#131 Comedian Brian Kiley Is Joking Around

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Jeff Dwoskin 0:31

All right, Laurie, thank you so much for that amazing introduction. You get this show going each and every week, and this week was no exception. Welcome, everybody to classic conversations, Episode 131. As always, I am your host, Jeff Dwoskin. We've got an amazing show for you today. Yes, we do. Brian Kiley is here. That's right, Emmy Award winning writer, comedian and actor Brian Kiley. Over 20 combined appearances on The Tonight Show with Johnny Carson Late Night with David Letterman, Conan O'Brien, late night shows he was with Conan O'Brien from the early 90s all the way to sign off in 2021 we talk all about Conan cluding going to the tonight show leaving the Tonight Show. Heading over to TBS the whole shebang It's all coming up in just a few minutes Brian Kiley spills it all

Jeff Dwoskin 1:29

for those of you into online dating or have online dated or about online date. Make sure you do not miss episode 130 with some are more because you're gonna want to hear all about her web series pandemic pillow talk which is all about online dating. She also has an awesome short called as in Kevin, all about online dating hilarious stuff, check out episode 130 Check out the show notes to that episode also is links to all her awesome shorts. So definitely check that out. Also follow some are more on Instagram. As you learned from last week's episode, her Instagram got hacked. So I'm encouraging everyone to head on over and follow her on Instagram. The link again is in the show notes. So check that out. Thank you very much.

Jeff Dwoskin 2:25

Oh my god, I gotta tell you I had the greatest geekiest experience ever this past weekend at the Motor City Comicon greatest time ever. So I had press passes. I got to interview everyone that was at the Comic Con for the Christopher Reeve legacy reunion. They had folks from Superman 78 So Superman 123 and four it was the 35th anniversary of Superman for so I got an interview with Sarah Douglas Ursa Krypton baddie Jack O'Halloran non another Krypton baddie Mark mccluer Play Jimmy Olsen and all the movies. Aaron Smolinski baby Clark cat you know it's one when he's a little baby and he holds the car up over his head and he's wearing the red little schmatta around his waist because the little baby Mark pillow nuclear man I met him I got a photo but the sound for that one didn't come out. So but it happened. Mariel Hemingway, Lacey Warfield and Superman for she was awesome and Robert Venditti and will Fredo Torres both artists for the comic book Superman 78. So I'm gonna be editing those all together. They're like little short interviews. I'm gonna have a Christopher Reeve legacy reunion episode. So anyway, that's coming up. I don't know when but soon in the future, you can look forward to that. It's gonna be awesome.

Jeff Dwoskin 3:48

I do want to take a quick second. Thank everyone for their support of the sponsors. When you support the sponsors, you're supporting us here at Classic conversations. And that's how we keep the lights on.

Jeff Dwoskin 4:01

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Jeff Dwoskin 4:49

Well, that's awesome. I'd say what else is awesome my conversation with Brian Kiley. Oh my god. We talk about Conan, we talk Jesse pa A comedian friend of mine that I used to do open mics with and Michigan went on to write for Conan. Brian shares some cool stories about him. And of course, I talked to Brian about his seminal role in D located John Glaser's awesome TV show so much, so much coming atcha buckle up, because it's coming at you out right now.

Jeff Dwoskin 5:22

All right, everyone, I'm excited to introduce you to my next guest, Emmy Award winner, writer, comedian, author, ladies and gentlemen, welcome to the show, Brian Kiley.

Brian Kiley 5:33

Hey, thanks for having me.

Jeff Dwoskin 5:36

So happy to have you here. You are a institution in the comedy world. I'm excited to talk to you about all your time at Conan O'Brien and your Emmy Awards and all that cool stuff. And you're, you've been on what the late night shows 20 times. That's an insane amount of times.

Brian Kiley 5:54

Yeah. Tony sometimes, yeah.

Jeff Dwoskin 5:56

Incredible. So tell me what's your origin story in terms of finding that comedy bug and knowing that comedy is where you're gonna go?

Brian Kiley 6:04

You know, it's so funny. I, we had this talk one time in the in the Conan writers room about our childhoods, and we were all comedy nerds, you know, whether it was you know, people have their different things, whether it was Mad Magazine, or, you know, SNL or whatever. But we were all comedy nerds from an early age. And I remember being a little kid in elementary school and checking a joke book out of the library, and then getting in trouble for not returning. It's like, Hey, didn't return the joke. And I feel like I was like, obsessed with jokes and stuff is at an early age. Yeah, I mean, I'd love to do q&a Show. And I saw that he was a comedy writer, and I was like, Oh, maybe I could be a comedy writer. And I would watch, you know, when I was a kid, you know, I couldn't stay up late and watch comedians on Johnny Carson or anything like that. But there'd be a comedian on like Mike Douglas, or Merv Griffin when I was a little kid. And my mother would be like, you know, I'd be playing outside or whatever. And she'd call me in and a lot of the comedian, I'd go back outside and play or whatever. So I think I was always kind of obsessed with comedy. And, you know, my brother and I had like a little Mad Magazine that a fake Mad Magazine that we wrote, and I used to write jokes, and I kept them on little note cards for when I needed them someday. If I ever found those no cares, I'm sure they're long gone. But if I were five, I'm sure those steps were horrendous. But you have to start somewhere. So even 13 years old, or whatever, or 12 or whatever. I was started comedy writing, you know, in my version of what I thought was comedy writing, so I did that. And then, when I was in college, I saw a comedy show. And the last comedian Barry Crimmins. I thought he was great. And I want to talk to him. And he was running a club called the Dean Hall, when Cambridge mass. I met with him one day and had a cup of coffee. And I brought my I brought, I typed up a bunch of jokes that I had written. He was saying, you know, you could couldn't make any money in Boston writing, you'd have to go on stage. And I was like, Oh, I quit. It was so terrifying. I couldn't he let me come to the shows for which I would do every few weeks. And that took a comedy class at Emerson College in the summer, taught by Dennis Leary. Really, yeah. And we did stand up in the class. And then the last class, we invited people in and perform for them. And they encouraged me to keep going. So I started doing open mics when I was in college, and I started getting some paid gigs. And then, after college, I just started doing it full time. And I did full time for 12 years or something. And then I got hired at Conan. And I kept doing it while I was working at Conan, and they would put me on somebody would, I guess would cancel, and it's a get out there. You know? Or they'd say, you know, we need to do the show tomorrow, because somebody pulled out the last minute. And I did the show, like 12 times, but only once did they give me a date, the rest of the time was going out there.

Jeff Dwoskin 8:56

How much extra pressure is that though? To not have? Because I imagine with the people that do know, you know, they're going over there like, yeah, like thing, right? They're going crazy.

Brian Kiley 9:06

So what happened is I would finish one, I would do a spot and then I would the next day or just start working on the new one. You know what I mean? Sometimes it was good to, to not have that lead out. But like you didn't have time to get nervous because you didn't know you're going out, you know, so I would keep a suit in my office. And I would always be working on my next set. And sometimes there were times when they say Hey, can you do the show tomorrow? And I'd say you know, I've only got like two thirds were sat and whatever. And they go, well, you'll be the second guest. And I would literally be reading jokes from the train that do that night. It's like it's sometimes it'll get old senses. What does that joke and I've heard that joke, even though it's coming out of my mouth. So

Jeff Dwoskin 9:43

that's funny, Chris, is it stressful though? I mean, to be able to have to, because I mean, I know you're on the show and so it's a thing Hey, yeah, Brian, just to hear get up here. But you're going in front of a national audience. And so yeah, you know, you don't know that you're, you know, you got the suit ready in the back office.

Brian Kiley 10:00

It's actually a little pressure just because you have to see everybody at work the next day and you don't want people avoiding eye contact as you walk down the hall I kind of boy. So you always you want to have a good set, you know, what's it like doing a hell gig, you felt like the crowd was going to be good so that you kind of you had that going for you.

Jeff Dwoskin 10:18

That is comforting. Let's do a backup at one second though, when you were doing stand up your first influences slash mentors, just happened to be Barry Crimmins and Dennis Leary.

Brian Kiley 10:30

Well, yeah, it was kind of funny. You know, kremens was the first person I met in comedy. You know, we ended up being lifelong friends. You know, he passed away a couple of years ago. You know, what an amazing person to stumble upon. You No kidding. So yeah, I mean, he was really, you know, he was such a brilliant guy. And he, he kind of evolved, like when I first met him, he was just a comedian, of any kind of morphed into a political comedian. And then he really kind of morphed into a political activist. So he had quite a transformation. He was such a brilliant guy. And I just kind of lucked out that I happened to he came to my college and I happened to meet him and and we became friends. And he kind of took me under his wings. So I was very fortunate.

Jeff Dwoskin 11:13

No, that's, that's incredible. When bob cat made the movie, call me lucky. How did you end up being a part of that?

Brian Kiley 11:20

Well, you know, bob cat knew the that Barry and I were good friends. And I didn't know I knew bob cat a little bit. But when I started in Boston, he Keith already left like he had a he made it so young. And so early. I remember a bunch of us went and saw the first police academy movie when he was in it, and have someone that we knew in a movie was for me unprecedented. You know, we were so excited. I think he was like 20 years old or something, you know that he was very young when he made it big. So when I used to go the dining hall before I started, I would see him performing. So and we talked a few times, and I knew him a little bit. But so he was quickly off the scene and on to bigger and better things. But when they who's making that movie about Barry, he knew that Barry and I were good friends. You know, he knew I had some berries stories. So he brought me in on that.

Jeff Dwoskin 12:12

When you were coming up what other people maybe they weren't famous at the moment later became very famous. So you just happen to be in the scene with Well, it's funny.

Brian Kiley 12:20

So Steven Wright was just becoming famous when I was starting out. And so he was another one who quickly was gone and you know, whatever. But I he would come back and I would see him at shows and we'd be working on our jokes. And we would always have long joke discussions and whatever. But when when I moved to the Bay open catch a rising star in Harvard Square in Cambridge. It was Louie CK and David Cross and Marc Maron and Laura Kightlinger and Janine, garofolo and so on. So there's a bunch of us there, that we're all kind of starting out together. They did much better than me.

Jeff Dwoskin 13:00

You did good. You did.

Brian Kiley 13:04

All right. And then there was some younger people like Bill Burr and Joe Rogan, and Patrice O'Neal, and so on some other people that came up, kind of like the class behind me in Boston that we didn't show, you know, so I mean, like, like, like Dane Cook opened for me once at a college, which is kind of funny to think about in retrospect.

Jeff Dwoskin 13:22

That's great, though. Yeah, it's

Brian Kiley 13:23

kind of funny where, yeah, so

Jeff Dwoskin 13:26

I opened for Patrice O'Neal. Once in Ann Arbor. It's whenever I think the documentary that came out that shows him in Ann Arbor. That was a show I opened for

Brian Kiley 13:35

Oh, nice, nice when he was awesome. That was so sad.

Jeff Dwoskin 13:39

So sad, talking about a guy exactly the same offstage as on stage. I mean, he was he was a real deal. He was absolutely my only connection with Barry Crimmins is it one before he passed away, I realized he followed me on Twitter. So that was a big deal.

Brian Kiley 13:51

Oh my god. Yeah, that's huge. The twitter follow

Jeff Dwoskin 13:54

is you can't beat that.

Brian Kiley 13:56

He wouldn't have done that. If he didn't like it, what you would put out there so it speaks highly of you.

Jeff Dwoskin 14:01

Now I just gotta get Brian Kiley to follow

Brian Kiley 14:04

one step at a time.

Jeff Dwoskin 14:07

Baby steps. So I was watching some of your clubs and you're you're super hilarious. And one of your jokes and I'll slightly butcher it. But I bought a box of animal crackers. The box said Do not eat a seal is broken. I open it up. And sure enough. The reason I love that joke so much was because you just stop. I always in the conversations I've had with comedians is the pause and controlling the silence and just letting the audience continue with it is such a thing you need to master and to me that joke was you could just watch as they all slowly got the joke. You just stood there going I'll wait. I'll wait. And I just I just wanted to kind of appreciate that in front of you for a second. Sometimes some crowds I'm still waiting, but it'll always be the case. At but brilliant. So I did have a question. What was the one where Bruce Willis was seemingly the host which show was that?

Brian Kiley 15:09

Okay, so this. So this is what happens. So when I was 25, I auditioned for the Letterman Show, and the producer came up to me afterwards and told me I was very good. And then they called me 17 years later, I didn't even know what's in the running. So I'm working at Conan, I'm at my desk. And Eddie Brill calls me and says, This weird question, but can you do the show today? And I was like, Yeah, okay. You know, when I hit by students, and you're on the hook in my office, and he goes, I'll call you back. So he calls me back and he goes, Okay, you're on. Dave is sick. Dave had shingles. So Bruce Willis is supposed to be the first guest. So now Bruce Willis is hosting. So Dave is sick. Bruce Willis is hosting. Don't tell anybody. That's okay. No, no, he said, so he said that whoever said David St. Louis was hosting. So okay, so hang up. I tell the guys should not take sick. They asked me to host Bruce Willis. Any book cosmetic don't tell anyone that Dave is sick. And it's like, well, the cats out of the bag, man. Tell me. But that was one of those things of I didn't know I was going to be on. It was one o'clock in the afternoon. I walked over there at you know, four o'clock. And they I was like, okay, just do your best five. And I don't think you know, when I was 25. I just, I wasn't ready. I wasn't ready. And I think I would have been too nervous. And not, I don't know that it could have gone well, but by the time I finally did get fun, at that point, it was like, Okay, well, I can't do it now, you know, so and then and then they would call me at the last minute to somebody who'd cancelled. So it wasn't until I moved to Los Angeles that they would actually i Okay, we actually have to give them a date. We can't get them at the last minute now. So

Jeff Dwoskin 16:50

think I'll highly They must think of you as a comic. I mean, that is the to put the trust to say, Oh, we can trust Brian Kiley, at the last second because I imagine they vet those. Everything I've I've ever heard they vet

Brian Kiley 17:02

it yourself. Absolutely. And but you know, it's funny because I have you know, I had a friend who used to go the tonight show one to do that. Have him be there last minute guy? And he said no, it's too nerve racking or whatever. And to me, it's a comic like you weren't your whole career to get on that. You know what I mean? So if you're a ballplayer, you're in AAA, and the big club calls you up to play the majors and I can go, No, I need more notice or whatever you, you know, you're like, Yeah, I'm pitching today. Okay, you know, whatever. So, you know, that's what you've been dreaming up to me your whole career. So, you know, I just kind of looked at it as an opportunity. And I was always excited. I remember one time, I was doing a fundraiser for the PTA in our little town and Westchester, and my wife was the VP of the PTA. So they called me the night before and they say, Hey, can you do Letterman tomorrow, whatever. So I told my wife, she's, oh, you can't do it. You've got to use this PTA. Like spoiler alert. I'm doing the literature. I don't know what you're talking about, but and actually ended up being the coolest thing because they offered me a car, a car service. So I did the Letterman Show. They put me in a limo, and then I show up to the to the PTA meeting in a limo and get out to do it's like, That couldn't have worked out better. It's like, I'll you know, all these soccer dads that didn't think much of me it was like, Well, I'm in the limo now.

Jeff Dwoskin 18:21

But yeah, check out this ride. And thankfully your wife's bakesale Didn't tank. She never would have let us down. That's true. That down. When you worked at Conan, did you know Jessie pop? Oh, yeah, yeah, yeah. I mean, Guy Jesse's from Michigan. Yeah,

Brian Kiley 18:40

hit submission was because you know, people, when people would submit their packets, you know that they're trying to get hired as a monologue writer. So everyone's got their monologue jokes. And there's some people that they have a bunch of jokes that you kind of think, yeah, we do that joke, you know, but at the same time, we also would have thought of it. You know what I mean? What I loved about Jesse's packet was, like some people, it's almost like him to use a baseball analogy with it. There's a ton of singles in there, but it's like, okay, but we could get these hits. And Jesse would have these homeruns that you like, Okay, we never would have thought about I remember there was some joke about there was talking about butchering jokes, but there was a house somewhere where people were away and they came back and it was infested with like, 8000 snakes or something like that. And then there was a joke of in snake news party at Steve's house this weekend. And it was such a clever joke. And so off the wall and it's like, Well, none of us would have come up. But you know, none of us are looking at that joke from the snakes point of view. I always enjoy Jack Jessie's comedy.

Jeff Dwoskin 19:43

Yeah, Jesse. All the comedians in Michigan. We would love to go listen to Jessie. There was one time where Jesse was opening for was a Comedy Central tour was Mitch Hedberg, Dave Attell, and Louis black. Oh my god credible. Jessie was like the local Winner guy. And the thing that I remember to this day he does is that does well and then Mitch Hedberg comes out and he's like that jazzy. His one Joel, motherfucker. Like, you know, design, Mitch, it was just like, I was like, he could have said something like that about me. That would be like the highlight of mine.

Brian Kiley 20:19

Yeah. That's so funny. That's great. Before we

Jeff Dwoskin 20:22

dive into Conan, even more, you worked with John Glazer. Is that how you met John Glaser?

Brian Kiley 20:28

Sure. So funny. He was he he did so many funny bits on Conan and he's one of these guys that most of us are either we have one strength we either good at writing or go to perform. You know, he's one of these. He's one of these few guys that are just he's equally as talented as a writer as he is or as a performer. So he did some great bits for us. You know, he was I always loved his stuff. Yeah,

Jeff Dwoskin 20:55

he's he's there. So you were on D located season one?

Brian Kiley 20:59

Yes. He came, He put me on the show, which was so nice of them. You know, I played his boss at the coffee shop. And and, you know, I was so honored to have somebody cast me in a show is, you know, playing up something other than myself.

Jeff Dwoskin 21:14

D located is a hilarious show. You can watch it on Amazon Prime. If you have Amazon, John Glaser plays a guy in the witness protection program. I asked John Glazer when I interviewed him, like, how did you even get this? How did you do this pitch? It's me, but I'm wearing a mask the whole time. So no one ever knows. He moves the family to New York and then does a reality show. Brian plays Rick the copy guy. This short episodes are like 11 minute episodes.

Brian Kiley 21:41

Yeah, absolutely. And, you know, that was a really cool thing when they had the premiere. You know, my kids were little and they came to the you know, and I think they were so excited to go to a premiere of a TV show and see the dad in it and all that stuff. You know, it was really I feel like I'm indebted to Glazer forever.

Jeff Dwoskin 21:57

Did you do any writing on the show? Were just perfect. Oh,

Brian Kiley 21:59

no, it was. I was still working at Conan and whatever. And they work on the show. And it was actually fun. It's so much fun to just actually go. I mean, it was a lot of improv and that kind of stuff. Yeah, I had a blast. I had a blast. And he kept finding new clever things within that within the concept. You know, it's amazing.

Jeff Dwoskin 22:19

So why weren't you in season two or three?

Brian Kiley 22:22

I think it's because I moved. I think we moved I think what was when we moved to LA, as I recall, because I could be wrong about the dates. But as I recall, when the when the show moved to LA, you know, I couldn't just stop by him and do that anymore. So I had a pretty heavy kind of schedule. So I think there was one week where they they were gonna have me come back and then the week got pushed up and I was back working accounting and couldn't do it or something. So

Jeff Dwoskin 22:49

that makes sense. So you had to prioritize Coenen PTA, PTA first place, and then John Glaser. I got a kick out when I was when I when I was looking at your IMDB and I'm like, Oh my God. That's right. It's always fun like you forget. And then you Sure sure. Oh my god, that was him. Alright, so you're you're doing all these appearances on Conan O'Brien show? And is that how did you just evolve from that to becoming one of the writers on the show? Or was there more of a, you still had to submit your packet while you're kind of being featured as a comedian as Oh, no.

Brian Kiley 23:25

So I actually got hired first as a writer before I got on Conan, I use some of the comics writers from Boston, my friend Tom Magna, and Chuck Sklar and Louie CK were all writing on the show, and somebody got fired. And at the time, I was doing a lot of topical jokes. So if I did 45 minutes back in those days, probably 20 to 25 minutes or so it was stuff from the news. So they knew I was writing those kinds of jokes. So they contacted me and said, Hey, can you submit a packet? So I typed up some jokes that I had been doing the last couple of weeks. And I you know, I just wrote some stuff from the newspapers in those days. And I submitted it and they said, Yeah, you start tomorrow. And the show was very shaky in the beginning. So I thought I was just getting this job for 13 years, 13 week contracts. So I thought I was you know, okay, we'll do this for 13 weeks or maybe 26 weeks or whatever. And there are constant rumors about the show being canceled and who's going to replace COVID And, and all that stuff, but the show just kept hanging in there and hanging in there. And then he was on for years. So I kind of lucked out.

Jeff Dwoskin 24:29

Right. So Late Night with Conan O'Brien debuts in 93. You joined 94

Brian Kiley 24:33

I did yeah. The Ides of March 94.

Jeff Dwoskin 24:36

That's in March so when Late Night with Conan O'Brien aired the reviews, and he even wrote I think something Sure. And like you said they kept I think the NBC kept threatening to put Greg Kinnear in Yeah, at what point during those initial years so from 94 to 2009 where it finally became this you know, just cultural thing when did it start to shift like what what was happening? We'll go Oops, where you're heading,

Brian Kiley 25:01

I think when we first got nominated for an Emmy that was kind of like, hey, we, somebody's acknowledging that they liked the writing on the show, and that the like that the show, you know, for us to get nominated kind of, because we weren't nominated the first couple of years, but it was almost like, hey, somebody decided, you know, it kind of allowed us in the club or something that somebody, it was kind of an acknowledgment that the show had reached a certain level or something, I guess. So I feel like that did it. And, you know, they gave us a primetime special for the fifth anniversary. And as we start hitting these anniversaries, and that's okay, we've we've kind of been on for a while, you know, but I do think I do feel like getting a getting some validation from the me people made us feel like, hey, you know, one time we were watching the Today Show, and the critic, TV guy was on, and he said, Conan has the best writers on TV. And it was like, what? That's us, you know. So we started to get some good press after after a few after a few years of not so good. So good press.

Jeff Dwoskin 26:06

I read a quote from Tom shales called it the one of the most amazing transformations in television history.

Brian Kiley 26:12

You know, even though Conan, you know, can you imagine learning stand up comedy on national television like that? Those are open mics, it's, you can't you know, you can't imagine that. But, you know, it takes so long to get good at stand up. Every day in the office, he would be unbelievably hilarious. You saw what a brilliant guy he was. So even though he was nervous on the air and wasn't polished, and whatever, just from seeing him off camera, we knew it's like, oh, this is actually a brilliant guy. Once he kind of figures it out. He's going to be amazing. We were fortunate and seeing how funny he was offstage.

Jeff Dwoskin 26:47

So that's your motivation to keep going.

Brian Kiley 26:49

Yeah, I mean, I think we were all because people would, people would bad opponent us in the beginning. But we kind of had this secret of like, Oh, you don't realize this is the funniest guy in the world. You wait till he gets comfortable on stage and get some experience and we kind of felt like he was going to be great. Just a matter of time.

Jeff Dwoskin 27:08

Right? Yeah. It sounds like he's a newbie. I mean, this. Conan was on sorry, writer for time I live it was a writer for The Simpsons. Absolutely,

Brian Kiley 27:15

absolutely. So he had, you know, he had a track record as a writer, but also just in the office. I've never seen anyone funnier. So I was really blown away by how brilliant he was

Jeff Dwoskin 27:26

amazing. And not shocking at all to hear that. Let me ask you about monologue writing. So, in your sense, where you have maybe 25 minutes of your act as you're going in is is of the day, right? Yes, you have the luxury to say, well, I'm going to do most of these things until they kind of die on the vine in terms of the news cycle. And then kind of filter man as you want. Maybe on a Monday you do one on a Tuesday throw 32nd new thing and right. So how is it going in day to day, I can't even imagine how many jokes you have to churn out and I don't want to say forcing inspiration. But now you're getting paid. It's a whole different thing. Right? Yeah. How did that whole thing work?

Brian Kiley 28:06

Well, it's funny because I, you know, as a comic, I will try to write like five jokes a day. And I thought, Okay, I'm hard working, you know, and here when you suddenly have to read 40 jokes, you do you like what? You know, and also say you had a great joke in your ACT about Michael Jackson. Well, you do that as a standup, you do it every night. And we'll do well. And you know, it's part of your act or whatever. But here was like, okay, you'd had a great joke. Michael Jackson on Monday. The next day, he wants another great joke on Michael Jackson, he like, what about the one I gave me. And we did that. So now you need a new one. So you have to write, you know, you end up having to write 50 Michael Jackson jokes for television, as opposed to the one that you had in your act, you know, I mean, so that's the hardest part to me is to have to keep replicating to keep going back to the same well over and over and over again, and try to find something new. That's where it gets tricky. And especially those days in the beginning, we didn't have the internet and start, you know, I feel so old saying goes, but we're reading newspapers and looking through and stuff. So sometimes the news was just tragedy. And I remember when the hit the Oklahoma City bombing was right around Jackie Onassis tight, and the news was just so awful. And he would come out and they have the little state by state things in the USA Today. And he'd come out and be like, Hey, did you hear about this comptroller in Des Moines, Iowa, and then was like, What are you talking about? But we couldn't talk about anything. There was so much tragedy in the big news. So it's gotten a little better now with the internet because there's more sources and more ways to find other stuff. At the same time. It's I think it's actually much harder now because everyone's tweeting jokes on Twitter. So you know, sometimes I'd read a joke at nine then three o'clock ago, somebody put that same idea on Twitter and you're like, but I came up with it. But it's old news by that time. So I think it's very hard to get monologue now because so many people are writing jokes on Facebook or Twitter off the news.

Jeff Dwoskin 29:59

I was going to ask about that, because right? You hear that all the time, like you're watching Bill Maher or something like these, especially these once a week or is and like, and then it's like, oh, that chokes been done 50 times already. Yeah. Yeah.

Brian Kiley 30:11

I'm sure when they wrote it, it was fresh. And it's just, that's, you know, I think it's very challenging now to write topical jokes.

Jeff Dwoskin 30:19

So when you're writing, are you writing trying to mimic Conan O'Brien's voice? Or do you write it in your voice or some hybrid and knowing that Conan will adapt it as he's reading it? While you're

Brian Kiley 30:31

trying to write in his voice, I mean, he'll, a lot of times he'll take it and he might tweak it a little bit, or rewrite a little bit and try to put it more but you are trying to write you do have that his voice in your head as you're writing them. And, you know, but I mean, you have to learn his voice. You know, there are comments that people that would write funny jokes for and it's like, well, that that's a funny joke, but that's too sarcastic for Conan, or it's too pointed, or it's too heavy handed or it's too the references too obscure or whatever. So, you know, when you work for somebody a while you find out what the things they like and don't like and that kind of thing. And I used to do a lot of sort of wordplay jokes, he hated those. So I had to learn not to do that. You know, when I was first started, there was a story about a woman had given birth in the New York City subway, and they wrapped the baby in the Sunday New York Times. And I said, you know, ironically, it was the C section. What I thought was a cute joke and whatever. No wordplay, corny blah, blah, blah, whatever. And you're like, oh, okay, so I stopped writing wordplay jokes, he kind of beat them out of me, and I stopped writing them for my act even because, you know, you just you learn, he has like that kind of thing. So use you stop going there. So it does take a little I didn't learn his get his voice pretty quickly. We have a lot of overlap in terms of our sensibilities and stuff, fortunately. But there's definitely you learn to write for the host voice. Hopefully, if you're going to make it dependent one on whatever show you are, you got to you have to replicate as best as possible the voice of the house.

Jeff Dwoskin 32:01

So when you're writing that many jokes every day for Conan, and in Conan's voice, do you lose a little bit of your own voice? Like how do you how do you maintain your voice as well as a comedian?

Brian Kiley 32:14

Well, you know what I did early on as I decided this, like, Okay, I'm gonna give him everything topical. And I'm just gonna write personal stuff for me. So I never want to have that dilemma. Who do I keep this job for my act or give it to me. So all the stuff off the news. So I stopped. I lost about 25 minutes of material. And I started because I was like, I stopped doing topical stuff. But then I had to build up my my app, but I kind of kept the division of those two and the stuff. So you can have your own voice when you're talking about your own life and whatever so that we keep it easy able to keep yourself in there.

Jeff Dwoskin 32:48

Well, I can imagine though, it'd be it could be. It wouldn't be crazy to think like if somebody comes to see you and you're like, Oh, you sound you sound like Conan now. Yeah,

Brian Kiley 32:57

it's funny. You know, one night he came on, and he was kind of mimicking me. And he even said on the it's like, oh, I'm channeling. And he does, he would do this bit sometimes in the dressing room, where he would do an impression of me doing stand up with my mannerisms and my demeanor, but he would be doing the filthiest act you ever heard. Certainly not magic, but he would just do. He would just do this parody of me, but but me being filthy. And people always. People always love the bit where he was doing the filthy version of me.

Jeff Dwoskin 33:32

That is funny. And such an honor. They have Conan O'Brien

Brian Kiley 33:36

it was it was. And there were times when he would meet other comics out somewhere. And they'd be like, You got to do the impression of blue Kylie. So yes, I was very honored that he would do an impression of me.

Jeff Dwoskin 33:50

Blue Kylie, that's awesome. It even had a nickname. That's great. When Late Night with Conan O'Brien was coming to an end, and you guys were all going to transition to the Tonight Show with Conan O'Brien, which I know is his dream he always wanted to host tonight didn't end dreamy. What was your point of view kind of going in and your feelings when you knew you were going to be part of that whole Tonight Show world?

Brian Kiley 34:17

I thought he was gonna be hosting that tonight show for 20 years, you know, and I kind of looked at it. Like, he followed David Letterman as a complete unknown and was able to make it work. I thought after all that experience and he was famous by this sport that that he'd be able to that it would work. Okay. And you know, there was a lot of a variety of circumstances, I think that were kind of conspiring against us at that time. It was I have to say that the Tonight Show was very stressful because really we were he was doing you know, the tonight show this history of doing a one month long monologue. So now he's doing 15 jokes instead of six jokes, whatever. So, you know, now I'm writing 70 jokes a day. And it was never enough. The whole was we always needed more jokes and the holes never filled. I remember the best day I ever had one day, I got seven jokes on, that's a lot of monologue jokes on one day was for me, and it wasn't enough, we still need more, it's like, you know, I just had the best day I've ever had. And it's not gonna, you know, I really did have a knot in my stomach the whole time. Because it was, it was the it was the output was just so much. And there was so much scrutiny. And you know, with the New York show, sometimes we'd be having a good day and would be in good shape. And I'd give my dad a call in Florida to see how he's doing or whatever, you know, my dad's voltage guy. And with the Tonight Show, there was never once a day where you can take a break, like I never called my dad once, you know, like, and by the time I get home at 730 or eight, he's long and bad. You know, it was just it was really a pressure cooker. And I thought it would eventually dissipate as as the show went on. But we get we end up going off the air before we ever got to relax.

Jeff Dwoskin 36:07

Well, it seems that the network couldn't like go there. Jay Leno crotch? Yeah. And so what were you did you guys have dark boards with Jalen was phase on it stuff like that?

Brian Kiley 36:18

No, I think everybody thinks that we're like, you know, whatever. I mean, I think we've all moved on. I do feel I would feel bad for Conan were a guest would come on the show, you know, when he was hosting a TBS show, and they bring the whole thing up, and he would just kind of dismiss it and move on. And then they actually are Conan still talking about that? Like, no, he's still talking about it. You know, he's moved on with his life. But he can't control something, a guest brings it up, and he would quickly move on. But, you know, I do think,

Jeff Dwoskin 36:48

Well, how did you feel in the staff feel? Not necessarily Conan about it? Well,

Brian Kiley 36:52

I think we, the problem was, to me, it was a much bigger audience. Like I mean, not only the home audience, but our studio audience was too big. Like, I think, you know, like, people that do stadium shows, not that we do a stage show, but more comics do stadium shows, their comedy is very broad and big and whatever. And when you're an indeterminate club, you can be subtle and, and have nuances. And I think that was the kind of comedy we did I think, Conan, I think we're better served when he's posting a show for 170 people as opposed to 450 people or whatever, because I think, I think a lot of subtlety and so on is which is more of his humor. You know, it was it's one of the things it's it's like, it's it's like a messy divorce. Looking back on it, it was it's still sort of painful. And, you know, but I do think the TBS show kind of reflected more of our sensibilities humor wise, you know, I think he wasn't really a monologist to go out there and do 15 or 20 jokes. You know, that's really not what he was about. And, you know, I think trying that with the tonight show you kind of sort of doing someone else's show in a way because it's has this these expectations were when we went on the TBS Show, the show was called Conan, we could do whatever we want, because there's sort of no history there or whatever.

Jeff Dwoskin 38:12

It sounds like, moving back to this Conan, on TBS format was better for everybody, but your relationship with your father and family at the time as well. So you could call everybody,

Brian Kiley 38:23

I, you know, I would come home, like just wiped out with and I can actually come home like a normal. Yeah, I think the stress was very, very intense. Yeah.

Jeff Dwoskin 38:34

How did you feel with the show ending?

Brian Kiley 38:37

The TBS show ending with CBS show ending? Yeah, yeah. You know, it's, I was very sad, you know, and I was at 27 years. And it's sort of this mixture of, you know, you're grateful to have a job for 27 years and TV, but you're still sad when it comes to an end. You know, we I really, the writing staff, I really enjoyed everybody. And we, you know, this past year with the pandemics, we would have zoom meetings every day. But that was the highlight of my day, you know, the people are gone, the meetings and everybody's funny, and you enjoy all your co workers. And it was really, you know, I was so fortunate to, you know, Conan and Andy are incredibly hilarious and other writers and so I laughed a lot every day and I was I'm, I was very fortunate to have that experience. You know,

Jeff Dwoskin 39:26

that's awesome. So as head monologue writer, how many people did you have writing monologue

Brian Kiley 39:31

jokes? You know, I feel bad when people say that with with the Tonight Show. We you know, we had six monologue writers. So we kind of need they need to kind of appoint person and often I would meet with Conan Malone at like, 11am to kind of say, okay, what are we going to talk about today and even before we've shown him any jokes, so and then with our staff got smaller when we went to the TBS show, and then some people left. So by the end, it was just Laurie kill Martin, who's a brilliant comic. It was just her and me writing the monologue. Sophie Like, Oh, you're the head monologue writer. It's like, it's just Laurie and me. And I don't have any special duties for you know, it's and I can assure you, I'm not bossing Lori around. So it's almost like my that title was kind of grandfathered in from the tonight show this but yeah, I mean, we're all just writers. And I mean, the head writer is actually he's in charge of picking the sketches. And I think I'm more of a figurehead as I guess, is what I'm trying to say.

Jeff Dwoskin 40:25

And I agree, Laurie Kumar is great. I had the opportunity to work with her once she wrote a tag for one of my jokes, so I can attest to her amazing,

Brian Kiley 40:32

nice, nice. And that doesn't surprise me at all. Did you also write skits? I would occasionally, yes. When the show was five days a week, I just really didn't have time to do it. When it was four days a week. On an off day. Sometimes I would write some sketches. And so I wrote. And sometimes what would happen is I would come up with the initial idea. And then one of the sketch writers would would fill it out or whatever. But yeah, I did write some sketches from time to time, you know, more so in the past year, because if he wasn't doing a monologue, yeah, it's much it's yeah, that was that was a little harder for me. But it was, we had a bit one time where they have outlawed straws in California. So we hit a bit where this is, you know, there's a guy doing a mountain of cocaine and the cops burst in and they take the straw away from him. And he's got this and they leave, you know, they carried him off in handcuffs, but they leave the the cocaine because, Yep, he's using a straw, you know?

Jeff Dwoskin 41:30

Awesome. And that's the guy just hilarious. It's on your website. Actually, I laughed my ass off watching that. Oh, good,

Brian Kiley 41:35

good. And there was a bit that we did about Conan trying to bring back the word thrice because he used to be once, twice, thrice. It's such a handy word, you don't hear it very often. And then we would have sketches where people would be using. So and that was a running gag for a little while. So

Jeff Dwoskin 41:51

I think that'd be amazing. They bring that word back.

Brian Kiley 41:53

Yeah, absolutely. Why didn't happen? How could it ever leave? I don't understand.

Jeff Dwoskin 41:57

Some mysteries will never be solved. Who were some of your favorite guests? You got to meet on the show, like personal favorites?

Brian Kiley 42:03

Sure. Sure. Well, you know, it's so funny, because there's a lot of actors and stuff that I really like, and I didn't meet them. Because what would I have to say to them? You know, if I met Harrison Ford, and I hit him with it, you know, it's like, okay. I mean, any. I'm sure I hear that a million times a day, and who cares, whatever. But I remember when Henry Winkler was on, he had written these children's books that my kids loved. And it was for like, eight to eight to 10 year olds, whatever. And I would read them to my kids, and they would read them on their own, and they would crack and they just loved them. And I kind of thought, I felt like this probably would mean something to him if I told them because, you know, if I said, Hey, the Fonzie he probably want to murder me. But I just met him and I just said it. You know, I just want to say my kids, we read your there. It's called the Hank Zipzer stories. And I said, my kids love your books, and we, you know, they laugh and they read them on their own and it was, you know, which is apparent you love when you kids actually reading, you know, and I just told them how much they enjoyed it, and he seemed very touched or whatever. And then a couple of weeks later, I get in the mail, he sends me three of his books, autographed to my kids. It was just so nice of him to do that. You know? So when people ask me who my who my favorite guests is always say Henry Winkler, that was amazing.

Jeff Dwoskin 43:21

Henry Winkler is the greatest person in the world. I've never heard one person ever say anything bad about Henry Winkler, I've had the opportunity to meet him twice, once at an event and once at a comic con. And then it was on a kind of a clubhouse thing, and I got to ask him a question. And my goodness, he's the nicest guy. I have an eight by 10 of his hero. Jeff is cool. So I got to picture the Fonz is as Jeff is cool. Oh, that's awesome.

Brian Kiley 43:46

Well, he does seem I have I've never heard a bad word about him. He seems so beloved. And and I'm glad that he's that. You know, he's on the show Berry, which is so great. And you know, yeah, he's awesome.

Jeff Dwoskin 43:58

That is awesome. So I'm happy I'm happy for your kids that they got those books those sometimes it's easier to I know he did it. You didn't know but some that is one of the backdoor tricks is to hey, my kids. Is there anybody who you don't have to answer if you don't want to to anyone that you're like, you just just cause such mayhem? Well,

Brian Kiley 44:18

it didn't have anything to do with me. So if there was somebody that did, I'm sure there's some guests that Conan was like, you know, whatever. But I had very little interaction with something you know, I'm from Boston and sometimes a Boston sports here I would be on the show, so I'd get to meet that person or whatever. But generally speaking, even guests I love I kind of shied away from because I didn't have anything to interest of interest to say, you know, I didn't have to like when the Red Sox won the World Series and they had guys I was like, Okay, I gotta meet this guy, or whatever. And it's so funny. I met with Jesse Papas on the show. Justin Verlander was on and pops a big Tigers fan. He and I Jesse's so shy. I actually was kind of like, oh, You know Mr. Verlander are scattered, you know, whatever it can be managed or whatever. And I turned around Jesse shook his hand and I turn around and Jesse was gone. He was so shy, that I'm standing there with Verlander. It's like, Wait, you're the tiger. But I think he was too. I think he was too overwhelmed to meet this star

Jeff Dwoskin 45:19

before Verlander left Michigan left the Detroit Tigers he was dating. I think it sends married to Kate Upton. So this is this is just to give you an idea of how much I am in touch with sports and sports figures. We're at a place in Birmingham, Michigan. A restaurant I turn. I go, Oh my God. That's Kate Upton. So that must be Justin Verlander. That's so funny. Yeah, that was that's the best I could do. The hat. The hat fooled me. Well, you know, it's I love I love the Tigers. I love the idea of going to the games and I love all the Detroit sports. I just don't know any of the specifics. I love it. Like I watch a movie. I don't know all the stats. I can just enjoy it. Sure, sure. Which is weird, but I just didn't. I didn't grow up. My dad didn't train me in the way this wife. A wife loves

Brian Kiley 46:13

it, though. Oh, that's great. That's huge. That's

Jeff Dwoskin 46:16

huge. The fact that she gets me every Sunday is fine. So cool. So one last Conant question. So you credited his writer for the White House Correspondents Dinner when he did it for Obama Care. Is there any other zingers that you remember you wrote that? He said?

Brian Kiley 46:35

Well, I remember he did it for Clinton too. Early on with the Clinton I'm traveling with the Clinton one. I remember. Sonny Bono was in the in Congress them so he was there. And he did a joke about you know, I'm walking the streets of wash in Washington DC leads to the streets that were walked by, you know, Jefferson and Madison and Adams and Bono, and they cut the Sonny Bono. It just that was a fun experience to cut this. Like we didn't we never had that before, because he would do jokes for the people. But they weren't there. Do you know what I mean? So if it was a joke about there was a joke about term limits. And Strom Thurmond saying I've been I've been in favor of term limits since 1910 or something like that. But what I remember about that joke was Conan bumped into Bob Dole the next day and Bob those I like that joke. Of all jokes for him to pick a guy was in the Senate forever, but that was kind of funny. And when Obama would do was very interesting. He would, you know, do joke and then catch Obama laughing and I saw this with the other with the other people when the other years when somebody because somebody was on a year or two after Conan and they did some kind of dicey jokes that that were kind of Obama's slams that you could tell he wasn't into and Conan didn't do that. But whoever that was, and they would cut to Obama instead of him. Like, he would just be pouring a glass of water. Like, I don't know what's going on over there. I'm so busy pouring this water for myself, you know, and it was such a, which I kind of thought was an ingenious way of deflecting an awkward moment.

Jeff Dwoskin 48:10

That is pretty ingenious. Yeah,

Brian Kiley 48:11

I'm sorry I can't think of any specific snap but I do. It was it was really fun to have him do a joke that of yours and then they catch the president laughing It's like that's a that was a pretty cool thing.

Jeff Dwoskin 48:23

That's awesome. Well, thanks I appreciate all these stories so many great it's so interesting to hear about just all your history with Conan and all that kind of stuff. i Where can where can people keep up with you on the socials?

Brian Kiley 48:37

They can follow me on Twitter at Kylie noodles calm Conan makes fun of my skinny legs and calls me noodles. So that's where that came about. And then I'm just on Instagram at Brian Kiley comic or my Instagram feed is pretty lame, but or they can go to Brian kiley.com and I haven't done much with my website since COVID. But I need to I need to kind of now that we're coming out of it. Get back to that.

Jeff Dwoskin 49:01

Awesome. Well, thank you so much. I can't thank you enough for hanging out with me. This

Brian Kiley 49:05

is so fun. This really flew by so thank you.

Jeff Dwoskin 49:08

Thank you all right, how awesome was Brian Kiley so cool, right right. I know I know. So cool. Go follow him on the socials. Do your thing everybody

Jeff Dwoskin 49:21

well with the interview over that can only mean one thing. That's right. It's time for another trending hashtag and the family of hashtags it hashtag round up follow us on Twitter at hashtag roundup download the free always free never cost a penny app called hashtag roundup at the iTunes App Store or Google Play Store receive notifications every time a game goes live tweet along with us and one day one of your tweets may show up on a future episode of Classic conversations, fame and fortune awaits you. This week's hashtag are going back back into the Twitter archives 2018 Four years ago, hashing with fan brought us #FastFoodAComedian. That's why I'm in a comedian mood. So let's do a mash up game with comedians and fast food. I guess I'm also hungry. You know how the Mashups work? You just take a comedian you take a fast food and mash them together and how they fit in zoos. Hi, let's take let's read some of these #FastFoodAComedian tweets, Fozzie the bear claws, Colonel Sandler won the shakes, Rodney Dangerfield rise, you get it? Get the matchup #FastFoodAComedian let's keep it rollin norm McDonald's John Cleese burger. Richard fryer. Would you like fries with that fan? Red Robin Williams amazing #FastFoodAComedian tweets but we're not done pizza Davidson. They messed up our order now. Kathleen's mad again. Ah. Laurel and Hardy is KitKat Williams. And our final #FastFoodAComedian Betty White Castle. Right there. Yeah, have it. All those tweeters will be retweeted at Jeff Dwoskin show on Twitter. Go show him some love. Tweet your own hashtag fast food a comedian tweet. I'll show you some live tag me on it. And we'll go from there.

Jeff Dwoskin 51:21

All right. Well, with that hashtag done the interview over it can only mean one thing. Oh, my goodness, Episode 131 has come to an end. I want to thank my special guest, Brian Kiley. And of course, I want to thank all of you for coming back week after week. It means the world to me, and I'll see you next time.

CTS Announcer 51:42

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Transcribed by https://otter.ai