Conan O’Brien Needs A Friend - Staff Review With Brian Kiley

Episode Date: February 26, 2026

Conan sits down with comic and staff writer Brian Kiley for a look back on their storied partnership over the years. Wanna get a chance to talk to Conan? Submit here: teamcoco.com/apply Get access to all the podcasts you love, music channels and radio shows with the SiriusXM App! Get 3 months free using this show link: https://siriusxm.com/conan. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Conan O'Brien needs a fan. Want to talk to Conan? Visit teamco.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, yes.

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 Senegal. What town? What town was that in? In Brighton. In Brighton.

You were in Brighton on a top of a high hill. These nuns taught Catholic instruction on Monday afternoons. I think you and my brother Luke started chatting with each other about the Bruins and the Red Sox. And I was in the corner doing bits for like a snowman. Yes. It's insane. We went to CCD, which is, you know, Catholic. Sunday school, the 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 and my brother's dance class. And then Dan, Dan, say that a little slow because it said you were in my brother's... It sounded like you were in my brother's dance class.

I was not in your brother's dance class. Oh, I thought that's what you 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 at Lamaz's class. What?

I was not in a Lamaz class. No, his name's Lamas. No, so Dan and Conan were in the same class. And then they went to Harvard together. Oh. 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. 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 S&L.

But I would have walked by you on the street not known you. Do you know what I mean? Because I hadn't seen you since we were. 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. Okay. 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 stand-up, 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 chat 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 Correspondence 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 you'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 I'm in and we could settle old scores. Yes. Yes. Right. Let's do it.

Ironically, my first day of work was March 15th in 1994. Oh, you're kidding. No. No, the eyes of March. So now that's where 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, uh, 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 got to. wash that ass. Ladies, you got to 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 and some of the other, but they always report back to me like, they're dying. Yeah, yeah. Yeah, yeah. You was a really filthy comic. And then the minute your sets 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 are even filthier the second time. Filthier. Then I go into my B stuff. Yeah, yeah. Yeah. So, yeah, but I'm just, I've got my oldest Kylie Rift, 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's going to say, too. He's 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't 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 onto their fork. And I mean, these bits would, they would go on forever. Yes. He's called them vermicelli, fibrichel. Fibre octa 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. You know, 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, you know, it's like, no, it's no good, he won't respond to anything.

Kylie's here. Verme Shelley legs. A child braided them together. AT&T wants to talk to him about micro fibers. And the same thing was 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 and I went, I mean, Berkeley, Johnson told me, I think, 20 years ago that his dad owned a flag store. Right.

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. Don't hold them now. Not a rift.

Not a riff. No, a riff will always be remembered. Yes. 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, 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 Correspondence 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. Sure. Your favorite things seem to be me making up jokes that I could never do in a million years and pitching those 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 me, buddy.

Yeah. 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.

It's going to give me an example. And I'll have a roll like that's of like 100 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 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 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 Ryan Kelly's hero. It's one of the coolest things. So Kevin Dorff came out with his great big. 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. A little glass box. A glass box. And if the show runs long, Bob Newhart's in the tube there. And if it shows long, then he dies. He dies. 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 wheel him out. and he's sitting on this stool, and I'm bringing this up for reason, because he's your idol, you haven't met him before, and we're at rehearsal, and we wheel him out.

The idea is we're going to 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 it 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 has 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,

Hart showed him you doing it. That was the coolest thing to have Bob Newhart. So 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 was 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, and we come back, and people are coming up to me offering their condolences. And about 80% are talking about my dad, but then I realize 20% are talking about the red sons. So they said, oh, man, I'm really sorry. I'm like, oh, thanks.

And they're like, well, there's always next year. And it's like, no. What do you mean next year? Oh, it's they're pitching. Oh, yeah. No, no, it's going to. They'll be back. Back.

Two totally different conversations. Oh, my God. Yeah, just so many, I mean, I can't, 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 help you this year. I mean, I know I'd be probably even better off. No, 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 and you can't tell anybody. 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. 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 was 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 lorry and i would meet you with you right after one for the second lady kill martin who's another amazing stand-up absolutely and then you were normal and we would talk about our kids we were talking about movie we'd talk about whatever do you know what was this when was that this when was that normal this is this is be like the one o'clock meeting. Oh yeah, one o'clock in the afternoon. Yeah. 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, no, he can't be normal. Like, like, no, no one believes. 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. I know. Let's see receipts. Here, one p.m. normal hour? Yeah. It's just not true. It just doesn't happen. And so I'm curious I mean this is really isn't a staff review This is just I love Brian Kylie And I want to talk to him Yeah You better

You better Be ship shape Better do more leg days Yeah That would crush me I know If you developed your legs Yes

It was powerful All right Also you don't you love about me Giving you shit about your legs Look at mine Yeah I mean yours It's so

I will I will get on other people about things that I'm far guiltier of, which is the most crazy thing. Well, also, like, 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. He was like, 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 was. And so, and you were obsessed. So every packet, I get the joke packet. You're obsessed? No, no, he was obsessed with Chris Christie Fet. 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 setup. 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, 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. Any time a truck turned over or a blimp crashed and fried chicken spilled on the highway, when he heard, comma, Chris, Chris. He said, is there a bullet, is there a jet that goes directly to that location? You, 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 hambs 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. Just for the setup.

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 for me offering their condolences. And I thought they were talking about my dad. Did you do all the Taco Bell jokes, too? Is that you? We did do a lot of Taco Bell. He was getting paid by Taco Bell into the table.

Well, that's, it was, we did a lot of Taco Bell Tyree 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. 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 got to stop this. Wow. I can't believe they bought Wendy's bought in. Yeah.

We had to send in a monologue for, 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 like 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? And they 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. This is very good, dude. They've checked all of our socially responsible boxes and diarrhea.

Yeah. You're going 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 do you like? What's more fun? I mean, the White House correspondent's dinner is pretty cool. Because he'd do a joke and then they'd cut to Bob Doehole laughing. And we had, or whatever, you know what I mean? So you see the people like that.

day I did 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 people like, once, you know, this guy's going to bomb. And you guys wrote just some amazing stuff when 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, D.C. for brunch. And I'm just really happy that I made it. And 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. I'm like, what, to have like one of the most powerful guys in the Senate say, good term limits

joke, which is probably your joke. But. Well, and I also remember when you had a joke about, you know, I walked with the streets of Washington and it's like, this is where Jefferson was and and Madison and Hamilton and Bono. 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. We got him while he was still around.

He was there, yeah. Jesus, why'd you have to bring up how he died? I'm sorry. I wanted to make sure people knew that this was, that he was hearing that 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 to. 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. I've tried it.

It's called a comedy killer. Yeah, tell that the Sonny Bono cut to. Hey! Oh, my God. Oh, my God. Well, Brian, I'm glad you. came in for your staff review. You know.

Well, thanks for all the laughs. Yeah, you too. I mean, just so many, 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 just, it's still every now and I think about it, which was like, Luciano, when Poverati'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, well, this wasn't mine. Oh, wasn't yours? Luchiano Pavarotti, you know, today Luchino Pavarotti released a cent, 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.

Oh, please. Well, I don't care. You know, I couldn't do every fat joke. No, that's true. Do you still remember all the jokes you wrote? Like, if you listened to his White House correspondence, dinner, would you be like, I wrote that one? You forget most of them.

Oh, okay. 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 on. I don't even know anymore. No, no. And people would compliment me 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, you. Yeah. Bring back. Chris Christie.

You know, anyone listening to, 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 declares just overturned in Newport, Rhode Island. When he heard Chris Christie said, get me to Newport. Cut to Leo DiCaprio looking confused. Simothy Shalamee

Kylie Jenner laughing really hard Oh she's like that's good Yeah yeah yeah finally She's your audience Yeah well yes and if he Chris Christie If he thinks it's the Oscar Meyer I'm making appearance guys

Oscars The Hot Dog people No the film award You're gonna be calling him saying Would you do a bit Will you keep running in with a bib saying, Oster's,

are the weaners 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, Pat. Uh-oh, this is going to... Oh, boy. Oh, boy. We just juiced it.

Yeah, over and out. Because when this air, they'll have already lost. Oh! I said it before. Conan O'Brien, Needs a Fan with Conan O'Brien, Sonam Obsessian, and Matt Goorley. Produced by me, Matt Goreley.

Executive produced by Adam Sacks, 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 Burm. Engineering by Eduardo Perez. Get three free months of SiriusXM when you sign up at SeriousXM.com

slash Conan. Please rate, review, and subscribe to Conan O'Brien needs a fan wherever fine podcasts are down.