Conan O’Brien Needs A Friend - Simon Rich

Episode Date: October 18, 2021

Writer and humorist Simon Rich feels extremely grateful about being Conan O’Brien’s friend.Conan sits down with Simon to discuss writing affable villains, choosing colleges courses for their comedic premises, and the inspiration behind the hilarious stories in Simon’s latest book New Teeth. Plus, Sona seeks advice for a child-rearing quandary as she makes a welcome return to the team.Got a question for Conan? Call our voicemail: [phone]. For Conan videos, tour dates and more visit TeamCoco.com.

Hi, my name is Simon Rich and I feel extremely grateful about being Conan O'Brien's friend. That was sweet. Thank you. And I think sincere, that was really nice. I went for it. We're going to run that through. We have a machine here called the Snarkometer. And just dial it up.

Everything comes out in Dennis Miller's voice. I feel really fucking great about being Conan O'Brien's friend, cha-cha. And welcome to Conan O'Brien Needs a Friend. This is a glorious day. My mother always uses the word glorious. I would say, mom, what do you think of this slice of pizza? It's glorious. She would say glorious all the time.

And I'm quoting my mom. This is a glorious day because for the first time since she left to go on maternity leave and give birth to Mikey and Charlie, her beautiful twin boys, Sonam Obsession is back in the podcast studio. Sonam. Yay. It's good to be back. You can't say something. It was good to be back.

Yeah. You know, it was nice. It was kind of emotional because you've, you zoomed in once. Yeah. Kind of recently. But to have you back here in the studio, and of course I've been here with David. David is Sonam's assistant. And yes, you heard that right.

What? My assistant has an assistant named David Hopping. He's more, he's more your assistant now. Well, yes. But what I'm saying is you used to have an assistant. That's right. Which enabled you to do absolutely nothing. Sonam was the best boss though.

Yeah, I was. Yeah. So any who, He says I was the best boss. Yeah. Because he lets you watch, you know, Big Brother or whatever it is you watch. Grey's Anatomy. Grey's Anatomy.

Okay. Whatever. Yeah. Whatever. I don't know. I haven't watched TV since maybe a RFD went off the air. Anyway. No one got that.

David, there's two people out there who got it and boy are they happy and both of them worked on that show. Listen, David has been doing his best to fill in for you and I think doing a lovely job. Excellent. Doing a fantastic job here in the podcast studio. But great to have you back, Sona. And people have missed you. People have told me how, everywhere I go, people say how Sona doing.

Yeah. Oh, that's nice. Yeah. I was really excited to come back and then I think five minutes into being here. Can I, can we, to my tell you what happened? Yeah, I think I want you to say it. Okay. So I see Sona in the parking lot.

We're here at the Ear Wolf Studios on Sunset Boulevard. Just a fun fact right across the street from where Greg Daniels and I got started in the business in 1985 at Sunset Gower Studios. Very cool. Not necessarily the news. Little fun fact. Anyway, I run into you in the parking lot as we're both about to walk up and we hug and it's kind of emotional.

You're back. You look fantastic. Doesn't she look fantastic? She looks great. Yeah. You look amazing. Thank you. You look amazing and we're just so happy to see you.

Thrill. And then we walk into the offices and there are a couple of people here and Ruthie's here from Team Coco and she's happy to see you and hugs you. So nice. And David's hugging you and everyone's hugging you. I want to say maybe at most two minutes went by. Yeah. When you found that there's these energy bars here, little snack bars.

Yeah. And so Sona unwrapped one of the snack bars and was eating it and you seemed really happy and everyone was really happy and you're about halfway through this bar and I said, what you got there, Sona? And you went, what is it? What was it? It was a kashi, chocolate almond, sea salt, delicious, you know, bar. Yeah.

And you were halfway through. You're really enjoying it. So tanky. And I said, what is that? And you went, oh, it's this. And I said, what flavor is it? And you held it out just a little bit and I smacked it out of your hands and it went flying across the room and shattered into a million pieces and you shattered out.

You deck. Yes. And I was thinking, that's what I do. Minutes. That's what I do. And you think just because you gave birth to two babies. Oh my God. That you get to come in here now and be treated differently.

And what I'm trying to teach you is no, you've got to get your reflexes back. I mean, I've done that on the team. I've done that to you hundreds of times. And it's actually featured in a very popular YouTube video that's out there where I demonstrate how I do it in front of an HR person. Right. No shame. And you held it out to me because you completely forgot.

I did. You were so busy giving life to the world that you forgot to guard your Kashi bar around Conan. I wasn't even angry at you. I was angry at myself. Appropriate. Because I should have seen that coming a mile away. Right.

Like you did that once when we were on the show where I was holding a plate of watermelon. You're like, what do you eat there? I'm like, oh, that's a plate of watermelon. And you didn't hit it. You kicked it. That was hard. I did a roundhouse kick. Because I had to kick it out of my hand.

Yes. And I kicked it perfectly. So it went flying. And you know, that takes real coordination. It was, I have very long legs and I did a spinning kick and hit the plate, which was paper, fortunately, but I didn't care. It could have been on a Ming vase and I wouldn't have cared. And the watermelon went flying.

Crew members were there. And they weren't used to this. And it's always right when I really want a snack. I find the perfect snack and it's almost as if something triggers in your brain. You're like, so does enjoying herself. Oh, yes. Let me ruin it. The way a shark can smell blood.

I can smell joy and I have to attack. If I sense joy, I must strike. And you get so happy about your snacks. All I need is food and you take it away from me. Yeah. Exactly. Oh, and you love it. You're so happy.

Oh my God. It made me so happy. I'm so glad you're back and I'm so glad you're snacking and then gullible enough to when I innocently inquire. So what, what flavors it? You hold it out a little closer to me. God. Well, it's actually it's chocolate, but it's got a little fudge swirl and what goes flying.

Minutes. Your hair is still up. Yeah. She hasn't done that yet. Oh yeah. When you just punch my, I have my hair in a bun and you just punch the bun for no reason. I punched the bun because I think that doesn't count as actually hitting you because it's, those are dead cells.

You never get my head. No, I've got no, that would be abuse. No. I wouldn't touch the skull or the head, but I figured out a way that if I punch quickly like a little rabbit punch, the bun of your hair, it completely falls apart and you go, oh man. So good to be back. Anyway, as you can tell, I've missed you.

Oh, I've missed you too. It was seconds. Just seconds. Well, we are happy to have you and the twins are doing well. You send me pictures every day and my wife makes fun of me because I run around the house and make everyone look at the pictures. I'm not related to you. We're all surrogate relations.

Yes, but I run around and I go, look, look, here's the latest of Mikey and Charlie. I love looking at them, but my wife said you are far more happy about these children than you were about your own children, which is true. That's nice. Thanks, Conan. Yeah. Well, you know me. I'm a real good guy.

Yeah. Now, what's that you're eating right there? One tang. Okay. Well, Sona, all I caution you to do is don't eat hot soup near me anytime soon. Okay. Okay. That's not a good idea because it's not my fault.

I can't control myself. It's your fault. You can control yourself. Clearly, I can't. Well, anyway, I'm very excited. My guest today was the youngest writer ever hired on Sona Live. He's a frequent contributor to the New Yorker and he's created such shows as Man Seeking Woman and Miracle Workers.

His latest book is a delight. I so love this man's writing. It's called New Teeth and it's available now, very excited to talk with him today. Simon Rich. Welcome. I don't find myself being envious of many people, but I envy you, Simon Rich, and I'll tell you why. Your writing makes me laugh out loud.

I was reading your new book, New Teeth, the other day and I kept shrieking and my wife and kids would come running in the room because they don't hear me laugh like that. Then I would say, wait, wait, wait, hold on, hold on, hold on. And then I would explain the premise of the story and then read them long passages. And anyway, this all leads up to you writing these stories. I've been reading your books for years now and looking at your stuff in the New Yorker and I'm always put it down and think, God damn it. How come he gets to do that?

How do you do that? So I'm so delighted to have you on the podcast. Thanks for being here. Well, thank you so much for the kind words. It is so thrilling to hear you say that. I'm a lifelong fan of your work and all your shows and your writing for some of my favorite shows of all time. The bigger influence on my comedy was absurdist 90s television comedy like your Late Night

Show and sketch shows that were tonally similar, that were silly and smart like Kids in the Hall, Mister Show, The State, The Short-Lived Ben Stiller Show, the last 10 minutes or so of SNL when they were allowed to be non-topical and totally weird. Oh my God, that was my, I'm sure for you too, but I loved writing weird things and some of my favorite things that I ever wrote lived at 1245 on SNL. Yeah. And I thought that's the sweet spot. That's where you want to be.

Absolutely. Totally. Yeah. You don't always have the best set. You have like one flat that's kind of wedged in between the weekend update desk and like a really cool like parody set. And it's just like, okay, we have this small flat that's big enough to fit one robot. And you're like, one robot.

And you're like, I'm on it. I'm your man. Here I am. Get ready. Because I'm pretty sure Bill Hader has a robot voice. Yes. Yes. Pretty sure he can do that.

And can I ask who, when you were writing for that show, like who your favorite people to write for were? Well. Was it Hartman? The best utility performer in the history of SNL Live was Phil Hartman. Yeah. Because Phil Hartman, he used to describe himself as a Mr. Potato Head. You could just, you could, you could put anything onto him and he would become that.

Yeah. Phil Hartman, improbably, but if you look back at his work, he could play the father. He could play the grandfather. He could play the guy in a leather jacket who's a tough, who's here to beat you up. Both Hartman and Hader, my favorite mode for them is when they're villains. Yes. Yeah. And for me, like Troy McClure, Lionel Hutz, I prefer them to be sneaky and oily and sneaky.

And that always was so thrilling to be able to write Charming Bad Guys, which you can get away with with Bill. And you can't get away with that with most performers. We have so many points of commonality that it's almost absurd. Like I look at your transcript, transcript, I look at, I'm going to call it a transcript. I looked up your comedy, comedic transcript, and there's so many of the, we've done so many of the same things. We both got started on the Harvard Lampoon, and that was sort of our awakening.

And I want to, you know, the Simpsons, Sarnat Live. So many points where you and I have had, I think, similar experiences. And where I honestly believe you've ripped me off completely. There was a period of time where you were wearing a red pompadour wig. Yeah, and stilts and the whole business. But you gave me 15% of your income. That's right. Which was, I thought, was incredibly kind of you.

But you brought up, when you bring up villains, I remember when I was at the Simpsons, all I wanted to do was write for Mr. Burns. Because Mr. Burns is evil, which is so fun to write, it is so fun to write evil. He's comedically old, so you can have all kinds of fun with him being an intern for Thomas Alva Edison, you know, or whatever. He also has limitless wealth, which is fun to write. Because he can have an underground lair that's filled with hyperbaric chambers, whatever you want.

And I remember when I was at the Simpsons, just constantly wanting to bring Mr. Burns into the story when he didn't fit at all. And them kind of telling me, no, you can't have more chocolate cake right now, Conan. You have to resolve Marge's issue with Homer over their marital difficulties. And I was like, God damn it, I'm telling you, I want to write about Mr. Burns' brain being put into a chimp. It really is like all you can eat in comedy buffet with Mr. Burns. The funniest villains often, or the kind of best constructed villains often are weak

in some way, because it gives them some level of sympathy that you're allowed to make them even more evil, which is why it's so brilliant that Cartman is eight. And overweight and mocked, and he's physically kind of has a hard time getting around. And I think that's like right out of the Burns playbook, or to make Stewie a baby is a brilliant choice. And a lot of my favorite villains have some kind of infirmity, because you like them just enough that when they decide to block out the sun or whatever, you're like, OK, yeah. I know exactly what you're talking about.

And let's start. I don't talk about this much. I don't know why I don't talk about it much. But I was fairly insecure about a lot of things, didn't quite know where I fit in the world. And then I get to this very prestigious college and went there with every intention of being a serious student and scholar, bumped into the Harvard Lampoon first semester freshman year. It was like stumbling into Willy Wonka's chocolate factory.

I just thought almost a religious experience of these people take seriously the stuff that is so important to me that I didn't think you could take seriously. I honestly didn't think you could take comedy writing seriously or being silly seriously. I mean, yeah. I mean, I distinctly remember like a four hour debate about which masturbating bear segment was the most important, you know, in terms of like, I'm glad I did my part to move the chess piece forward. It was literally like intense, like four hours, like no, when that's when bear quits smoking.

Yeah. That's the best one. And here's why. And then somebody else being like, I disagree. I think that's when it lost its way and like that you cannot and just like heated debates about the silliest sketches. When you're 18 years old and just at a high school and I went to a public high school and I was a Rube, I mean, I didn't know anything about anything.

I got into the Lampoon and suddenly 21 year old seniors are saying, hey, I really like that piece you wrote or I really like that cartoon you did. And to an 18 year old, a 22 year old is the president. He's the president of the United States. You can't believe you cannot believe that this person's making eye contact with you. A man with a full mustache is looking you in the eye. Someone who needs to shave. Yeah.

It isn't an affectation. They actually need it. Yeah. Because hair grows out of their face. Out of their face. Every day, daily. I used to at that age, I was inserting hairs into my face and painstaking ritual hours to wake up in the early pre-dawn hours with the tweezers and the glue and just, I remember,

yeah, I still do it. But these adults, they were adults to me and they were full on adults and looked like adults and talked like adults. They would drink like nice beers. Not just any beer. Like they would be like, I prefer this beer to that beer. I prefer the taste of this beer as opposed to just like get it in my throat by the fastest physical mechanism that we have.

I'm told you had a tracheotomy so you could get the beer in even faster. It's like, no, this beer, I prefer it. What is it? What's sophisticated world of mine? It's like James Bond. Yeah. If you have an Amsterdam still light, I'll take it. That guy's the coolest man in the world.

The coolest thing in the world. I mean, the miracle of writing for me has been basically, it's this thing that I started doing because I didn't always feel like I fit in with other people in school and I often felt like, okay, the things I think are funny, kids at the popular table don't necessarily think that they are funny and I wasn't on the sports teams and I was not, you know. The fact that you called them the sports teams. The sports teams. Yeah.

And so I was alone in my room studying the Simpsons and Kids in the Hall sketches and writing as a kind of way to deal with the social weirdness that I felt. And then somehow through the writing, I ended up with this community of friends who saw the world in the same way that I did and who even wanted to collaborate with me. And that's the thing that I'm so grateful is when I started writing, I loved it from moment one. As soon as I started writing as a child, I was like, this is what I want to do forever. But I did not think that it was going to make me lifelong friends.

It is, it's a little like Robin Hood where you start off and then you pick up people along the way and then before you know it, you have your gang of merry men, your posse of people that you collect along the way. The other amazing thing is you, in my case, I've learned so much from the people I've met along the way. Like at every stage at the Harvard Lampoon and then at SNL and then at later on when I worked at Pixar and then on the other TV shows I did after that, I learned so much from the other writers.

That's the thing that I really like is if you can say there's your, you know, there's Malani's and, and, and, you know, your Jack Handys and your Jim Downey's and Robert Smigel and, and, you know, you, there are all these people that come up with these ideas that I think, oh, this is going to be really funny. This is just funny the way it's like an ore. You can put it in a furnace and melt it down and it will just be a, it'll be a funny goop that then can reform into a cell and it's still funny. It's a mass.

It's solid. Um, it's not attitude. It's not getting by on a buzzword that it's not trading on your emotions. It's just got this, um, this worth that I think is so cool. I got to write most weeks at SNL with, with two writers, Merica Sawyer and John Malani and the three of us wrote together most weeks and they are the two funniest people I've ever met. Yeah.

And I learned so much from getting to work with them. And to this day I still can't believe they like let me tag along because they were both so much funnier than I was. Not only was everything they were doing stronger than what I was doing, it was happening at a speed that blew my mind. I mean, it's like watching, it's like, it's like being a sprinter and then racing against Usain Bolt. And you just, it's a level of speed that it almost seems magical.

Yep. It's hard to explain how surreal it, it, it, it felt to write with Malani and Merica because it, it's like it, it would be like meeting somebody who spoke in perfect rhyming verse and I am a contender, you know, without even trying. It's funny when people have an access, this makes me think of Downey and I think it's also true of, obviously of Malani, if they have immediately access to the right phrase. Perfectly every time. So, so I remembered when I was going to go see John's show, Downtown in LA and he said,

oh terrific. And then as a joke, I just said, I plan to walk in, you know, a few minutes into your set. They try to rattle you. You know, no, I like, and my idea was I, and you know, I'm just expecting, I'll use the center isle so that you can hit me with a spot and say whatever you want to say about me. And I said, I'll walk in, I won't walk in too quickly.

And he wrote back immediately. He said, you'll walk in at a King's pace. And I was like, shit, that's the phrase. It's King's pace. He always has it. He has it instantly. Yeah. Every time.

A King's pace, I thought, but for my entire college career, I thought about comedy and, and thought about different ideas and what's the best way to be funny and why does this not work, but that works. That got me started a lot earlier, I think, than I would have otherwise been thinking about it. Oh yeah. Yeah. I was the same way.

And I even, even the courses that I took were designed to get material. Like I purposely would take classes that I thought would like yield interesting premise ideas. So if you look at my transcript. Okay. Well, wait, really? It's all like, yeah. No, literally.

It's like medieval medicine. Yeah, any, any class I could find that had, any class I could find that had monkey in the title. Uh-huh. Like sometimes they'd be like really hard science classes. I could barely understand what was happening, but I was like, eh, there might be some fun stuff. That's hilarious.

About monkeys in here. You're at Harvard and you're choosing courses that might help you with a comedic premise. So you probably, I find if I looked at your college records, like four times you, you took classes on pirates. Exactly. I literally took a class on pirates. Any class I could take about talking animals. I took a robotics class.

I mean, it was just like, you know, anything I could do to try to get, get new premises that other people were going to get. I saw you do something on your show, which absolutely floored me, a man seeking woman and you did a piece where Hader is Hitler at a party and he's like in a cool loft party. Yes. And there's a guy there who's like, and it's Hitler now, he's like 130 years old. Yeah. That's based on one of my short stories and the premise is actually the pilot of man

seeking woman. Yes. The very first episode we led with, we led with 135 year old Hitler. But I loved it because it was, it was Hitler is at this party and now he's dating this guy's girlfriend. Yeah. And it was at this guy, he finds out that his ex-girlfriend, this 20-something guy, his ex-girlfriend has moved on to someone new and he's still in love with her and it's,

now she's dating this older, richer guy and he becomes even more upset when he finds out that that person is Adolf Hitler, who is 135 years old, apparently faked his death and you know, met his girlfriend or his ex-girlfriend and but he's there and he's got money and he's in a wheelchair. He's in a wheelchair. I mean, he is, he is 135. Right. He's reasonably old, but he is still with it and his friends, his best friend, played

by Eric Andre, is like, you know, give him a chance. Like, like I know he's sort of sketchy, but like he's got great stories and like I think maybe- He's got a really cool apartment. Cool apartment and I think maybe you just don't like him because he's dating Maggie. He's like, he's Adolf Hitler and they're like, you know, you know, like maybe cool with that because like we're at his apartment and like there's like really good shrimp and like-

It's completely insane and I love how it was a really good hipster party and of course Hader, as you said, is so great at being, he's charming as an old, old Hitler and you know, it's all, it's, there was some bad, you know- He knows. He knows. He's done some, some questionable things, but he also kind of has a sense of humor about it all and Maya Erskine, who now is this brilliant show, Pen 15, is great as a, as the, as Maggie, is the ex-girlfriend.

Yeah. Who basically it builds to the point where she tells Jay Barshall, who plays the main character, that he needs to apologize to Hitler for, for ruining his party. Exactly. And he has to say, I'm sorry, Hitler and then, but then Hitler is so, it is, and is improvised. Yeah. Hitler is so old that he's extremely deaf and so, so Bill Hader is like, what? And then, and then Jay has to apologize to Hitler louder.

Yeah. And so we had like one extended improv take where he has to apologize like 12 times because Hitler keeps forgetting- So it's just so funny because I saw that and I thought, shit, you've ramped it up where Jay Barshall has to say sorry, Hitler, because he's really being a drag at Hitler's loft party. At his really cool party. Yeah.

I mean, yeah, I, because when I was growing up, I really loved, like I said, I loved absurdist sketch comedy. And the other thing I was obsessed with was heartbreaking, realist fiction. And so I would be watching kids in the hall and then during commercial breaks, I would be reading like Carson McCullers and, and like Richard Yates, like stuff that is not necessarily depressing, but, but like stuff that like can make you cry because it's so emotionally brutal. And I always thought like, I wonder if you could do these at the same time.

Like I wonder if you can write a story about like unrequited love that is as brutal as Flannery O'Connor's story. But also have robots and also have time travel and also have talking monkeys. Like can you jam those two things together? And I remember asking like my English teachers, like, do you know any writers who like do that? And, and one teacher I remember told me it's impossible because the funnier something gets the more superficial and hollow it becomes.

And I remember thinking, I don't think that's true. And the reason why I don't think it's true is because of the Simpsons. Because the Simpsons, especially the era of the Simpsons that, that you were a part of, it's super silly, super absurd and also incredibly emotionally grounded and moving and poignant, sometimes all within the same scene or even within the same joke. And so I was like, I know this can be done and, and I've been trying, trying with varying degrees of success to try to kind of do that thing of being silly, but also emotional at the same time.

And you know, it's, it's, you know, I want to make sure I talk about this because New Teeth is that your new book of short stories and I've devoured all of your short stories over the years. But there's so many stories in here where I found myself really laughing because it's so funny. But then there's something that feels sweet and real to me at the end that's earned. There's this story you wrote called Clabo. Please, if you're listening, go out and get New Teeth and read Clabo because I read it,

the entire story out loud to my family because I kept laughing so much. I'm so happy you liked that one. But Clabo is, when I talk about being envious, I wish I had written Clabo. And in fact, I'm going to start telling people I wrote Clabo and just, you know what's going to happen? Most people won't bother to look up that you and find out that you wrote it. So there'll be a 3% will end up thinking I wrote Clabo and that's all I want. But Clabo is a giant, like superpowered ape that has saved Earth many times.

And now, it's a couple of years later, no creatures have come from the sky in a long time and they bring Clabo in and they tell him, basically, we can't afford your giant fortress of solitude. We can't afford. They tell him there's been some budget cutbacks. So we're actually going to put you into a management situation. Yeah, because they're polite because he was a big hero many years ago and they don't want to slight him.

So they, as a conciliatory, they kick him upstairs, essentially. Yeah. And they say, you're going to be our new senior coordinator for the Office of Community Affairs. And Clabo is impressed. You're going to get your own office and Clabo, now of course, Clabo speaks the way you would imagine Clabo would speak. He is a giant ape creature. So Clabo's excited and says, Clabo, going to need new clothes.

Clabo need tie, Clabo need shoes. And Clabo need to go to bed by 10, he's saying this to his wife, Clabo need to leave early in the morning, Clabo need to allow time for learning new commute. He's so excited. And then you get to this passage where he has a whole suit that he's picked out to where to work. And I'm just going to read this because I just loved it so much. Clabo got to work four hours early.

He didn't have a key card yet, so he spent the morning pacing around the lobby, stopping at each mirror to scrutinize his outfit. He still wasn't fully confident in his executive look. At 12 feet tall and 1,900 pounds, shopping for business clothes had been a challenge. Mimi, that's his wife, had managed to find him a pair of Quadruple X khakis. But when he tried them on at dawn, the seams had exploded, leaving him no choice but to tie the garment over his crotch like a diaper. In lieu of a tie, he painted a red stripe on his chest.

His shoes were buckets. This is so delightful. He shows up to work like that. And of course, he's used to battling space aliens. And now people at work are kind of snarky because he doesn't know anything about management. There's a lot of eye rolling, inner office politics. And he's just trying to hang this new environment and trying to fit in and do a good job and serve the city in this new way that he just doesn't have.

He really only had one skill that everyone needed. Which was, when it was clobbo time, he could bash aliens. Nobody was better at bashing these worms from space, but when it comes to figuring out the Wi-Fi password, it's very tricky for him. Yeah. And they're trying to get him the Wi-Fi. And he's trying, and he just says, get me numbers, get clobbo numbers. He knows that his job involves numbers in some way.

He thinks that he can fake it, you know, that if he just keeps demanding, if he keeps demanding numbers of people, that somehow he'll succeed. Yeah. Clobbo need numbers, he would say. You could have clobbo numbers now, and Kevin, who's like the young guy at the firm who has to kind of look after, is like, what numbers? You tell me, clobbo would say, you are supposed to know which numbers. You find out which numbers, and you show to clobbo, I don't know what you want.

I have no idea what you're talking about. And poor clobbo, but I read it, and I had so much, and there's a really sweet ending to the story, but I think one of the things you do so well is don't spend any time trying to massage a crazy premise. Just start by saying, clobbo was a giant ape who protected Earth for years. That's the way you do it. You don't mean this? Thank you.

Well, thank you so much. I'm so happy you liked that story. Yeah, I mean, some of my favorite short story writers are not comedy writers, like they're genre writers. So like Stephen King, and Bradbury, and Phil K. Dick, and Shirley Jackson, and TC Boyle. These are writers who take really big swings. The first sentence of a Bradbury short story. They're transported.

Like by the end of the sentence, you know, okay, I guess I'm on the spaceship now. And there's an alien loose, like you're right there. And I try to emulate those kinds of writers where that's why I prefer to write short story collections to novels, so I have written a couple of novels, but I mostly write short stories because you can take these really big swings. You can just say, okay, yeah, here's a giant monkey man trying to learn how to be a middle manager in a bureaucracy. And then 10 pages later, you know, when you're on to the next story, it can be a 1930s style

noir, or it can be about a... You wrote a great noir story in here about it's a baby who's basically the detective, and there's another baby, a young girl baby who is the femme fatale who wants... Who's hiring him to find out what's going on. And everything lines up with a great detective story, but you're talking about people that are what, a year old? Yeah. So the...

Well, Charlie, he can move, so I'm thinking he's about a year and a half old. He's two. Yeah, he's two. He's two. And he's... It's called the big nap, and it's kind of modeled after, you know, the Chandler, Hanlon novels. And he's two years old, and he is just...

Life is hard for him, you know. He is weary and tired. He's hitting the bottle all the time. He often will wake up and not know where he is. He's just, you know, trying to keep it all straight and keep it all together in a world that makes no sense. And then, yeah, this femme fatale, this baby girl shows up with a missing unicorn, and she wants him to find it.

And he's not sure whether to get mixed up with her, because she has this, like, shady pass. She doesn't exactly know where she came from, like, did some people say that she came from the hospital, but then there's also this rumor that she once lived inside of mommy's tummy. And so he doesn't really trust her, you know, but she has Batman stickers. She's gonna pay him. So he's like, hey, a job's a job. Oh, I love it.

Yeah. And then, like, as the story progresses, like in all of these, in a lot of these detective noir novels from the 30s, 40s, 50s, he realizes, you know, there's something about this screwy kid. And I kind of like her. She's getting under his skin. She's getting under his skin. Yeah.

But then, of course, she ends up betraying him. And then, ultimately, there's a happy resolution. And so it's like, it is like a parody, it's satire, but what I was hoping to do is, like, emotionally, I was hoping to tell a story about, like, two siblings becoming friends, you know, about a toddler learning, maybe my baby sister is not so bad, maybe we can coexist. Maybe we can work this out. Yeah.

And that's something you do exceptionally well, which is you take a story we all know, which is, in this case, the Chandler story, the tough Humphrey Bogart, the, you know, the woman coming into the detective office who's in trouble. He's not going to fall for this, but he starts to. And then you flip it around. So we're seeing it through the eyes of these babies, which makes me see it in a completely different way. It's very disarming.

One of my favorite things you did in that, it's a spoiler, but it doesn't matter because it's just that funny when you read the stories. There's a great moment because we all know that in detective stories, at some point, they slipped the detective a mickey. And they slipped the detective a mickey. It's inevitable. It's inevitable. They put something in his drink.

Yeah. And then he wakes up somewhere and he realizes that the bad guys drugged him. And in this one, he's trying to get away and an adult clearly gives him, like, some robitussin. He wakes up in his crib and it was great because it was just, it slid over perfectly. It worked really nice. Yeah. And then that story, thank you.

And that story, the grownups are essentially the mob. They're the enemy. Yes. Yes. And it's like he knows. A big nefarious group of grownups, which is perfect. Yeah. Right.

And they're speaking code. Right. They're constantly disappearing. You don't know what they're up to. And he knows that it all goes back to mama somehow. Like, he knows that she's at the top. Right. And then everybody works for her.

Yeah. Including especially Dada. Yeah. But like, he doesn't know more than that. Doesn't know. He's just trying to. It's a shadowy world. It's a shadowy world.

They have their secret after hours, hang out at the TV room where, you know, they stay up late doing God knows what. And yeah, he's justly terrified of them. Yeah. Well, this is, I'm going to really get into the weeds here with a question for you, which is something that has always fascinated me in comedy. And I see you do it sometimes really well. There's a story that you wrote in here, which is a really great, funny story about these

two pirates that are just the worst, cruelest pirates ever. They literally, their beards are soaked with the blood of their victims. They talk like pirates. They're tough. And then they find this little girl that they've got to take care of. They're talking like pirates, but trying to figure out basically how to ferberize the baby like in a sleep schedule. Yeah.

They end up having different parenting philosophies. And yeah, they were a great duo, you know, when it came to killing people and stealing their gold and sailing the seven seas, they got along perfectly. And then when it comes to the question of how do we deal with this three-year-old girl, it's like, you know, like, ah, maybe we should be getting her on some kind of schedule. Yeah. And then the other one's like, ah, no, you know, because one pirate wants to keep a rep all night and let her have fun.

And then there's like saying, ah, I think we should put her on a schedule. And then the first one saying, ah, well, you know, if she makes noise at four, we'll just handle it then. And then the second one, as we've all heard this conversation in relationships many times, oh, so you'll be the one getting up at four. And I thought, but one of the things I love is there'll be a character like a Homer Simpson or whatever, who's clearly not very bright. And the whole premise is that he's not very bright.

But at a given moment, he'll suddenly be a savant and he'll have full knowledge. At a given moment, if it's funny for Homer to suddenly have access to great knowledge, he will. Yes. I was rewatching some episode that was not from my era, but, you know, Lisa makes some kind of joke about, or she's worried about her college career. And she says, you know, I don't know if I'll get into an IV. I might have to go to Vassar.

And he spits out. He says, no daughter of mine. Yeah. And, but he's also like enough Vassar bashing in this house. Oh, that's what it is. Yeah. Yeah. Vassar bashing in this house.

And I'm thinking Homer doesn't even know what Vassar would be in any other reality. But suddenly he knows that there's an old trope of Vassar bashing in the IV leagues. And he defends it. And he defends Vassar. That's right. I miss him. Yeah. It's so great.

So, you know, and I've noticed that I bring it up because obviously that's a trick that you can do in comedy is suddenly a character has knowledge to just what to say. I've noticed that sometimes in your stories, you're really getting into the rhythm of this pirate language. And it's really great. And then suddenly a pirate knows, all right, you're just being passive aggressive now. And suddenly he has access to something to a level of knowledge of human behavior. We in the 21st century use the word passive aggressive all the time.

But this pirate. Yes. Yes. And sometimes, sometimes I'll be in situations where there'll be like a, you know, either at the New Yorker or with one of my publishing houses, there'll be a very sweet fact checker who is like, because I get the copy of it, and I don't think an 18th century pirate would know this term or like, I don't think this slang word, you've been consistent for many paragraphs in a row, but I don't think that the elephant man would say that something

was played out. Yes. Yeah. That's what I was going to bring up. You wrote this piece that I love called Case Study, and it's about, it's basically, it's the story of the elephant man, and it's all the diary. It's the diary of the physician who's helping him. But suddenly you'll keep doing this great rhythm thing where you'll change it up.

It's all written as a medical report would be in the 1880s. But then, you know, he'll notice that the elephant man is kind of coming onto his wife by reading poetry in front of her. He becomes obsessed with the theory that there's something going on between his wife and the elephant man. Yeah, and the elephant man, and he's writing, and he's still writing in that 19th century style, but at one point he'll say things like, he's reading poetry again. I mean, he's really pushing it.

And you'll think, well, no, no one would have said that, but it's hilarious. At one point he asks, he asks rhetorically why she would do him like this. Which is extremely, extremely, extremely anachronistic. Yeah. And there's another point that I really loved where you're suggesting that, you know, it's brought up that, well, possibly that they're having some kind of affair. And someone says, that wouldn't happen. This is Victorian England, because there's something akin to that where people are very

aware that this is the Victorian era. Well, the wife, yeah, because the wife says we're not, you know, you're being jealous and ridiculous and insecure, but also like he's clearly gay. Yeah, yeah. He said, how do you know he's gay? Did he come out? And she said, well, no, he wouldn't come out. It's Victorian England.

Yeah, he's got enough going on. He doesn't need that. Also, so they somehow have knowledge of the time period they're in. They're very self-aware. Yeah. So that's, yeah, I mean, in terms of that whole trick, that sort of the inconsistency that you're describing, like, I mean, the simple answer is I love it. I think it's hilarious when all of a sudden you were in a Simpsons episode that I wrote,

you find out that Homer at one point self-published an autobiographical novel about his father, which is completely ridiculous. So I love that device, but my rule is always, if it's emotionally honest, you can be as inconsistent as you want. It's fine. It's that old David Letterman line of just accept the premise and go. And I remember there was a Simpsons episode again, I'm quoting stuff that I had nothing to do with, but Lisa's citing different people who, I don't forget what it is, I forget exactly

what the context is, but she's saying something and she says why, you know, even Supreme Court Justice Souter thought so, and Homer just goes, oh, no, not Souter, Homer wouldn't know her care who Justice Souter is, oh, no, not Souter. But it's emotionally raw, you know, like. I swear to God I could do this all day, and maybe we should just have a podcast where you and I break down, get really into the weeds on comedy, but this has been absolutely joyous for me. So.

Thank you so much for having me. Oh, yeah. I mean, I didn't want to. Again, I'm just incredibly embittered by your success and your talent, but no, this was a delight, absolute delight. And I want to make sure that I tell people, you know, the nice thing about this podcast is I don't have to plug anything. That's what I love about it for years and years and years.

I was saying, well, OK, let's get to the clip, and what's really nice is I'm mostly talking to people and I mention what they're up to or I don't. But new teeth stories by Simon Rich, if you're, we're all need to laugh more. And man, this is a funny collection of stories and also really sweet, but hard, hard laughs. So please keep making this stuff. Thank you. It's really good. Thank you.

It really means the world to me. Thank you. All right. Show yourself out. Once again, Sona is back with us in studio joining David and I. The team is reunited. We're thrilled to have you. Yeah.

How's it going? So I wanted to talk about this one thing that happened to me and I wanted to get your take on it because I know Liza was always very open with your kids. So two of my friends were at my house and they have a seven-year-old daughter. And she was like hanging out with me and whatever, feeding the kids. And then at one point I went to go change one of the diapers for one of the boys. And I take off his diaper and she goes, why does he have a tongue in between his legs? And I go, well, that's his penis.

She goes, his what? I go, that's his penis. You have a vagina and he has a penis. And she goes, what do I? Oh, no. Oh, no. How old was she? She was seven.

She was 27 years old. That's the scary part and she's from Arkansas. This is horrifying. I just don't know. She graduated law school. Wait. Oh, sorry. She's seven?

She's seven. Yeah. She should know things at seven. That's what I was saying. Well, first of all, Liza, my wife, is from the, you explain everything and you just are very like, that's a fact. That's what you have. You have a penis.

You have a vagina. Yeah. I'm uncomfortable even talking about it. Those things weren't mentioned in my home and my dad's a doctor. I know. So I grew up thinking I have a vagina and was actually told by several doctors that it resembled. But anyway.

You know several doctors to tell you? There was later, there was a surgery and we're fine. But the point is, and they can do miracles. So you know. I don't understand what you do. In the medical community. Okay. They can, whatever.

From scratch, they pretty much built me functioning. Anyway, my point is that my wife is just very much, that's what it is. And so there's no squirming or, so my question is, what is this girl's parents saying to her? So she was very confused and then, you know, and also it's very complicated now because it's, there are men who have vaginas and women who have penises and I didn't even want to get into that. So I kept it very simple.

No, you don't have to get into that. You can give it a simple, yeah. And I was, you know, and then later on I went downstairs and I had to say to her parents, I go, I just told your daughter what a penis and a vagina was. And they were pretty, they were kind of upset at me. No, really? Yeah, but how can they be upset? What are you supposed to do if she follows you into the room and it's not like you introduced

the subject. No, no. And then, oh my God, I forgot at one point. And it's not like you gave her a book like, and here's the big book of dicks, you know. It's a Dr. Seuss book. Mr. Wix's has dicks's, you know, you didn't do that. You were confronted while you were changing your boy's diaper. Yeah.

The question. Yeah. You know, this part, so I was chatting and I was like, you have a vagina and then she goes, and then she was like confused and then I go, you know, I was like, did you not know this? I was like, he has a penis, you have a vagina. And then she looked at me and she goes, I don't think you're supposed to be talking to me about.

Oh no! And I got really uncomfortable and then I just finished changing their diaper, one of their diapers in complete silence and this was so awful. So, and you say the parents were not happy with you, what would they have had you do in that situation? I don't, I feel like they would have been like, they would have probably been better with me being like, ask your parents. Yes, I see, I see.

And I, you know, I just, that's not your jam. You don't. Well, a similar thing happened with my niece. My husband's parents are divorced and they're both remarried. And so Ava was asking me, she goes, why does Tac have four parents? I go, well, because his parents are divorced. And then she goes, well, what's divorce? And I said, well, it's when two people who are married aren't, don't want to be married

anymore. And then she goes, well, why wouldn't they want to be married anymore? And then we got deep. And then I was like, you know, love changes, things happen. Yeah, love's pretty much a myth over time as people age and they see the encroaching shadow of death. They realize we're here, but for a short time, they should probably taste other fruits. Oh no.

Wait. Don't say taste other fruits. Well, aren't I just saying what, maybe I went too far. Yeah. Honey, I love you. But anyway, baby, you're the best. But no, how deep did you get with it? Well, we got deep.

And then Danny and Lucy said that every time they would have like even a slight disagreement after that, Ava would ask them if they were going to get a divorce. Like she was kind of traumatized by it, but. All you have to say to Ava just before she's going to sleep is don't worry, statistically it only happens 50% of the time and then turn the lights out and shut the door and then start loudly arguing with your spouse. You don't make enough doing the best you can. You're not a real man.

How am I supposed to live off this? Ava just sitting there listening in the dark. Single tier. Single tier. Wow. Well, I don't know, Sona, I don't think you did the wrong thing. I hope not. I got really uncomfortable by it.

Yeah. Has it ruined your relationship with these people? No. No, we're fine. We're fine. You know, you should tell them they should be happy because if I had been in the room with you and the little girl had said, what is that thing between his legs? I would have said, it's a cock-a-roo, it's a cock-a-roo, and I would have followed her

down the stairs going, ah, cock-a-roo, come on. I'm guessing Liza's the one who had to have all these talks with your children. Yes. What would happen is a question like this would come up and Liza would look at me, I'd look at Liza, and we usually keep the windows in our house open so I can just roll right out and I would roll out onto a hedge below and then I'd just run all the way till I hit the 405 freeway and then I'd go north and I'd look for water up in the hills to try and live off of for a while and then I'd come back when the coast was clear.

But no, I think you answered that, you know, the right way. I mean, yes, maybe you could have said you got to ask your mom, but that's weird too. That is weird. Because it's like- Then you're making it weird, right? Yes. Then she can become like you and you don't want that. Well, I mean, clearly whatever happened to me yielded an incredible gift to the world

and really if you think about it, I hear crickets, we should put crickets in here, a genius, a solitary lone voice that could unite a torn world. More crickets please, this is good, a real genius, the Michelangelo of comedy, more crickets please, Conan O'Brien needs a friend, with Conan O'Brien, Sonam of Sessian and Matt Gorely. Produced by me, Matt Gorely, executive produced by Adam Sacks, Joanna Solotarov and Jeff Ross at Team Coco and Colin Anderson and Cody Fisher at Year Wolf, theme song by the White Stripes, incidental music by Jimmy Vivino, take it away Jimmy.

Our supervising producer is Aaron Blair and our associate talent producer is Jennifer Samples, engineering by Will Beckton, talent booking by Paula Davis, Gina Batista and Brick Kahn. You can rate and review this show on Apple Podcasts and you might find your review read on a future episode. Got a question for Conan? Call the Team Coco hotline at 323-451-2821 and leave a message, it too could be featured on a future episode.

And if you haven't already, please subscribe to Conan O'Brien Needs a Friend on Apple Podcasts, Stitcher or wherever fine podcasts are down. This episode was produced and edited by me, Brett Morris.