Inside Late Night with Mark Malkoff - Inside Late Night: Brian Kiley

Episode Date: March 10, 2026

Brian Kiley spent 27 years writing for Conan O’Brien across Late Night, The Tonight Show, and the TBS run of Conan, earning an Emmy and 16 nominations along the way. On this episode of Inside Late Night, he joins Mark Malkoff to talk about joining the show in 1994, the relentless pace of writing dozens of monologue jokes a day, and his many last-minute stand-up appearances when comics canceled. Along the way, Kiley shares memories of Conan’s writers room, performing on Letterman and The Tonight Show, and what it’s like working with O’Brien again now as part of Conan’s Oscars writers team.

From late-nighter.com, it's Inside Late Night with Mark Malkoff. Welcome to Inside Late Night with Mark Malkoff. Today we talked to comedian and longtime Conan writer Brian Kiley. Brian Kiley, nice to see you. Nice to see you, Mark. Thanks for having me. It's amazing to get a job in television with longevity. If you go past maybe two seasons three, it's winning the lottery.

How many seasons or how many years were you with Conan? I mean, you're still writing for the Oscars with Conan now, but how many years has it been? Well, 27 with the show have been the last two years with the Oscars. And then I did, after the Conan show ended, I jumped on the last season of Ellen. So, yeah, 30 years altogether. Unbelievable. I love hearing this. Did you join Conan and was it 93 or 94?

What year was it? I started in 94. So I started the Iids of March in 94. So you have all these Boston comics because you were, or did stand up in Boston, Massachusetts. You had Tom Agna, Chuck Sclar, Louis C.K. They recommended you because they needed to replace a monologue writer. That's right, exactly.

So they recommended me, and I sent a packet in, and they called me and said, okay, you start tomorrow. So it was like, okay. Did you not meet with Robert Smigel or Conan beforehand to go in to do an interview, or was it just based on your material and the recommendation you got the gig? I did not meet the one. This is a little bit of a crazy thing.

So when I was a little kid, I went to Sunday school, like Catholic Sunday school, they call CCD. And it was at this place. It was taught by nuns in Brighton. And Conan and his, Conan's brother was in my class. And Conan was in my brother's class. And so we had this a little bit of a weird connection. So I hadn't seen him since we were nine or ten years. old. But we did have this little weird coincidence.

And then your brother, didn't your brother go to college with Conan? He did. My brother went to Harvard also. Yes, the class of 83 did not do nearly as well as the class of 85. But yes, so my brother went to Harvard. It's funny, when we used to go to CCD, we would carpool with this other family. And there was a girl my age and a girl in my brother's age. And the girl my brother's age also went to Harvard. So this class of 15 kids, I'll end up going to public school and at Harvard, which is crazy. How much time did you have to do a packet? Did you have monologue jokes ready to go? Was this something that you were looking to do?

Well, no, but, you know, it was funny. At that time, I was writing, I was doing a lot of topical jokes in my act. So I was writing new stuff for them, but I did have stuff that I had been doing, you know, topical stuff has a short shelf life. as you know, but I had been writing and doing it for, you know, a couple years anyway. So I was kind of used, I kind of had that muscle, was already being used, you know. Very few writers at Conan, especially earlier on were let go. I don't want to say the gentleman's name, but the person that you replaced, wasn't he a Boston comic originally? Yes, yes. And, and, you know, sometimes things don't work out. And it's not that somebody's not funny or that

they're not good. It's really a grind when you do a show like this. And when you're writing on a monologue, like a monologue, a late night show, you're writing 40, maybe 50 jokes a day. So people burn out. Also, that may just not be the right medium for them. You know, that doesn't mean they can't, you know, I've known people who got let go on shows and they went and had huge success for writing a different kind of show. So it's, it's no mark against him. I just want this, you know, It's just, and people do get burnt out on those late night shows. At what point did you become head monologue writer? Was that at the Tonight Show or TBS or late night at 1230, did you become head monologue writer?

Well, it was never something I saw. I think what happened was I was working with this guy, Chris Albers, who had, he had worked on, on, I think, the Daily show, or at least John Stewart's, previous. Yes, it was the Paramount syndicated show, and then he was got a lot of jokes in on Letterman when he was Paul Schaefer's assistant. He was getting a lot of opening remark jokes in the monologue.

So they kind of, they named us co-head writer, a co-head monologue writers, which is kind of, I mean, there's only three of us, so it's kind of, four of us at some point. So then, um, uh, when we got to the tonight show, um, Chris was working in the,

remotely. So, it was just kind of went to me by default. Interesting. Usually on those shows, or at least back then, Letterman, you had opening remarks, writers, monologue writers, and then you had everyone that was doing the rest of the pieces. A lot of times it was so separate, but you were still writing as monologue. You were still contributing in the year 2000 and cable stations, correct? Yes, yes. That was actually very fun for me to write some of the other pieces. I probably only got one or two sketches on a year, but I would, the jockey pieces were it be year 2000s or celebrity surveys or, you know, SAT, you know, those kind of things. I enjoyed writing on those and and satellite TV channel was one of my favorites. So yeah, that's stuff. The jokey pieces, I, I, I, um, I, um, I weren't difficult for me. The one that I never cracked, we would do a thing which called new characters, which is just as it sounds.

And it was so abstract. It wasn't rude in anything, and it was too abstract for me. Your creation was allergic zookeeper, correct? Yes, yes. I'm amazed at the research you've done. We had a bit called, Guess We'll Never Have Back. And it was just a fake bit where we would pitch someone coming on and they would, you know,

there'd be an author, there'd be something. And so Johnny Carson used to have, and then as he started it, I think, he would have the zookeeper from San Diego come on and bring his different animals. So the late night shows that became a staple. So I had one where the zookeeper is bringing on the animals and he's allergic to the animals. And Matt Walsh played the zookeeper. and he improvved just hilarious stuff and just made it so funny. So you really appreciate that as a writer when that performer just brings it to life. Originally on Conan's show, I think it might have been before you were there.

The warm-up before the show with the audience was Joel Goddard, the announcer, did it. And then it went to Mike Sweeney. And then after that, Brian McKin, were there any time since you're a stand-up comedian that they needed somebody last minute to do warm-up? Did you ever do the warm-up? If so, what was that like? I didn't. Fortunately, I don't like that kind of thing. But also, I was meeting with that.

The warm-up was happening while we were in picking the monologue jokes. So I really had to be in the monologue meeting, and I couldn't be out there for that, thank God. But one time we had to do an extra taping where the show was over, and we had to have the audience stay because we were shooting something else. And Conan and Andy had to go change or whatever. So they did throw me out there to do a few.

minutes of stand-up, but the audience was leaving. You did Conan's day, Conan's late night show 12 times. How much notice did they give you the first time? Some of these times were they needed somebody last minute, correct? Except for the first time, it was all last minute. I remember, I would say, hey, can you do the show tomorrow? Because somebody would cancel or somebody would get sick or they missed their flight or something. So Paul Davis at work, I said, can you do the show tomorrow? and I'm like, well, I've only got about two-thirds of a set. And she said, okay, well, you'll be the second guest. And I just remember on the train in that morning, I'm writing jokes for that, you know,

that had never tried before. And I'll watch, like, that old set. I'll watch some of the old sets on Conan. And there's some jokes that I never heard in my life. And there I am doing them. It's like, I don't remember that joke at all. Yeah. Did it get to be almost like going on Johnny Carson, a lot of the comedians would have several

sets prepared just in case Jim McCauley, the talent booker of comedians, would call it last minute. Was that the case with Conan where you would have these in your back pocket if they asked you last minute to do stand-up? Well, whatever I did stand-up on the show, as soon as I went over, as soon as I finished, that night I'd start to go, okay, what's my next? And I'd start building the next one. So I was always in the process of trying to put together another six minutes or whatever. When Conan originally started, he would do his monologue, which we'd cover.

the conologue. And occasionally a sketch would bomb. I don't think people probably remember this, but a monologue would bomb and he would give the cue card. He would take it and give it to an audience member. Now, at some point, those silences stopped and the audiences would either laugh or clap, but the jokes weren't bombing almost ever. It was almost always clapping. When did that change? Do you remember and why that would change in terms of, you know, Carson used to cover up monologue jokes that wouldn't go well, but that didn't become an issue with late night. host anymore. Do you know why that changed around when that might have changed? Do you agree with what I said? Yes, yes. I definitely think that happened. I think it is, here's the thing. Conan is the

funniest guy. He's the funniest guy I know. And I've been to comedy for 40 years. I think what happened was he was brand new in the beginning. So I just think as he got more skilled, as he got more confident than he then the jokes worked more. So I think it's all because of him. Who are some of the guests that you got booked on based on suggestions? Any stand-ups? Anybody during those years of you working for Conan, anybody? Yeah, you know, I would definitely recommend other comics to them. And one thing I'm proud of was I was able to convince them to go to Boston a couple times and do a showcase and see the comics there. So, you know, that made me feel good when they went and did that and they,

and they saw some of my friends, like Tony V and Frank Sinarelli and so on. And when they got on the show, it made me feel good to help them out. Because when you were at Boston College, this Boston, everybody in Boston can be a comedy knows Barry Crimmons. You befriended him. He was a headliner and he would let you hang out at the comedy club in Cambridge, where Stephen Wright, Paula Poundstone, all these Bobcat were doing sets. Was that pre-Steven Wright doing the Tonight Show that you were going to watch him?

It was, yes. He was on, you know, I was 18 or 19. I had met Krimands He'd done a show at my school, and I thought it was great, and I talked to him, and I had wanted to get into comedy, and I'd been writing jokes for years, so I met with him, had a cup of coffee, and I showed him my jokes or whatever,

and he was like, oh, well, the only way you make money in Boston is by performing, and I was like, oh, it's too scary. but he would let me come to his club, The Ding Ho, and I would come every couple of weeks, and I'd watch the comics, and Stephen Wright was unknown, and I thought he was incredible. And, yeah, it was kind of a really an incredible, very special time for me. Your dream was to do Carson Show. Eventually, you did the Tonight Show four times. You did so many late-night shows.

Did you ever audition for Jim McCauley to do Carson? I did not. I did not. You know, it's true. Early on, I realized I set that goal for myself because as a kid, you know, all comics really idolized Johnny Carson. And so I would, you know, I would work TV clean and in whatever bar, circumstances, which wasn't always popular.

But I really kind of stuck to my guns and worked clean for years. And so when I did get the Tonight Show, it was. It was about a little over a year after Johnny left, but it was still very thrilling doing that. And then when I was 25, I auditioned for Letterman, and the producer was very complimentary and so on. And then they called me to do the show 17 years later. Was that when Eddie Brill was book in the comics,

and did you know him from Boston? I did, I did, because Eddie would come down from New York and do shows in Boston. And I didn't know why I was in the running, and I don't know how many people he called, before me, but Dave got sick one day. So I'm at my office at Conan, and it's one o'clock in the afternoon, and Eddie calls me and goes, hey, this is a weird question. Can you do the show today? And I was like, sure, because I always kept a suit in my office, and I was always preparing for to do Conan. So he said, I'll call you back. He said, Dave's sick.

Bruce Willis is going to host, because Bruce Willis is supposed to be the first guest. So he called me back, told me, he said, you're on. So I turned and I told a couple of people, my, I, office mate Michael Gordon and he called back and said okay but don't tell anybody it's like well it's too late now I just said that but I just went over and did it and then subsequently I did it six more times and once again it was last minute when somebody got sick I was the emergency guy so it wasn't until I moved to L.A. the last time that they actually had to give me a date um it was always uh the the day of or the next day or whatever. Lederman was watching at how he was sick. He had, it was either his heart issues or shingles when they'd guest host, and he would

watch those when he wasn't feeling well. So he obviously loved you because he kept having you back. Did you have any interaction with Dave other than the handshake after the monologue? Because someone like Brian Regan, apparently, when people ask him what Dave is like, he said, I don't know. I've never had a conversation with him. Did you get to talk to Dave at all? Well, I didn't when I would do the show. It is funny because you don't meet him beforehand. You do the show and he comes over. And he's He always says a funny quip when it goes before it would go to throw to commercial. And he would just say, how's Conan doing? Or I would just say, how's your son?

And we'd have a quick exchange. And then one of the craziest things that happened was I went there one time and they said, we don't have a dressing room for you because you too was on the show. And they took up all the dressing rooms. So we're going to put you in the green room. So the green room's on the first floor where the showtapes, and the dressing rooms are on like the third or fourth floor or whatever. So I'm in the green room, and before I come on, they go,

hey, listen, would it be okay if you two hung out in your dressing room while you're on? Because they have to set up for you two or whatever. So I said, you tell those Irish. No, I was like, show, sure, sure, of course. So I go out and I do my set and I come back and I go in my dressing room. And it's you two, the four members are you two and me. And they're setting up for them for five or ten minutes. So the five of us are just chatting.

And it was the most surreal moment of my, they all introduced themselves. Bono introduces himself. The Edge just says, hi, I'm The Edge. Nice to meet you, The Edge. And we just talked to, we just were like five dads and we just talked about our kids for 10 minutes. So then they went out and did it. But that was really my most surreal moment. in show business, I think.

Did they watch your set? They did, they did. They were very, they were very complimented, very nice guys, and that was very cool. What was it like in contrast doing Jay Leno show? I'm guessing Jimmy Brogan when he first did it in 93, he was booking comics? Yes, yes. So what happened was, I had, it's funny how these things kind of come full circle, where when I was in college and I was an open micer,

Jimmy Brogan came in. So Lenny Clark, who was an amazing comic. he would I would do his show every week in Cambridge and Lenny's show it was like the Old West I mean the show would start at 9

it would go to 1 a.m. And it got crazy at the end and whatever and Lenny you know Lenny drops a lot of F bombs and so on so Jimmy Brogan came one time he was visiting

he did 50 minutes squeaky clean killed all the comics were amazed Lenny was amazed, Cremans was amazed. We were all just couldn't believe it. And it was really one of the best sets I've ever seen still. So he ended up booking the Tonight Show,

and I had to come out, and I came out to L.A. and auditioned, and he said, you know, you've got about three quarters of a set. So he went through my set, and he approved maybe 17 out of 24 a joke, something like that. So I needed six or seven more. So I went back, and I worked on my set. And in those days, you had to hire somebody to come and videotape you. And then you would send them the VHS.

And I remember I was doing one show where I was doing a benefit. Everyone's just up. Everyone's just up. The crowd couldn't have been nicer. It was just me doing the show. They just had me do 20 minutes for the thing. And everything's going great. And with a couple minutes left in my set, out of the kitchen,

I was at this restaurant out of the kitchen. Six chefs with those tall white hats and flaming cakes came out of the kitchen with flaming cakes. And they all parade around this stage and go back in the kitchen. It's like, I can't send this tape. I was so incensed. But I finally got a tape I sent to him. And I was doing a gig and I came home and there's a message on the engine machine. It was Jimmy Brogan saying, yeah, I saw your set and let's book a spot on the show.

And I was like, I'm sorry, what? I think I had to replay it about 10 times. But yeah, then I got to go out and do the show, and then they had me on three more times. I want to point out when you did Jay show the first time, it was still in Johnny Carson's old studio. They didn't move over to Studio 3 by then, correct? Yes.

And it was a different thing where Jay changed the set because Jay was a nightclub comic, and he wanted more like a comedy club. set up. This was set up more like a theater where you came out and there was a, the audience that was going up like this and, you know, 500 people or something, but you couldn't see anybody. It was just a sheet of black. So you're just kind of coming out and doing your set into the void and hoping there's people out there and hoping in their laughing. So yes, that was, that was the old, that was the old. So even though I didn't get to do Johnny, I

did get to do his studio his uh his studio what did you prefer dave letterman not saying hi to anybody before the trip was that's what pretty much johnny carson unless he knew the person well wanted to save it for for air whereas jay would be backstage paling around with the guests before the show did you have a preference and what was that like when jay would stop by your dressing or before the show yes you know conan would do the same thing conan would like to go meet the guests and make them feel comfortable and whatever i i didn't have a preference you know i i would was I was always such a Letterman fan as well. So just seeing him, I might have been too nervous to meet him beforehand. So I think it was fine just to meet him after your set and then he comes over.

I do remember one time I was doing, you know, one of my later spots, because in the beginning, you start with your opener, you end with a closer and so on. But as you're doing progressive, of you kind of just doing stuff in the middle. But I remember I had, I was doing one bit, and I didn't know how to get from point A to point B just in terms of segues. So I had this very tortured segue to the next joke or whatever.

And I just heard Dave behind me laughing like, what was that? And I wanted to turn around. I go, I'm sorry, I didn't have a segue there or whatever. But it was, and I almost burst out laughing when he was laughing at me for having such a tortured segue. I remember Louis C.K. would crush on Dave Letterman's CBS show, and he had one set where the audience for Dave was just, it was not a good audience. And it was the first time I saw Louie, he was doing, not doing well. And he bombed a joke and just looks over at Letterman and start, you can hear Dave laughing. I believe that's my recollection. And Louis kind of throws his arms up. I mean, what can you do? Would you go over? Like on the Tonight Show, Dolly Parton was a guest when you were there. Would you go over and say hi to the other guest or get photos or would you stay in your dressing room? Uh, no, well, beforehand, I was just so nervous and I didn't, I didn't want to bother anybody or anything like that. I had, um, but I do remember the first time I did it was, uh, Kenneth Branagh, was a great, um, Irish, British actor.

He, uh, after the show, he came by my dressing room just to congratulate me or whatever, which was very nice. But Dolly was very nice, and I remember Fay Donaway was very nice, but they were very nice to be sitting down on, the couch and just, you know, you appreciate that when it's on the air and you have someone like Fay Dunnoy saying, hey, you're funny or whatever, you know. When you were going on Letterman and Leno and Conan, how many people would you hear from your past? I mean, I don't think Facebook was around back then, but would you hear from people you hadn't heard from in a long time? Did anybody on the street recognize you? It's so funny because whenever I've been recognized, generally, until recently, until recently,

generally speaking, it was somebody who's at a live show. And it just makes more of an impression. And I remember when I was in Chicago years ago, we were at this club that wasn't doing well, and we were getting about 10 people a show. And I kept getting recognized every day because they were tourists, and I was a tourist who were all doing the same touristy things. And I'm like, how do I keep getting recognized?

There's nobody at these shows, you know? So in Boston, I got recognized fairly frequently because I was doing a lot of shows and it's small enough and you'd go to Fenway Park or you'd be somewhere. But I remember her a week after the Tonight Show, I was at a Red Sox game, and this guy came up and he was like, hey, Brad, I saw you on the Tonight Show last week. I was in the audience.

Even then, it was somebody who was actually at the show. When you were at Conan on any of the different versions of Conan, who had the best writing packet of anybody that you met, that you hired one or two people that stand out, if any? I remember, well, I remember when they hired Andy Blitz. They said, we got hiring this guy, and they loved his packet. And in the writer's room, they showed, they put it in, once again, it's just how old him, his VHS, and they popped it in, and it was his stand-up.

And he was incredibly hilarious. And I was like, who is this guy? And I watch a lot of stand-up, and a lot of times I'm thinking, oh, that's funny. and I'm not laughing out loud, but I'm thinking, oh, that's a great joke or whatever. I was dying, and I'm like, who is this guy?

And he was just a brilliant comic and a brilliant comedy writer, and we'd be in the meetings, usually when someone would pitch an idea, halfway through the idea, you see where they're going. He would pitch something, and I would be bewildered,

and then he would add the last little piece and it would all come together, and it would be brilliant, and I'd be like, how did he think of that? You know, so he, he really stood out to me as just having such a unique comedic mind. Yeah, he was really funny.

I know Jonathan Groff would see him down at Luna Lounge and Bliss would crush with that crowd down on Ludlow Street. Really funny guy. Who were some of the guests at Conan that you went backstage to say hi, that you just couldn't help yourself, that you grew up watching? I knew someone like a Bob Newhart was a big influence on you. Who were some of the people that you went backstage that stand out to say hi to? I got to meet Mary Tyler Moore.

That was huge. And she was like my sister's hero. And I had her book she signed for my sister. I had, you know, meeting Bob Newhart was incredible. I'll tell you a story about meeting Bob Newhart. And I'll get to meet Ted Williams as as, as, that was amazing. And I got to meet Tom Hanks. I'll tell you story.

I usually didn't bother the guests. Even, you know, like if Harrison Ford's on, I love Harrison Ford, but I don't have anything interesting to say to him other than, hey, I'm a fan where it's like he could hear that all day long forever, you know? So, but when Henry Winkler was on, Henry Winkler, he was writing these children's books for kids around 8, 8, 9, and 10, and my kids loved his books. And I would read them to them, to my kids, they would read them by themselves. and we would laugh and they really, it was really like something they loved. So I kind of thought that that might be something kind of near and dear to his heart,

as opposed to going, hey, the Fonzay. Whatever, I wouldn't do that. But I said to him, I just, I just wanted to thank you. My kids love your books and we laugh and we read them all the time. And unbeknownst to me, he got my name from the producer, Dan Ferguson, and he, a couple weeks later in the mail, got three books from Henry Linkler, signed to my kids, just sent to my house. That's so nice

to hear. A lot of people stayed at Conan for years and years. There were very few people that were like, oh, did you have to let anybody go? Just, you know, people get burned out with the, with the monologue. Johnny Carson, there were a lot of people, unfortunately, they just couldn't keep up the pace. Did that happen much or at all when you were there? It did happen occasionally. And a lot of times, a lot of times people would get burned out and they would just, and they would quit. And I think it is, you know, you're working long hours. And as a monologue writer, it can, it's the same thing every day. So I think people felt like they wanted to do something else creatively.

And, you know, it was interesting because you did have people leave like Bob Odenkirk and then, you know, or Alison Silverman or someone like that and go on to much bigger and better things, Jonathan Groff and other people. But then you had some people that had some success. And then you had some people that they left and then they never got another job in TV again. So it was certainly risky leaving. I didn't want to take that risk because I had children and they needed food and shelter. And I liked my job and I liked the people I worked with.

So part of me would have liked creatively to go. go write on sitcoms or write movies or do other things. But I was a little afraid to give up a good job, you know. And I don't regret it because I had so many laughs every day. And, you know, I'm grateful for how it turned out. When you got hired, was Marsh McCall the head writer? Was Smigel still there? Smigel was, yeah.

Smigel was such, he was this revered comedy writer. And I knew there were his sketches, you know, there was that famous S&L sketch where it's William Shatner yelling at the Trekkies. I had been a fan of those sketches and those things. And I didn't know it was like, this is the guy that wrote those, you know? So I was in awe of him. And he's really an S&L legend. So I was definitely, you know, I was in awe of him when I started. But, and, you know, he was amazing.

So, yeah, Marsh got hired. of, you know, I think Smygel went ahead, other projects happening. And I'm not sure it was a year or two in that Marsh got hired. Yeah. Yeah, Smigel was burned out and then eventually did the Dana Carvey show. Was it difficult? For example, when Bill Clinton was president, you had to be churning out these Clinton jokes constantly. On the weekends, can you turn off your brain when you're with your family? Or is it constantly you're just coming up even subconsciously with Clinton jokes and jotting them down? How hard is. That was that? Well, you know, it actually helped me with that was doing stand-up because, like, if I had to spend the weekend not doing stand-up, I would be obsessing about work the whole weekend.

And even there would be times when I remember pushing my daughter in the swing, and I'm just thinking about work, and I'm thinking, I am not even paying attention to this, my cute little daughter here, you know, and I was like, this is what I should be focusing on, you know. So it was hard to get that out of your head. But the nice thing about doing stand-up is it's such strong stimuli. It just knocks everything out. So in a weird way, I would do a show Friday night, and that would kind of clear the palette for the rest of the weekend. And I wouldn't be obsessing about work.

But if I didn't have a show, then all weekend, I would just be thinking about work. To your knowledge, when you were writing monologue jokes, was there any public figures that were upset with a joke? that you wrote that you later heard about it? Sure, sure. That would have... Can you name one or two? If not, no worries. This is a terrible story.

So when I was growing up, I used to watch the Dick Van Dyke show, and that was my favorite show, and I still love it, and it had such a strong influence on me. And watching that show, because I knew I wanted to get in the comedy, but I didn't know how people became comedians.

You know, and I was such a comedy buff, and I remember I got in trouble in the second grade because I took out a joke book from the library, and I didn't return it because I just wanted to keep it. But, and my mother knew that I was such a big comedy fan where they'd be a comedian on, there were these daytime talk shows like Mike Douglas and Murph Griffin, and I'd be playing in the yard or something, and she'd say, Brian, there's a comedian on. I'd come in and watch a comedian, and then I'd go back out and play. But when I was about, I don't know, 11 or 12, I, watching Dick Van Dyke, I realized it's like, oh, these shows have writers.

So that's an actual job. And so I wanted to do that. And that kind of inspired me to, I knew I wanted to be a comedian or a comedy writer at that age. So I love the Dick Van Dyke's show. He was great. So we had a joke.

We used to do a lot of jokes about CBS having older viewers back then, because they had Matlock and they had Jags, and these shows that were for senior citizens, you know. So Dick Van Dyke was on a show called Diagnosis Murder, and CBS announced they were canceling the show.

And the joke I wrote was CBS is canceling diagnosis murder when they realized all their viewers died four years ago. And it was just a joke about CBS News or whatever, but it got back to and it was put in, and they published it in that, magazine entertainment weekly they would have jokes sometimes from and it got back to conan that dick van dyke's feelings are hurt and it's like here it's like oh i hurt my hero's feelings i felt terrible and conan wrote him an apology letter and then he ended up coming on it actually worked out for me because he

came on the show and then i got to meet him a couple times and i didn't tell him i was going to ask that so you became a hero can you did you know norm macdonald from stand up before he started doing your And do you have any Norm stories from him doing Conan? I didn't meet him beforehand. I remember being a fan of his because he was so funny. What I do remember was I did the show one, I did the Conan show one night, and the next night Norm was on. And the Conan show was starting and we're in the hall watching the monologue in the monitor.

And Norm came up to me, and he knew my name. He said, I saw your set last night, great job, whatever. and I was kind of shocked. And I was so flattered to have Norm recognize me and know my name and be complimentary. That was a huge thrill. That's really great that happened. To your recollection, you know, they almost never stopped taping. They tried to do live to tape the 1230 show.

Do you remember a few times when they had to, for whatever reason, either stop tape or something wasn't airable? Well, we would have some sketches that we had to cut out sometimes. I do remember the first time I did stand up on the show. I'm backstage. I'm ready to go on. And I don't remember what the sketch was, but the sketch bombed. And they were like, we've got to figure out what to put in that place. And they had to me. So Smigel and Conan and I don't know what other writers there were meeting at his desk, this is for about 20 minutes or 25 minutes. And I'm backstage waiting to go on and the crowd's getting mad because they're just sitting there while they're trying to figure out what to do and um do you recall what the sketch was the premise i was so nervous and focused on my set i wasn't focusing on what we were doing uh but i just remember being backstage and the band's playing and i'm waiting and i'm waiting and um and um i you could it i when i came out there the first joke or two you could see the crowd's was kind of mad and then they came around thinking.

Did they ever, to your knowledge, have to sweeten any of the standups that just didn't do great? The audience was off or anything in post-production? No, as I recall, we didn't sweeten anyone's sets. And there were times when somebody would bomb or, if not their whole set bond, they would have some weak moments and things like that. So we kind of, and even with the monologue with Conan,

I mean, it was just on him. And so it's hard to cut out a joke with a camera's just on, you know. That's true. When you did Jay Leno's Tonight Show the four times, did he ever call you the next day to thank you? I knew he would do that with sometimes with comics. I don't know if that ever happened. Oh, really? I never got a phone call.

He knows me. He owes you for sure. You moved, you were living outside of New York and you moved to Studio City to do Conan's Tonight Show. When you walked in the studio for the first time, the 50 million. dollar studio at Universal. Looking back, a lot of people were worried. They thought the studio was not conducive for live audience. Did you have those inclings, those worries in the beginning when you first saw it?

Yes, I just thought it was too big. And the thing about comedy is, as the audience gets huge, like we would do these shows on the road, we'd go to Chicago, or we'd go to San Francisco, whatever. And with these, doing these giant theaters, it's very difficult. out to be subtle. Comics who work stadiums, I mean, luckily no one's having me work stadiums, but it's just a different thing.

It's very hard to be subtle with huge crowds like that. So I actually prefer, I liked our audience of, you know, 185 or 190. It was just more intimate and you could be more subtle. And so I did worry that it was too broad for our, broad comedy was not our specialty. Is that what we really did? So I felt like a big audience was too much for us.

What was it like backstage with Conan at the 1230 show? Because most of the writers obviously weren't with him in his dressing room before the show going over jokes. You had this unique position. What would that be like when you were with Conan? Was he lose? Was he nervous? What was that like?

Generally, you know, he certainly loosened up as the years went over. And, you know, every once in a while we'd get. a bad crowd because what would happen is sometimes we'd have a band on the show and it would just be fans of the band that came and they didn't and sometimes they were fans of the band but they were also Conan fans

sometimes they were just there for the band. That is very hard. That's that ruined shows and yes Saturday Night Live episodes. You know Lord Michaels is much more hands-on with Jimmy Fallon. He'll go down stairs sometimes and give Jimmy tips

or suggestions on what analog jokes don't work or maybe tweaked at this. Did Lauren Michaels ever come down at all when you were there to give any punch-ups or suggestions? He came in one meeting one time. We were in Conan's dressing room and he came in and it was like, and that was the one time I met him. He wouldn't know who I was. He wouldn't know my name. It was just, you know, he really, I think what happened was I think that he, because Conan used to write on SNL,

Conan's the funniest guy in the room and I think Lauren was well aware of that so I think he when he picked Conan I think that was because he knew what a comedic mind he had so he kind of just let us do our thing

we really didn't I think Conan would go out to dinner with them once in a while but he didn't interact with us at all or come down to our studio at all yeah there was one time I was going to the early Conan tapings 93-94 where they couldn't fill the studio audience because nobody wanted to see him. It was those 13-week renewals. And I remember Lorne, I remember seeing him by the double

doors one time during, I think before a taping or during a taping, but I was like, oh, I didn't know he even showed up at all. But yeah, it was rare. Now, when it was announced that in whatever it was, five years or whatever, that Conan was going to be taken over the Tonight Show, was it almost instantly, instant that the monologue for Conan at 1230, that they started to add jokes knowing that Conan, you know, couple years was going to have to do a longer monologue. Was that almost instant? I don't know that it was almost instant, but it became a thing.

And then we started doing five shows a week to kind of prepare for five shows a week. I think there was the thinking that, you know, Johnny had this history of doing a long monologue and Jay had this history of doing a monologue. And we kind of felt like we were supposed to, you know? So we ended up with the Tonight Show, ended up having six monologue writers and then um you know it had started out at three when i started at conan and then uh by the end of the run on tbs who was just lorry kilmartin and and myself and luckily lorry's great and she's so funny and prolific but ended up just being the two of us at the last year or so

can you talk about the contrast at being 1230 and you could you know maybe call somebody on the phone and say hi your wife uh versus the tonight show where literally you're working through lunch and you can't really leave your desk for a minute or two maybe to go to the bathroom and that's about it. Yes, you know, we were only on the Tonight Show for seven months or something, but I had a knot my stomach the whole time. It was, it was, we had to churn out so many jokes and we had to go from churning out, say, 40 jokes a day to like 60 jokes a day. And you, and the problem with that is it doesn't give you time to really craft a joke and get the wording. You're just putting sort of every first draft on the page and keep going. And yeah, I had to have to work through my lunch

Sharwood and I remember in New York, if we were having a good day, I'd give my dad a call and see how he was doing. Here, I never had a, you know, it was never in that situation. It was, we were under the gun the whole time. And by the time I would get home at 730 or 8, you know, it's 11 o'clock in Florida and I couldn't call my dad. So yeah, it was very, um, the hole was never filled. We just never had enough drugs. One day I got seven jokes on, which was the best day ever had, and it wasn't enough. We still needed more. So I always felt like I felt like I was failing every day, you know. One of the versions of Conan, I forget which one, were you not doing Fridays with Fridays off? Yes, well, Fridays we would work. We would work on the prepare for the next week, but yes, because TBS had had that dinner and a movie thing on Friday night for years. The old show, we would have. have Mondays to prepare for the week. But then TBS we had Fridays, not off, but we didn't have a show those nights. So it gave us some time to prepare. I was going to ask, in terms of being topical,

was that possible to write jokes Friday for Monday knowing the news might change? Was that, was that your strategy? Did that work? No, no. We didn't write monologue jokes on Friday, or at least I didn't. That's Friday I would work on this, you know, the year 2000. So Sleps series or sketches and things like that. Yeah. At what point during the Conan's Tonight Show did you realize that there might be some trouble? I didn't know until I was Michael Gordon and I were working in our office and the head writer Mike Sweeney came in and said go to go to TMZ and we went in and said the Conan's out and let you know, whatever. So I didn't have any inkling of that.

It was really caught us completely by surprise. You know, I thought because, you know, Conan with no experience was following David Letterman and able to last the show for years. So I thought that he would. I knew that our ratings weren't great and so on, but I thought that they'd give us some time and we'd get our footing and everything would be fine. So, yeah, I was totally caught off guard. I just remember everyone was very emotional when this happened. and we had a couple weeks to go before we were off the year. And I think I was just in shock.

And then I remember about a week later, it was my wife's birthday. We went out to dinner with this other couple. And it just kind of hit me that I moved my family across country and I put my kids in new schools and bought a house and now suddenly we're out of work. And I don't think I said a word for about two hours of dinner. They're all talking and I'm just suddenly. It suddenly hit me, you know. Yeah, I bet.

For the final Tonight Show, when Will Farrell played with Conan, was there a party afterwards? I mean, it's such a somber occasion. There was a party? It was. And actually, you know, it was fun. It was kind of cool. My son came with us. And I think he was 13 or 14.

And there was a party there, and there were some celebrities in there, whatever. So we get the car to leave. And I was like, who are you talking? He's like, he got Steve Correll. and Will Ferrell, my son's wearing like a New England Patriots shirt or something, and they're like, oh, you're a Patriots fan. And they talk to him for 15 or 20 minutes. And what a thrill for this kid. And I don't know those guys. You know what I mean? It's not like their friends of mine or they know who I am. But that was really what a incredible thrill for my son. And I think they'd rather talk to a kid than talk to an adult for whatever.

but that was a great moment for my son. Up until that you found out about the TBS show, you were depressed. Were you able to get out of that depression? If so, how? Well, I was fortunate in the sense that I was, you know, I'm a stand-up, so I was able to, I went and worked on the road,

and I would open for my friend Gary Goldman, and I did some touring. But also, I wrote a book in that time. I wrote a novel because I was taking this class and I wrote what I thought was a short story. And the teacher was like, oh, that's not a short story. That's the first chapter of a novel. So each week I'd bring in the new chapter.

So that gave me something to work on every day. I would just, I would get up and I would shower and shave. I didn't want to just be unshaven and walking around in sweatpants all day. I would get up and shower and shave, and then I would go to a room just with a legal pad and no computer and whatever and no distractions. And I would just write for about three or four hours. And that was a nice distraction for me to do that. That's smart. Yeah, the book is called The Astounding Misadventures of Rory Collins, everybody by the book.

So you're on a plane. It's really sad. You're going to Boston. Your aunt had just passed away. you're going to her funeral, very, again, somber. You land and get maybe some of the best news of your life when you land. You turn on your phone and what happens? Well, I'm so impressed by you.

You know my life better than I do. I shut the, you know, you have to shut your phone off. You get on the plane and it's six hours or whatever. And I got off and I must have had 30 or 40 messages where we, the rumor was Conan was going to Fox. So I get off the plane and there's a thing of Conan's TBS has picked up Conan. You have a job in September and just knowing I had a job and was back. And it was really great news. And the TBS people, they let us do our thing.

They really, very rarely did the sensor have a problem with anything. And we didn't get any network notes to my knowledge. we could do the kind of show that we wanted to do. And, you know, we didn't have to do a long monologue, which wasn't what Conan wanted to do. We could just do whatever we wanted because it was our show, you know. What stands out in 1989 and 1990 when you did the Johnny Walker National Comedy Search? I mean, it was you, Ray Romano, Judd Apatow, Steve Harvey,

all these people before they were well-known. What was that like? Oh, I didn't know about Ray or Judd. When I did it, it was... IMDB was wrong, surprise. Well, this is what happened. So they had a not dish, they had like a cattle call. They had different parts of the country were having,

they'd pick a representative from different parts of the country. So my grandmother's sister, my aunt, Jim was sick, and I had gone to Mass General to visitor. And I came in and it was something like 110 people that signed up with this thing. We're all doing two minutes. So I signed up and I got picked to the, get in the finals, and then for the finals of Boston. So they had eight of us, and I got a lucky spot, and it went well.

And so I got picked. So I went out. They had somebody from New York, somebody from Boston, somebody from Atlanta. So Steve Harvey was the guy from Atlanta. And the winner ended up being this guy, Rocky LaPorte, who was from Chicago, a great comic. and Mark Brazil was one of the people and he ended up creating that 70s show. So it was kind of a nice group of comics.

And I do remember hanging out with Steve Harvey at the time. He's gone on to such bigger and better things. I don't know that he would remember him. We were so long ago. But that was actually very cool. Yeah. How hard was that if all to every year go to the MAs knowing that the Daily Show or Letter

was going to win. Chris Rock would always say the best writing in late night was easily honed and they would, the people that were voting, a lot of times would just go for the more quote high brow. But I mean, finally, I know that in 2007 you guys won for, you won for writing the show did. But was that hard knowing almost going into it that that's probably how it was going to go? No, I mean, you know, of course we would have liked to have won all those times, But being at the Emmys was, he just felt like you were in show business. And for my wife, it was a thrill because she'd walk around and she'd check out the cast of ER or Seinfeldor. You know, she would just be mailing her up kind of doing stargazing.

But, you know, you really felt like you were in show business and you felt like it was cool being in the room and they'd bring Bob Hope out or they'd bring Milton Earl out or something like that. And so, yeah, it was, you know, I loved going even though we would lose most of the time. Yeah, I really was, I was so excited when your show finally, when your show finally, how did you get hired on the last season of Ellen's talk show? Did you know Ellen? And what was that experience like, weren't right in on her final season? Well, I didn't know Ellen. What happened was there was, they had two headwriters. One of them was a guy named Gilreef, a very nice guy and a funny guy.

And I would do his daughter's fundraiser for, she was going to some, it was like a, some school at her synagogue. I would do the fundraiser every year. And so when the show ended, and I would bump into him because Ellen was on the same lot as us when I was at the TBS show. So after Conan ended, I said, are you looking for anybody? And they said, we are actually. So he had me send a packet in, they go, yeah, okay. So I was able to jump on the last season. The problem was it was, COVID was still going on.

So we were all masked up and we had to socially, so even in the meetings, everyone was wearing masks and whatever. And we had to kind of socially distance. And it was just, it was sort of surreal, you know. So, but I had fun. I mean, the writers were fun. and it was her scandal, I guess, what I call it, had already kind of happened.

So all the stuff that people had said was going on, I didn't see any of that. It was perfectly fine. I had trouble adjusting to a daytime talk show after working on late night, where I'd pitch something and they'd laugh and they go, we can't do that. And I'd be like, what?

It's so innocuous, you know? But then sometimes they would have something risque, where it's like, how does that get on or whatever? And it was just a different style because I would write jokes and that wasn't necessarily what they were looking for. I would get stuff on by accident. You know, Wordle had just started. Do you play Wordle?

Oh, yes, I do. So Wordle had just started and we're in the room. We were just talking and I said, you know, that's going to be the easiest job in the world. You show up at noon. How about Dwell? Well, 12's good. Okay, I'll see you guys tomorrow. And they go, that's a good idea.

And then ended up being the monologue the next day. I was like, oh, I was just kidding around in the room. So I would get stuff on more by accident than Ellen than on purpose. You are so nice to be doing this because you're currently getting up early in Los Angeles to write for the Oscars. Conan is going to be coming. Becky did such a good job. I think it was the fastest they ever said a host was coming back. When you're working on the Oscars right now, is it remote or do you get together at Conan's house or an office?

No, no, I'm going to be going into his office in a few minutes. Oh, wow. We'll get off soon. What was that like? What are one or two things that stand out from writing for the Oscars last year with Conan, who did a Grand Slam hosting job. Well, he prepares and prepares and prepares. You could see why he was an A student at Harvard

because he just prepares so hard. The coolest thing for me, we're backstage, and I peek out, we're in a curtain behind, the writers of this little curtained off room because we'd come up with some stuff on the fly, and I peek out and he's 10 feet away talking to Mick Jagger. It was like, oh, my God, that was really cool. I think the coolest part when you were in that

because you love it when you wrote a joke and he does it on the Oscars and it does well but coming up with one or two jokes on the fly because something happened there that was even a bigger thrill I think because you know just something happened off the cuff you know Brian Kylie,

thank you so much for doing this. I know you're super busy so I'm grateful that we got to do this and can you just tell us your website and where people can check you out. Sure. It's just briancailey.com. And if you want to, I have a dry bar special on YouTube that you can check out. But yeah, I'm here working on the Oscars until mid-March, but then I'll be back out on the road doing stand-up. And hopefully somebody will hire me for a show.

Aren't you teaching classes as well or were you teaching? Yes, yes. A young guy from Israel contacted me a few months ago. and he's got this workshop called the Comedy Society, and he has bookers, he has other comics, he's got comedy writers,

he's got comedic actors, whatever. So he asked me to do this joke workshop. So about every six weeks or so, I talk about joke writing, and there's other people that have questions about their acts and things like that, and we just talk comedy for an hour and a half or so.

And I'm a comedy, nerds, so I love talking to other comedy nerds. Like myself, Ryan Kiley, thank you so much for doing this. This was fun. Mark, you're incredible. Your research and you're so perceptive, it was really, it was great. Thank you so much. Thanks for listening.

Please subscribe so you never miss an episode. On Apple Podcast, please rate it and leave a review. Be sure to go to late-nighter.com for all your late-night TV news. And you can find my podcast at Late Nighter. dot com forward slash podcasts. Have a wonderful week and I'll see you next Tuesday.