Staff Review With Brian Kiley

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1:12hey conan o 'brien here uh normally on thursdays we drop a fan episode but i want to do something a little different today on monday i talked to dennis leary and he was chatting about a comic we both love, a Boston comic, Brian Kiley. Brian is working with me in my office right now on the Oscars. And I thought, hey, Brian's in the building. Let's get him in here. He knows all the dirt on me. Anytime I do anything where I need great jokes and everyone else is busy, I get Brian Kiley. I'll take it. I need the work. I mean, I really cast a wide net and no one wanted to work with me. No, Brian, we've, I mean, our story is kind of crazy.

1:56We've known each other since we were kids because you would chat with my brother Luke at our Catholic instruction class that met at the Cynical. What town was that in? In Brighton. You were in Brighton on the top of a high hill. These nuns taught Catholic instruction on Monday afternoons. I think you and my brother Luke started chatting with each other about the Bruins and the Red Sox. Yes. And I was in the corner doing bits for a snowman. Yes. I mean, it's insane. We went to CCD, which is, you know, Catholic Sunday school, same place. I would sit next to Luke and we would talk about the football games the day before, which we would still be doing now.

2:39We were like eight years old or nine years old. You were in my brother's dance class. And then Dan, Dan. Say that a little slower because it said you were in my brother's. It sounded like you were in my brother's dance class. I was not in your brother's dance class. I thought that's what he meant. No, no, no. I'm sorry. My brother Dan and Conan were in the same class. And then they both. You were in my brother Lamaze's class. What? I was not in a Lamaze class. No, his name's Lamar. No, so Dan and Conan were in the same class. And then they went to Harvard together. And then my brother Dan would show me the Harvard lampoons.

3:21And he'd be like, remember Conan O 'Brien? And he would show me these things, which were great. First of all, the class of 83 didn't do nearly as well as the class of 85. We didn't go to Harvard, Luke and I. You dummies. I know. But we'd read these lampoons, and then I kind of followed your career because I knew you were on The Simpsons and SNL. But I would have walked by you on the street not knowing you. Do you know what I mean? Because I hadn't seen you since we were there. Well, you would have been like, wow, who's that guy? He's got Riz. In like the 80s and the 90s and stuff? He'd be like Riz?

3:56He was using Riz back then. Oh, wow. With me exclusively. That guy's got Riz, and I don't know what that is. I still don't know what it is. But so I think you came to work on Late Night. I'll never forget. You came in one day and you were wearing an Irish cap. Sure, sure. And you were, because you were a very funny standup, everyone knew who you were. And you were chatting with a bunch of the writers in the hallway because you were visiting. Right. And this is early, early days of, very early days of the Late Night Show, like 93. And I see you in the hallway and I'm like, hey, we know each other and we chatted a little bit.

4:36I pushed a button that said, please get him out of here. You were immediately taken away by NBC pages and a robot. I kept asking, what's Riz?

4:49And then shortly after that, there was an opening for you and you came and started writing jokes for me. And you've, I mean, my White House Correspondents Dinner, both of them with Clinton and with Obama. I mean everything I ever did the two Emmy shows and all the late night shows I've ever done and then last year's Oscars you wrote amazing jokes and now we're working again on this year's Oscars March 15th, tune in and so I thought wait a minute this is a chance to get Brian to come in and we could settle old scores Yes. Yes. We had some grudges. Let's do it. I write it. My first day of work was March 15th in 1994.

5:35Oh, you're kidding. No. No, the eyes of March. So now that's when the Oscars are. And that's when the Oscars are. Yeah. Oh, cool. It is. No, you have, as you know, I've told you this a million times, you're one of my favorite comedians. You have such insanely great jokes and you're so disciplined about having great jokes. my favorite thing to do is an impression of you doing the filthiest material ever at the Apollo Theater. Because you and I are the whitest comedians in the world and you are the cleanest comic. You never go blue. And you always are wearing, in my impression, you're wearing a blue blazer, which is very you.

6:14Sure. And hello, hi, how are you? And then you go into the filthy, I mean, stuff that would make Red Fox blush. And you do it at the Apollo and kill. and it's just really like, you gotta wash that ass. Ladies, you gotta wash that ass. So I'm going at, and your enunciation is always so perfect and you're so friendly and pleasant. And so I would do this routine called Kylie at the Apollo and it was one of my favorite things to do because I get to be really crazily blue, but it's not me, it's you. Right, right, right. Well, you've done it for my friends like Gary Goleman and some other people, but they always report back to me, like they're dying.

6:55Yeah, yeah, yeah. You was a really filthy comic. And then the minute your set's over, you go back to your dressing room and you open up a giant book on Truman and sit on a metal stool, a little metal chair, and read it in your perfectly creased, you know, chinos and blue blazer. And then eventually the guy comes back and says, get your ass back out there. And you're like, oh, okay. And you go out and then you completely, you're even filthier the second time. Filthier. Yes, then I go into my B stuff. Yeah, yeah, yeah. so yeah but I'm just I've got my oldest Kylie riff because I like to have riffs on each writer was that you're you work out a lot you're very disciplined you have this very powerful I know it's coming right I know what he's gonna say he's got a powerful very strong chest arms shoulders I mean this guy is just you work out but I noticed a while ago that I don't think you work your legs out as much and so So I started to riff on this.

7:52And then eventually your legs became vermicelli. And there were whole riffs about people in a restaurant. You can't go to Italian restaurants because people try to twirl your legs under their fork. And I mean, I would, these bits would, they would go on forever. Yes, he's called them vermicelli, fusilli, fiber optic cables, ribbon candy. I was late one day last year because I had a doctor's appointment. And Conan told everybody I was late because I fell asleep and a little girl braided my legs together.

8:27And I mean, this is the stuff I'll be doing on my deathbed. And what I remember, I forget all kinds of things and my brain gets goofy, but the stuff I will never forget. And I don't care how bad my brain goes. I don't care what happens to me. I could be in a deep coma and if someone came into me and said, Conan, Conan, you know, it's like, no, it's no good. He won't respond to anything. Kylie's here for my jelly legs. A child braided them together. AT &T wants to talk to him about microfibers. And the same thing with like Berkeley Johnson, one of the writers, a hilarious writer. He, I haven't seen him since he worked on the Oscars last year.

9:12He came into the writer's room and sat down and within a minute and I went, I mean, Berkeley Johnson told me, I think 20 years ago, that his dad owned a flag store. Right. And I just like, yeah, I want you to tell that to your dad at the flag store. I said that instantly. Those things I'll never forget. If I can find a little thing on a writer, that's going in the vault. Right. You'll forget your children's names, but not a riff. A riff will always be remembered. Yes. It's funny because you were always there in the... room with me just before I went out and did a monologue in any situation. I mean, all those late night shows, hundreds and hundreds of thousands of late night shows, you were always in the writer's room with me and in my dressing room.

9:58And it's just about time to go out and we're going over the jokes. And the thing we noticed, and whether it was the White House Correspondents Dinner, I'm just about to go out there and perform for Clinton or Obama, any of those situations or the Emmys or all the other different award shows, you and I would be together in a room and i would start um saying the worst things i could think of like if i sure my your favorite things seem to be me uh making up jokes that i could never do in a million years and pitching those and um and then acting out the crowd turning on me right we would be doing that instead of me reading the real jokes oh my god and there are things that you can't tell anybody yeah and they don't because they don't make sense once you when you're in the room it's it yes there's a room reality where it's working in this room but then the minute you leave that situation if you go home and try and tell your wife they're like what are you talking about it makes no sense and and they'll like people say oh this is conan really funny i'm always hilarious can you give me an example and i'll have a rolex of like a hundred things i go nope yeah i can't tell any of those you know what i mean because they don't make sense they don't make sense but yeah

11:19I was at the airport. I was waiting in one of those long lines. And I kept saying, hey, let me through. I'm Conan O 'Brien. And they said, shut up. You'll wait in line. And I went, okay. That's so sad. It's a really good story. But I was hungry. I didn't have a snack with me. You got to keep... And I didn't want to lose my place in line and go try and find something. I know. That's when you got to have Nutri-Grain on you. You got to always have a snack in your bag. And when it's a Nutri-Grain, it's perfect. It's perfect because it's the right size. It's handy. It's also nutritious. Yes. Okay. You can go anywhere.

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14:31One of your heroes, Bob Newhart, you were so excited when we thought of a bit for Bob Newhart. Oh, yeah. Bob Newhart was one of my heroes. And very much like Bob Newhart, you're a clean comic, amazing jokes, and you do not have a hurried rhythm. And so you have your own thing, but you could see why, oh, this makes perfect sense. Bob Newhart would be Brian Kelly's hero. So Kevin Dorff came out with this great bit because we didn't want the Emmy show to run long. So the show's supposed to go three hours. So we have a tube with exactly three hours worth of air. Like a little glass box. A glass box.

15:10And if the show runs long, Bob Newhart's in the tube there. And if the show runs long, then he dies. He dies. And the great thing is he could do this without speaking. So who's better than Bob Newhart? With his face. With his face and his big, sad eyes. And so he's out there and we put, we wheel him out and he's sitting on this, uh, stool. And I'm bringing this up for a reason. He's, cause he's your idol. You haven't met him before. And we're at rehearsal and we wheel him out. We're going to, the idea is we're going to wheel Bob Newhart out in this box and then announce that he has three hours of air.

15:43And then, um, if the show's still going, he'll, he'll die. And he's sitting in the box. and it was great because we decided it's great if Bob doesn't know that. Right. So he comes out and he's kind of sitting on the stool and he's kind of happy to be there. And then I announced that he only has three hours worth of air and he'll die. And you just see, because no one could do it better than Bob, that it registered with him what I'm saying. And he doesn't say a word. And he's also in an airtight box so you can't see him. And he's just, it's registering. Wait, what? And so Bob couldn't be there for rehearsal.

16:21So we had you sit on the stool and be Bob Newhart and we shot you. And then when Bob Newhart showed up, we showed him you doing it. That was the coolest thing to have Bob Newhart. So to have me being Bob Newhart for Bob Newhart was the coolest thing. Yeah, it was so great. You were standing. Yeah. And there was so many, like everyone on the show knew each other so well. and there were so many amazing moments. I remember when everyone knew I was a big Red Sox fan. So in 2011, the Red Sox were in first place like September 1st, and then they couldn't win a game for the last month. So at the very end of September, my dad dies, and we fly to Florida, we go to the funeral, we come back, and people are coming up to me and giving off their condolences.

17:07And about 80 % are talking about my dad, but then I realized 20 % are talking about the Red Sox. you know so they said oh man i'm really sorry i'm like oh thanks yeah like well there's there's always next year and it's like no there isn't that what do you mean next year oh it's their pitching oh yeah yeah no no it's gonna they'll be back two totally different conversations oh my god uh yeah just so many i mean i can't i associate you with just almost every uh moment of my career you're always there and you're there again. And I don't know what I would do if you told me, yeah, I can't help you this year.

17:49I mean, I know I'd be probably even better off. No, I'm kidding. No, I just wouldn't know what to do. Well, you know, we've had this long bond and it's also just so many laughs. It's just so nice to actually have laughs every day at work, which is unusual. None of them translate and you can't tell anybody. Yeah. But we still have the laughs. There's so much, I always thought the... just the meeting just before I go out and do a show, um, the card meeting, that could be so funny and not because of the jokes. Right. and then, and then the meeting after the show was always just fantastic. Well, the other thing is, cause then I could talk about like, if a guest was really didn't deliver, we would talk about that.

18:34And it was, um, that was so much fun. That was so, but also I rooted against guests. Yeah. I wanted the show to tank so I could have a good postmortem. meeting but also i remember you know laurie and i would meet you with you right after lunch for the second laurie kilmartin laurie kilmartin who's another amazing stand absolutely and then you were normal and we would talk about our kids we were talking about movies we'd talk about whatever do you know what i mean when was this when was this would be like the one o 'clock meeting oh yeah one o 'clock in the afternoon yeah and then the meeting right before the show was total insanity and so the other writers only saw the insane parts right it was like no actually and be like no, no, he can't be normal.

19:11No, no, no one believes us. The fact that I was shocked that I was normal at some part of the day. I know, you were like, when was that? Yeah, prove it. I know. Let's see receipts. Here, 1 p.m. normal hour. Yeah. It's just not true. It just doesn't happen. And so, I'm curious. I mean, this really isn't a staff review. This is just, I love Brian Kiley and I want to talk to him. Yeah. You better, you better be ship-shaped. Better do more leg days. Yeah. That would crush me. I know. If you developed your legs. Yes. It was powerful. Also, you know what I love about me giving you shit about your legs?

19:47Look at mine. Yeah. I mean, yours, it's so, I will get on other people about things that I'm far guiltier of, which is the most crazy thing. Well, also, there are so many riffs on different things. And I remember when that Tommy Lee sex tape came out. Yeah. And so we wrote all these big penis jokes about Tommy Lee or whatever. So Tommy Lee's on the show and Conan's walking down the hall and Tommy Lee says, hey, Conan, I heard you've been doing jokes about me. And Conan said, yeah, about how big your penis is. Feel free to do the same about me. And he was like, oh, yeah, right, right. And then he got it.

20:29And that's actually not a bad thing for people to be joking about. Yeah, I remember that. He was like, oh, yeah. He was kind of menacing and then he totally turned around. Do more of those. That's a good thing. Yeah. One of your obsessions was you just always wanted to write jokes about how heavy Chris Christie was, Governor Christie. And he just. And so. And you were obsessed. So every packet. I get the joke packet. Obsessed? No, no. He loves. Because it was all jokes. It's all jokes like there was a 3.2 magnitude earthquake in New Jersey today when that story would be in the news in the morning, like a slight tremor near Trenton.

21:15I knew on the way in, oh God, this is all Kylie's gonna write today. And then every joke was that set up. And then, yeah, apparently Chris Christie joined a jazzercise class. Look how proud he still is. Apparently, and you would do this, and then God forbid, God forbid anywhere in the United States, these stories would come out, these human interest stories, and it would be like a semi truck filled with candied hams overturned on Interstate, you know, seven, and 900 hams covered the highway in Iowa, period. When he heard Chris Christie said, I'll see you. Whatever. I'll see you in Denver. You know, like he has to immediately get on the scene.

22:05Yeah. And I don't know why he just didn't go to the supermarket and buy ham. As opposed to. Anytime a truck turned. It just seems so fiscally irresponsible. Anytime a truck turned over or a blimp crashed and fried chicken spilled on the highway. When he heard, comma, Chris Christie said. Is there a, is there a bullet? Is there a jet that goes directly to that location? You, it was just, and to this day, when those stories break, and I eventually accused you of shooting out the tires of semi-trucks. I came up with this idea that Kylie finds out what trucks are carrying giant hams and roast beefs.

22:49And there's a giant truck carrying candy apples and it's headed through Nebraska. cut to Kylie on a high hill. He's got the itinerary of the truck. He's got a scope with like this. Just for the setup. And he fires, blows out the tires. It spills. You know, roast beef spill all over the highway and Kylie starts submitting jokes. Even before USA Today has it. Well, I remember when they came out with the memo of like, no more fat jokes. And I was like, what? He was devastated. And then people are coming up to me offering their condolences. And I thought they were talking about my dad.

23:29Did you do all the Taco Bell jokes too? Is that you? We did do a lot of Taco Bell. You were getting paid by Taco Bell. Well, we did a lot of Taco Bell diarrhea jokes. And then we had to stop because they started becoming our sponsor, which is a great way to blackmail people into becoming a sponsor. You drove more companies into becoming our sponsor. And you know what would help? I mean, for the podcast, we're doing great. Yeah. But to have Kylie come in occasionally, let's pick a top brand that hasn't bought into the show. Yeah. You go after them. Sure. With your special humor. And then the next thing you know, they'll call up and go, we got to stop this.

24:10Wow. I can't believe they bought Wendy's bought in. Yeah. We had to send in a monologue for, like a Writers Guild Award or something. So we had to type it up. And we went through a bunch of them. So we came with one. It was like six jokes, like five, like really smart political jokes. We're like, this is perfect or whatever. And then of course the last one is a Taco Bell diarrhea. We're like, oh, we can't send that in there. You thought you were going to have a smart monologue and then Taco Bell crept in there. Anytime there was a moment where we thought, maybe we'll get a Peabody award this year.

24:44Whatever we submitted had one Kylie diarrhea joke in there. And you just could see the Peabody committee. Well, this is very good, dude. They've checked all of our socially responsible boxes and... Diarrhea. Yeah. You've got to keep it real, guys. Yeah, I know. I know. I owe you a lot. Oh, please. You've cost me terribly, but I still owe you a lot. No, this was really fun. I know. What was your favorite event thing to work on with him? Like, what do you like? What's more fun? I mean, the White House Correspondents Dinner is pretty cool. Because he'd do a joke, and then they'd cut to Bob the whole laughing.

25:19Or whatever. You know what I mean? So you see the next day I did the, the Clinton and it went the one for Clinton and it went really well. And this is when I'm still pretty new to people. I've only been on the air for like two years and, um, people like, what's, you know, this guy's going to bomb. And you guys, uh, wrote just some amazing stuff when I get up and I do it. And then the next day I took my parents, my parents had come to see it. I took my parents out to dinner in Washington, DC for brunch. and I'm just really happy that I made it and it worked out well. And I'm sitting with my parents at a table and Bob Dole walks by and he points at me and he says, good term limits joke.

26:02I'm like, whatever. To have like one of the most powerful guys in the Senate say good term limits joke, which was probably your joke, but. Well, and I also remember when you had a joke about, you know, I walked through the streets of Washington and it's like, this is where Jefferson was. and Madison and Hamilton and Bono. Sonny Bono. Cut to Sonny Bono, who was a congressman. And he's just kind of like, whatever. What the hell? Of course, tragically died two years later in a skiing accident. All right. We got him while he was still around. He was there, yeah. Jesus, why'd you have to bring up how he died?