The Three Questions with Andy Richter - Conan O’Brien

Episode Date: May 12, 2020

Conan O’Brien sits down with Andy Richter on the season finale of The Three Questions to discuss stories from his time at the Harvard Lampoon, writing on The Simpsons and SNL before becoming a late-night icon, and the future Conan envisions for himself.

all right well let's start the podcast hey show a little enthusiasm you again how often do you get to talk to me. Well, I just want to finally confront you about your habitual pants shitting. Okay. Confront you. You're a pants shitter and admit it. I'm going to clap back at you for that.

How are you? Seriously, I mean, see, this is what's fun about this podcast is that I get to talk to people that I know and love and have known for a million years. And they just like ask them prying personal questions that I normally wouldn't. So wait a minute. You always ask me prying personal questions. Yeah.

And you always come up with a joke. You always deflect with your comedy. Oh, so no jokes today, huh? Yeah, no, Yeah, no. No, I know. But I mean, seriously, how are you holding up during this? I am doing OK. I would say if it's all relative. because my wife comes from this breed of sort of Welsh, Scotch, English, WASPy people that just

want to stay at home anyway. And I've always joked that they're hobbits because they're very content to like make granola, look out the window. They're wonderful people, great people, but the last thing they want to do is get on a plane and go somewhere or rush around. And both my kids, 14 and 16, are very good at living online and very sort of built for this. I think there's a generation that's kind of built for, they game with their friends, they're really smart about taking their online classes, they know how to upload their homework. I mean, it's just, they've been preparing for this somehow. And then I'm the one that's having trouble, as you can imagine, because you've known me for years and i'm uh hyperkinetic i'm always moving i need to constantly be physically putting my hands on people uh that's a problem no i know i know i

know but biden told me it was fine right uh no i like i grew up uh in family of six. And so the boys in the family were constantly wrestling. And I just never got over that part. As you know, I'm always wrestling our head writer. I just need to physically touch a lot of the writers. I don't touch the women. I'll make that very clear because I've asked them if it's okay. And they've said no right um and then uh but they didn't really say no they yelled no they yelled they banned symbols together and just scare you away yeah and uh but i don't know i'm very uh so and of course i invented this whole other job for myself, which is traveling the world and jumping on planes and going places and jumping into crowds of people.

That's always been the essence of, I think, what made me happy. So everyone stay inside and don't move much. Yeah. And stay away from other people has been frustrating for me. Do you miss the studio audience? Because I know, I feel like you get a charge out of that. I do. I think it's funny because I think, I've noticed this is something that you and I are very different. We have similarities and then we're very different in some ways. I get something from an audience. I get a charge. And you're always, in a good way, I think, uninfluenced by, meaning if a crowd is terrible, I think I lose some of my energy.

And if a crowd's really great, I get energy. And I think I've noticed that you're a strength of yours is that when a crowd isn't giving you what you want, you're still yourself and you're very comfortable with your own rhythm and knowing what to do. And I think I've gotten better at it over the years, but I used to live or die by the crowd. And you would say like, well,

what do they have to do with it? We're making a funny show. And. Well, and especially it's the studio. The studio audience is just a soundtrack that we actually can, can manipulate. Whereas it's the people at home watching the show that are the true audience.

But I used to get my feelings hurt. Honestly, I'm very thin-skinned, and I'm very influenced by, you know, if one random person says, you suck, you know, if one random person says you suck, you know, if a million people tell me I'm great and one person says you suck, I'll obviously think about the person who said you suck for months afterwards and wonder, why would my father say that? There we go. There's your joke. Well, that's a common that's a common malady though i mean i think it's like you know because i definitely notice that in in our studio audience if there's one person sitting with their arms crossed and like without smiling and just kind of like right the person that looks like the you know the dad that was dragged to this thing and never thought much

of the show yeah and that's the person i see the smiling happy faces enjoying themselves are like a visual white noise but the only thing i see is the person having a bad time and i and it's not like that they panic me i just am like fuck you motherfucker like what just at least when you know but it's when you say that and you're rolling. That's the problem. I know, but you know. No, but I've gotten a lot better. I mean, you've, you know, we've met you and I in, you know, like May or June of, it might have been May of 93. And so we've known each other a really long time. And, uh, you've been there for just a lot of, you've been in the nose cone

with me watching stuff happen. And so, uh, you've seen what my real, uh, I don't know how vulnerable I can be in front of people. If I think they're not getting what they want or if the customer's not happy and I've gotten much better at that, I would say I don't miss our studio audience as much as I miss. I love a theater crowd. Just before, um, this whole thing happened, happened uh judd apatow asked me to uh join him and adam sandler and eric idol and a couple of other people to do something uh at um largo largo yeah and i did it and you know largo is they have such sweet crowds at Largo. They're just the best crowds in the world. They're so smart. They're so generous. They're so great. And so I came out and I was a surprise and it was really, I had so much fun. And I do feel like if there are times where I feel like

if I had, you know, an infection or if I had a cancer and I went in front of a crowd like that, there'd be no sign of it afterwards. The disease would be gone just because I do feel like I really do get something very positive. And I feel like I give something positive and I get something positive and no one gets hurt and it just feels lovely. And I have to say that was one of my last experiences before everything shut down. And yeah, I've I do miss humans and making humans I don't know laugh. I do miss that a lot. Do you think because for me, it's different. Like I don't the people that I like to make laugh and also to like, I didn't set out to become a live performer.

I set out to be, you know, I went to film school and I wanted to be in television or or movies, but not in a not in front of a studio audience. Just and I like I still to this day, like the feeling of being on a film crew. still to this day like the feeling of being on a film crew yeah and being sort of this like little band of people that packs things up into trucks and then shows up and plays makeup world and then leaves yeah yep um and so it and when and even in our studio the people that i like to make i like to make the cameraman laugh you know like i like to make the the stagehands laugh and when i hear them laugh that's like the most rewarding thing for me and i think and that is a difference between us and i want like i wonder because you were in such a big family and because you are i mean you joke about being the middle kid and like needing attention but do you think

that that is like a serious kind of result of of that kind of dynamic oh yeah i mean i you know freud says there are no jokes uh he's a bummer he was really no fun you know freud used to go to comedy clubs this is true and comedians would be telling jokes and he'd stand up and go there are no jokes yeah yeah and uh you want to fuck your mother. You want to fuck your mother and kill your father. He got thrown out of the laugh hut and the laugh factory. And I just love doing laugh. Yeah, I love it. But the chuckle barn, the chuckle bunker.

The chuckle barn. a big family and you know the irish catholic cliche but it's true my my parents had a child a year for you know like six years i mean there's some little gaps here and there but really uh i think they had four kids under under five at one point which is which is madness that's just absolute craziness well it's just you know it so funny. But if you look around other families I knew growing up, other Irish Catholic families and cousins, they all did the same thing. There were like nine kids in this family and seven kids in that family. And we had six. And it was just it's it's what we did. And it was it was the time people people I think I don't know if it was overtly because the pope didn't want people using condoms. That's what I was going to say,

because I'm not Catholic. Was it really a religious thing or is it just a cultural thing? My parents are religious, but I really do think my mom also told me when I was young, I said, how come there are so many of us? And she said, I just always wanted to have a lot of kids. So I, I, I do think that she wanted to have a lot of kids, a lot of children. So, but what happened was I just remembered there was so much, uh, when I look at like a bunch of puppies and they're all climbing over each other, you know, sometimes you'll see video of, or you'll see a bunch of puppies in a pen and they're literally crawling each other. And one of them is sleeping in the water dish and they're tumbling and there's one jammed under three others. I feel

like, oh yeah, I kind of know what that's like. That kind of looks familiar. Uh, I think what, uh, what, what it did is it made me, I think there was a lot of my youth where I didn't know who I was. I remember thinking very clearly, I don't have a personality. Like my brother, Neil, the oldest. Like at what age? This would be in would be very strongly i think i felt that way from like nine till like 16 i remember just there's like a bunch of years in there where i think well i don't know what it is i contribute because my oldest brother was really big and physically strong and also incredibly mechanical and knew how to fix cars and just

was off doing his thing. And he had a very clear thing. And then my brother Luke is to this day, one of the smartest people I've ever met and kind of a Renaissance man and was, um, knew everything about sports, but also knew how to make a creme brulee, but also knew how to, I mean, just knew everything, but also had read, you know, Dante. I mean, just. He's a dick. Let's just say. Yeah, no, he is. He is. And also saintly, like an incredibly nice guy. And I'm moral. I think I just used to feel like, yeah, very moral. And I used to just think I'm no Luke, I'm no Neil.

And I just remember thinking, I don't know what it is I do. And I didn't like I didn't like the way I looked. I didn't like having I had orangish hair and freckles. And I remember hating that. And I had a weird name. And I just thought the whole thing was I remember thinking, I wish I looked like Hogan on Hogan's Heroes. I wish I just had black hair and was sort of good looking in that generic way. And I wish I don't know. And I didn't have who has freckles.

What an embarrassment. And I'm not good at sports. So there's there was a lot of not knowing and looking and trying to figure it out. And then slowly living in reaction to the people around you, too. Yes. You know what I mean? You know, because you couldn't be. Even if you because I know that, you know, my ex-wife was from a big family and I think there were four girls and it was kind of like, I can't do that because that's my sister's thing. Yes. Even if they had, you know, like an inclination towards a thing, it'd be like, that because that's my sister's thing yes even if they had an you know

like an inclination towards a thing it'd be like so now that's her thing this is a true story uh my um i love when people say that as if everything else i've said is a sociopathic right right i know i mean i'm gonna put a big disclaimer on this get ready for the horse shit he's the ted bundy of comedy i'm a good guy yeah i wear a turtleneck and i just want to go on a date um but uh i the thing that i remember very clearly it's so ridiculous to think about it now uh but because i grew up i came of age in the 70s and so i should have been watching like movies like the french connection and listening to punk rock and all that instead for some reason because i was in such a bubble uh the movie that's entertainment came out oh yeah and it was this mgm uh it was a collection of all the greatest mgm song and

dance routines from their best movies during their musical period it's like a clip show yeah clip show yeah and my dad took me to see it and i saw donald o'connor doing make him laugh make him laugh make him laugh and he does this in crazy dance routine where he's smashing. And I saw that and I really felt like someone had taken my hand and put it on the third rail of a New York subway. Electricity went through my body. And I just was like, that hit me like a ton of bricks. And I wanted to be a song and dance man and a vaudevillian. And I think to this day, I want to be a vaudevillian. I think I'm really happy in theaters. I, I love, uh, you know, packing them in the seats and giving them a great time and then

giving them more than they thought they were going to get. Uh, and I love old love old um kooky theaters and and you know even when when you and i you and i have done so many shows together where we do a week in chicago a week in atlanta a week at the apollo theater yeah i'm in love with that i mean i'm on cloud nine i love backstages i love and i think uh all of those things led me to sort of, that's the kind of show business I wanted to be in. And I think I willed myself. I mean, I was a writer producer on The Simpsons and people were really happy with me there. And there was a feeling I remember by agent at the time saying, hey, you could stay here and you could run The Simpsons and this thing's going to go on forever. And it's the most respected.

And I was like, I got to get out of here because I'm in a lab. I'm in a comedy lab. And it's the funniest group of writers I may ever work with. But guess what? I'm sitting in a room. I mean, people have said to me over the years, oh, you must have loved The Simpsons. I'm like, no, I love what we made. And I had such respect and have such respect for

those writers and for that what that but it wasn't my creation and also it didn't involve it involved me sitting still and just using my brain it was like i can't i can't stay here or i'll die but everybody that worked with you there talks about how you were. It was the Conan show in the room every day. Yeah. Yeah. And I can totally, I mean, having,

you know, having been your TV wife for all these years. Yeah. I know. Like you can't, you don't stop. No. And it's funny because,

you know, when we did the tour after the tonight show craziness, and we did that, you and I did that tour and, and it was such a traumatic slash great it was a common it was a combo platter of so many things it was uh and rodman flender made this documentary about it and for a long time he was putting it together long after the tour ended and i said what are you going to call this thing and he went oh i know

what i'm going to call i'm not going to tell, oh, I know what I'm going to call it. I'm not going to tell you yet. And then finally he came out and it was called Conan O'Brien Can't Stop. And I said, oh, that's interesting. And he went, yeah, it's a documentary about addiction and you're the addict. And I was like, oh, okay. And I don't think he's wrong. I think he's right in that there was some. And you can see in the documentary, which I won't watch any, but but he did a very good job. Have you never seen it? I know I watched it when it came out. Yeah. And then I haven't wanted to look back at it because it's just a time I I don't want to go back to.

And I think I will look at it again. but i think more time needs to go by it's only been a decade yeah but uh i think it'd be good to watch it with your kids when they're older you know what i mean but i think one of the things that's interesting is this this dynamic of i remember very clearly there was a moment when uh when i was over just being pulled in so many directions. And I just said to my wife, they keep making me do this and they keep making me do that. And she said, there is no they, it's you. And it's really, I mean, powerful, but she wasn't saying it in a mean way. She was just saying, you're enabling all of it. You're saying yes to everything. And when someone doesn't, when something isn't scheduled, you wonder why there's a hole in the schedule. And then you complain about it. And I was like, oh, that's sick. But, you know, we we get.

We get. I don't know. We get. I was going to learn to, you know, I and I think you've done a very good job of this where you take your neurosis. I mean, if you if you. Well, you're a very complicated person. Well, A, you're a very complicated person. You're not, you know, you are in no way a simple person. And you have taken what one could very easily call neuroses and kind of turned it into a helpful bacteria, a beneficial bacteria that in some way I think could be, you know, left in some unexamined way. It could be very toxic, but I think that you've sort of like gotten a handle on it. You learn like what you need. And while some of the need might be, you know, it might be a little bit more than what you like, you know, you know, that I think that you do though, kind of,

you do have a sense of perspective, you know, and it does. You know, you're three years older than me, but it does seem like it takes this long. It does. To kind of figure out, oh, yeah, right. No, this is what I need and this is what I don't need. And, you know, and to calm down about stuff. You know, it's interesting. uh we have we are in this culture that uh really fears um it really fears age it really fears people getting old or it's it's cool to be young and you know people get disparaged for being uh

you know if you've been around the planet too long you can be disparaged and as i get older i have more and more. I'm just I'm happier. Yeah. I'm just happier the older I get. And I think that there's something I always think about erosion. Like, you know, we think about erosion is a bad thing, but it's not always a bad thing. Erosion, like, you know, we think about erosion is a bad thing, but it's not always a bad thing. It smooth surfaces, you know, and it it it makes things erosion eventually. I mean, yeah, too much erosion and you lose your backyard, but it also makes things softer and more gentle and mountains are easier to climb and more pretty because of erosion. And I think, yeah, it's just been, I'm 57 and I've had all these years of erosion. And I look at, you and I both experienced this, but our digital team is constantly putting stuff up and I love it. It's great. It's great. They've gone back and they've

digitally enhanced all of the catalog of our stuff starting from 93 and they'll just post stuff and it's so i'll wake up in the morning and i'll just turn on my phone and suddenly it'll be me doing a bit with you and some actors from 1993 oh yeah, yeah. You know, where you're throwing a drink in my face and, you know, it's sort of like that soap opera parody we used to do. We would shoot it film style. And I'm looking at that guy and I'm thinking, you don't know anything. You don't know anything.

I'm like, I have affection for him because I think his heart's in the right place and I can see what that guy wants to try and do. But I think, oh, you just you just need to be whack-a-mole for about 15 years and you'll get better. And so that's I mean, I figure out what's important and what's not important. And right. Exactly. Well, now let's go back to when you were a kid and you find out this identity. What do you do with it? Like you said, like when you get into sort of like 14-ish, 15-ish? Well, I've always said, I think it's true that you kind of, I think we all do this, it's evolution, it's Darwinism, but you click through, what's the hand you've been dealt?

And so when you look at someone who's been dealt a hand, they're taking all of their cards that really aren't worth anything and they're shuffling them around and putting them off to the side and discarding them do you know what i mean yeah and they're and they're focusing on the good cards they have and so i imagine that i was dealt this hand and i could see all the things that talk about how I was like a brilliant student because people know I went to Harvard and I'll think, oh my God, I spent years and years feeling stupid. And I was very phobic about math. And my brother Luke, who's just a year older than me, is a genius at math. And so I decided I was terrible about math. And so I struggled a lot in math and felt stupid and felt slow. And so I just kept saying, I don't have this, I don't have that, I don't have that, I don't have this.

And then I could make people laugh. And I knew that from about third grade. And then I noticed I'm doing it with my friends, but I start writing. I really did this. And starting in third grade, fourth grade, fifth grade, I would write plays and put them on for my, for,

and they would let me use the theater for a bit. And then I, I would get into theater at school. You mean? Yeah. Yeah. And I would, and,

uh, is this public school? You went to public school, right? Yeah. And I would. And is this public school? You went to public school, right? Yeah. Yeah. Yeah. And why did they send you to Catholic school? Just out of curiosity, I've never thought to ask you that. Well, money. They that's the other thing, too, is my my my mom didn't go back to work for a long time. And my dad's a brilliant guy he's in academic medicine but it's not like he was yeah you don't make money doing that yeah and so and there's a lot of us so uh we and and brookline has a really good school system so my parents were interested like yeah this is great you know brookline massachusetts is a great public school system so

that was a no-brainer that we all go to public school and, uh, and they let you use this theater in that, you know, that's pretty great. Let me use the theater. And they let me, uh,

um, you know, uh, and it's funny because I wrote one of the plays and with my friend, Jake Fleischer, and we, we cast our, you know, we, we were And we wrote it for ourselves,

this sort of musical kind of fun romp that the two of us would do about two guys making it to the top of the business, like literally straight out of the 30s. And we wrote this play. And of course, we wrote it like in 1974, 75, which is ridiculous. But then we put it on. We convinced the school to let us put it on and they did uh and all the kids were happy because it they they let the kids out of class

for half an hour whatever it was to watch our ridiculous play and um so on my last tour that i did which was just stand up with some other stand-. A guy stood up in the middle row, I think when I was in Seattle and said, I have something for you, Mr. O'Brien, you might find of interest. And I was like, who is this? It looked like I was getting a peanut. Yeah. And I looked at the guy and I think I think I know him. It's Jake Fleischer. Oh, wow. And he's got the play we wrote together and he handed it to me and I have a copy of it. And it's written in my handwriting on that carbon paper that you put through a video. I mean, I mean, yeah, ditto paper, something that anyone listening to this right now has no idea what you're talking about. But that's how you used to make copies of things and uh carbon

paper carbon paper yeah and so anyway uh that was so you were doing were you now and i was zeroing in i was zeroing in on yeah i like this i like this this i can do and then at some point, I want to say fifth, sixth grade, I decided this, you can't be in entertainment. I don't know anybody in entertainment. That's silly. Be, grind it out. Be a great student. I'm naturally, I was naturally good at English, creative writing, stuff like that. So science and math make it happen yeah and i

that's when i really became like uh um i am going to if i'm going to make and it's so ironic because i thought i'm i'll never make it in entertainment because i don't know anyone from entertainment and that's just seems like a fantasy and a silly fantasy so and also down also you want to be donald o'connor in the in the mid 70s yeah right when there's no need for donald o'connor anymore and people want people are like it would make more sense if i wanted to be one of the remotes yeah and instead and instead i'm like those ruffians you know i want to be in vaudeville so uh so i buckled down and i was a grind and it's not pretty to admit but i was an incredible grind i worked really hard through grade school and through high school and then also i could get into this really great college and what do i do when i

get into the great college i stumble onto their humor magazine and get, it's like the line Pacino has in the third Godfather, I get sucked right back in and getting on the lampoon at Harvard totally changed, you know, like I did my- Where was the grind leading? I thought the grind was leading to me being like an author or statesman. I'm not even kidding. Like I go to the Kennedy School, I I or I, you know, and I go to law school and I get legitimate credentials and I become a man of great affairs, whatever that means. a great affairs whatever that means you know uh a man of letters or a guy i mean i didn't know i didn't have i had uh a very murky sense of what it would all be but it was my ego telling me no you've got to do something big and it needs to be in this legitimate arena so i ended up getting to go to this school that's like you know harvard is the this will this will prove to everybody that i've made it and that i'm legitimate and then

the first thing i do when i get there is get sucked into the comedy magazine and uh you know, was still a good student. It's not like I... Yeah, but you didn't get sucked in. No, I didn't get sucked in. Yeah, yeah, yeah. I entered in, but the minute I made contact with that place, it was, oh, my God, where has this been all my life? And you know what it's like. When I got on, I would have been 18.

When you're 18 and the place is run by 21 and 22-year-olds, they are adults to you. Yeah. The chasm between a freshman and a senior, and those seniors were saying, hey, you're really funny and i was i was blown away yeah i was just like head over heels in love with the building the people history writing stuff all day making really funny people laugh and have them think i was funny and i that's when i was hooked yeah and for me that was that was improv that was when i got into improv it was i was a little older

you know 23 24 but it was that was the same thing it was like oh christ this is why i've been sort of i mean you know brain chemistry is one reason but this is a kind of a reason that i felt kind of shitty for a long time is because i wasn't around these people i wasn't around these like funny here they are here are the people i should have been with the whole time yeah it is uh i don't know it's all wizard of oz sort of you're on this it's the cliche but it's so many so many great tropes and so many great films but people want a journey meeting their friends along the way yeah and finding them and yeah and and it can be robin hood and it can be lord of the rings and it can be like but you find your people on the

road you pick them up and then you become this merry band. And that's what that's what I dreamed about. And that's essentially. Where it sort of started and when does that become I mean, is it the performing for them, just making them like, excuse me, making them laugh around the that that building which is like also too it's crazy that it's got a fancy old building you know it's not just it's not just a fancy old building it's i mean it's one of the things that uh i'm sure makes people hate the lampoon or harvard in general but um it really is magical it's hog. It's the Hogwarts. It's like a Hogwarts for comedy. It is. The story is that most if a college is lucky enough to have a hero magazine, they all have to meet in some closet off the cafeteria, you know, or an old rec room or some some horrible space. And then, of course, in 1876 it's the oldest g-room magazine in america uh in 1876 they start the lampoon at harvard and uh just to put that in perspective that's the year custer

is defeated that little bighorn so these guys with like wax mustaches um uh you know dating dating women in hoop skirts. Who bathed every two weeks. Exactly. They started a humor magazine in 1876. And at one point, I think in the 1880s or 90s or whatever, they let a young man get on. There's two ways to get on the lampoon. One is, well, three ways actually. One is, there's the literary board, which means you're either a writer, which I was, or a cartoonist, which I was, I did that badly, but I was sort of a writer,

but I also did cartoons. And then there's the business board, which means you sell ads. And so there's a business component to it. And they let a guy on the business board whose name is William Randolph Hearst. And so he gets on, has a good time, and then he leaves. And shortly after he leaves, he says, you know, it'd be nice if we had a building of our own to congregate in. And they went, well, that would be nice. Oh, it sure would. building of our own to congregate in and they went well that would be nice oh it would and he says i'm thinking of a miniature flemish castle that has architectural tricks and illusions in it and i'm also thinking it should be filled covered on the inside with Delft tile. That's, uh, and it's been shipped in from my private collection. So for future generations to puke on.

Yeah, exactly. So that's, so you can imagine I was a rude. I mean, um, I never drank. I grew up in a dry house. I never drank, uh, or did drugs. I never took a I never had a sip of alcohol all four years of college. And I'm quickly running an institution that's famously filled with alcoholics. And it's like my job to help get the liquor in there. And it sort of like i'm running animal house but it's not animal house it's the people are really brilliant i mean some of the some of the people they're just absolutely brilliant funny uh minds and great artists but they getting some of them are just seriously getting destroyed whenever we would have a party.

And I'm always stepping over them to go answer the door. And it's the it's the Cambridge police because someone's called them. And I was like, hey, guys, I'm totally, you know, yeah, I've been I've been drinking Coca-Cola out of a flagon all night. But but yeah, do people live there? Like, can you I know you can't live there. You're not supposed to live there? Like, can you? I know you can't live there. You're not supposed to live there. I live there. I so became and I so fell in love with the place that I get. Elected onto the lampoon as a first semester freshman, which was kind of unusual. And then I just decide this is it. I'm throwing in, I'm putting everything into this. Everything I have is going into this place and this idea. So I ended up pretty much living there the first summer. Yeah. Cause I, I helped,

they did a Newsweek parody and I was not, I was too young to be selected for the staff, but I just said, that's okay. Don't mind me. And I. You stayed there all summer. I stayed there all summer. Did you sleep at your parents' house and like I would go back and forth. I would like. But yeah, it was I mean, I slept there many nights on the couch in the president's office. And there's a red couch that might still be there. And it was surreal. a red couch that might still be there. Uh, and it was surreal.

You'd wake up, you'd wake up in the night and you're in a Flemish castle on, on Mount Auburn street. Uh, and you know, school is out for the summer. And I mean, it was very strange. And the place is filled with gargoyles and weird posters from 1922.

Uh, and, um, you know john updike what had all these great people like you'll pass a drawing and it's like oh that's by john updike or or um george plimpton or um you know soupy sales soup Yeah. Damn it. I wish it was soupy sales. Can't you tell my loves are growing? And you get into this milieu, if you will, and you're now like, OK, this is somewhere in here is going to be what my life is. At what point does that become overtly about performing? I would say it didn't. I really liked performing and I was always the writer that made other writers laugh. Like I was the performing writer. I always say I was the Maury Amsterdam, if you know the Dick Van Dyke show. Yeah. Like the guy who you think could be on the show, but he's in the writer's room. show. Yeah. Like the guy who you think could be on the show, but he's in the writer's room.

And so I, um, I got the bug. There was a singing group at Harvard called the Radcliffe pitches. I'm not making any of this up. Right. And they're, uh, acapella group. But they said, hey, we're doing a big show in Sanders Theater, which is this classic old theater at Harvard, beautiful space with multiple tiers. And they said, we need someone to emcee it. You're the president of the Lampoon. So do you want to do it? They just assumed I would know how to do that. And I said, yes. So it was one of those things where I said yes, without knowing what the fuck I was doing, which I built a career on. And so I said, yes, and then started writing jokes on little blue cards on index cards and trying them out on people. And then not knowing anything, I went and I found a friend of mine had like a yachting cap as a joke. So I took his yachting cap and I put on like a third rate tux that was from a place

called Kieser's, which I think is since closed, where you could buy used tuxedos that like a homeless man wouldn't wear. That smelled of formaldehyde. Yeah. And I got it. Exactly. Suspiciously of formaldehyde. And I got a cigar like an asshole and walked out and told jokes and i was petrified before i went out there uh this is your first time doing anything like that yeah i mean i had been up on stage in shows and stuff like that as a as a as an actor in various plays but this was my first time like here he is conan o'brien And I went out on stage and I did my thing. And I remembered being petrified, but it went well. And recently, I want to say about two years ago, I got a package in the mail from this

woman who said, I was the head of the pitches and I found this cassette. And I think it's that performance. I haven't listened to it because i'm too afraid oh my god i'm too afraid because i just think it's gonna be i am always afraid that i'll listen to it and go like oh you shouldn't be in show business and then retroactively everything else will go away so uh now how long did you did you just do the top of the show or did you do in between i'd go in betweens too yeah and i i really liked that but i was very also aware that like man this would the the the safety of being a writer is it's the tension between the safety of being a writer versus uh but you have to then deal with the frustration of being anonymous versus the glory of being on stage versus the absolute horror of it not going well.

So those forces are all fighting each other. Yeah. Now you have I mean, you have what I mean, to say yes to doing something like that. I mean, to say yes to doing something like that, it's like a preternatural sort of confidence that probably I would imagine that having been in this among this group of funny people doing this stuff. Encouraged you to feel that confidence, and I'm wondering if it played out into other areas of your life, like were you confident with your schoolwork then? I mean, did you did it take away from the grind i mean were you confident in your social life was it easier to talk to women yeah yeah it definitely the big revelation to me is i think before comedy i used to think that goodness good things could only come through pain just just classically Catholic. But I really did believe that, that suffering, there's some Latin phrase through tears, wisdom. Like if you really suffer, then,

then wisdom and good things will come. And I think to a degree, my dad encouraged that kind of thinking, which is you've really got to, my dad said to me once, and he's a brilliant guy and a really funny guy, but he told me once, if you agonize long enough, ideas will come. And I thought he used the word agonize in a positive way. And I think, yes, that is true. Kind of. Kind of. Well, the thing is, everything's partial. I mean, it's partially true.

Yes. But. You know, at what cost? Yeah. And also like Elton John wrote Rocket Man in like six minutes. Like great stuff can happen quickly through just joy and inspiration. So I think that's the part he was leaving out. And I think what was really nice for me is the idea that

when I did comedy, it was the first time that I didn't overthink it. I didn't, I just, I did it. It brought joy to other people. It made me happy. It brought joy to other people. It made me happy. It brought me a certain kind of status. And I thought, wait a minute, what is this? I didn't agonize.

There was no misery. Now, occasionally there is, yeah. I mean, once you make it your profession and you're either a writer at Sound Out Live or The Simpsons or whatever, you know, or hosting a late night show when someone's attached a giant machine to it. It can get very complicated, but still there's a lot of joy in the doing and i would say you know the biggest revelation to me in finding comedy was that thing that it didn't have to be painful it sometimes is but i mean think about um so many of my favorite moments uh or flashes of just great memories from all the stuff you and i have done over the years a lot of it i don't associate with any kind of pain

there's just yes there's been times where it's incredible amount of pressure and or there's a bit that you that took two days to edit you know yeah yeah yeah and was exactly going to shoot yeah yeah but there's so much of it which is just the laughing really hard at rehearsal or my favorite thing we do is scraps yeah the shit the the mistakes and the stuff that we're not trying to do that's the stuff that i feel like is the most joyous and that's kind of what you know there i really think there's not a lot of comedy where you're watching somebody doing the comedy and they're not enjoying themselves right you know like the there has

to be a certain level of joy even if it's you know like sort of like a pathetic kind of comedy or something it's it's always people kind of they know they're making people happy you know, like sort of like a pathetic kind of comedy or something. It's, it's always people kind of, they know they're making people happy, you know? And so there's like a joy to it. Yep. I, and I, I think that's, uh, you know, there are, there's, I think in the, in the, if you're looking for this through line, to really try and simplify it, it was that revelation. When I think back, I know a lot of people idolize their childhood. I don't.

I remember being very anxious, probably should have been talking to somebody, maybe should have been medicated. But what do you think for what? For anxiety, anxiety? Yeah, yeah. Yeah, just just anxiety, waking up in the middle of the night, really hated school, really feared it, really feared tests, really worried about failing, was obsessed with the idea that i would fail and so not a not an my mother had said much later on yeah you never took things easily like she just had this when you've got six kids you can kind of sum them all up and i was the one that that uh took things really hard and was worried all the

time and um so i think comedy was this great escape from all that and just the the joy of of uh i mean i knew when we did happy happy Show, which is a stage show that I did with Robert Smigel and Bob Odenkirk and a bunch of other talented people in Chicago in the summer of 88, we made no money. It was in a tiny equity waiver theater. We didn't get good reviews. I had my apartment. It was an incredibly hot, muggy summer in Chicago is, as you know, all too well. I had no air conditioning and I was joyously happy. Yeah, I just was like, I would rather. Rule in heaven than serve in hell.

I just love being part of this little group of people and I love making the opposite rule in hell than serve in heaven. Yes, that's what I say. Well, really, in hell than serve in heaven. Yes. That's what I say. Well, I want to rule in heaven. I know heaven really is the best. So that's my first choice. I didn't miss this. Right.

That's first. Right. But if I can't, I'll rule in hell. Right. But I'd like to rule in heaven. Yeah. Okay. I'd serve a little,

you know, I'd switch it up, rule and serve. Be versatile. I do. I'd like make thursdays the day that i serve yeah yeah just to feel good about yourself okay well you leave you leave uh you end up meeting greg daniels yep and you guys become a pair a writing yeah and that was really

i mean we were we became friends like junior senior year and we hung out we hang out more and more senior year and then we decide i think we were both in i mean i knew i think i knew more than greg did but i really knew i wanted to get into show business somehow greg uh what had like taken Greg had taken the LSAT and gotten a perfect score because he's a brilliant guy. And I think he was probably getting a little pressure maybe from his family like, you know, really? You would do this? I might be wrong about that, but I think his mother might have been somewhat skeptical. So he was getting some pressure maybe and i just i i kind of think i maybe quasi talked him into come on because i wanted to do it with someone i was scared and greg's funny and uh it just felt like a no-brainer

so we teamed up yeah and we started applying to different shows. And later on, when I hear how lucky... And like your senior year or after you're out of school? We graduate. We graduate. And then there are very few options back then. It's not like today. Today, there's literally 600,000 shows being made constantly. Back then, I had a rule, which Greg reminded me of recently which is i was adamant we don't

write for sitcoms we don't write for sitcoms and we don't write for anything that's beneath us like beneath like what an ad but i really was and i'm still that way i was like i'm not gonna i used to say uh don't learn to pitch the ball poorly in order to someday pitch it well. Like you've got to build our form now. I was very strict about that. So I said, we'll work for Saturday Night Live or we'll work for Late Night with David Letterman, which was like in its golden era, you know, just or we'll work for a show that makes a sketch comedy where we can control our input. And then there was a show called Not Necessarily the News. And we knew a guy.

We had a connection there. We submitted. And we got really lucky because a writer named George Meyer quit just as our packet came in. Literally one of those things that if that hadn't happened, we could have... Just been left in a pile somewhere at a desk. Yeah. So you get that first job. We came out to LA.

We worked there. And I mean, coming out to LA from my experience in Boston, it was like coming to the moon. Yeah, it's weird. It's really weird. And I was scared of this place. And I thought it was, I just thought, I mean, I didn't like it here. When I first came out here. It's so big and sprawling that you just don't know where to go.

You know, it's like, I mean, you know, it's as big as, you know, two of most other cities just in terms of the, you know. Also, I think I maintain that L.A. has gotten a lot better. Yeah. I mean, L.A. now has there's people come out here. There's so much more culture, I think, out here now than there was when I came out in 85. It's much hipper. I think LA got a lot hipper. And then you go to these different neighborhoods and I'm blown away. I mean, I remember going to, I'm trying to think of the name of the place, Atwater Village or some of these places. And they weren't like this now.

I mean, back then they were just kind of, you know, now. You know, UCB wasn't out here. Yeah. Yeah. Yeah, it is true. It is true. It's kind of I don't know. It just seems like a lot of people in the time that we've been here have made L.A. more like other places rather than just kind of succumbed to L.A.

Because L.A. is kind of full of shit, you know, left to its own devices. At least the show business part. The show business part, the show business, the show business part. But then you realize, I mean, I didn't have access to or I didn't know. And I think it's grown a lot. But now there's just these thriving art communities and yeah, and and little theaters and people, you know, crazy diversity and cultural diversity.

Yeah, just, you know, yeah. And and everyone's aware like you know like i probably didn't eat korean food till i was 30 and like my my kids knew all about korean food when they were seven you know yeah i i think that's the other thing too is uh um i've always, I learned, it took me a long time to learn it, but LA has everything you need culturally, uh, cuisine, everything. You just have to go find it. Yeah. I mean, LA in New York, it's right in your face. There's the Guggenheim there's, you know what I mean? There's the, there's, uh, Lincoln center. There's this amazing, you know, I'll go down to Soho and there are these great restaurants. I actually think L.A. has gotten, it's more affordable than Manhattan.

So artists can still- Weather's certainly nice. Yeah, artists can live here. And so there's a lot that's really very cool, I think, and it's gotten a lot better about LA, but I hated it at the time. But we came out, we got started, we got our Writers Guild cards, that sort of got us launched. Then that job went away. I think through no fault of our own. I think they just contracted the staff. And then Greg taught SAT prep.

I worked at Wilson's House of Suede and Leather for a little bit. And then we got a job on this show that turned out to be a cataclysmic disaster called the Wilton North Report. But I got to be on camera some. And this whole time I'm taking improv and I'm meeting people like Lisa Kudrow and I'm making all these friends

and I'm doing improv and getting laughs in front of an audience and thinking, hey, OK, this this I like this. I like this. I don't know if I have the guts. I'm not going to throw away the writing gigs because that's what pays the rent. But very interested in this. Yeah. And then then start out live. And, you know, yeah. Were you and Greg hired for SNL together? Yeah. And is it after SNL that you guys ended up splitting? Yeah, we went to SNL together, but we had also, it was interesting, we were hired as two writers that worked together. So it wasn't like we split a set.

We weren't a team, meaning you get one salary. We were each hired as individual writers. And so we would work together on a lot of stuff, but we'd also work separately on things at SNL. And then I, in this period, get more and more interested in performing. I think Greg is more and more interested, obviously, in... Not performing. Yeah. And he didn't want to perform. He wasn't interested in that. And so that was just kind of natural. He left SNL to go and be with his girlfriend at the time like the most successful, you know, she's she's fantastic. And she has ended up having every important job you can possibly have in show business. And she's really brilliant and fun and one of the great, really great laughers of all time. brilliant and fun and one of the great, really great laughers of all time. And, you know, Greg, of course, went off to make 35, you know, important television shows. And so he did that.

And I did, I decided I'm going to strike out and try my thing. First, I went to The Simpsons, because I was always afraid to let go of the writing thing and i really wanted to work with those writers because i thought that's the best writing room in america and i want to be in there been on when you went there i think it had been on for three and a half seasons yeah maybe and that's really too like when it was its golden age too yeah and i got in there at a good time uh and you know you're sitting there with it was its golden age, too. Yeah. And I got in there at a good time. And, you know, you're sitting there with it was very intimidating. But but found my sea legs and.

Pitch some shows that they liked and sort of really started to click in and feel good about it. And I think that was a phase of my life when I started to really feel like I'm doing improv, I'm writing on the Simpsons, I'm building up the nerve to, you know, and then, uh, that's when this whole craziness of late night rears its head.

And, uh, I mean, that's such a, what's the, what's the, what's the first whiff of that you get? First whiff of that I get is that Lorne Michaels wants to talk to me and he was interested in having me.

They had put him in charge of trying to find the person to replace letterman and i at first and so he was thinking of me as like the you know head writer slash producer yeah you know the sort of the the the tina fey on 30 rock maybe whatever who right show together and i i was sort of thinking well i'm intrigued and i idolized late night as a format i was intrigued and i had a few meetings with lauren and then i said you know what i i'm very instinctual and i just was like no i can't i can't do it i don't i don't want to be that person you know and i was very uncomfortable i never wanted to be a producer like i know that i have producer titles occasionally but to this day you are a producer i mean you and

i are both producers of the show yeah but but yeah but it's i don't i just the idea of like i don't want to make phone call i don't want to have a phone call sheet yeah there's all this stuff that they're supposed to do. And I, I was like, no, I want to be the person who plays the game. I don't want to be.

So I wasn't, was that it too, is that you didn't want to be the person servicing and be in proximity to what you really kind of want. I think, but I couldn't, I mean, it's hard to couldn't verbalize.

Yeah. I couldn't verbalize that. And also at the time for me to have said, no, I'd much rather host this show would have been insane because that was an insane idea. Given, you know, the idea that they would hire an experienced stand up comic. So I back out and I immediately feel better. I mean, I was getting like hives and stuff and I backed out and then immediately. How long are you mulling it over? It wasn't that long, I don't think. I think I was mulling it over for a few weeks and then got out.

And then there was like at least five weeks or more of just, I'm out. They're going to go ahead and do this. And I don't have to be the one who has to worry about how do you replace David Letterman. And I remember telling a friend, I'm glad I'm out because there's no way to replace. You're never going to find anybody to replace David Letterman. That's a fool's errand. I really did say that. And I think that's probably, I mean, there was an email then, but I wish there was because I would. God damn it. I have an email where I said, no, it's I don't want anything to do with this because you can't replace David Letterman. No one can. And then cut to Lauren calling me back.

After a while, and I guess they had looked at a bunch of different stand-ups and it wasn't sitting right with Lorne and he pitched he said how would you feel about auditioning and then something in me was like well why wouldn't you audition and I like why not just audition what's the worst that could happen you won't get it but what's the so i did did you ever put an idea in his mind that you would like to be the host or i did not first he said he said it first and i i mean later on i had people say you know oh did you you machiavellian genius and i was like uh i'd love to take credit for that. But I mean, first of all, it's now, was it 28 years ago now? So I think it's 28 years.

Yeah, 27, 28, something like that. 27 years ago. I'd love to be able to think that I, like LBJ, somehow figured it all out. figured it all out uh but i honestly i think i honestly did feel like they were going to i remember hearing that they were going to get gary shandling and thinking well that's it you know like they're going to get gary shandling who at the time with uh it's gary shandling show and and and then he had come out with, he had just, his, why am I blanking on this? His famous, Larry Sanders was killing it. And so I just thought, well, yeah, that would be if,

if he wants the job, he'll do it. So, so when Lauren called me up, I remember having some trepidation, but then thinking I'll do it. I'll audition for it. And I auditioned for it and immediately loved the audition was in the Tonight Show set when everyone was gone. And, you know, with Jason Alexander and Mimi Rogers. Yeah. And it was very funny. Yeah.

It's, I mean, I think it is. Does it exist like that in the world? Yeah. We put it up online. But, you know, one of the things that was, I think, made it funny was I was so loose. Yeah. And I don't know why I was that loose, but I was loose in a way that I wasn't again for a year on the late night show. on the late night show.

I just was loose because I, I, you know, it's, it's one of the frustrating things about this is, uh, is that the comedy is so mercurial and so hard to, it's like this superpower,

but it's not always there when you need it. You can't just say Shazam and it's there. It's there sometimes. And sometimes when you need it the most, it's not there. And I find that to be maddening. And you learn all these tricks to compensate. You learn all these over the years and thousands and thousands of hours of doing this. I've learned all the different ways to be able to compensate for the superpower didn't show up. But it's still, it's there sometimes and it's not there sometimes and when it's there everything's easy and joyous and when it's not you're relying on muscle memory this that and people will still say oh that was a good show afterwards. But, you know, no, it wasn't.

There was no pixie dust in the air. There was not that special thing. So that's why I think the audition went so well. And that's around the time you and I meet. Because then we have, I mean, you think about it now. We had no time to put the show together. Yeah. I knew nothing.

I had Robert Smigel and I had these ideas, very strong, sort of almost religious ideas about what the show should be. We both love silliness. We both we could have talked for hours then and now about, well, Letterman is the answer to Carson. So it's irony. We're going to be post irony. Post irony is, you know, silliness. It's going to be sort of like a Pee Wee's Playhouse, but it's also going to have a subversive this, and it's going to include puppets and animation. I won't wink at the audience and tell them we all know this character is false. I will if a sketch calls for me to break down in tears, I'll break down like the whole thing. Yeah. But I want it to look like a 60s talk show, which is why. Yeah. We tried so hard to make it look kind of square.

But then and I was square looking and you and i looked like kids that were dressing up like johnny and ed but we weren't you know so well also too like i remember uh john stewart was doing a talk show on comedy central pre-daily show i was wearing like a leather jacket and a t-shirt and stuff like that and i you know and i think that that was kind of expected of us at the time that we're, cause we're young and we're supposed to look and we just were like, no, we'll look like idiots. And I do.

And I, you know, yeah, because also, you know, I've told this to people since then, if you want to do something really revolutionary, sometimes it needs to look the way in is to look acceptable

but in a way do you know what i mean yeah and i know uh i'm much more of a beatles fan than you are but like the beatles and not to compare anything like that in that way but just like they you're saying you're more important and more popular than jesus christ that's yeah there you go there you go yeah uh what i'm saying is they did a lot to make the pill go down easy and then you know what i mean i just like they looked like they dressed in these edwardian suits and yeah they had long hair but they had edwardian suits and beetle boots and they bowed after each song and you're like they did all they did that shit and i remembered in the beginning thinking yeah it i

really want it to look like uh all i have all the classic tropes there classic classic and then be totally insane like i want it to you know it's in and and uh and really fuck with your mind in some ways and i think that that's the thing i was really proud of is i would say it wasn't there wasn't detachment no because that's really what dave had been kind of about yeah he was always a little bit outside of and above. Yeah. A lot of what he did. And it was very funny, you know, and incredibly formative for me, just personally, but I think a lot of people in comedy our age.

But, yeah, but that was like, that was kind of, and it also just wasn't our thing, you know? Yeah. It was so nice because you know we came out we did the show and there was of course uh people you know a lot of hate and a lot of just like we're gonna get canceled and i mean i i think that however long i live uh i would have lived three years longer if i hadn't gone through that like whatever my expiration date is it was accelerated by three years because of this year and a half or two

years of just absolute uh misery but i always remember the show was fun and that was the escape i could feel like wait we did that thing and the crowd laughed and it all seemed to go really well. And then I would read a horrible, you know, headlines. Conan, worst person ever. You know, America wishes he would die. And I would think that's interesting because the show is so much money by says Blandy Slicker. It says an insider. Yeah, insider, mustachioed insider. Yeah, I don't know. So I think that what's so nice now, this is another thing about getting older,

is there are all these really funny people who blow me away with their talent, whether it's a Bill Hader or a millennia or nick kroll and the list goes on and on and on and i talk to them now they're like oh yeah that was the show you're you're you guys i used to watch that when i was a kid and that was the show made us laugh so hard and i was thinking why couldn't i have known? I just wish, I wish that I could have had like one night like screwed where these ghosts came to me and said, look, this sucks right now. And you're getting hit from every angle, but these are the ghosts of the superstars of the future. And they're telling you, they really like what you're doing.

superstars of the future and they're telling you they really like what you're doing and it's influencing them and i would say okay thank you ghost of you know mysterious person ghost of tina fey yeah yeah you know i that that to me is one of the i mean one of the truly special things about it is that people that were like me looked at our show the way that i looked at the shows that i looked at and and looked to and was affected by and didn't sit there and think like i'm gonna be a comedian but definitely soaked that shit up and was like okay i see what they're doing here you know and started to sort of think about comedy and think about what they were doing. Yeah. And, you know.

No, I, you know, I would say, I mean, that has been, that's all, that's really all I wanted. Everything else is gravy, but all i wanted was to do that and i still find nuggets like that when when if you talk to someone and they say yeah i was watched it when i was in high school or i i was depressed and i used to watch the show to make me feel better i whenever i walk away from those and I walk away quickly, uh, I feel like,

you know, yeah. Who wants people? Exactly. Uh, how is this making me money? Um, no,

whenever I get a moment like that, I truly am. Uh, it, it is nutrition for me. And I just think that's really all I wanted out of the whole thing. And, you know, which makes, uh,

you know, where we are now. So interesting. Cause people, I don't know about you, but I get a lot of people saying, Oh, so when do you think, you know, you'll end that people have a, I don't think they're being, they're not being malicious, but they just, it gets talked about so much like the longest serving hosts, you know? Yeah. And so you can always detect, especially if you're me, a hint of like, so shouldn't you be leaving now? Yeah. Maybe it's time you left the party. You got here early and you've been here the longest. And so he liked tennis. Yeah, exactly.

Johnny liked tennis. Yeah, exactly. You could marry again. And I think, you know, the thing I just go by is I like to make stuff and it's fun to make stuff. And sometimes it's also very annoying to have to make stuff. Right. But, you know. If you're having fun, you know, have to make stuff. Right. But, um, you know, if you're having fun,

you know, and it's like, yeah, you gotta do something, you know? Yeah, I know. I know.

It's funny at a certain point, you know, I mean, the early years of the show, 93, 94, 95, 96 was such a,

such a must, must, must survive. Kind of, kind of like running through the woods, being chased by hounds and just dodging and, you know, getting a piece of your arm torn off, but grabbing a branch and wrapping it while you're running. It just, and then it's so funny to be like, now it's like, you gotta do something. It's kind of true. Like the stakes aren't the same yeah and it's a different show and i mean we have built up a business and you know now that uh late night was it 16 years that it went on or i think it was 16 and a half 16 and a half yeah dave dave did late night for 11 yeah We did it for 16, I think. And at what point in that do you start thinking about trading up to The Tonight Show? Well, I think it started to be questions about, well, you know, there have been questions like in the press and stuff about

where do you go next? And Conan's in a commodity and this show is really hot and then we get uh i think it was when fox came to me and i'm i'm not i'm gonna be hazy on all this but i think it was fox peter churnin at fox coming to me and saying that they really would want me to come and make it worth your while yeah and do a show there and he's such a that's one of the smartest people i've met in all of show business in all not even just show business he's just this incredibly intelligent guy peter churn and and i and i'm saying that just because he he was right about everything he said. He pretty much told me how everything would lay out and lay at night. And I listened and I went, yeah, you're probably right, but I think I'm going to stick it out here. And my biggest reason for

wanting to stick it out at NBC was my body of work. I really had seen what happened to Dave when he switched networks. And I thought, I want the idea that my network would hate me and that I wouldn't have access to 16 and a half years of all this stuff we made. Yeah, that was my nightmare. So the great irony is that I stayed with NBC because I thought I want to stay connected to all this stuff. And then they were interested in having me, uh, move on up and make the show younger and, uh, make the demographic younger.

So I, I did, uh, I said, okay. And it was like, okay, will you do that in five years? And I remember thinking,

wow, that's a long, okay. All right. So, and then we all know how that played out so you know there's plenty of footage of that crash yeah but uh um yeah but i mean when they when that idea came to you of like doing the tonight show had it been something that had been on your mind yeah i think it had well first of all

the first couple years of late night, obviously not. It was just like, if I can write, no, of course, if I can keep the late night shot, but I think over time thinking,

yeah, when you're on a 1230 for a really long time for a decade and a half, you're thinking, yeah, being on 1130 would be, it'd be nice, you know, and Letterman had set that precedent.

Yeah. Yeah. So I'm going to'm gonna say yeah that had and i think i also had this probably mistaken notion of you know i grew up watching johnny so i could wouldn't it be great to make, you know, do that show and do it in this certain way that I, I think would be like a great, you know, I don't know. I, I, I think I had aspirations of doing it in a way that we're probably, or, you know, thinking rightly or wrongly that, oh, I could, you know, uh, make the show, um, more like that show that I grew up watching, which I think is probably mistaken. Yeah. You know, if you could like. If you could go back and keep The Tonight Show, would you like if there was some sort of magical lever that could be pulled? I wouldn't change a thing about any of it. And I really mean that. I think people sometimes say,

really, you know, I think, no, I. I think I think the everything that happened when that went down the everything that happened when that went down was excruciating but also in some ways magical and beautiful like the whole movement that came rose up out of it and the i think it it the tour was really meaningful to me and i think moving over to tBS and being able to do things exactly the way we want to do them. Yeah. And I mean, that's something that when people have talked to me about it, I'd say that, you know, you own this show and it wouldn't matter how long you were on The Tonight Show. Yeah. You would have been an employee. yeah and i think you know i think at the end of the day there's again we're going to go back to you know rule in hell that's not that's no slam against tbs but i think i have to do things the way i need to do them and i don't know if that was going to be possible in that other scenario and uh i'm it's funny because i'm very ambitious i'm not going to lie about that i am very ambitious but also i can't compromise certain

things for my ambition and so that's a sticking point you know and i don't know if uh i'm sure that you know and i i do think the way everything happened was quite unusual and it's a very strange show business story yeah but if you think about the fact that i got the late night show in the first place that's completely unprecedented and then what happened with place. That's completely unprecedented. And then what happened with the tonight show is completely unprecedented. Like they don't anoint the seasoned tonight show replacement. Do you know what I mean? And then have that dissolve so quickly in such a weird way. And the person before the,

that you replaced goes to 10 o'clock and the whole thing's a mess. I mean, I don't know it to quote a great man, Jeff Ross, it was what it was, you know, it is what it is. And it was what it was.

And so, uh, I've had the whole team Coco movement and the, um, the whole explosion of stuff that we've done on digital and the travel shows and the podcasts and all of it, I don't see any of that happening in that other reality. And that would make me sad, you know?

Do you think there's something good? You know, we've never talked about it. Like, you know, there is kind of that, you know, it's the Colbert versus Fallon versus Kimball do you think that it's good for us to be kind of like off to the side of that a little bit yeah I I think uh I mean we're old you know which I don't feel like we're old but we are definitely in this business we're the old ones you know well you're you're old i'm as you know you're older than me andy look at wikipedia it's been changed this morning oh my god i'm 40 i'm 44 yeah you don't pay for all those surgeries if it doesn't turn back the clock um yeah no i I 100% agree. I couldn't agree more.

I think there's a natural thing. Sometimes I think the media, if you look at it, there are individual exceptions. But if you look at the mass media, they like things simple. And so what they like is a clash of the titans. They want Godzilla versus Mothra. Do you know what I mean? is a clash of the Titans. They want Godzilla versus Mothra. Do you know what I mean?

Yeah. They want two giants clashing. That's, they want Fraser Ali. That's what they want. Yeah. And so I've always thought that's great. And it works so well in sports. And it can even work in politics. It doesn't work in comedy, in my opinion.

And so when people are trying to just, you know, be like, who is going to beat which funny person is going to beat the other funny person with their funny ray? It doesn't work. And so, of course, there's much less. It's beside the point. Yes. And so I always thought the whole, it's Leno versus Letterman. You know, and the only thing that they could do is come up with ratings. Who's ahead in the Niedelsons? And I was like, well, it's just who makes you laugh?

Who makes you laugh? Who did something that made you laugh tonight? Who's your cup of tea? Yeah. No, no. It's a battle to the death. It just serves. It serves the industry of talking about the show business industry.

Right. It's creating content for the people that have to say, you know, you know, Laurie Laughlin's got a new show. And then, you know, but they also love this whole notion of the late night wars they dined out but it doesn't but it doesn't it doesn't work it doesn't exist it doesn't exist and so i think uh you know um there was a piece i wrote for entertainment weekly when Dave brag much. Must be nice to get right in work. I love bragging about an article that I,

I think I got no weekly that I got no money for, but there was probably only online. But Dave, when Dave went off up there on CBS, I wrote this piece and I was just trying to make the point that this is what he meant. And then I, I was saying the whole late night wars and the, whatever this, the scandal and the, it's all noise. What really meant something was what did it, what it meant to me to be 15 16 years old and seeing this guy on tv who looked completely like nothing else i've seen on television and being

this voice and this wit that's what counts that's, it's completely beside the point. So yes, to be locked in some goofy. And I mean, I think they've given up on it because there are just too many late night shows now. So they can't do, there literally are so many late night shows now that when they do a late night roundup there's like they there's like 35 people in there yeah yeah it really well and the ratings too are like so much lower like what's a good rating now is a third of what a good strong rating used to be yeah in our day yeah well it is just everybody's watching other things and on those video games. Oh, I hate those things. Yeah. I think on any given night on the late night show, we were seen by as many people as see a Super Bowl now. That's a true story. Really?

No. No. I was going to say, that doesn't sound right. Can't you tell my love's a-growing? The main reason I had John here is just to say, what's in our future? Do you have any kind of game plan? I don't. For what it goes forward?

Do you just take it as it comes? I know those 40 just well, no, I will take it as it comes. I think anybody I mean, you know, I try and keep my podcast evergreen. But I think these days you have to accept and not mention dates or anything. But we are smack dab in the middle of this quarantine and this coronavirus. And anybody who makes a prediction on what they're going to do next in the midst of this is crazy. Yeah. I don't know. I feel in a very healthy way. This has got me thinking, what am I doing today? What am I going to do today? And then and how is the world going to change?

And how is the world going to change? And, you know, who's. Are these shows, I don't know when there's going to be an audience again. And I don't know when I'm so sick of that awful phrase, the new normal. But, you know, what is. What are things going to look like in two months three months uh and i i don't know i don't know so i know that we're doing this now but i have absolutely no idea how this uh pandemic is going to change what we do i I always know that people adapt and I know that we'll keep, I think, making or trying to make funny stuff, but I don't know what that's going

to look like down the road or when it's going to, is it ever going to go back to completely what it was before? I think a lot of us assume it will, but I don't know. Well, before the pandemic, what was your notion of what your future was going to be i honestly didn't know i think um i think i probably could see the business of and here he is conan hi everybody welcome and then you know comedy bit comedy bit and let's sit down now we've tried to change it a bunch just because i started to lose my mind and i really started to think this business of and then i come out and i'm in a suit and tie and you're like, what are you doing? It's and there's a desk and a microphone. And so we changed it up a bunch and we changed it to half an hour.

And that was feeling a lot closer to something that felt like, yeah, this is more appropriate now. Do you know what I mean? Yeah, of course. But. I honestly wasn't thinking that far ahead because I didn't know, I just didn't know how much this business is changing so quickly and streaming and, you know, late night shows existed initially as time killers at 11 o'clock. Yeah. Cheap, cheap ways to get commercials on yes and promote other things that's the history of the late night show that's the dirty history of the late night show is a a cheap way to you know and now and now look then they became these monstrosities and not not in a bad way but they became these behemoths under cars Carson and then on into the 90s and 2000s. And we, you know, really got to live doing the late night show during the sort of big time era of these

shows. But now when you think about it, when your local news is over, if you're even watching your local news you have a choice it's not like well you know before i turn in i'm gonna see what's going on on the tonight show or the late light show whatever i mean yeah you can you can do that or i'll see what you know kimball's up to or conan or whatever you can do that but you can also watch anything that's ever been created in the history of the world. Yeah, yeah. Anything. From exactly when, from the beginning. Right. Director's Cut, David Lean, Lawrence of Arabia.

Right. So it's so... Or things like, you know, Uzbeki TV. You know, you can find it all. It is pretty amazing. So I don't know i wish i could tell you i've never been more aware than during this you know time of covid that uh that i'm it's about today it's about today and it's about what are we doing today? And so I'm doing your podcast and then I'm shooting some stuff for tonight's show.

I mean, it's actually that we've got tonight's show all set. I know. No, actually, I'm shooting the wraparounds, the intros for tonight's show. And then we're doing a bit. We're doing a bit. And then you did a funny piece uh that i think is great where you're making uh you take you're going off of um stanley toots bartending yeah stanley toots bartending video went viral so you you did a thing of well i'll make cocktails out of what's left in the liquor cabinet which is really funny uh i so i'm like that's where I am is I'll do that. And then, um, I'll talk to Hank Azaria in about 45 minutes after that, you know, uh, for the show later this week. And then,

uh, I'll, I'm really trying not to watch CNN because. Yeah, me too. I can't. It's just the same thing over and over. Yeah. It's again, it's needing to talk about something when we don't have enough information. Still. Well, now, do you think do you think much about a day when you're not doing a daily show like about, you know, like, yeah, your time when you don't do that anymore? And yeah, your life looks like. A future time when you don't do that anymore and what your life looks like?

I don't know. I've always dreamed of one day living in a city like London for a year. I've always wanted to do that. So sometime I'd like to write a book at some point about my, you know, I want to create a religion, basically. It'll be my dinos. Sure, sure, sure. Right, right, right.

Have a lot of acolytes. No, I've always thought... Get some celestial wives. If I could get it together, I'd like to write a book about some of what I've seen and witnessed and have it be a good one of those. Yeah.

I just, it's such a mammoth undertaking, but I'd like to do that someday. I really love, you know, I don't know what your experience is, but I really love doing the podcast because this is such a nice way to talk to people and to use a much different lens, you know, to use a much different lens than the lens of. All right. That was a great four minutes. You got some good laughs. Let's go to commercial. Come back and do another four minutes and then I'll get rid of you. You know what I mean? Yeah. I'm just saying it's time people had podcasts. They do. They really, truly do. I really want to ask. I thought it was just me and you.

That bust of Roosevelt behind you has one. It's all about Josie and the Pussycats. Well, what, I mean, what's the point of it all? That's, you know, that's, you know, in this podcast, we kind of gets to the what you've learned part. And I mean, what, what? It's what you do now. It's what you do now. I will tell mean what what that's what you do now it's what you do now i will tell you this it's what you do now it's uh it is there's no big mystery to it it is i don't believe in legacy i don't believe in uh i i mean whatever i used to believe about any of

that stuff and what will my place be in the pantheon? It's not about that. It's about, did you behave well? Did you, um, you know, day in and day out, try to do good work. Did you, um, you know, try to enjoy things as, as best you could. Did you make lives better for Pete? You know, I don't know. Yeah. Just try to pay it forward a little bit and, and also have humility about the whole thing. You know, just, I, I, I, uh,

really have humility. Don't think you're, don't think that you're, uh, don't think that you're, uh, I don't know. I think I have, I don't know, may not always come across, but I do have real empathy for people. And I like to joke around a lot that I don't have empathy or play the guy who's like out of touch. But, uh, I, I, I do empathize with other people and I realize in a bunch of ways I've been lucky. So I don't want to get a big head about it, you know, and just sort of play it close to the bone. Yeah. But I don't know what it's all about. I just know that my grave will be a monument.

It will make the pyramids look small. And people will know my name for millions of years as the overcompensator conan the overcompensator and they will come and witness my massive giant phallic tomb all right well that's enough of this. Thank you for doing this. Yeah. I love you very much. And thank you for taking the time.

Well, you know what? And now we have to shoot more stuff. I know. Yeah, I'll see you in like six minutes, I think. Yeah, yeah. We'll do. We'll. But yeah, you know, this is the thing is that I always wanted to do this kind of crazy thing.

I always wanted to do this kind of crazy thing. I always had a dream of doing this thing, making something and having my band of people. And I don't know why you and I met in 93. I don't know. I mean, I know specifically how it happened. Yeah. But you were the perfect person at the perfect time.

Yeah. And you compliment me. And I don't mean compliment because you've never complimented me. But you compliment me. You are such a great partner in comedy. And you're very honest. And I think the fact that I have a lot of affection when i look when these things pop up on my phone and i see you and i doing something in 1995 or you know we're shooting some remote and we're dressed literally like children yeah uh i'm just i'm

really grateful i'm like god bless that andy he he was there uh he was there and he saved the day so well i mean listen i i i definitely i i'm a 100 an agreement with you that we do we work well together yeah both on and off camera and and i mean and you know this show has given me the opportunity to kind of find my place in the in the comedy world. Yeah. And I mean, and I, you know, I went off and did sitcoms and stuff and I came back just because I love the immediacy of it. Yeah. You know, I love the fact that we get to just put shit on TV today. And I have to sit and wait for somebody to come back from, you know, Maui and judge what I've written. You know, I've been sitting for three weeks. Now we have a little clubhouse, but we can pull up the rope ladder and not let anybody else. Yeah. Yeah, it's great. All right. All right.

Well, this is actually this is actually the end of my podcast season. You're my big season closer. So I do want to say that. Oh, that's all. No, no. I mean, I designed it that way. Oh, good. I do want to say to the people out there, the people, the people, as Sybil would say, thank you so much for listening to this show. And I've gotten nothing but wonderful feedback. And it really is meaningful to me, all the nice things that people say about this show and I've gotten nothing but wonderful feedback and it really is meaningful to me, all the nice things that people say about this show. And I'm glad that it means something to the people that listen to it.

And I'm sure I'll be coming back to you soon with more of them. So thank you, Conan. Thank you, listeners. And we are out. Bye. The Three Questions with Andy Richter is a big, big love for you. The Three Questions with Andy Richter is a Team Coco and Earwolf production. It's produced by me, Kevin Bartelt,

executive produced by Adam Sachs and Jeff Ross at Team Coco, and Chris Bannon and Colin Anderson at Earwolf. Our supervising producer is Aaron Blair, associate produced by Jen Samples and Galit Zahayek, and engineered by Will Becton. And if you haven't already, make sure to rate and review The Three Questions with Andy Richter on Apple Podcasts. This has been a Team Coco production in association with Earwolf.