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Hey, Konan O'Brien here. Normally, on Thursdays, we drop a fan episode, but I want to do something a little different today. On Monday, I talked to Dennis Leery, and he was chatting about a comic we both love, a Boston comic, Brian Kyly. Brian is working with me in 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 Kyly.
I'll take it, guys.
I need the work. I really cast a wide net, and no one wanted to work with me. No, Brian, our story is crazy. We've known each other since we were kids because Because you would chat with my brother Luke at our Catholic instruction class that met at the Cenzacle. What town was that in? In Brighton. In Brighton. You're in Brighton on the top of a high hill. These nuns taught Catholic instruction on Monday afternoons, I think you and my brother Luke started chatting with each other about the Bruins and the Red Sox. I was in the corner doing bits for a snowman. Yes, of course.
It's We were the same. We went to CCD, which is Catholic Sunday School, same place. I would sit next to Luke, and we would talk about the football games the day before, which we would still be doing now. We were eight years old or nine years old. You and my brother's dance class. Then 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, I'm sorry. My brother Dan and Konan were in the same class, and then they both- You were in my brother's Lamaze's class.
What? I was not in a Lamaze class. No, his name's Lamaze.
No, so Dan and Konan were in the same class. Then they went to Harvard together. Then my brother Dan would show me the Harvard Lampoons. He'd be like, Remember Cohn and O'Brien? And he would show me these things, which were great. First of all, the class of '83 didn't do nearly as 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 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- You would have been like, Wow, who's that guy?
He's got Riz.
In the '80s and the '90s and stuff, he'd be like Riz?
He was using Riz back then. Oh, wow. Okay. With me exclusively. That guy has got Riz, and I don't know what that is.
I still don't know what it is.
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. Because you were a very funny stand-up, everyone knew who you were, and you were chatting with a bunch of the writers in the hallway because you were visiting. This is early, early days, very early days of the late night show, like three. I see you in the hallway, and I'm like, Hey, we know each other, and we chatted a little bit. I pushed a button that said, Please get him out of here. You were immediately taken away by MBC Pages and a robot. Right.
I kept asking, What's Riz?
Then shortly after that, there was an opening for you, and you came and started writing jokes for me. My Whitehouse Correspondence dinner, both of them with Clinton and with Obama. I mean, everything I ever did, the two Emmy shows and all the late night shows I've ever done. Then last year's Oscars, you wrote Amazing Jokes, and now we're working again on this year's Oscars, March 15th. Tune in. I thought, wait a minute, this is a chance to get Brian to come in, and we could settle old scores. Yes.
Let's read some good job. Let's do it. Ironically, my first day of work was March 15th in 1994. Oh, you're kidding. No, the Eyes of March. Now that's when the Oscars are.
That's when the Oscars are. Oh, cool. 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. You always are wearing, in my impression, you're wearing a blue blazer, which is very you. Sure. Hello, hi, how are you? Then you go into the filth, I mean, stuff that would make Red Fox blush. You do it at the Apollo and kill. It's just really like, You got to wash that ass. Ladies, you got to wash that ass. So I'm going to... 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. Well, you've done it for my friends like Gary Goldman and some other, but they always report back to me like, They're dying.
. Yeah, you was a really filthy comic. And then the minute your set's over, you go back to your dressing room 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 Chinos and blue Blazer. And then eventually, the guy comes back and says, Get your ass back out there. And you're like, Oh, okay. And you go out, and then you completely are even filthier the second time.
Filthier. Then I go into my bee stuff.
Yeah, but I've got my oldest Kylie Riff, because I like have riffs on each writer was that you work out a lot. You're very disciplined. You have this very powerful- I know it's coming, right?
Powerful. I know what he's going to say, too.
He's got a powerful, very strong chest, arms, shoulders. I mean, this guy is just you work out. But I noticed a while ago that I don't think you work your legs out as much. I started to rift on this, and then eventually, your legs became vermicelli. There were whole rifts about people in arrest, you can't go to restaurants because people try to twirl your legs onto their floor. I mean, these bits, they would go on forever.
Yes. He's called them vermicelli, fusilli, fiber-active cables, ribbon candy. I was late one day last year because I had a doctor's appointment, and Konan told everybody I was late because I fell asleep, and a little girl braided my legs together.
I mean, this is the stuff I'll be doing viewing on my deathbed. 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, Konan, Konan. It's like, no, it's no good. He won't respond to anything. Kylie's here. Firm a Chilly legs. A child braided them together. At&t wants to talk to him about microfibers. The same thing with like, Berklee Johnson, one of the writers, a hilarious writer. I haven't seen him since he worked on the Oscars last year. He came into the writers room and sat down and within a minute, I went, I mean, Berklee Johnson told me, I think 20 years ago, that his dad owned a flag store. I just like, Yeah, I want you to tell that to your dad at the flag store. I said that instantly. Those things I'll never forget. If I can find a little thing on a writer, that's going in the vault.
Right. You'll forget your children's names, but not- Don't know them now.
Not the baby.
But not a rift. Not a rift. It works.
No, a rift 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 monolog in any situation. I mean, all those late night shows, hundreds and thousands of late night shows, you were always in the writer's room with me in my dressing room, and it's just about time to go out and we're going over the jokes. The thing we noticed, and whether it was the White House Correspondence dinner, I'm just about to go out there and perform for a Clinton or Obama, any of those situations or the Emmies or all the other different award shows, you and I would be together in a room and I would start saying the worst things I could think of. Sure. Your favorite thing seemed to be me making up jokes that I could never do in a million years and pitching those and then acting out the crowd turning on me. We would be doing that instead of me reading the real jokes.
Oh, my God. There are things that you can't tell anybody. Because they don't make sense.
When you're in the room, there's a room reality where it's working in this room. But then the minute you leave that situation, if you go home and try and tell your wife, you're like, What are you talking about?
It makes no sense. People will say, Oh, is Cohnen really funny? Oh, he's hilarious. Can you give me an example? I'll have a roller deck of like 100 things. I go, Nope, I can't tell any of those.
Because they don't make sense.
No, they don't make sense. But yeah.
One of your heroes, Bob Newhart, you were so excited when we thought of 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 Calleigh's hero.
That's one of the coolest things. So Kevin Dorff came out with this great bit because we didn't want the Emmy show to run long. So the show is supposed to go three hours. So we have a tube with exactly three hours worth of air.
A little glass box.
A glass box. If the show runs long, Bob Newhart's in the tube there. If that show runs long, then he dies.
He dies. The great thing is he could do this without speaking. Who's better than Bob Newhart? With his With his faces? With his face and his big, sad eyes. He's out there and we wheel him out, and he's sitting on this stool. I'm bringing this up for a reason because he's your idol. You haven't met him before. We're at rehearsal, and the idea is we're going to wheel Bob Newhart out in this box and then announce that he has three hours of air, and then if the show is still going, he'll die. He's sitting in the box. It was great because we decided it's great if Bob doesn't know that. I remember that bit. So it comes out and he's sitting on the stool and he's happy to be there. Then I announced that he only has three hours worth of air and he'll die. 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. He's also in an air tight box, so you can't see him. It's registering. Wait, what? Bob couldn't be there for rehearsal. We had you sit on the stool and be Bob Newhart, and we shot you.
Then when Bob Newhart showed up, we showed him you doing it.
That was the coolest thing, to have me being Bob Newhart for Bob Newhart was the coolest thing. Yeah, it was so great. You were standing. Yeah. 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. In 2011, the Red Sox were in first place September first, 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 offering their condolences. And about 80% are talking about my dad. But then I realized 20% are talking about the Red Sox. So they said, Oh, man, I'm really sorry. I'm like, Oh, thanks. They're like, Well, there's always next year. And it's like, No. There isn't actually.
What do you mean next year?
They're like, Oh, it's their pitching.
Oh, yeah. No, no. They'll be back.
Back. Two totally different conversations.
Oh, my God. Yeah, just so many. I associate you with just almost every moment of my career, you're always there, and you're there again. I don't know what I would do if you told me, Yeah, I can't help you this year. I mean, I know I'd be probably even better off. No, I'm kidding. No, I just wouldn't know what to do.
Well, 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. You can't tell anybody, but we still have to laugh.
There's so much... I always thought the meeting just before I go out and do a show, the card meeting, that could be so funny, and not because of the jokes. Then the meeting after the show was always just fantastic. Well, the other thing is- Because then I could talk about, if a guest really didn't deliver, we would talk about that. That was so much fun.
But also- I rooted guests.
I wanted the show to tank so I could have a good postmortem meeting.
But also, I remember, Laurie and I would meet you with you right after lunch for the second-Lauri Kilmartin. Lauri Kilmartin, who's- Another amazing stand-up. Absolutely. Then you were normal, and we would talk about our kids, we were talking about a movie, we were talking about whatever. Do you know what I mean? When was this?
When was that normal?
This would be like the one o'clock meeting.
Oh, yeah. One o'clock in the afternoon.
Then the meeting right before the show was total insanity. The other writers only saw the insane parts. It was like, No, actually, and be like, No, he can't be normal. No, no, no one believes us.
The fact that I was shocked that I was normal at some part of the day. I know. You were like, When was that? Yeah, prove it. Let's see receipts. Here, 1: 00 PM, normal hour. It's just not true. It just doesn't happen. I'm curious. I mean, this really isn't a staff review. This is just I love Brian Kyly, and I want to talk to him. You better be ship-shaped.
You better do more leg days.
That would crush me. I know. If you developed your legs. Yes. That's powerful. Also, you know what I love about me giving you shit about your legs? Look at mine. Yeah. I mean, 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. I remember when that Tommy Lee sex tape came out. We He wrote all these big penis jokes about Tommy Lee or whatever. Tommy Lee's on the show and Konan's walking down the hall and Tommy Lee says, Hey, Konan, I heard you've been doing jokes about me. And Konan said, Yeah, about how big your penis is. Feel free to do the same about me.
He was like, Oh, yeah, right. Then he got it. Then that's actually not a bad thing for people to be joking about. Yeah, I remember that. He was like, Oh, yeah. He was menacing, and then he totally turned around. He was like, Do more of those.
That is a good thing.
One of your obsessions was you just always wanted to write jokes about how heavy Chris Christie was, Governor Christie. He just... It And you were obsessed. So every packet, I get the joke packet. You were obsessed? No, no. He was obsessed. He loved it because it was all jokes. It was all jokes like there was a 3. 2 magnitude earthquake in New Jersey today, when that story would be in the news in the morning, like a slight tremor near Trenton, I knew on the way in, oh, God, this is all Kylie is going to write today. And then every joke was that set up. Then, yeah, apparently, Chris Christie joined a jazzercise class.
Look how proud he still is.
Apparently, and you would do this. Then, God forbid, God forbid, anywhere in the United States, the These stories would come out, these human interest stories, and it would be like a semi truck filled with candied hams, overturned on Interstate 7, 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. He has to immediately get on the scene.
I don't know why he just didn't go to the supermarket and buy ham as opposed to flying across the country. It just seems so fiscally irresponsible.
Any time a truck turned over or a blimp crashed and fried chicken spilled on the highway, when he heard, Christie said, Is there a jet that goes directly to that location? To this day, when those stories break, 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. 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 this- Just for the set up. He's like a sniper, and he fires, blows out the tires. It spills. 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 no more fat jokes, and I was like, What?
He was devastated.
People are coming up with me offering their condolences, and I thought they were talking about my dad.
Did you do all the taco Bell jokes, too? Is that you?
We did do a lot of taco Bell. He was getting paid by taco Bell on the table.
I know. Well, we did a lot of taco Bell, Tyree jokes, and then we had to stop because they started becoming our sponsor, which is a great way to blackmail people into becoming a sponsor for the show.
You drove more companies into becoming our sponsor. I know. You know what? It would help? I mean, for the podcast, we're doing great. But to have Kylie come in occasionally, let's pick a top brand that hasn't bought into the show. You go after them with your special humor. Then the next thing you know, they'll call up and go, We got to stop this. Wow, I can't believe Wendy's bought in.
We had to send in a monolog for... Remember, they would have a Writers Guild Award or something. We had to type it up, and we went through a bunch of them We came with one. It was six jokes, five really smart political jokes. We were like, This is perfect, or whatever. 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 monolog? Yes, every time. And then, taco Bell crept in there.
Any time there was a moment where we thought, Maybe we'll get a Peabody Award this year. Whatever we submitted had one Kylie diarrhea joke in there. You just could see the Peabody committee, This is very good. They've checked all of our socially responsible boxes and...
Diarrrea.
Yeah.
You got to keep it real, guys.
Yeah, 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? What do you like? What's more fun?
I mean, the White House Correspondence dinner is pretty cool because he'd do a joke, and then they'd cut to Bob Dole laughing, or whatever. You know what I mean? So you see the people like that.
The next day, I did the Clinton, and it went the one for Clinton, and it went really well. And this is when I'm still pretty new to people. I've only been on the air for two years. People were like, What? This guy's going to bomb. And you guys wrote just some amazing 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. I'm just really happy that I made it and it worked out well. I'm sitting with my parents at a table and Bob Dole walks by and he points at me and he says, Good term limits joke. To have one of the most powerful guys in the Senate say, Good term limits joke, which was probably your joke.
Well, and I also remember when you had a joke about, I walked to the streets of Washington and it's like, This is where Jefferson was and Madison and Hamilton and Bono. You cut the Sunny Bono, who was a congressman, and he's just like, what the hell?
Of course, tragically died two years later in a skiing accident. We got him while he was still around.
He was there.
Yeah. Jesus, why did you have to bring up how I'm sorry. I wanted to make sure people knew that he was hearing that joke before he died. Okay.
You were making fun of him after he tragically died. I would never do that. That's nice. Okay, good.
Because he's not there to cut away to. Oh, my God. I have a heart and I'm practical. You can't cut to a grave. It just doesn't look good. Well, I'm sorry. Jesus Christ. I've tried it. It's called a Comedy Killer. Tell that to Sunny Bono, Cutoo. Hey.
Oh, my God.
Oh, my God. Well, Brian, I'm glad you came in for your staff review. Well, thanks for all the laughs and all that fun. You, too. I mean, just so many great jokes. There was one I remembered when every celebrity was coming out with a cologne, and I thought you wrote this one, but it's still every now and I think about it, which was like, Luciano, when Pavarotti is like, Luciano Poverati is alive. Hello. It was true. It was in the story that he had come out with a cologne and you said- No, this wasn't mine. Oh, wasn't yours? No, it was a great joke. Luciano Poverati. Today, Luciano Poverati released Ascent, this time on purpose.
Oh, my God.
I was so happy with that one. I still think about that one.
But that was not your joke. That was not mine. Oh, please.
Well, I don't care.
I couldn't do every fat joke.
No, that's true. Do you still remember all the jokes you wrote? If you listened to his White House correspondence dinner, would you be like, I wrote that one?
You forget most of them.
When I look through my whole career, I never know. People will say to me sometimes, Oh, that's so you, that joke.
You must have written that one, and I don't even know anymore. No. People would compliment me in a joke, and they go, That wasn't mine. Then I look on my computer, it's like, There it is. It's like, Oh, I didn't even know about that at all. That definitely happened.
How are we going to do this year at the Oscars?
Taco Bell Diaria jokes. Well, if Chris Christie.
Yeah.
Great back for Chris Christie. You know what? Anyone listening, listen to the Oscars. If I walk out there and the first thing I do is say, folks, we've got a great Oscars tonight. So many stars are here. But quickly, I just got to mention a truck carrying 900 éclairs just overturned in New Newport, Rhode Island. When he heard Chris Christie said, Get me to Newport. Cut to Leo DiCaprio looking confused. Timothy Chalamet, Kylie Jenner laughing really hard. She likes it. She's like, That's good. Yeah. Finally.
She's your audience.
Well, yes. Chris Christie, if he thinks it's the Oscar Meyer, he could make an appearance, guys. Oh, God, it's a work.
Oscars? The Hot Dog People? No, the Film Award. You're going to be calling him saying, Would you do a bit where you keep running in with a bib? Saying, Oscars, are the Wieners here yet? No, Chris Christie. You're the worst. I'm just realizing right now, you have crippled my career. Get the fuck out of here. Brian Kiley, God bless you, sir.
Thank you so much. So good to see you. Go Pats.
Go Pats. Uh-oh, he's going to... Oh, boy. All right. Oh, boy. We just juiced it. Controversial. Yeah, over and out. Because when this airs, they'll have already lost. I said it before.
Konan O'Brien needs a fan with Konan O'Brien, Sonam Obsesian, and Matt Gourley. Produced by me, Matt Gourley. Executive produced by Adam Sacks, Jeff Ross, and nick Leal. Incidental music by Jimmy Vivino. Take it away, Jimmy. Supervising producer, Aaron Blaird. Associate talent producer, Jennifer Samples. Associate producers, Sean Doherty and Lisa Burm. Engineering by Eduardo Perez. Get three free months of SiriusXM when you sign up at siriusxm. Com/conon. Please rate, review, and subscribe to, 'Conon O'Brien Needs a Fan' wherever fine podcasts are down.
Conan sits down with comic and staff writer Brian Kiley for a look back on their storied partnership over the years. Wanna get a chance to talk to Conan? Submit here: teamcoco.com/apply
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