some elderly people and uh 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 you're like the one successful couple that they can boast of. I know. I didn't, I it's one of the unfortunate thing is like, it's not like you can get then a free membership. I know. I didn't, I, 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. Um, yeah, we met on a dating app and I, and I, um, uh, 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 for, it's supposed to be like, quote unquote creative types and and what that meant at least when i joined it was for like uh beautiful women some of whom were quite talented and accomplished and some of them are just beautiful and like uh like uh successful men yeah who are or like hot guys in front of like a ford bronco with like wide brim hats and like um you know like like a picture of them with their dog sir you know rented puppy yeah yeah yeah a vintage puppy and uh uh you know like a lot of bracelets. So no, we met on there. And I find it actually kind of romantic. It served us 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, and it was trying to figure out a way to meet someone outside of my circle. And, uh, and I did it and, uh, now we're married and have a child. So nice. Yeah. Yeah. Cause I was, I've been single for a couple of years now and, and I attempt rise. The only attempt I've made at a dating app and I, attempt rise. The only attempt I've made at a dating app. And I, I scurried away as quickly as I could. It felt so I I've told this before, but the thing that did it was seeing a woman who's her, her job was listed as denim architect. And I just was like, I don't think this is my crowd. 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. And yeah, no, I, I,

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 but 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 yeah mort from madagascar you know it's like yeah yeah i mean i i would have been like oh i want to date the guy from quintuplets well of course you would um but no i think i mean ironically my wife told me that she was like had she 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 ruxin she's like i hated your 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 i may as well like swipe right or or whatever approve just like at the very least i might have like a laugh you know and um and uh so i'm glad she she chose to uh 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 f18 is flying um that's um if you only watch the league you'd think my i mean ruxin was like a truly deplorable human yeah he's an asshole yeah the worst yeah and i'm only and i'm just i'm just

a pain in the ass i'm just right right You aspire to those levels. Yes, exactly. 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 they're 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 know you play some charming people too occasionally i i seem i seem to get cast i've gotten gotten, I have been very, I've been very fortunate to get cast and, and, or, uh,

to do different things, but I definitely, for a long time, at least my sweet spot was like douchebag assholes, which are, which are always fun to play. It's, you know,

it's like, it's a fun, I trust me. I don't, I, I, I'm not complaining about it, but,

but at some point specifically, there was something about the league where like Manzoukas, Jason, who is, was played my brother-in-law, who's a on the show, a stone cold maniac, like pure id, 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 very emotional guy and also a massive ocd germaphobe yeah yeah quite reserved because of he's you know yeah prison of his own making yes and so but people before the world like before covid uh you know before the collective trauma of covid that we've all gone through um he we would be out and about and like every real life rafi his character in the league would come up to him and be like you rafi i'm rafi and he'd be like please don't, I can't like you touching me, scares me so much. Like, but I kind of enjoyed it. Cause I am like, you've, you know, you've chosen this. Right. Right.

So just, you know, this podcast is sort of a, you know, it's a, as a John Gabrus called it the origin story which makes it sound like i'm only interviewing um villains um so uh you grew up on the east coast new york yes where many villains come from where many villains come from and um and it's i mean it's not a secret your dad owns a pretty big business like a pretty big company that's like well-known out in the world. Uh-huh. And, uh, so, you know, you, you had kind of an East coast.

I had a privileged East coast upbringing. Yeah. Yeah. And, um, how'd you end up so nice? That's the crazy thing. Um, you know, it's so funny. It's just weird. It's a it's a very I mean, it's I mean, it's I mean, I feel incredibly blessed growing up in my family because 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, the no, if you if on the internet, it says that, like, I have ten million dollars. I don't I do not have ten million. I don't have anywhere near ten million. Well, if you don't have ten 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. We grew up very comfortably growing up, but it was something that he built over 40 years or so. But I grew up with yeah, I grew up very comfortably. And, but also my parents just did, were, are nice people. And, and it would never even have crossed my mind to not be nice to people. Cause that's how I think, cause that's kind of how my parents were with people, with everybody. So, 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. And I have found life to be easier being nice to people. Like from a purely pure pragmatic way as an i it 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 like even if you're evil and all you care about is productivity and that people are machines that 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 a 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. 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 if you are nice the world is there to work with you uh 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 uh or your room you're not getting the room you thought you were going to get at a hotel or like you're like you're the the 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? Oh, I'm the baby. By how much? Like who's, what's the age spread?

It's a seven year spread from oldest to youngest. So there's, 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, you know, and then there's this three year 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 and sister from my mom was married twice i have an older brother who's three years older than me and then i have a younger uh brother and sister from my mom's second marriage so we have a different dads uh and they are twins and they are uh 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 uh you know because when then I was like the middle. Right. Because when there's two at the same age, that's functionally the same person. You don't have to treat them as two individuals. You can't separate them. You can treat them as one entity. Right. It's a time saver. I believe very much in birth order. Conan always did, too. He always believed in that. Really? Yeah. order yeah i'm a big and always did too he always believed in that really yeah it's i 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 what where do you fall in your birth order yeah i think that that has a massive impact on, on, uh, on who you are. Um, and what's Lily? Uh, she's also a Gemini. She, no, no, I mean, I mean, uh, birth order wise. Oh, she's, she's the old, 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 sibling older girls to younger boys and so i sort of make sense on some level uh 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 the, that like sister was a little older than me, like where you, 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, like, how do you talk to women? How do you, uh, how, whatever that relationship was, I think became a central one for me. And I think,

and I think as the youngest, I think of the youngest oftentimes as performers, as the ones who end up becoming performers. Cause I think they have been like, um, I think they're verbal younger, uh, 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 standup 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. Can't give that away, baby. But, um, but I, I, yeah, I don't know. Do you feel like a youngest

or an, and do you feel like a middle? Like where, where do you, um, I do feel like, Um, 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. When is your birthday? 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 you're 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 right like Yorkville Illinois in the, they're like, you're born and you're born here. That's the year you're 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 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, birth wise, like, I definitely think 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 kind of i mean i had i had friends my age and and all different ages but i always kind of was around a lot of older people and then when i started 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 it was kind of like halfway through. The my first in on the Conan show that there started to be writers younger than me, and I started to feel like, Hey, wait a minute. I'm supposed to be the youngest.

I'm a little wonder. Can I bet 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 my- He was an improviser, producer and UCB. Yeah. Incredibly talented guy. Yeah, it was my intro into UCB and through him, I met, you know, Shear and Hubel and, and, and then through just all of those relationships, it was like Manzoukas and Brian Husky and Seth Morris and, and that whole crew of folks. And I was like, I was used to that. I was like, 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 if like UCB shows, I would go do UCB shows that somebody would say, would say hey you know this person that you know is going to do this show will you come do the show and i'd say okay and they would turn out the person that i know wasn't doing the show and it will would all be people i don't know and it would be me and then what felt like a just a room full of people that are 20 years younger than me so i i just was uh yeah no i know it well i'm like oh fuck i feel so old yeah well go get on a go get on a kid's dating app and then you'll feel much better i don't know i couldn't not a kid's dating up i take that back because there also is the internet rumor that i'm because of my show about kids sexuality, that I'm also a pedophile. So, well, I want to, you know, just wait.

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 a you know an older sister i was and 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. Don't let it touch the ground.

So anyway, hopefully my mom won't listen to this one. Your mom loves it. She's a big fan of the pod. She's a big fan of the pod. She's a big fan of the pod. Uh, I'd say it's, it's unfortunate that she does know about things. Now there was a, like a little brief window where she didn't know about anything. Right, right, right. And then it's like, well, we were listening to Andrew's podcast and we heard, yeah, I

wish you'd say nice things about the family sometimes. Yeah. I'm like, well, things about the family sometimes. Yeah. I'm like, well, maybe you should have thought about that 30 years ago. Nice. Yeah. When you were being such a, oh, never mind. Here's your ventilator bag. Now, I want to back up a little bit from you starting in New York.

Because, like, you know, is it a funny family like are you fine your mom and dad funny funny siblings you know yeah sorry i finished your question no no that's i mean are you funny i mean in the family like are you like is it's like oh nick's so funny yeah i mean i feel like you probably talked 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 always, my family's got, I think has a very good sense of humor. I think my dad and my dad is, is got a fair, is funny. My brother's got a very like really dry sense of humor um and i and i see it in myself too where it's like when you meet people and he like um 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, Soner Owen brought me to a party at Walsh's and you might've been there. It was like, you know, 1999 or something at whether. 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 on 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, you know, um, 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 um but i would i've always said that like i think amongst my family and definitely my like growing my friends growing up if you've been 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

being successful i just talked to bill hater and uh 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 Mullally saw him on stage, recommended him to Lorne 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 okay which that's so nuts that's such a you know yeah my i think my trajectory was much has been much more gradual i mean i've been very privileged to to work at each stage but mine was like start at ucb like take 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,

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 SNL after party. And then four years later, it was like, boom day i could go to an snl after party and then four years later it was like boom a friend was on snl yeah like four years later it's like boom yeah i was allowed to sit in lauren's office and watch saturday night live

oh man yeah now uh 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 it was a school and it was a private high school in Westchester. It was like grooming people to, I guess, like be like finance-y kind of folks. Is it a boarding school or is it? No, it was a, it was, 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. It 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 one, I had a, I had a nice teacher mr uh fuller who who like was a cubby on the original uh mouseketeers wow um who like put me in a play and 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 wanted 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. One semester, you live on this like organic farm, fully self-sustaining, 45 kids. No, everybody worked the farm and worked 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 spoiled is that yeah well the kids like the kids of the mountain 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 were like it was this was well before it was like binary non-binary it's just like oh i'm gonna 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 would, I remember doing like a lip lip sync to like James Brown in like a, like a weird orange jumpsuit and wearing like kitchen clogs and was like, oh, this feels fun. feels fun and feels and but even still i then went to college and went to georgetown and did improv there and met berbiglia and melania and everybody else even there i started doing improv

and i was i remember the first time i did improv or the first 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 and I was like oh this is what I want this is it like and I don't think I'd ever realized but even when I graduated I still was like I wasn't like well of course I'm gonna go become a professional comedian like it didn't I don't know why it didn't cross my mind that like I I was like, I knew I was like, I grew up watching Saturday night 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 likened it to like, if I was a kid and I thought, it was similar to like thinking like, I'm going to be an astronaut. Like, like the, the be an astronaut like like the the 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 i don't have a fucking clue as to get there it felt like that and it also felt uh 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 yeah so like like you must think you're hot shit don't

you buddy you know yeah i think you're gonna get but i mean but it is like well you do the idea is you have to think you're hot 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 so i that 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 haven't heard it, but secondhand, 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, you're friends with Kroll. And he's like, and again, not to toot my horn. He's like, I like Kroll. He's funny. He's like, but I had to stop following him. I just saw too many pictures of him like as a young kid smiling like he had a normal childhood. Marin said this or David? 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 watch the guy, you know, who seemingly had a had a well, you know, well adjusted. Yeah, well adjusted. Exactly. But yeah, but I but I do think it was not like, so I had a supportive family 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, we're like, oh, how's it going? Like, or like, like when we were dating and when Lily and I 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 uh and so and that's a that's. You know what I mean? Like, it's not like, like, I bet he's very successful. No, like, no, no odds are, you know, he's also, he's also doing DoorDash and Uber, you know? 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. it was not assumed that it would it would work or succeed um 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 that do you have you ever have you looked at your wikipedia page lately i have not looked at it in because you know it's just there's a, like one thing made me laugh because it mentions you go into Rye Day, Country Day or whatever the fuck it is. And then he went for one year to this school in Vermont. It was here that he developed his love of hiking. Like somebody felt the need to like, you you know point like as if people are out

there wondering like where did he get this love of hiking story of hiking what 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 i know 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, like about how how you look to others 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 oh yeah a proof sheet like yeah like so where you can look

over all the photos and 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 where 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'm the same way i i make some i have someone else do it because i have no it's just like no, it was just like, cause if it was up to me, none of these would be, none of these would be approved. I did a movie with Ashton Kutcher and he, it was, 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, 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 but in that movie you're an idiot you know like the name of the movie is dude where's my car and you're 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 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 uh uh take on it yeah and it is and it's also like if they'll make you like you have bags under your eyes they'll like get rid of the now they'll make you like you have bags under your eyes, they'll like get rid of them. 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 percent of independent films. You look at the movie poster and you're like, why did they put their heads? You can tell that those are so weird. Yeah. Always. Always always you're like how did we how is this possible can't you tell my loves are growing so what makes you just head out to new york after college you went to college and went to college in dc and and then moved to new york and was like i'm gonna give it a shot and again my 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 yeah and i'd already been going to like i mean i remember going to see in college we would do weekend workshops we do like one workshop uh uh and during the year with at use you know with ucb folks like you know walsh did one andy secunda did another you would go to new york or they would come 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 like one of the senior level peoples and And then we'd see an ass cat. And I remember seeing you at an ass cat, um, at,

on the, 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 a, I don't know, maybe a hundred, 150 seats, a hundred, maybe a hundred seat theater.

Yeah. Yeah. And like, we, I remember very clearly sitting on the floor on the side of the stage little that was like a 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 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 to watch you guys perform and inspiring. And we just went back and was like, you know, trying to force college audiences to watch us do long form improv poorly. Yeah. And it was terrible, but it made me be like,

I want to go to New York and, and I started taking class at UCB and then started doing sketch and, and, and, and started doing characters and then was sort of like realized, like at first I was doing standup, but I wasn't, I was so much more enjoyed doing, honestly doing the characters on stage than I enjoyed doing improv or standup. Cause 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 that my stuff that way and that became sort of my more of my entree to stuff than either straight improv or straight um uh stand-up or yeah at first um and i 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 from 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, to do an open mic and then went from there. Wow. And did you just then end up doing mostly just the character work? Like, did you, you know, I kind of like it. Would you mix it up? That was really kind of where I kind of, I did like did you you know i kind of like it 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 payamas and he was all of his jokes were kind of like nico payamas and he was all of his jokes were kind of a 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 that's the i think that's the first time I saw you doing character work. And it was at 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. 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 satire-y kind of way. And he wasn't prepared for it because he said some things to me that still sting. That still haunt you. Yes, he said, the one I remember most was he said that I look as if the Michelin

man just smelled shit. And it's really that's pretty fucking good. It's very ill. Yeah. Come on. Come on. But it sticks. That's the thing with roast is like and I think I'm doing this in character.

Yeah. Don't because I don't want to. I can say whatever I want. That was the beauty of being in character. You can say whatever you want and get away with it. They're like, Nick would never say that. Fabrice, that's Fabrice Fabrice. Yeah, that's nice.

I did one roast. I did the roast of James Franco. It was like me and Rogan and Sandberg and Aziz and Hader and Natasha Leggero and Sarah Silverman, Jeff Ross, Jonah Hill. It was like a really great, like very current group.

And it was the one of them. 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 gonna make fun of you and then or they're not gonna 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 yeah uh i just to me it's just like i mean you know comedy comedy it always has like a little pinch to it or you know it 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. 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 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. And it's just trafficking and meanness. I don't. Yeah. I, I, I have, I have a tremendous amount of skill for the, the math of it. Um, cause it is math. Um, 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 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, yeah it really hurt my feelings it 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 because, you know, you are it's 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. I mean, I I think it was 2002. I started really 2007. I booked I'd come out to L.A la that year for pilot season um and i booked um uh cavemen the hit show cavemen uh based on the geico cavemen based on the geico caveman the beloved geico caveman commercials um so and you know say whatever you will about that show. It was a, it was to get cast on a network TV show, especially that was nearing the end of the, 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 face. 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 like 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 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, the sound person and how do you, uh, you know, who do you, do you, do you take orders from the writer or from the director who's really running thing? 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 i did that and i uh the show got canceled then the first the writer's strike happened uh this is 2007

and then i put on a right a writer's strike show uh that period of time to, like, raise money for the Motion Picture Television Fund, like, below-the-line worker folks. And just kept me busy. And then from there, started booking, you know, stuff. Yeah. And have been able, luckily have worked ever since basically. But so that was, so it was about five years till I got like a, a movie or TV show of sorts. And, and then the size, that's not that fast. I, you know, I mean, no, it's, it was pretty, it was like, 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 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 i think yeah no i as i i really do believe like i 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, yeah, that guy is already in movies or why is why? Why does she get to like go out and 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 of this. It was less like unhappiness for them as it was for myself. Yeah. Because I think it's sort of that, that competitive, ambitious quality inside of you.

And again, I attributed that, that honestly a lot of it to being the youngest we're 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 you can keep 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 yeah 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've 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 of years older than me and the women a couple years older than me being 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 I, it, none of it came so quickly that I was like, Whoa, I, 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, 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 Titan. I don't know. She might be. I know Billy Zane and his eyebrows are. Oh yeah. Great head. Great head eyebrows. Kroll show was so fucking funny.

Was so good. Kroll 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 characters I was doing fabrice and his character bobby bottle service and me and john daly you guys rich dicks 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 Service. I did an Oh Hello bit with Mulaney. And I don't think we did it. I don't know if there was one more or not. And then stand up. And then Daly and I with John

Kreisel did a pilot presentation of Rich Dix, which 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 standup special was basically function as like a backdoor pilot, like a proof concept of all these characters. And so they, so, so we then, yeah, out of that came Kroll Show um which 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 of more narrative driven stuff alongside these characters,

but that it was going to be like Seth Meyers, 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 sketchuational 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 third the third beat where all of your stories are hopefully now coming together uh and yeah we did three seasons of it and another internet thing people are always like why did they cancel crawl show and i was like they didn't cancel it i mean like it was not a it was not a wild success

yeah but they but i was like i'm i i was i was creatively um exhausted creatively emotionally exhausted i you know sketches sketches a fucking beast. Yeah. And also, too, just the things that... Some things are... Movies can't go on forever. Books can't go on forever. And TV shows. That's like the strength of some of these English shows like Fawlty Towers.

Like, you know, how... What a strong, funny show that is. I mean, you know, it's kind of... There's some racism and cruelty and, you know, whatever. Nothing, nothing as well. Nothing. 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'm like yeah that feels about right like I was like that feels like we did what we set out to do and and and I agree I think it's I think it's I 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 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 got to keep them all hooked. Yeah. And I think that's the weird thing now with with with all the streamers is sometimes they're like, no, three, three. Now it's good. Like, we're good. We need more. But they also want it serialized. 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 right on air you know like it's this weird thing um well the streaming that the reason you know the three seasons seasons, they dump things after three seasons, 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 renegotiate. Yeah, it's not economically feasible. 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. And it's like how I do heroin. Right. Like a vacuum cleaner, like a Dyson, sucking up dirt. Well, what's next? Where are you going now? I mean, not tonight.

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 um um i'm doing uh let's see we're doing big mouth um which are is actually now made it through those the three seasons and out they've held on to us. It's so funny. 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 on the show that I'm getting out of puberty than I did in real life. But yeah, we're still doing that. We're doing a spinoff of that called Human Resources. That is in the workplace of the monsters 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'll that will come out next year sometime, you know, spring ish.

And then we've just started, ironically, talking about how sketch is exhausting. We've just started writing History of the World Part Two 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, he's kind of my number one. Um, and I watched that movie hundreds of times as a kid and, and, and he came to me and, um, and we put together, you know, to be like, do you want to do this? And I was like, yeah. And so we put together a great team. It's, you know, uh, uh, Wanda sykes and ike bernholz and dave stassen

who i'm sure you know i do chicago days and beyond um and uh 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 that those are the and then i'm i've got a um i'm trying to produce for other people so i'm helping people uh get their hopefully get their shows and movies made um with a sort of a just helping to produce so um i'm doing a bunch of stuff and i i'm i i, I really like doing all of it. It's incredibly lucky. I really enjoy doing it. Are you going to stay in LA? Like does having a child make any difference to you now? Geographically? Uh, you know, I'm from the East coast and I missed my family and we spent, we just spent a lot of time this past year. Um, in the last couple of months on, uh, upstate,

like on a lake. Um, I love being like, you know, I think that's the thing about COVID is you're like, oh, I could do, I can't kind of go anywhere, you know? Yeah. I mean, I like LA. I have so many friends and, and, and 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 do. I learned to love at the mountain school.

Right. But 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 around here. Where would you go? I would very possibly move back to Chicago.ago 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 uh wherever they are yeah um 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 true good luck buck oh yeah well what um what is the 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's your path is taught um so it's a huge question i don't know what i don't have to

answer it 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 yourself enough to be willing to perform, but you also kind of, while I am incredibly, you know,

as a weird joke, like I, 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. Um, and I think, I think, I think it's like really trying to figure out self love. Um,

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 you will have a capacity to love others and be loved. Yeah. 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 only tolerate this much of me. Like, you know, a bad tendency that I have, or, you know, taking advantage of other people. Like being hard enough on yourself to not excuse the bullshit, but also enough love for yourself to forgive yourself for whatever your shortcomings are. And that I think for all of us is like a lifelong journey. But I am, 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 fellow a hug, you know?

Ah, 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're, you know, you got a lot going on. You got babies and dinners and, you know, the desert nightlife. Well, and let's not forget the horse track where I spend 85% of my time. Oh, that's nice. Yeah.

Well, I'm very addicted to horse racing. You got to have a job. Got to fill the day. Yeah. You got to fill your heart with parimutuel gambling. Exactly. But thank you for having me again. As I said, seeing you on stage at UCB over 20 years ago was an insane highlight for me.

And the idea that 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 it's like a friend is is like tickles me to no end so i'm privileged to be here that i mean i i it's very flattering to hear you say that it's weird to hear you know like 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 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. I have had an effect on people in a real way. And I'm what I've done matters. And I have been a super impactful person 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 Wolf production. It is produced by Lane Gerbig, engineered by Marina Pice, and talent produced by Kalitza Hayek. The associate producer is Jen Samples, supervising producer Aaron Blair, and executive producers Adam Sachs and Jeff Ross at Team Coco,

and Colin Anderson and Cody Fisher at Earwolf. Make sure to rate and review The Three Questions with Andy Richter on Apple Podcasts.