Conan O’Brien Needs A Friend

Staff Review With Brian Kiley

27 min
Feb 26, 2026about 2 months ago
Listen to Episode
Summary

Conan O'Brien interviews longtime writer and collaborator Brian Kiley about their decades-long working relationship, starting from Catholic school in Boston through their work together on Late Night, award shows, and the upcoming Oscars. The episode is a nostalgic celebration of their creative partnership, featuring stories about inside jokes, memorable writing moments, and the unique humor that develops between comedy collaborators.

Insights
  • Long-term creative partnerships develop unique, non-transferable humor that cannot be explained to outsiders but drives daily workplace satisfaction and output quality
  • Pre-show preparation meetings with comedy writers serve dual purposes: refining material and managing psychological readiness through absurdist humor and worst-case scenario rehearsal
  • Comedy writing for high-stakes events (White House dinners, Emmy awards, Oscars) requires writers who can maintain discipline and quality while operating under extreme time pressure and visibility constraints
  • Personal brand consistency in comedy (clean material, specific comedic style) can become a creative asset that other writers build running jokes around, strengthening team cohesion
  • Sponsorship acquisition can be strategically influenced through targeted comedic content, creating a feedback loop where brands become sponsors to stop being the subject of jokes
Trends
Long-form podcast interviews as vehicle for entertainment industry retrospectives and relationship documentationNostalgia-driven content celebrating pre-digital era comedy writing and collaboration methodsAward show writing as premium creative work commanding top-tier comedy talent and long-term relationshipsInside-joke culture in comedy writing rooms as competitive advantage and retention mechanismCross-generational comedy mentorship and knowledge transfer through formal and informal channels
Topics
Comedy Writing for Award ShowsLate Night Television ProductionWhite House Correspondents Dinner WritingEmmy Awards Writing and ProductionOscar Ceremony Writing and HostingStand-up Comedy Performance StylesComedy Writer Collaboration DynamicsBoston Comedy Scene HistoryJoke Development and Refinement ProcessPre-Show Preparation RitualsCelebrity Guest ManagementSports Fandom in Comedy WritingClean vs. Blue Comedy MaterialComedy Writer Retention and LoyaltySponsorship Integration in Comedy
Companies
Taco Bell
Subject of recurring diarrhea jokes in monologues; eventually became show sponsor, stopping the jokes
NBC
Network that employed Conan during Late Night era; mentioned in context of early 1990s show production
Sirius XM
Current podcast distribution and sponsorship partner offering three free months to new subscribers
People
Brian Kiley
Longtime comedy writer and collaborator with Conan; subject of the staff review interview
Dennis Leary
Boston comedian mentioned as mutual acquaintance who recommended Brian Kiley to Conan
Bob Newhart
Comedy idol of Brian Kiley; featured in Emmy Awards bit where he sat in airtight box with three-hour air supply
Chris Christie
Former New Jersey Governor; frequent subject of weight-related jokes written by Brian Kiley
Bill Clinton
U.S. President; Conan performed White House Correspondents Dinner jokes for Clinton administration
Barack Obama
U.S. President; Conan performed White House Correspondents Dinner jokes for Obama administration
Sonny Bono
U.S. Congressman and entertainer; subject of joke at White House Correspondents Dinner before his death
Tommy Lee
Musician; appeared on show after jokes about his sex tape; handled ribbing well according to Conan
Lori Kilmartin
Stand-up comedian and writer who participated in pre-show meetings with Conan and Brian Kiley
Bob Dole
U.S. Senator; complimented Conan on term limits joke at White House Correspondents Dinner
Luciano Pavarotti
Opera singer; subject of cologne joke about releasing a scent 'this time on purpose'
Quotes
"Anytime I do anything where I need great jokes and everyone else is busy, I get Brian Kiley."
Conan O'BrienOpening
"You'll forget your children's names, but not a riff. A riff will always be remembered."
Brian KileyMid-episode
"There are things that you can't tell anybody. They don't make sense. When you're in the room, there's a room reality where it's working in this room. But then the minute you leave that situation, if you go home and try and tell your wife, they're like, what are you talking about?"
Conan O'BrienMid-episode
"I rooted against guests. I wanted the show to tank so I could have a good post-mortem meeting."
Conan O'BrienMid-episode
"You've crippled my career."
Conan O'BrienClosing
Full Transcript
Conan O'Brien needs a fan. Want to talk to Conan? Visit teamcoco.com slash call Conan. Okay, let's get started. Hey, Conan O'Brien here. Normally, on Thursdays, we drop a fan episode, but I want to do something a little different today. On Monday, I talked to Dennis Leary, and he was chatting about a comic we both love, a Boston comic, Brian Kiley. Brian is working with me in my office right now on the Oscars. And I thought, hey, Brian's in the building. Let's get him in here. He knows all the dirt on me. Anytime I do anything where I need great jokes and everyone else is busy, I get Brian Kiley. I'll take it. I need the work. I mean, I really cast a wide net and no one wanted to work with me. No, Brian, we've, I mean, our story is kind of crazy. we've known each other since we were kids because you would chat with my brother luke at our catholic instruction class that met at the cenacle what town was that in brighton in brighton you're in brighton on the top of a high hill these nuns taught catholic instruction on monday afternoons i think you and my brother luke started chatting with us with each other about the bruins in the Red Sox. Yes. And I was in the corner doing bits for a snowman. Yes. I mean, it's insane. We went to CCD, which is, you know, Catholic Sunday School. Same place. I would sit next to Luke and we would talk about the football games the day before, which we would still be doing now. We were like eight years old or nine years old. You were in my brother's dance class. And then Dan, Dan... Say that a little slower because it said you were in my brother's... It sounded like you were in my brother's dance class. No, you weren't in dance class. I was not in your brother's My brother's dance class. Oh, I thought that's what he meant. No, no, no, I'm sorry. My brother Dan and Conan were in the same class. And then they both... You were in my brother Lamaze's class. What? I was not in a Lamaze class. No, his name's Lamaze. No, so Dan and Conan were in the same class. And then they went to Harvard together. And then my brother Dan would show me the Harvard lampoons. and he'd be like, remember Conan O'Brien? And he would show me these things, which were great. First of all, the class of 83 didn't do nearly as well as the class of 85. We didn't go to Harvard, Luke and I. Oh. Yeah. You dummies. I know. But we'd read these lampoons and then I kind of followed your career because I knew you were on The Simpsons and SNL. Yeah. But I would have walked by you on the street not knowing you. Do you know what I mean? Yeah. Because I hadn't seen you since we were there. Well, you would have been like, wow, who's that guy? He's got Riz. In like the 80s and the 90s and stuff? He'd be like Riz? He was using Riz back then. Oh, wow. With me exclusively. That guy's got Riz and I don't know what that is. I still don't know what it is. But so I think you came to work on Late Night. I'll never forget. You came in one day and you were wearing an Irish cap. Sure, sure. And you were, because you were a very funny standup, everyone knew who you were. and you were chatting with a bunch of the writers in the hallway because you were visiting. Right. And this is early, early days of, very early days of the late night show, like 93. And I see you in the hallway and I'm like, hey, we know each other. And we chatted a little bit. I pushed a button that said, please get him out of here. You were immediately taken away by NBC pages and a robot. Right. I kept asking, what's Riz? Yeah. And then shortly after that, there was an opening for you and you came and started writing jokes for me. And you've, I mean, my White House Correspondents Dinner, both of them with Clinton and with Obama. I mean, everything I ever did, the two Emmy shows and all the late night shows I've ever done. And then last year's Oscars, you wrote amazing jokes. And now we're working again on this year's Oscars, March 15th. Tune in. And so I thought, wait a minute. This is a chance to get Brian to come in and we can settle old scores. Yes. Yes. Let's do it. My first day of work was March 15th in 1994. Oh, you're kidding. No, no. The eyes of March. So now that's when the Oscars are. Yeah. Oh, cool. It is, no, you have, as you know, I've told you this a million times, you're one of my favorite comedians. You have such insanely great jokes and you're so disciplined about having great jokes. My favorite thing to do is an impression of you doing the filthiest material ever at the Apollo Theater. Because you and I are the whitest comedians in the world and you are the cleanest comic. You never go blue. And you always are wearing, in my impression, you're wearing a blue blazer, which is very you. Sure. And hello, hi, how are you? And then you go into the filthy, I mean, stuff that would make Red Fox blush. And you do it at the Apollo and kill. And it's just really like, you gotta wash that ass. Ladies, you gotta wash that ass. So I'm going out. And your enunciation is always so perfect and you're so friendly and pleasant And so I would do this routine called Kylie at the Apollo. And it was one of my favorite things to do because I get to be really crazily blue, but it's not me. It's you. Right, right, right. Well, you've done it for my friends like Gary Goldman. Yeah, yeah. But they always report back to me like they're dying. Yeah, yeah. You was a really filthy comic. And then the minute your set's over, you go back to your dressing room and you open up a giant book on Truman and sit on a metal stool, a little metal chair and read it in your perfectly creased, you know, chinos. and blue blazer and then eventually the guy comes back and says, get your ass back out there. And you're like, oh, okay. And you go out and then you completely, you're even filthier the second time. Filthier. Yes, then I go into my B stuff. Yeah, yeah, yeah. So, yeah, but I'm just, I've got, my oldest Kylie riff, because I like to have riffs on each writer, was that you work out a lot, you're very disciplined, you have this very powerful. I know it's coming. Right? I know what he going to say too He got a powerful very strong chest arms shoulders I mean this guy is just you work out But I noticed a while ago that I don think you work your legs out as much And so I started to riff on this. And then eventually your legs became vermicelli. And there were whole riffs about people in a restaurant. You can't go to Italian restaurants because people try to twirl your legs under their floor. And I mean, I would, these bits would, they would go on forever. Yes, he's called them vermicelli, fusilli, fiber optic cables, ribbon candy. I was late one day last year because I had a doctor's appointment. And Conan told everybody I was late because I fell asleep and a little girl braided my legs together. And I mean, this is the stuff I'll be doing on my deathbed. And what I remember, I forget all kinds of things and my brain gets goofy, but the stuff I will never forget. And I don't care how bad my brain goes. I don't care what happens to me. I could be in a deep coma. And if someone came into me and said, Conan, Conan, it's like, no, it's no good. He won't respond to anything. Kylie's here for my chili legs. A child braided them together. AT&T wants to talk to him about microfibers. And the same thing with like Berkeley Johnson, one of the writers, a hilarious writer. He, I haven't seen him since he worked on the Oscars last year. He came into the writer's room and sat down and within a minute I went, I mean, Berkeley Johnson told me, I think 20 years ago, that his dad owned a flag store. And I just like, yeah, I want you to tell that to your dad at the flag store. I said that instantly. those things I'll never forget. If I can find a little thing on a writer, that's going in the vault. Right. You'll forget your children's names, but not a riff. A riff will always be remembered. It's funny because you were always there in the room with me just before I went out and did a monologue in any situation. I mean, all those late night shows, hundreds and hundreds of thousands of late night shows. You were always in the writer's room with me and in my dressing room and it's just about time to go out and we're going over the jokes. And the thing we noticed, and whether it was the White House Correspondents Dinner, I'm just about to go out there and perform for Clinton or Obama, any of those situations or the Emmys or all the other different award shows, you and I would be together in a room and I would start saying the worst things I could think of. Like if I sure my your favorite things seem to be me making up jokes that I could never do in a million years and pitching those and and then acting out the crowd turning on me. And we would be doing that instead of me reading the real jokes. Oh, my God. And there are things that you can't tell anybody. Yeah. And they don't because they don't make sense. When you're in the room, there's a room reality where it's working in this room. But then the minute you leave that situation, if you go home and try and tell your wife, they're like, what are you talking about? It makes no sense. And people will say, oh, is Conan really funny? Oh, he's hilarious. Can you give me an example? And I'll have a Rolex of like a hundred things. I go, nope. I can't tell any of those. Because they don't make sense. No, they don't make sense. But yeah. one of your heroes bob newhart you were so excited when um we thought of a bit for bob newhart oh yeah bob newhart was one of my heroes and very much like bob newhart you're a clean comic amazing jokes and you have you do not have a hurried rhythm and so you have your own thing but you could see why, oh, this makes perfect sense. Bob Newhart would be Brian Kelly's hero. That's one of the coolest things. So Kevin Dorff came out with this great bit because we didn't want the Emmy show to run long. So the show's supposed to go three hours. So we have a tube with exactly three hours worth of air. Like a little glass box. A glass box. And if it runs, if the show runs long, Bob Newhart's in the tube there. Yeah. And if the show runs long, then he dies. He dies. That's dead. And the great thing is he could do this without speaking. So who's better than Bob Newhart? With his face and his big, sad eyes. And so he's out there and we put, we wheel him out and he's sitting on this stool. And I'm bringing this up for a reason. He's, cause he's your idol. You haven't met him before. And we're at rehearsal and we wheel him out. We're gonna, the idea is we're gonna wheel Bob Newhart out in this box and then announce that he has three hours of air. And then if the show's still going, he'll die. And he's sitting in the box. and it was great because we decided it's great if Bob doesn't know that. Right. So he comes out and he's kind of sitting on the stool and he's kind of happy to be there. And then I announced that he only has three hours worth of air and he'll die. And you just see, because no one could do it better than Bob, that it registered with him what I'm saying. And he doesn't say a word. And he's also in an airtight box so you can't see him. And he's just, it's registering. Wait, what? And so Bob couldn't be there for rehearsal. So we had you sit on the stool and be Bob Newhart and we shot you. And then when Bob Newhart showed up, we showed him you doing it. That was the coolest thing to have Bob Newhart. So to have me being Bob Newhart for Bob Newhart was the coolest thing. Yeah, it was so great. You were standing. Yeah. And there was so many, like everyone on the show knew each other so well. and there were so many amazing moments. I remember when everyone knew I was a big Red Sox fan. So in 2011, the Red Sox were in first place like September 1st, and then they couldn't win a game for the last month. So at the very end of September, my dad dies, and we fly to Florida, we go to the funeral, we come back, and people are coming up to me and offering their condolences. And about 80% are talking about my dad, but then I realize 20% are talking about the Red Sox. So they said, oh man, I'm really sorry. And Michael, thanks. And they're like, well, there's always next year. And it's like, no. There isn't that. What do you mean next year? Oh, it's their pitching or whatever. Oh, yeah, yeah. No, no, it's gonna, they'll be back. Back Two totally different conversations yes Oh my God Yeah just so many I mean I can I associate you with just almost every moment of my career You're always there and you're there again. And I don't know what I would do if you told me, yeah, I can't can't help you this year. I mean, I know I'd be probably even better off. I'm kidding. No, I just wouldn't know what to do. Well, you know, we've had this long bond, and it's also just so many laughs. It's just so nice to actually have laughs every day at work, which is unusual. And none of them translate. You can't tell anybody. Yeah. But we still have the laughs. There's so much. I always thought the meeting just before I go out and do a show, the card meeting, that could be so funny. And not because of the jokes. Oh, right. And then the meeting after the show was always just fantastic. Well, the other thing is... Because then I could talk about like, if a guest really didn't deliver, we would talk about that. And it was, that was so much fun. That was so, but also... I rooted against guests. Yeah. I wanted the show to tank so I could have a good post-mortem meeting. But also I remember, you know, Lori and I would meet you with you right after lunch for the second. Lori Kilmartin. Lori Kilmartin, who's great. Another amazing standup. Absolutely. and then you were normal and we would talk about our kids we would talk about movies we would talk about whatever do you know what I mean when was this? when was that normal? this would be like the 1 o'clock meeting oh yeah 1 o'clock in the afternoon yes and then the meeting right before the show was total insanity and so the other writers only saw the insane parts and it was like no actually and be like no no he can't be normal I'm like no no no one believes us the fact that I was shocked that I was normal at some part of the day I know you were like when was that? yeah prove it let's see receipts your 1 p.m. normal hour yeah it's just not true it just doesn't happen uh no and so I'm curious I mean this is really isn't a staff review this is just I love Brian Kiley and I want to talk to him yeah you better you better yeah be ship shape better do more leg days yeah that would crush me I know if you developed your legs yes powerful also you know what I love about me giving you shit about your legs look at mine Yeah. I mean, yours, it's so, I will get on other people about things that I'm far guiltier of, which is the most crazy thing. Well, also, there are so many riffs on different things. And I remember when that Tommy Lee sex tape came out. Yeah. And so we wrote all these big penis jokes about Tommy Lee or whatever. So Tommy Lee's on the show and Conan's walking down the hall and Tommy Lee says, hey, Conan, I heard you've been doing jokes about me. And Conan said, yeah, about how big your penis is. Feel free to do the same about me. And he was like, oh, yeah, right, right. And then he got it. And that's actually not a bad thing for people to be joking about. Yeah, I remember that. He was like, oh, yeah. He was kind of menacing. And then he totally turned around. Do more of those. That's a good thing. Yeah. One of your obsessions was you just always wanted to write jokes about how heavy Chris Christie was, Governor Christie. And he just it. And so and you were obsessed. So every packet I get the joke packet. Obsessed? No, no. He loves because it was all jokes. It's all jokes. like there was a 3.2 magnitude earthquake in New Jersey today when that story would be in the news in the morning, like a slight tremor near Trenton. I knew on the way in, oh God, this is all Kylie's going to write today. And then every joke was that set up. And then, yeah, apparently Chris Christie joined a jazzercise class. Look how proud he still is. Apparently. And you would do this and then God forbid, God forbid anywhere in the United States, these stories would come out, these human interest stories. And it would be like a semi truck filled with candied hams overturned on interstate, you know, seven and 900 hams covered the highway in Iowa, period. When he heard Chris Christie said, I'll see you, whatever, I'll see you in Denver. You know, like he has to immediately get on the scene. Yeah. And I don't know why he just didn't go to the supermarket and buy ham as opposed to flying across the country. It just seems so fiscally irresponsible. Anytime a truck turned over or a blimp crashed and fried chicken spilled on the highway. When he heard, Chris Christie said, is there a, is there a bullet? Is there a jet that goes directly to that location? you it was just and to this day when those stories break and I eventually accused you of shooting out the tires of semi-trucks I came up with this idea that Kylie finds out what trucks are carrying giant hams and roast beefs and there's a giant truck carrying candy apples and it's headed through Nebraska cut to Kylie on a high hill he's got the itinerary of the truck he's got a scope with like this, he's like a sniper and he fires, blows out the tires, it spills, you know, roast beef spill all over the highway and Kylie starts submitting jokes even before USA Today has it. Well, I remember when they came out with the memo of like, no more fat jokes and I was like, what? He was devastated. People are coming up to me offering their condolences and I thought they were talking about my dad. did you do all the taco bell jokes too uh is that you we did do a lot of you're getting paid by taco bell well that was we did a lot of taco bell diary jokes and then we had to stop because they started becoming our sponsor which is a great way to blackmail people into becoming a sponsor for the show. You drove more companies into becoming our sponsor. I know. And you know what would help? I mean, for the podcast, we're doing great. Yeah. But to have Kylie come in occasionally, let's pick a top brand that hasn't bought into the show. Yeah. You go after them. Sure. With your special humor. And then the next thing you know, they'll call up and go, we gotta stop this. Wow, I can't believe they bought, Wendy bought in yeah We had to send in a monologue for when would they have like a Writers Guild Award or something So we had to type it up And we went through a bunch of them So we came with one. It was like six jokes, like five really smart political jokes. We're like, this is perfect or whatever. And then, of course, the last one is a Taco Bell diarrhea. We're like, oh, we can't send that in there. You thought you were going to have a smart monologue? Yeah. And then Taco Bell crept in there. Anytime there was a moment where we thought, maybe we'll get a Peabody award this year. Whatever we submitted had one Kylie diarrhea joke in there. And you just could see the Peabody committee. Well, this is very good. They've checked all of our socially responsible boxes and... Diarrhea. Yeah. You got to keep it real, guys. Yeah, I know. I know. I owe you a lot. Oh, please. You've cost me terribly, but I still owe you a lot. No, this was really fun. I know. what was your favorite event thing to work on with him like what what do you like them what's i mean the white house correspondence dinner is pretty cool because he'd do a joke and then they'd cut to bob the whole laughing and we had or whatever you know what i mean so you see the next day i did the the clinton and it went the one for clinton and it went really well and this is when i'm still pretty new to people i've only been on the air for like two years and um people like once you know this guy's going to bomb and you guys wrote just some amazing stuff. And I get up and I do it. And then the next day I took my parents, my parents had come to see it. I took my parents out to dinner in Washington, DC for brunch. And I'm just really happy that I made it and it worked out well. And I'm sitting with my parents at a table and Bob Dole walks by and he points at me and he says, good term limits joke. To have like one of the most powerful guys in the Senate say good term limits joke, which was probably your joke. Well, and I also remember when you had a joke about, you know, I walked through the streets of Washington and it's like, this is where Jefferson was and Madison and Hamilton and Bono. And you cut to Sonny Bono, who was a congressman. And he's just kind of like, whatever. What the hell? Of course, tragically died two years later in a skiing accident. All right. We got him while he was still around. He was there. Yeah. Yeah. Jesus. Why'd you have to bring up how he died? I'm sorry. I wanted to make sure people knew that he was hearing that joke before he died. Okay. You were making fun of him after he tragically died. I would never do that. That's nice. Okay, good. Because he's not there to cut away, too. Oh, my God. I have a heart and I'm practical. You can't cut to a grave. It just doesn't look good. Well, I'm sorry. Jesus Christ. I've tried it. It's called a comedy killer. Yeah, tell that to Sonny Bono cut to. Hey! Oh, my God. Oh, my God. Well, Brian, I'm glad you came in for your staff review. Yay. Well, thanks for all the laughs and all that fun. Yeah, you too. I mean, just so many great jokes. There was one, I remembered when every celebrity was coming out with a cologne. And I thought you wrote this one, but it's still every now and then I think about it, which is like, Luciano, when Pavarotti's alive, hello. And I said, and it was true, it was in the story that he had come out with a cologne and you said- No, this wasn't mine. Oh, wasn't yours? No, it was a great joke. Luciano Pavarotti, today Luciano Pavarotti released a scent. This time on purpose. Oh, my God. I was so happy with that one. I still think about that one. But that was not your joke. That was not mine. Oh, please. Well, I don't care. Please. You know, I couldn't do every fat joke. No. Do you still remember all the jokes you wrote? Like, if you listened to his White House Correspondents Dinner, would you be like, I wrote that one? You forget most of them. Oh, okay. I can't. When I look through my whole career, I never know. You know, people will say to me sometimes, oh, that's so you, that joke. You must have written that one. And I don't even know anymore. No, no. And people would compliment me and make a joke and they go, that wasn't mine. And then I look at my computer. It's like, there it is. It's like, oh, I didn't remember that at all. Yeah. That definitely happened. How are we going to do this year at the Oscars? Taco Bell diarrhea jokes. Well, you know, if Chris Christie. Yeah. Bring back Chris Christie. You know, anyone listening now, listen to the Oscars. If I walk out there and the first thing I do is say, folks, we've got a great Oscars tonight. So many stars are here. But quickly, I just got to mention a truck carrying 900 eclairs just overturned in Newport, Rhode Island. When he heard Chris Christie said, get me to Newport. Cut to Leo DiCaprio looking confused. Timothy Chalamet Kylie Jenner laughing really hard Oh she likes it She's like that's good She's your audience Well yes and if he Chris Christie if he thinks it's the Oscar Mayer He could make an appearance guys Oscars? The hot dog people? No the film award You're going to be calling him saying Would you do a bit where you keep running in with a bib? saying, Oscars? Are the wieners here yet? No, Chris Christie. You're the worst. I'm just realizing right now, you have crippled my career. Get the fuck out of here. Brian Kiley, God bless you, sir. Thank you so much. Go Pats. Go Pats. Uh-oh, this is gonna... Oh boy. Oh boy, we just changed it. Controversial. Yeah, over and out. Because when this airs, they'll have already lost. Oh! I said it before. Conan O'Brien Needs a Fan with Conan O'Brien, Sonam Avsessian and Matt Gourley Produced by me, Matt Gourley Executive produced by Adam Sachs, Jeff Ross and Nick Leow Incidental music by Jimmy Vivino Take it away, Jimmy Supervising producer, Aaron Blair Associate talent producer, Jennifer Samples Associate producers, Sean Doherty and Lisa Berm Engineering by Eduardo Perez Get three free months of Sirius XM when you sign up at SiriusXM.com slash Conan. Please rate, review, and subscribe to Conan O'Brien Needs a Fan wherever fine podcasts are down.