
Comedian and actor Denis Leary feels like he could give a f*** about being Conan O’Brien’s friend. Denis sits down with Conan to discuss their shared Worcester roots and finding out they’re related, making healthy lifestyle choices, founding the Emerson Comedy Workshop while in college, and shooting his television series Going Dutch entirely in Ireland. For Conan videos, tour dates and more visit TeamCoco.com. Got a question for Conan? Call our voicemail: (669) 587-2847.
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Conan O'Brien
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Dennis Leary
Fools. Yeah. Fools.
Conan O'Brien
Fools. Yeah. Yeah. Visit usbank.com smartlycard to learn more. The creditor and issuer of this card is U.S. bank National association, pursuant to a license from Visa USA, Inc. Some restrictions may apply. Steve Carell stars in the new HBO original comedy series Rooster, premiering March 8. From a creator of Ted Lasso and Shrinking comes the story of an acclaimed author who finds himself teaching on a college campus alongside his adult daughter. Navigating their complicated relationship and Greg's late in life first chance at the college experience he never had. Is there anyone funnier than Steve Carell? I do not think there is. So I will watch this. Don't miss the world Premiere of Rooster, March 8th at 10pm exclusively on HBO Max. Subscription required. Visit HBOMax.com for details.
Dennis Leary
Hi, my name is Dennis Leary, and I feel like I could give a fuck about being Conan o'.
Conan O'Brien
Brie.
Dennis Leary
Cause I'm already his fucking cousin.
Conan O'Brien
It's true. It's true. You know, first of all, we were just acquired by pbs, so I'm gonna reduce. You're gonna reduce the fuckage?
Dennis Leary
Yeah.
Conan O'Brien
Folly's here. Hear the yell back to school. Ring the bell Brand new shoes Walking
Dennis Leary
loose Climb the fence Books and pens
Sonam Vaidya
I can tell that we are gonna
Conan O'Brien
be friends Yes, I can tell that we are gonna be friends hey there. Welcome to Conan o'. Brien. Needs a Friend. Joined as always by Sonam Obsessian. Yeah. Hi. Matt Gorling. Hi. And I'm gonna let people have a little peek behind the scenes of how we work here. I noticed something recently, which is we always have the interview start with the guest saying, hello, my name is. And then blank. And I feel blank about being Conan o' Brien's friend. And we give them a physical piece of paper. And that's the way we've been doing it now for. Is it five years? Six years?
Matt Gourley
Almost eight. It's over seven years.
Conan O'Brien
Oh, my God, we're speeding towards the grave. All right, Anyway, Walking hurriedly towards the grave. And what I noticed is that guests, not every guest, but maybe one in three, they get fidgety. And so there's this piece of paper in front of them. And they would do this a lot with their paper and slide it around. And it would distract me. I think sometimes you would hear it, Eduardo.
Dennis Leary
Yes, every now and then.
Conan O'Brien
And I just started to notice. There must be a better way. And so finally, for the first time recently, we started, I suggested, isn't there a better way where there's no physical piece of paper? So we started putting it up on a screen over there on the wall, so there's nothing in front of them and they can't fidget. We try it out for the first time recently, and we're doing it. The guest says, hello, my name is blank. And I feel blank about being Conan o' Brien's friend. And we're off to the races, everything's great. And then I start to hear, oh. And I'm like, what the hell? And I look over and you, Matt Gourley, the podcast maestro, the producer, you were like, you were shuffling your paper and you kept crinkling it and uncrinkling it. And I kept looking at you and you were looking at me. You weren't picking up on my signal. And then I had to point at you during the interview at your paper, and you made this oops face. What were you doing?
Matt Gourley
In my defense, it was in the Kevin Nealon episode.
Conan O'Brien
Yeah.
Matt Gourley
And you guys were just insane. So I think I was just like disassociating, you know, because it was uncomfortable. Because. No, no, it wasn't uncomfortable. I just normally don't do that kind of thing. But I was rolling the corner of my paper.
Conan O'Brien
Oh, my God, it was so loud.
Matt Gourley
I apologize.
Conan O'Brien
Yeah, well, no, listen. Apology not accepted.
Matt Gourley
Oh, then apology rescinded.
Conan O'Brien
Oh, how do I get that apology back? Because now I'm reconsidering and I would like the apology.
Matt Gourley
You really show me that you want it.
Conan O'Brien
Where is it stored, the apology?
Matt Gourley
My apolog safety deposit box.
Conan O'Brien
Okay, I've got to get in there. That's my new heist movie with my friends. Me and my friends gotta get into that vault and get that apology back. Oh, my God, the worst heist movie ever.
Sonam Vaidya
The worst.
Conan O'Brien
Yeah. I can't. It's all of us in some villa in France that we can't afford because we got no money. And we're all toasting each other as I unbox the apology.
Sonam Vaidya
Wait, and you open it and there's nothing in there.
Conan O'Brien
You just hear, I apologize comes out and it disappears into the air. I apologize into the ether. Yeah. And then someone comes in and says, get out of my villa. You don't pay anything.
Sonam Vaidya
You're Italian accent.
Dennis Leary
I thought they were French.
Sonam Vaidya
I know. What is. Was that?
Conan O'Brien
Italian. An Italian can own a villa in France. And in this movie, because I can't afford the really good French villa, I go to the Italian villa in France. Asshole. Eduardo.
Sonam Vaidya
So the Italian villas are subpar, is what you're saying?
Conan O'Brien
No, this one just happens to be. I would never generalize, but this guy really doesn't have his shit together. Except he's on it with the billing. Anyway. Yeah. So I think I have to start taking paper away from you because I'm going to have other interviews that go
Matt Gourley
up that happened one time in hundreds, three, almost 400 interviews.
Conan O'Brien
But it happened the first time that we had removed. That was the best part. It was the first time I had removed paper from the guest to try and stop this problem. When I hear crinkle, crinkle, crinkle, crinkle, crinkle, crinkle. And I'm like, who's ordering crinkle cut fries? And I look over and there's Matt Verley. Crinkle.
Matt Gourley
You're not above this. You're often doodling on your paper.
Conan O'Brien
Yeah, doodling is different. No, because you can. That is the artist expressing himself.
Dennis Leary
Oh, no. Oh, you.
Conan O'Brien
Oh, like, you know about noises that come up in the. Oh, yeah, you do listen to the podcast. Do I make a lot of dink, dink, dink noises?
Matt Gourley
No, what you do is this.
Conan O'Brien
Yeah, yeah, that's me. Well, I'm very. I have a high moral standard, but the audience wouldn't know. Like, I kind of. Me. That's me disapproving of the morality of the people around me. I'm tisk. Tisking them. That's not.
Matt Gourley
So I should leave those in?
Conan O'Brien
No, you should take them out. But you should put them in a box and put them in a safety deposit box.
Matt Gourley
I've got one of those movie.
Conan O'Brien
Me and my gang at an Italian villa in Switzerland. No, an Italian villa in Ireland. What? And we open up the box and all these come out. And then a guy comes in and says, are you in the. Bail you bill. Now get out or I throw this pile of potatoes at you. Oh, Ireland.
Sonam Vaidya
Because it's Ireland.
Conan O'Brien
I tied it all together. God, he's good. Who's talking? Conan. About who? Himself. Anyway, no more paper for you. No more paper for me. And I'll try not to do.
Sonam Vaidya
Yeah, why do you guys.
Conan O'Brien
When do I do that?
Matt Gourley
When do it? No, but when you do it, usually as you're about to begin a thought, so you go, like. Another thing you always say, coming Into a response to a guess is, you know, it's interesting that. Or it's very funny that. And then you'll go. And then say something.
Conan O'Brien
Yeah, yeah. It's very erotic when I think about it.
Sonam Vaidya
It's erotic.
Conan O'Brien
Do you think that's a turn on for women?
Dennis Leary
Not at all.
Matt Gourley
What sign?
Dennis Leary
Erotic?
Sonam Vaidya
Yeah. What do you mean? Yeah, what do you mean?
Conan O'Brien
When I was single. When I was single, I used to go, oh, yeah, this is really good.
Dennis Leary
Oh, my God.
Matt Gourley
It sounds like you're trying to.
Sonam Vaidya
I love it when guys make creepy noises at them. Like, that really works for a lot of girls.
Matt Gourley
Summoning a horse.
Conan O'Brien
And that's me. I'm in the bathroom. They're in the bedroom. I'm just talking to the mirror. I don't know what's happening in this scenario.
Sonam Vaidya
I don't know what happened. You know what? Why do you guys even need paper? Like, I never have paper in front of me. Well, don't have paper. What do you need?
Matt Gourley
If you want, I have to write notes.
Conan O'Brien
When you were my assistant, you never had any paper. Yeah, I used to ask you write things down and you wouldn't do it.
Sonam Vaidya
Yeah, but you never. Who's not making noise? This guy.
Conan O'Brien
Will you admit that you rarely had paper when you were my assistant?
Sonam Vaidya
You know why I didn't have paper? Because I was using an iPad with the writing stylist. Because I was trying to save people.
Conan O'Brien
You weren't drawing. You were drawing dicks and butts with your stuff.
Sonam Vaidya
But I was also taking certain notes. It wasn't all just. It wasn't all dicks and butts.
Conan O'Brien
I remember the time I. I went over your notes, I looked over your shoulder, and you were drawing butts.
Sonam Vaidya
Okay, I. I think there was a reason that I was drawing butts. Wait, remember when Gorley made a lot of noise with paper?
Conan O'Brien
You know what? You're right.
Sonam Vaidya
Yeah, yeah, yeah, yeah.
Conan O'Brien
Oh, I love it.
Sonam Vaidya
Also, remember when he sneezes and blows his nose?
Matt Gourley
Remember when you spilled water all over the table?
Sonam Vaidya
That was one time.
Conan O'Brien
Hey, remember? Remember when we got along and made a great podcast?
Matt Gourley
No, I don't.
Conan O'Brien
I don't either. All right, all right, let's get started.
Dennis Leary
Yes. To prove a point.
Conan O'Brien
Here we go.
Sonam Vaidya
Here you go.
Dennis Leary
Adam gave me.
Conan O'Brien
Here we go. No, I didn't know if we were doing it, if that was a segment. I, like, forgot. Is that a segment? Is that. No, I'm serious. I don't know. My guest today is a comedian and actor who you can now see in season two. Of the Fox comedy going Dutch. Are we related? Are we not? We just don't know. But you'll find out. Dennis Leary, welcome. I want to say one thing before we get started, which is you and I have known each other a long time. We've hung out. We've enjoyed each other's company. You always go out of your way to tell me that you've been listening to the podcast and then tell me what happened on the podcast. So some people say, I love the podcast, and you can tell they're just reading it off their phone that I have a podcast. But Dennis is a true blue fan, and he's always going on and on about two other people in the room who aren't me. Okay, all right. This enrages me.
Dennis Leary
So listen, this is a perfect opportunity for me to say this. I don't know what this means. I don't really fucking listen to podcasts, okay? But I listened to this because it was on the radio. And I drive everywhere in Manhattan. I drive everywhere in Brooklyn. I drive everywhere. So I fucking was like, oh, my God, Conan has a podcast. And once I got in. Now, one of my favorite things on the old TV show, I can't remember which iteration.
Conan O'Brien
Who knows? Colin?
Dennis Leary
But when you and Kona were doing the bits.
Conan O'Brien
Yes.
Dennis Leary
Okay. Those film bits were fucking genius.
Conan O'Brien
Right?
Dennis Leary
So I love those. So once I started listening to this, I just told these guys this backstage. I was like, listen, I like the podcast. I like most of the people that are on this show. I know I've either worked with or I've hung out with or I've known for, like, forever before we were famous, like Ben Stiller, whoever.
Conan O'Brien
Right? Yeah.
Dennis Leary
So I'm interested, but not. What really brings me in is when these two. When Gorly and fucking Sona are arguing and shitting on you. It's some of the funniest fucking shit.
Conan O'Brien
Fuck you, man.
Dennis Leary
Fuck you.
Conan O'Brien
Maybe a little more artistic than that. Okay. Not just better. Now you're onto something.
Dennis Leary
It's so fucking funny. And also, it's just when you're firing back at them, that's really my favorite part. So, like, when I met Sona just before. You can't. I've been here for, like, four hours. Conan doesn't get here until, like, a minute before you start shooting. He's too big of a star.
Conan O'Brien
Yeah.
Dennis Leary
I was downstairs, and you could hear
Conan O'Brien
my helicopter landing on the roof of the building.
Dennis Leary
Well, I thought it. Does it land where the pool used to be? Why the fuck would you. Why would you wait There was a pool.
Conan O'Brien
When we bought the pool, there was a building, and I covered it right away.
Dennis Leary
Why? Because you can't go in the sun. What about everybody else? Sona obviously can go in the sun again.
Conan O'Brien
I want to take it away. Take it away.
Dennis Leary
I can't go in the sun anymore at all. I used to go in the sun all the time. I can't now. I'm just. Every time I go in the sun, I get a melanoma.
Conan O'Brien
Okay, so wait. It happens instantly.
Dennis Leary
Instantly. If that light here. This light. This light is going to. I'll have melanoma before the podcast.
Conan O'Brien
This is how I know that we
Dennis Leary
are related, is that it's from the skin cancer.
Conan O'Brien
You are. It's so funny because people get hung up, you know, like, who? What's your skin color, race, all that kind of stuff. And we're not just white. You are a deathly pallor, and I think I'm whiter than you. Except. Yes.
Dennis Leary
But we are not even white. We're like. We're into a different. It's like translucent.
Matt Gourley
You guys are ultraviolet.
Conan O'Brien
Yes. Yes.
Dennis Leary
It's like a UV form of skin.
Conan O'Brien
Yes.
Dennis Leary
Yes. Yeah. It's see through.
Conan O'Brien
We emit light.
Dennis Leary
Yeah.
Conan O'Brien
That's how white we are.
Matt Gourley
We have prisms.
Conan O'Brien
Yeah. People have used me, and people have used me in mines to get copper out.
Dennis Leary
We are literally walking lamps. Okay, so.
Conan O'Brien
Oh, here he comes. Good, good. Open the old text and we'll read.
Dennis Leary
I can find my phone. Get Conan over here. Conan. Look in there.
Conan O'Brien
Always keep a Conan or a dentist by the bed.
Dennis Leary
So funny.
Conan O'Brien
Just right there in case there's an emergency. All right, let's crack into this right away because there's a lot to talk about.
Dennis Leary
I want to say another thing about how old we are.
Conan O'Brien
Yeah.
Dennis Leary
Because when he told me, I just. Out of the. I know. I just did a gig with you. I know how old you are, but I'm not in my mind. I think I'm like, 40.
Conan O'Brien
Yeah.
Dennis Leary
And then when I see somebody like you who's in my age group, I go, huh. Conan doesn't look like he's 40 anymore.
Conan O'Brien
Yeah.
Dennis Leary
And that's what reminds me that I'm fucking almost 70.
Sonam Vaidya
I feel older by looking at Conan.
Conan O'Brien
I provide that service for everybody.
Dennis Leary
By the way.
Conan O'Brien
Can I just say that I don't just admit light, but I will help you determine how old you are by just looking at me.
Matt Gourley
Wait, I'm just aging in your presence?
Conan O'Brien
Yeah.
Dennis Leary
Oh, my God.
Conan O'Brien
Yeah.
Dennis Leary
I saw Brian Kiley downstairs.
Conan O'Brien
Brian Kiely has Been with me from the beginning. Those guys are downstairs. They're working on the Oscars. And Brian Kiley's been with me since, I think, 1993.
Dennis Leary
Yes.
Conan O'Brien
Brian Kiely from Newton, Mass. And part of the Irish Mafia. And he went to my Sunday school. We had Sunday school instruction. That happened, I think, on a Monday night. It was called the cenacle. And we'd go out to, like, Brighton, and we were taught by nuns. Once a week, you know, parents would send their kids to make sure they got proper Catholic instruction. Sons and daughters. And so I would get driven out there with my brothers. And Brian Kiley was one of the kids that we used to talk to.
Dennis Leary
That's so crazy.
Conan O'Brien
Yeah. And it was always about.
Dennis Leary
Because, you know, I played hockey with him.
Conan O'Brien
Yeah. Oh, really? You did?
Dennis Leary
Yeah. In Charlestown, of all places.
Conan O'Brien
How does he play hockey? He has no leg muscle, so he works. He's a guy that works out all the time. And he has this incredible, you know, buff torso and then two pork slim Jims hanging off of his. Hamming off his pelvis.
Dennis Leary
Well, this is how good. Well, you don't have to waste a lot of time talking about Kylie, but Kylie looks the same. Yeah, he looks. Literally. Because he was bald when we were like, 20 and he was always in shape. And so now he looks the same. He looks exactly the same. He's Brian Kylie with glasses, you know. Cause he's getting old. His eyes are getting older.
Conan O'Brien
He's 110 years old.
Dennis Leary
He's 110 years old.
Conan O'Brien
He fought in the Korean conflict, which.
Dennis Leary
Yeah. So we played. And he was a comic from my generation. He's a great joke writer.
Conan O'Brien
Just a great joke writer.
Dennis Leary
Why are we talking about him?
Conan O'Brien
You know what? I have the same thing. When we're talking about another comic and it's not one of us, I have an egg timer that goes off after three seconds.
Dennis Leary
Like, why are we talking about this person? He's a great writer.
Conan O'Brien
I may have mentioned this, but we had Gene Simmons on the Late Night show years and years and years ago, and we had some sketch that he was going to be in, and I can't remember the context, but for some reason, he said okay to a lot of the different jokes. But then there was one joke that involved him just saying. And I take a. Like a Jazzercise class with Richard Simmons, the workout guy, and he put an X through it. And our head writer at the time said, well, you don't like that joke. Was her problem with it. And he said he's welcome to mention me anytime, but I don't need to mention him. And our writer said, well, wait a minute. Do you have a beef with him or something? He went, not at all. But he said, no free rides. That was the thing that haunts me. He said this. He said, no free rides. And what that means is, why would I mention someone else unless I'm getting something for it? Literally another person, like, hey, Gene Simmons, how are your children doing? No free rides. No free ride. Oh, my God.
Dennis Leary
Isn't that crazy? Well, if you can't monetize it, right?
Conan O'Brien
If you can't turn it into a kiss, Cuisinart, what's the point? Anyway, I want to get to the bottom.
Dennis Leary
I'm very impressed, by the way. A couple. I'm going to say something nice about you now.
Conan O'Brien
Oh, God. This. These go nowhere, by the way.
Dennis Leary
I'm not gonna say it.
Conan O'Brien
Nice, nice, nice, nice. And then you can come in with, you know, eat a dip.
Dennis Leary
I just want to say he did the Comics Come Home concert I do in Boston every year for the Cam Neely foundation, which is a charity I've involved with.
Conan O'Brien
It's a big charity you've been doing for, like, 20 something.
Dennis Leary
29 years.
Conan O'Brien
29 years.
Dennis Leary
Anyways, he did it this year. He was. We knew he was gonna be funny on stage. The fucking band loved doing Roadrunner.
Conan O'Brien
Roadrunner, yeah.
Dennis Leary
Which was really funny. But he was so fucking nice to everybody, including, like, my baby sister backstage and all these other people there. We went up to the VIP donor dinner, which is people who really donate a sh. Shitload of money to the hospital and the cause and everything. And. And was funny up there. Took all the pictures with every. He was so nice to everybody. And then he was a complete asshole later on.
Conan O'Brien
I know when to turn it off.
Dennis Leary
Yeah. It only lasts for, like, nine minutes.
Conan O'Brien
I'd look around, and when I'd see it was only me and Dennis or Maniscalco, too, I just. I'd be like, okay, I'm gonna tag out now. Screw you guys.
Dennis Leary
I mean, he was still a dick. Part of it. He was like, no, you were really. It was fucking nice of you to do that. And every. And you killed. And when you were backstage talking to my baby sister, she loves you. And she was like, my God, Conan was so nice. I was like, that's fucking front. But he was nice to you for, like, five minutes.
Conan O'Brien
Yeah.
Dennis Leary
But thank you for that.
Conan O'Brien
Oh, no, no. Well, this is the thing. And then we'll get to the question I had for you eventually, at the
Dennis Leary
end, Skin cancer question.
Conan O'Brien
I want you to look at something and tell me, because there's got a ridge around the edge of it.
Dennis Leary
Oh, yeah, yeah. No, that's. You got to get that taken out.
Conan O'Brien
So. And you said to me, hey, can you come do the Cam Neely thing? And I said, yeah, I've never been able to do it before. Cause I'm always taping. And I said, no, this year, I can do it. So I said, yes. I go to Boston, and I'm not thinking. And then I get to. I'm like, okay, where am I going now? TD Garden. So this is an arena, okay? And I think, oh, it's an arena. And I get up to the stage, and I peek through the curtain. Completely packed. I swear to God, I think everybody in Boston was there. And you have a moment of Jesus. Jesus Christ, look at this. I mean, an arena. This is what people see when they're playing the last game, you know, in the basketball season, in the championship. This is what you're looking at. And it was packed the next day. The next morning, I'm walking around Boston like Newbury Street. I'm over near the Hancock Tower. I'm just running some errands. I'm gonna go hang with some of my family. And people are just yelling out windows. Great job last night.
Dennis Leary
Hey.
Conan O'Brien
Had a lot of fun. Like, everyone in town had been to this thing. It's really impressive what you've built, because, yeah, there's. There's a lot of different charities, but I'm hard pressed to think of one where everybody in that city goes, well, listen, it's all. It's really cool.
Dennis Leary
Cam Neely, you know, who played for the Boston Bruins and is a Hockey hall of Famer, you know, he's the president of the Bruins. He runs the team. So it's like, you know, they respond to the cause. Boston's such a great fucking comedy scene, and it's still thriving there. So the guys coming back and who came out of that scene, but people like you as well, who were from Boston, anybody that comes in to do, they appreciate that. But Cam, you know, has turned that charity into such a big success. And he's, you know, he's a very present guy in that city. People love him. They love the Bruins. It's a hockey town. It's a sports town. So I think they see us within that light as well. You know what I mean? Like, we're at the Garden where the Celtics and the Bruins play. Like, I saw Conan at the Garden
Conan O'Brien
last Night, which is so cool for me growing up. The idea that anybody saw me at the Garden. I know, it's crazy because it sounds like I. I mean, to me, it just makes me think, yeah. And I drained a three pointer, you know, it's like, no, I didn't. No, I fucked around for you.
Dennis Leary
It's ok. Funny is like, because of our families backstage in my dressing room. And a couple of the areas are like my sisters and my older brother and a bunch of my cousins, right? And then I go and introduce Conan to my baby sister, like in the cafeteria where they're serving some food or whatever. And then the show gets done and I was like, I gotta go in and thank again, thank Conan, because he was so fucking good. And I go in his dressing room and there's a cousin. I don't know if she's a cousin of mine, but she's a cousin of yours from Worcester who's in there? Was she espousing a conspiracy theory?
Conan O'Brien
If it's a cousin of mine, then probably.
Dennis Leary
So I walk in and he goes, hey, this is my cousin, blah, blah, blah. And she's like. I just remember she went, this is my. Was it her?
Conan O'Brien
Her name's Catherine, but we call her Boo.
Dennis Leary
Okay. And her husband is Artie.
Conan O'Brien
Let's just say he's Artie. She's married to Artie Lang, which is not going well. Anyways.
Dennis Leary
It was so funny because she was telling us some weird story about Worcester and she was like, this is my husband Neil, or whatever his name is. And he's just like a guy saying nothing in the corner. It's because she's.
Conan O'Brien
There's no room to talk around any o' Brien or Reardon.
Dennis Leary
I know, it's so funny.
Conan O'Brien
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Sonam Vaidya
Loves me some couch life.
Conan O'Brien
Without ever leaving the house, T Mobile still has you covered. Find plans, including Netflix plus deals on DoorDash. The more benefits you use, the more value you get. I mean, why go anywhere when you can get your favorite takeout, binge a show and brag to all your friends? You won't believe what I'm not doing tonight. That's a brag. When you get to hang out on your couch and live life at its most supreme.
Sonam Vaidya
It's so comfortable.
Conan O'Brien
I have T Mobile. It's great. And I always like to watch those survival shows and I like to get meat. So like a steak and then like a survival show. Yeah, and then the monster's eating the person you like. The meat monster. Exactly. You're a sick guy. Check it out@t mobile.com Magenta status. Wow. Receive Netflix standard with ads while you maintain a qualifying line in good standing. See dashpass details in the TeaLife app. The best B2B marketing gets wasted on the wrong people. Man, this tears me up. So when you want to reach the right professionals, use LinkedIn ads. LinkedIn has grown to a network of over 1 billion professionals, including 130 million decision makers. Hmm, I wonder if I'm one of those. That's why LinkedIn has the biggest B2B ROAs of all online ad networks. Spend $250 on your first campaign on LinkedIn ads and get a free $250 credit for the next one. Pretty good deal. Just go to LinkedIn.comconan that's LinkedIn.comconan Terms and conditions apply. Steve Carell stars in the new HBO original comedy series Rooster, premiering March 8. From a creator of Ted, Lasso and Shrinking comes the story of an acclaimed author who finds himself teaching on a college campus alongside his adult daughter, navigating their complicated relationship and Greg's late in life first chance at the college experience he never had. Is there anyone funnier than Steve Carell? I do not think there is. So I will watch this. Don't miss the world Premiere of Rooster March 8th at 10pm exclusively on HBO Max. Subscription required. Visit HBOMax.com for details. You've gotten me to what I want to talk about, which I didn't even know this, but a number of years ago you said, hey, I'm your cousin, we're related. Because I think you didn't know it either.
Dennis Leary
I had no idea.
Conan O'Brien
And then I. So we try to look into it. You're from Worcester, Mass.
Dennis Leary
Yep.
Conan O'Brien
All my people are from Worcester, Mass. My father's side of the family is from just outside Worcester. My mother's side of the family is from Worcester. So the Reardons are from Worcester. The o' Briens are from like towns outside Milbury, Sturbridge and so basically Worcester. Basically Worcester, yeah. And my grandfather was directed traffic downtown in Worcester and that was the job he had. Or as we say, Worcester, Worcester, Worcester. And I used to go and hang out with my cousin there when I was growing up, I'd hang out in Worcester and there was one thing to do and one thing only, which is for some reason there was a museum of armor.
Dennis Leary
Oh, yeah.
Conan O'Brien
From like the 14th. Yeah.
Dennis Leary
AMA Museum of Armor.
Conan O'Brien
So people would say, did you go
Dennis Leary
to the armor museum?
Conan O'Brien
Yeah. And literally what it was, it's not even that well curated. It was just. It was a big old office building that hadn't been used, that had been shut down in like 1920. And they filled it with armor that they didn't clean. It was just, I think some of it, most of it wasn't on a mannequin.
Dennis Leary
It was just horrible.
Conan O'Brien
It was horrible. And it looked like a hoarder's attic of armor. And so I remember I'd be staying, my cousin and my aunt would be like, go see the honor. Why don't you go see some armor?
Dennis Leary
And that was a big highlight.
Conan O'Brien
And literally, like, we did that yesterday. Do it again. And because it's Worcester and that's what you do, there's not a lot. And you'd walk around and go, yep, there it is.
Dennis Leary
Now they have a minor league baseball team for the Red Sox. Pola park, which is downtown, used to
Conan O'Brien
be the Pawtucket Red Sox. And they moved.
Dennis Leary
They moved to Worcester.
Conan O'Brien
Yes.
Dennis Leary
And it's polar poc. Nice little ballpark in downtown Worcester. And they have a minor league hockey team. And so things are looking up.
Conan O'Brien
This is how. And the thing is, when you're from
Dennis Leary
Worcester, it took us 150 years.
Conan O'Brien
It's a really funny thing. Yeah, the mill closed in like 1902.
Dennis Leary
Listen, let me tell you, when I was growing up and some people are still bemoaning this, it was the heroin capital of New England for a while, when I was like a teenager.
Conan O'Brien
Why do you think I was there?
Dennis Leary
But we were literally like, hey, we're famous for something. Yeah, right. And then I think it's now Lowell. Anyways, it's like 10 years ago, Lowell took the crown. Lowell took the crown.
Conan O'Brien
We can get it back.
Dennis Leary
And I was like, so now we have nothing. So Lowell took the stone capital of New England. We don't even have that.
Conan O'Brien
I think we still have the armory. But yeah. And the thing is Worcester, this is how Worcester centric people get. And don't get me wrong, I love Worcester.
Dennis Leary
And so do I.
Conan O'Brien
My whole family's there. It's a big deal. And the people are lovely. And it was a big part of my growing up. Cause that's where I'd go see my grandparents and cousins. So it's very near and dear to my heart. But I will say that when you're in Worcester, everything's Worcester centric. And nothing exists outside Worcester. When you're there. So I had the experience of when I got the Late night show in 1993, there was all this specula. First of all, my own relatives were like, what the hell? You're gonna take over for Letterman? I'd be like, yeah, I guess so. I mean, what the hell are you talking. You can't take over for Letterman. They were. I think they.
Dennis Leary
I remember my family, my. You know, because my. Everybody still lives in Worcester. And they were all like, hey, do you know this guy? Yeah. I'm like, no, I don't know this guy.
Conan O'Brien
No one knew that guy.
Dennis Leary
And for Letterman?
Conan O'Brien
Yeah.
Dennis Leary
I was like, yeah, I don't know.
Conan O'Brien
I don't know.
Dennis Leary
I don't know.
Conan O'Brien
Good luck to him.
Dennis Leary
Yeah. So look at us years later. Here you are covering up pools in Hollywood. That's how I close that fucking pool. Everybody inside,
Conan O'Brien
fit it with cement. So I am there. I'm in Worcester visiting my uncle, Jim Reardon. We called him Gavin. And wait a minute.
Dennis Leary
What?
Matt Gourley
Makes perfect sense.
Conan O'Brien
Yeah, his name was Gavin. That's what we called him, Uncle Gavin. And Uncle Gavin said to me, I know who your first guest should be. And at the time, people were saying, when you have your talk show, you can have pretty much anyone as your first guest. Anyone will be like, oh, my God. First guest on a talk show. And if it goes, then I'm always gonna be the first guest. So you pretty much have whoever you want. And he went, I know who it's gonna be, and this is what you gotta do. And I said, who? And he said, bob Cousy. And I said, what? And he said, bob Cousy. Bob Cousy.
Dennis Leary
Oh, my God.
Conan O'Brien
A big star out of Holy Cross College in Worcester who was a big star for the Celtics in the 1940s and 50s, back when people shot, he would shoot his whiter than me. And he would shoot his free throws between his legs, like granny style. He would shoot them between his legs and. Great player, but this is 1993, and I'm being.
Dennis Leary
By the way, he's still alive.
Conan O'Brien
Yeah. Oh, yeah. He's 100 and God bless you. I'd have him now. I'd have him now. But as my first guest in 1993, can you imagine if I said, bob Koozie, Bob Cousy when I was a kid? But that's how. And I said, I don't know if that's gonna work for the first. And they're like, what are you talking about?
Dennis Leary
It's Bob Cousy.
Conan O'Brien
It's Bob Cousy, everyone's gonna go crazy. Yeah, everyone in Worcester is gonna go crazy.
Dennis Leary
He lived in the night, what they call the nice section of Worcester, which I can't remember at that time when it was when we were growing up. But on Sundays, you know, when your parents would drive around and look at houses that you're never gonna live in after mass on Sundays. Cause we lived in Maine South. We lived in an apartment in a two and a half decker, not even a three decker. So my father would drive us by Bob Cousy's house in the nice neighborhood. He's like, bob Cousy's house? And we're like, yeah, we know. We go by it every Sunday.
Conan O'Brien
Yeah.
Dennis Leary
You know what I mean?
Conan O'Brien
We go to the Armory now.
Dennis Leary
He had a driving school for a while in Worcester.
Conan O'Brien
What?
Dennis Leary
Yeah, had driving school. Bob Cousy's driving school.
Conan O'Brien
I want to drive like Bob Cousy.
Dennis Leary
Yeah. Like, what is that? Why the fuck does he have a driving school?
Conan O'Brien
So this I want to ask you about because this is something you can relate to because of what you just said. Said. And I wasn't going to talk about this, but when you're Irish Catholic and growing up in, you know, and you're in Boston or you're in central Massachusetts, there's this whole thing of, what kind of Irish are you?
Dennis Leary
Yeah, yeah.
Conan O'Brien
My mother was, you know, had been the first in her family, like to. I'm not the first in her family, but her generation was the first in her family, obviously, to go to college.
Dennis Leary
Yeah, yeah.
Conan O'Brien
And she. She had really worked hard and she had become a lawyer. And she used to sometimes talk to us about how we are not, you know, we are not. We are lace curtain Irish. And my brothers and I would, you know, my sisters would be sitting around being like, what are you talking about?
Dennis Leary
What?
Conan O'Brien
And she'd say, you know, we're not triple decker Irish. You know, she.
Dennis Leary
She would come out of Worcester and become Lace Curtin Irish.
Conan O'Brien
No, exactly. And I'd say, mom, what are you talking about?
Dennis Leary
It's because you moved to Brookline.
Conan O'Brien
Yeah. And also, also I' in the corner, it'd be like a ham hanging on a rope and my brother Neil was hanging off of it like a bear in the woods. I mean, all of our behavior, we would have potato fights. There was. I mean, there was nothing about us that was at all respectable in the way that we behaved, but she was just willing it to be so. Do you know what I mean?
Dennis Leary
It's so crazy because when I heard Lace, Kurt and I, when. When you grow up in. In Massachusetts, especially in our age group, like the fucking Kennedys.
Conan O'Brien
Right? Yeah.
Dennis Leary
This is before, you know, RFK Jr. This is like when the Kennedys were the Kennedys. Right. So I still remember. Actually, this is like one of my first memories as a kid growing up. Like, I don't know why. It's the summer of 63. My parents couldn't afford to go back to Ireland. When they came over in 49 and 50, they couldn't afford to go back then in 1963 was the first time they could afford to go. But they can only take one kid with them because they didn't have enough money. So my older brother Johnny got to go and the rest of us got dispersed to other apartments as cousins.
Conan O'Brien
Now, by the way, let's keep in mind, this is 1803.
Dennis Leary
Yeah.
Conan O'Brien
We ate coal for breakfast.
Dennis Leary
So I remember that summer really well because that's the summer that JFK went to Ireland.
Conan O'Brien
Yep.
Dennis Leary
But I remember Logan and my mother and my father get on this plane with my brother, who I really hate now. Cause he's going to Ireland. And I got stuck with my Aunt Betty, who had no kids and who gave me a Bible. It's the summertime. She gave me a Bible.
Conan O'Brien
It was a summertime Bible.
Dennis Leary
I had a good fun.
Conan O'Brien
Charlie XCX Summertime Bible. It's Bible summer.
Sonam Vaidya
Bible summer.
Conan O'Brien
I don't know why that didn't catch on. She keeps flogging it and it's not catching on.
Dennis Leary
Oh, my God. She took us. I had to go to Mass every day. I had to go to Mass every day. And then she'd walk me over to where my sister Emery was at my house. My cousins, the Lucy's, they were a couple blocks away where all the kids were having a blast in their yard. And she was like, I don't want you to get too dirty. We have to go back. And I'm like, that was a month. But anyways, also that when my parents came back, which I still remember that Kennedy was in Ireland, which was a big thing. But then he spoke at Holy Cross that summer at the end of the summer. So he drove through the neighborhood with the COVID on the car.
Conan O'Brien
Yep.
Dennis Leary
Unfortunate choice in Worcester.
Conan O'Brien
Yeah.
Dennis Leary
Right. There's nothing to worry about. Worcester.
Conan O'Brien
Yeah.
Dennis Leary
He went to.
Conan O'Brien
Yeah.
Dennis Leary
And that was like three months later when he got.
Conan O'Brien
Right.
Dennis Leary
Killed. And I remember that because that. I remember the nuns telling us to go home because we lived in the. We went to school in the neighborhood where we lived. So you Know, it was. I think I was. I was in art class. I think that day we were in art class, and the nuns were like, everybody go home. We're like, what? Because they had. They knew the.
Conan O'Brien
If a nun told me to go home, I wouldn't question it for a second. Wait a minute. Are you sure we can't have more Catholic instruction? Cause I think we got 40 minutes left. Sit down, Mr. O'. Brien.
Sonam Vaidya
I just got a new Bible.
Conan O'Brien
I just got my summer Bible.
Dennis Leary
My summertime Bible.
Conan O'Brien
Yeah.
Dennis Leary
That summer lives in my. That was so horrible, living with Aunt Betty. Oh, my God. She dressed me up with a tie every day in the summertime. It was horrible.
Conan O'Brien
Mass every day.
Dennis Leary
Mass every day.
Conan O'Brien
Okay.
Dennis Leary
With this stupid Bible.
Matt Gourley
Did you ever question why you were chosen to go with Betty and the other one.
Dennis Leary
Because she didn't have any kids. And they felt bad later when I asked them, but they were like, we wanted her to have a kid, but
Conan O'Brien
why did you get.
Dennis Leary
Why did you have to go to Betty?
Matt Gourley
There must have been a reason.
Dennis Leary
I was her godchild.
Conan O'Brien
Oh. Oh, there you go.
Dennis Leary
Yeah.
Conan O'Brien
And that's a sacred.
Dennis Leary
Husband was dead. You drew the short straw. Oh, my God. It was so horrible. Anyway. Was. But thank God I lived past it, so.
Conan O'Brien
Well, she's here today. Yeah, let's bring her out.
Dennis Leary
She's 100, and I'm still alone.
Conan O'Brien
No, it's so funny, because there's this.
Dennis Leary
There's no.
Conan O'Brien
There's this life that I knew growing up, and it's. Everyone's Irish.
Dennis Leary
Everybody's Irish.
Conan O'Brien
Everybody's Irish and Massachusetts. And so. And, you know, we don't get to choose what our makeup is. That's just what we are. And it's so interesting to me how comedy. I don't know. It just felt like a cellular thing. It didn't even feel like a choice. It's just something.
Dennis Leary
But in your family. I know from what I've heard you say before, I know in my family, this was true. My parents were really funny. All my aunts were really funny. Everybody was sarcastic. Yeah. And so I'm sure your family was the same thing.
Conan O'Brien
And really funny stories and people just laughing their asses off around the table eating some of the unhealthiest food that you can imagine.
Dennis Leary
Oh, the worst.
Conan O'Brien
The worst.
Dennis Leary
Oh, my God.
Conan O'Brien
I keep waiting for the surgeon general to say, you know, ham is fried. Ham with butter is. Actually. Lengthens your life. Cause then I'd be in great shape.
Dennis Leary
I remember there was an Italian family that lived next door, the Corelli's Their mother used to cook, like, while you were out playing football or baseball or street hockey in the street in the summertime, she would come out with. With homemade pizza or. Yeah. I mean, just unbelievable. So my brother. My brother and I. My brother ended up marrying an Italian girl. My brother was like, you know, mom, Mrs. Corelli makes the best. And she's like, I can make pasta. I can make spaghetti. And we were like, oh, please don't. Right? And so one night, she made this. I'll never forget this. I loved her. I loved my mother. She just passed away this year. She was 98. And she was lucid right up to the end, but she was. She was Irish cook. You know what that. Yes, I do boil it. It's like that. You remember Don Gavin, the comedian from Boston? He had a great line one time. He was like, I was eating my mother's food, and my brother turned to me and said, this tastes like shit. And I went, you can taste it. That sums up Irish food, right?
Conan O'Brien
So I remember my. What I remember very clearly is my mom would say, wanted to make. She used to make spaghetti with meat sauce. Was. You know, she thought was spaghetti, meat sauce. Basically, what it was was many packages of hamburger meat that are. That are fried up in a giant. And then you put some pasta in there, and there was. I don't even know if there was sauce, but for years. And I loved it, but I thought that that was spaghetti with meat sauce. And so when I went to. When I, you know, finally left home, and then I'm in New York and I go to an Italian restaurant. I think I was berating a waiter, like, sir, there should be six hamburgers. There should be at least three pounds of ground beef that's been fried in this. I mean, basically, I thought it was
Dennis Leary
a burger, and there's too much flavor. What's going on here?
Conan O'Brien
Why do I suddenly taste things?
Dennis Leary
Why does it taste good? Yeah, it was crazy. And also then my brother married an Italian, and there was a lot of Italians in the neighborhood. There was Armenians in our neighborhood. It was crazy. We went to the same school for 12 years. Right. So you had all these different Puerto Ricans, these different kinds of food, and every night you're eating stuff that you can't taste.
Conan O'Brien
Yeah.
Dennis Leary
And then on Fridays, when they have fish, it's fish sticks.
Conan O'Brien
Fish sticks.
Dennis Leary
Oh, my God.
Conan O'Brien
Yeah. Yeah.
Dennis Leary
Oh, my God. And my dad putting ketchup on the pasta.
Sonam Vaidya
Oh.
Dennis Leary
Oh, yeah.
Conan O'Brien
Well, that's. I mean.
Dennis Leary
I mean, what. Where do we live? And, like, you're like, listen, go out the back door on the porch and look across at the porch across the alley. There's Puerto Rican people eating really good food. Can we go over there? The Corelli's are right over here. Oh my God. My father ate. Literally, he ate meat. At everything he ate had to have meat. Bacon and eggs, steak and eggs. You know, he smoked five packs a day. I should talk. I smoked for 52 years.
Conan O'Brien
Well, I remember very clearly getting the talk show and doing the talk show. It's like two years in, it's starting to level out. It looks like I'm gonna make it. I went to some, with my girlfriend at the time, some fancy kind of resorty place in California, because I had a week, I think I had a week off, which never happened. And we went out and I think it was, you know, sort of north of San Francisco, right on, you know, cliffs and. And it was a very. Supposed to be like a very wonderful health conscious place. And I'll never forget I went in the morning to get my breakfast and they had laid out this table today that I'd be delighted with. Fruits, granola, different, you know, juices, all that kind of stuff. And I started to get mad and I was holding my plate and I was sh. Like shaking. I was so mad. My girlfriend was like, what's your problem? I was like, there's no eggs, there's no bacon. And she was like, hey, chill. And then I went outside, I put the plate down, I walked outside and I started kicking a tree.
Dennis Leary
What?
Conan O'Brien
I was so mad.
Dennis Leary
And you were like, at what age are you?
Conan O'Brien
At that point I was like 32. Yes. I was like, oh my God.
Dennis Leary
Hey, listen, I'm winning because.
Conan O'Brien
And keep in mind, at that time I went and got a cholesterol test and they said my cholesterol was like 350. And they basically. And I remember having this image in my head that if I stopped fast at a traffic light in my car, a cholesterol me would come crashing through my chest because I was made of fucking cholesterol.
Dennis Leary
But it's not your fault. That's your parents and your grandparents. It's Ireland's fault.
Conan O'Brien
Yeah, but this morning my wife makes granola. I put some berries in there.
Dennis Leary
That's what I had this morning.
Conan O'Brien
But I still, when she's not looking, put six slices of ham. Ham on a rope.
Dennis Leary
I love bacon. Oh, yeah, I love bacon. And by the way. And I love Ireland, but I've got a lot of cousins there and I'm shooting a Television show over there.
Conan O'Brien
Yeah, I want to talk about that.
Dennis Leary
Yeah. So it's funny because my generation, like, two of my cousins, took over the family farms, which are very close to each other in Killarney. My mother and my father met in Killarney. And so it's so interesting because healthy food, like many other things, have come to Ireland. Ireland's doing great financially, and it's. The film and television industry is booming there. Yeah. And other. As I've grown up, Spanish food and all these other kinds of food have come into. Even in Killarney, you go into Killarney, you can get French food in Spanish, which is fantastic. I went. This is not that long ago, 15, 20 years ago, maybe, went back to Ireland with my mother, and we went to a restaurant in town, a bunch of cousins my age and their kids and my kids. And it was this, like, really nice Spanish restaurant, which I'd never been to. And they're like, it's great. And we get there, and my Uncle Dennis, who I'm named for, my mom's brother, and my mom, it's like 20 people at the stable. We go in there and we order, and they. I think they're ordering, right? And then next thing I know, we're all talking everything. One of my cousins comes in, and he's got fish and chip bags from the. From the fish and chip place across the street. Like, they're just dripping with grease, brown bags. And I'm like, this kid's gonna eat. And hands a bag to my mom and a bag to my Uncle Dennis, who are way down there. So I go to my cousin Mahal, I go, what's going on? He goes, oh, they. They won't eat the Spanish food, so, you know, they're allowed to bring in fish and chips. I go, ma. She goes, I'm not having this stuff. This Spanish stuff.
Conan O'Brien
Yeah, everyone knows Spanish food is awful.
Dennis Leary
She literally. She wouldn't even eat a real Italian food. She didn't like. She was like meat potatoes I had when I lived in Charleston.
Conan O'Brien
Oh, so we're like vampires when you show us a vegetable.
Dennis Leary
When I lived in Charlestown, my girlfriend, my wife. Now we have my sister Ann Maria, and my mom over, because my mom was in Boston getting some health stuff done. And so she steamed some salmon and some broccoli and some kind of potato dish, and she served it. And my sister Emery, my mother, we're all talking and everything, so they bite in. And my sister Emery goes, hey, this broccoli, it's hot.
Conan O'Brien
And it's green.
Dennis Leary
My girlfriend Ann Goes, no, no, no, I know. I steamed it. And she goes, no, no, but it's hot. And she takes her plate and my mother's plate and goes into our kitchen in the apartment and reboils the broccoli.
Conan O'Brien
Yeah, I understand.
Dennis Leary
I was the same apartment where my mother. Literally, my mother said to me one day, she goes, she was there when we were growing up. It was in the 70s. My parents got the, like, avocado green refrigerator and stove.
Conan O'Brien
Yep.
Dennis Leary
You remember this?
Conan O'Brien
Yep.
Dennis Leary
So my mother's in the kitchen of that apartment, and she. She picks up an avocado, and she goes, now, this is an avocado, right? This is like. This is 1985.
Conan O'Brien
Yeah, yeah.
Dennis Leary
This is an avocado, right? And I go, yeah. She goes, huh? Yeah. And I go, what, you've never seen an. No, no, I've seen avocados. I'm just saying, that's an avocado. And I go, yeah.
Conan O'Brien
Spoken like someone who really is around avocados a lot.
Dennis Leary
I'm like, matt, I said, when we were growing up, didn't you have an avocado colored? Yeah. She goes, we had the color design, and the kitchen was avocado, but I wouldn't eat those things. She goes, they're so greasy and soft. I'm like, oh, my God. Greasy and soft. Who would describe an avocado as greasy?
Conan O'Brien
And also, people who eat grease eat grease.
Dennis Leary
Ma. It's green. You came from a green emerald isle. It ties into our whole. I remember saying this to my mother.
Sonam Vaidya
Like, I can't.
Dennis Leary
My mother said this one time, this kid that we grew up with, one of my best friends, raging alcoholic, died from alcoholism very young. And she goes, this is just a theme. You don't recognize this one? I go, yeah. So listen, he's coming over. He quit drinking. This is at her house in Worcester. He's coming over. He quit drinking, so don't give him anything. She goes, okay. He walks in the door, she says, hi. We sit down, and the next thing I know, she cracks a beer and puts it in front of him. I go, mo, what are you doing? And he. Of course. He's like, hey, like this. She goes, what? I go, he can't drink. You can't drink. And he goes, I know. Yeah, I can't. She goes, no, that says beer.
Conan O'Brien
Yeah, Beer doesn't count.
Dennis Leary
Guinness doesn't count. Beer doesn't count, right?
Conan O'Brien
No, Guinness is. Guinness is like a glass of milk.
Dennis Leary
Oh, that's growing up. Yeah. It's like a loaf of bread.
Conan O'Brien
Yeah.
Dennis Leary
Oh, my God, he can't be an alcoholic. All he drinks is beer.
Conan O'Brien
He had 35 beers. He's okay. He's driving a school bus in the morning. He'll be all right.
Dennis Leary
My brother. I would be in a car with my. Or a van with my brother when we were, like, in our twenties. And he'd be. He'd have a cooler full of beer. And I'd be like, you're driving and drinking beers. He goes, yeah, it's not like I'm drinking booze. What is happening?
Conan O'Brien
You know what's so funny? You know what's so funny? This all makes perfect sense. It doesn't even sound like comedy to me because it's just. You're like. We're like two fish and you're describing water. And these two lizards over here are going, water, water. And I'm like, what are you talking about? Of course no one would have a hard vegetable. You need to boil that until it's a paste.
Dennis Leary
And it's great. I have to tell you.
Conan O'Brien
Like a great paste.
Dennis Leary
So funny. I have my. Because of my algorithms. My. On my Instagram feed, on my phone. Every day comes up, comes cl. Like, from last night. There was one this morning I saw, you know, people fighting at a hockey game in Massachusetts, right? A kid's hockey game. The one this morning was. You see these two guys go, oh, yeah, say it again. Say it again. It's a girls hockey game. You can see the girls stopping at a glass. And then you see a woman come in. A woman. Of course, it's Massachusetts. And she hits the first guy. Hey, you shut up and leave him alone. There's always a woman. Every girlfriend I had that was from Massachusetts could fight. Yeah, The Nebraski sisters. Oh, my God. You did not want to mess with them. Now it's crazy.
Sonam Vaidya
God, these are kids hockey games.
Dennis Leary
Kids.
Conan O'Brien
Yeah.
Dennis Leary
Last night.
Sonam Vaidya
Oh, my God. I thought you were going to say, like, fans from, like, you know, Bruins and another Massachusetts.
Dennis Leary
A fight can break out at any time.
Conan O'Brien
I'm under the gun all the time. Would you say so, Sona? Yeah. Constant. Constant.
Sonam Vaidya
Yeah.
Conan O'Brien
Everyone wants a piece of their conesy woansy. So when you're crunched for time and you want something wholesome, something's gonna give you some energy. Yeah. Nutrigrain delivers nutrition and great taste. No trade offs required. Nutrigrain's made with 10 grams of whole grains, 10 vitamins and minerals, and no high fructose corn syrup. It's the hardworking snack that fits into real life. Portable con. Portable It's a portable snack, perfect grab and go option for busy days. Nutrigrain has flavors people generally love. Hey, you got your strawberry, apple cinnamon, blueberry flavors that are familiar. And new. Nutrigrain Crunchy brings you another go to snacking option. This is what you want to do. Like here at Team Cocoa. We're slammed all the time. Grab that Nutrigrain bar, take a chomperoo, and you're ready to go. I love chomp. Apple cinnamon flavor is my favorite.
Dennis Leary
No one asked.
Conan O'Brien
Okay? Okay. Find nutritious and always delicious nutrigrain bars at your favorite store. Why don't you go shovel some papers, buddy boy or online retailer today and look for new Nutri Grain Crunchy bars in a store near you. A simple yeah, I'll come by is perfect for bringing a pack of Miller Lite. And when things go from low key to legendary, everyone knows it's miller time. For 50 years, beer lovers have trusted Miller Lite for a taste they can depend on. Made with simple ingredients like malted barley, it delivers rich, balanced toffee note flavors and the iconic golden color. You gotta have that golden color. Yep. The original light beer since 1975. You know, when I get together with my gang, my posse, my squad.
Sonam Vaidya
Your homies.
Conan O'Brien
Yeah, my homies. We like to crack open a Miller Light. We toast each other, we bump chests. We have a good time. And you know what? It's a reliable, reliable experience.
Sonam Vaidya
You guys will not stop high fiving each other and crack an open Miller Lights.
Conan O'Brien
I high five more than most people that have ever lived. My hands are raw by the end of a day. And that's what I think when I look around at my buddies. We've all got a Miller Lite. Every decision was correct. All my good friends and the right beer.
Sonam Vaidya
Yeah.
Conan O'Brien
Cheers to legendary moments with Miller Lite. Great taste. 96 calories. Go to millerlight.com conan to find delivery options near you. Or you can pick up some Mirror Lite pretty much anywhere they sell beer. It's Miller time. Celebrate responsibly. Miller Brewing Co. Milwaukee, Wisconsin. 96 calories and 3.2 carbs per 12 ounces. But you know what's interesting is the whole culture. There's something in the whole culture and it's in the comedy scene and everything. There's this people think of like, New York is tough. And you think, yeah, Boston. You can almost hear people have like gravel when they talk. Like in their. It's in their Persona, it's in their language. Everything is very Abrasive. And I remembered we used to have. In the early days of late night, I would have all these Boston comics come on. And some of them, you know, you'd have a Comic Con who had only been in the clubs in Boston.
Dennis Leary
Yeah, yeah, yeah.
Conan O'Brien
And I'd be there and I'd say, all right, everybody. And now we got a great. You know, here he comes. And I'd throw to a. Here's a brand new comic in Boston. He's been big deal in the Boston comedy scene. Here he is. And a guy would come out and he'd have his hat pulled down over his eyes, and he'd be like. And it was pure vitriol and anger. And I remembered my audience would be like, jesus Christ, make that monster go.
Matt Gourley
I know.
Dennis Leary
It's so crazy. It's so crazy.
Conan O'Brien
Cause they had lived in a. They had grown up in a sea of lava. And this was their first time out.
Dennis Leary
One of the most amazing. I mean, there's a lot of great comedians over the years, from my generation through Bill Burr's generation and even now. But that. I went to college at Emerson College with Steven Wright. So in college, Stephen was the shyest human being on the planet, right? But really funny. Quietly, really unbelievably funny. And he. So when he started doing standup, that was one of the reasons I got into it, is because somebody told me, hey, Steve Wright's doing standup. After we graduated at a Chinese restaurant in Cambridge where there's a talent, I was like, a Chinese restaurant in Cambridge where there's a talent, Steven Wright. And I went. And he was. He was so different from Lenny Clark was hosting that show. That's how I went.
Conan O'Brien
I was gonna bring up Lenny because I saw him at the Cam Neely Theater. Lenny Clark, just this absolute Mount Rushmore icon of Boston comics. And I loved hanging out with him because it was like, I'm so glad he's here. He was really funny.
Dennis Leary
He's like the Fred Flintstone of Boston comics. He literally looks like Fred Flintstone come to life.
Conan O'Brien
And he talk. He's really loud.
Dennis Leary
He's a great actor, too, but this is the way he talks. He loves you. But he was hosting that show, and it was a talent show. And Steve Wright was just so. His jokes were like haiku. It was so beautifully written. But he was the only person like that Bobcat Goldthwaite came outta my generation. Everybody was loud. Bill Burr, everybody was sarcastic and loud and quick. The crowds were tough. Stephen, to this day, he's like a. It's like, he's a diamond, you know?
Conan O'Brien
No, he's. I mean, I always think if Steven's standup was always these jokes that are polished stones that are really precise, like
Dennis Leary
some of the most famous ones, like, small world, but I wouldn't want to paint it.
Conan O'Brien
Yeah, yeah. It's incredible.
Dennis Leary
That joke is just like, what are you talking about?
Conan O'Brien
So you're coming up from that in that scene. And I know that you were interested. When you're at Emerson, you're interested in comedy.
Dennis Leary
Yes.
Conan O'Brien
Right. And you started like a comedy group that's I think, still going today, the
Dennis Leary
comedy workshop, which was.
Conan O'Brien
So you knew. This is something I'd like to do at a very early age.
Dennis Leary
Yeah. So when I was growing up, my dad was a mechanic by trade, but he was a great musician and he played in Irish bands and he played accordion. Like, after a wedding or, you know, any kind of big family event, people would come back to our apartment and eventually the house we lived in. And my dad would play accordion and there was always music in the house. But my dad was. And my mom so fucking funny. Like, so funny. And so sarcastically. The moment you walked in the door from school, what the hell are you so happy? Like, they would start in on you. Right. So we were all funny in response to that, naturally, as you know. And then when I was a kid, a teenager, I saw fucking Monty Python and Richard Pryor, like, almost like the rebellious new Richard Pryor. Like 1972, 73. I was like. And then George Carlin and I was like, what the fuck is this?
Conan O'Brien
Right?
Dennis Leary
Monty Python just fucking made our heads explode.
Conan O'Brien
Yeah.
Dennis Leary
I mean, that was crazy.
Conan O'Brien
That was the new. I always. I've told Eric Idle this a million times. That was for me, anyway. That was the atomic bomb blast. That was the Oppenheimer moment of, oh, sketches don't have to end. Like.
Dennis Leary
Well.
Conan O'Brien
And so it was, you know, I guess we really are the Fathead family. And then the curtain comes down. They just blew everything up.
Dennis Leary
It was lovely way. They were like the Beatles of comedy. I never. To this day, nothing has ever done that atomic thing, although I did prior. And Carlin, especially Carlin, because he was talking like he was in the neighborhood. He was talking about Catholic school and nuns and seven dirty words and all that stuff. So then I was like. And then Saturday Night Live happened.
Conan O'Brien
Yeah.
Dennis Leary
And that first cast. And I was like, belushi especially, I was like, what the fuck is this? You know, it's still true. Like, I. At that same time in music, although I was A. More of a Stones fan. I mean, I don't really remember seeing the Beatles on TV and stuff, but I liked the Beatles. But David Bowie. The first time I saw Bowie, I was like. Like, my brother and I were like, what is this?
Conan O'Brien
Yeah.
Dennis Leary
Which was that? Just music.
Conan O'Brien
I was like, he's androgynous. I'm androgynous. I remember that really clearly. You know, you felt seen. I felt seen for the first time.
Dennis Leary
David Bowie was singing to you, and he was also saying, hey, Conan, you want to try this outfit on?
Conan O'Brien
Yes, I do.
Matt Gourley
And yet he still seems tougher than me.
Conan O'Brien
Yeah. Oh, he beat the shit out of me. Along with the Sikorsky twins, whatever their name is.
Dennis Leary
The Sikorsky Twins.
Conan O'Brien
No, but I. It's so. So it's interesting to me that you see that happening. You start this group, and then you start getting up on stage.
Dennis Leary
Well, to be fair, though, I. The group was started by me and a. And a bunch of other friends of mine at the time. Yeah, we. Because we couldn't. The. The juniors and seniors would get the acting roles, rightfully so before they graduated. You had to wait in line. There was a seniority system. Everybody had to play a major lead role in a play or a musical before you left the school to get your degree. Cause it was acting and writing. Right. So when we got there, we were like, we're never gonna get on stage. Then we found out you can get money from the student government to form a theater group. We were all comedy nerds. We loved snl, which is the beginning of SNL at that time. And Python, Pryor, Carlin. We all loved those shows, like the Mary Tyler Moore. All those funny women on the Mary Tyler Moore Show. It was. So a bunch of us formed the group, and it was packed with talent. Lauren Dombrowski was my girlfriend at the time. Ended up being one of the producers of MADtv. Mario Cantone was in the original group, who's just, like. Who was as funny at that time when we were 18 years old as he is now. There were so many talented people in that era. And then there was a couple of guys later in the Comedy Workshop who ended up writing on the Simpsons. John Frink.
Conan O'Brien
Yep. Yep, I know John Frink. He was hilarious.
Dennis Leary
And at my generation, after I left the Comedy Workshop, then there was David Cross and, I mean, Laura Kightlinger. I mean, it was an insane amount of talent at that school, and still
Conan O'Brien
is, I have to say. I'm often back there in Boston. A lot of my, you know, siblings live around the area. And so I find myself in Boston a lot, and I'm always talking to people who are really sharp, really funny. And then it turns out they're Emerson. Yeah, yeah, yeah, Emerson. There's something in the water at Emerson. So many great people have come from there.
Dennis Leary
Well, it's just. It's the type of kids. It's the theater kids from high school, the funny kids from high school, the best dancers, the filmmaker. Those are the kind of kids who go to a school like Emerson. So that's like. It's more. You're fighting people more like yourself.
Conan O'Brien
Yeah.
Dennis Leary
You know, like in high school, I was really funny. You know, I. I wasn't going to make it as a hockey player, but I was really funny in the back of the class, right? And then I was trying to make my friends laugh, but I didn't think that that was going to turn into something. But here we are. You're covering up pools. I'm your guest. You own a building. You own a fucking building.
Conan O'Brien
I own a building.
Dennis Leary
I had nuns who told me. I had one Spanish nun, and she was right in her way. I flunked Spanish twice in high school. She's like, I'm just going to give you. You a passing grade to get you out of the building, Leary. And she was like, what are you gonna do with yourself? What's gonna happen to you? You're not gonna go anywhere. Hey, Sister Judith Kapman. That was her name. Sister Judith Kapan.
Matt Gourley
No free rides.
Dennis Leary
Yeah, no free rides.
Conan O'Brien
Don't mention her, right? Somewhere right now, Gene Simmons is going like, why did he mention. Why should she get a free ride? She's a Catholic nun who's probably deaf. Why should she get a free ride?
Dennis Leary
Listen, she has to be dead. She has to be dead. She was, like, 90 then.
Conan O'Brien
You say it like someone who hired three hitmen. No, she has to be dead. I've hired the best.
Dennis Leary
But Conan, seven times. You know, that That's. That really is the same nuns and the same priests for 12 years. There are nuns where I'm like, is she dead? She's gotta be dead, right? She's gotta be dead.
Conan O'Brien
That's not a good sentence. She has to be dead. She has to be.
Dennis Leary
How could she still be alive?
Conan O'Brien
No one survives.
Dennis Leary
We put her in a barrel with some cement blocks and we dropped her in the Mystic River. How is she alive? We drove her to Charlestown, threw her off the bridge.
Conan O'Brien
And she. Know what it reminds me of in the first. In the Godfather, the first one. The first Godfather. When Sollozzo finds out that the Don is still alive, they shot him. And he goes, he's still alive. He's still alive. That's bad news for me and worse for you if you can't make this deal, Tom. But I always. I always. That always is like a. It's a thing in my brain. Still alive.
Dennis Leary
Yeah.
Conan O'Brien
And that's what you're. Somebody, they're gonna come and tell you. No, no, she's around. She's 150, still alive.
Dennis Leary
Well, I'll tell you, there was one great nun there, and that was the theater nun at St. Peter's I love a theater nun. She put me in place.
Conan O'Brien
Yeah.
Dennis Leary
And I loved it. Cause the hottest girls were in the place. And eventually, like, my brother and all the jocks were like, yeah, we want to be in the place, too, now and hold the girls and everything.
Conan O'Brien
Everything.
Dennis Leary
But she.
Sonam Vaidya
She hold the girl.
Conan O'Brien
Yeah.
Dennis Leary
Because.
Conan O'Brien
Hey, are there any good holding plays? How much holding is there in Othello? That's how they rank the plays.
Dennis Leary
No, because she would tell you, like, grab her by the. The bosom and by the rump and lift her up for the dance numbers. Right?
Conan O'Brien
I want that part.
Dennis Leary
Yeah. I told my brother and those guys. They were like, what do you mean, you get to grab? I'm like, yeah, that. Anyways, Bill Murray told me the same story.
Conan O'Brien
Whole acting philosophy around as much grabbing as possible.
Dennis Leary
So Bill Murray said, I heard him tell the same story one time, and he was at a Catholic school, and a nun made him be in the. In a musical, right? And he went in, and it was the Hottest Girls. And he was like, what is this? Anyways, that nun, Sister Rosemary Sullivan, at St. Peter's and I wasn't a great student. She said, listen, I can. I. I took a night class at Emerson. I have connections there. You just audition, you do a written essay, and then you do, like, a live audition, and you can get a scholarship. And that's how I got the scholarship at Emerson. She got me the audition. So that's how I got into Emerson. It changed my life. And I stayed friends with her till she died. She followed my career. She was a great nun, but there was a lot of nuns that I literally still think, like, she can't. Is she alive? Is she out there? Because they were so fucking mean. They were like. They were like, just like a cult of angry fucking women who just hated fucking kids.
Conan O'Brien
Okay? That's all the time we have. I hate.
Dennis Leary
You could hit you.
Conan O'Brien
This microphone isn't working. I can't even my microphone.
Dennis Leary
He's still afraid.
Conan O'Brien
I'm terrified. Nuns at the Cynical when they wear the habit.
Dennis Leary
Oh, my God.
Conan O'Brien
I mean, the thing is, you have to remember, there's the habit, which is black. They're like. It's like, you know, it's a Marvel Universe villain.
Dennis Leary
No, no, no. They were literally villains. Like, this girl. You weren't allowed to have pierced ears. And this girl showed up with pierced ear right at the beginning of after the summer. And we were, you know, you're changing classes, you're all in the hallway. And we heard this scream. And this nun had torn this girl's earrings out of her ear. So she's bleeding.
Sonam Vaidya
Oh, my God.
Dennis Leary
And. And threw the things down and gave her detention. We're like, this is crazy. And they used to grab the girls and hit them on the back of the legs and grab them and measure their skirts. But they could hit you in. Like when you went home and said, ma, I got hit by Sister Judith Kapman.
Conan O'Brien
What'd you do?
Dennis Leary
What'd you do?
Conan O'Brien
Yeah, what'd you do?
Dennis Leary
What did you do? Sure, you had it coming, which. But most of the time I did have it coming, but I'm just saying they didn't. They hit you. Sometimes they hit you just because they could.
Conan O'Brien
To be fair, your skirt was the proper length.
Dennis Leary
I want.
Conan O'Brien
I got to make sure I mention, oh, my God, this show going Dutch, which you've been working on.
Dennis Leary
In my defense, I was wearing the skirt because David Bowie was so fucking good.
Conan O'Brien
He was huge. And I had a crush on this girl. Conan.
Dennis Leary
Yes.
Conan O'Brien
Going Dutch. You know, I just. Cause one of the writers who's helping me out, Skyler, is a fantastic writer, and he's been working for you. And he worked on the show. And I said, how is it? And he said, oh, it's in Ireland. And I said, you're shooting it in Ireland, which is not where the show takes place.
Dennis Leary
No.
Conan O'Brien
But it's fascinating to me that. Yeah, that's where so much production is done now.
Dennis Leary
Yeah, well, we're shooting there because the show is set. It's based on a real army base that was in the Netherlands that got shut down.
Conan O'Brien
It's a funny idea. Yeah.
Dennis Leary
It's because of black market get. You know, drugs are legal, sex is legal, prostitution is legal. In. In.
Conan O'Brien
You've been sent to the least necessary base.
Dennis Leary
Now that base in real life is closed down. Right. So we're telling the story. Our military advisor was at that base. But Ireland matches the Netherlands in terms of landscape Right. And we have villages where we can shoot. So we were. We shot it in Ireland, so we didn't have to deal with the military or anybody in. In Amsterdam in terms of what we were gonna do. But my son developed that project, and he's the executive producer. So it's the first time I'm like, my son is my boss. But what is that? Which is bizarre.
Conan O'Brien
What is that like, your son telling you? Let's try it again.
Dennis Leary
It's interesting. Cause we do a lot of improv, Right. It's great writing. And the showrunner is on set, Joel Church Cooper. He's the guy who did Brockmire with Hank Azaria. He's a brilliant writer. And some of the writers are on set, and. And their pages are great. So we do the pages, but then we always improvise from that. And sometimes he comes in in the morning and goes, forget the pages. I changed my mind. Or we come in and go, hey, what if we did? So there's a lot of improvisation. So my son has a great sense of humor, and I trust him. He developed the material with Joel. He'll just come in like anybody else and go, dad, that sucked. You guys were great. Dennis, you were terrible. Let's do something else. You try something else. You guys do what you were doing. Or he'll come in and go, hey, Dennis. That was funny, you guys. That was great. So it's like, I'm just another guy on the set. I happen to, you know. And he's. You see my son, he's huge.
Conan O'Brien
He was. He was backstage.
Dennis Leary
Yeah. He produced. He produces the concerts.
Conan O'Brien
Yeah, he was backstage at the Cannameali thing.
Dennis Leary
It's funny because I have to. I've been looking up to him since he was, like, 14, but he's 6 7, my son. So it's like when I. When I'm. When he goes like, hey, that wasn't very funny, Dennis. I'm like, okay, Jack. But he's got a great sense of humor. My son is really funny.
Conan O'Brien
He puts. When I met him, he put his plate on top of the.
Dennis Leary
Yeah, he did. It's so funny because.
Conan O'Brien
Having a beautiful Caesar salad.
Dennis Leary
Because my son's name is Jack, and he's 6 7. And Cam Neely's son is also named Jack, and he's like, six six. So the two of us are, like, you know, looking up at them. It's so. I think we have a psychological advantage, but neither one of us wants to find out if we would actually win in a fight.
Conan O'Brien
Yeah, don't get into that.
Dennis Leary
Not getting into that.
Conan O'Brien
Listen, I wish we could do this all day because this is not. You know, I always say about the podcast, this is not work. I don't know what this is, but it is not work. And then there are days like today where it's just. I mean, you and I can finish each other's sentences. So I dedicate this episode to the Learys in Worcester. The Reardons in Worcester. O'. Brien. Scattered all around Massachusetts like a disease. O'. Leary's.
Dennis Leary
We found out when we were at Comics Come Home. Cause one of my sisters was there. Like, I think we chased it down. Somebody chased it down to a Reardon or a Daily. There was a Daily on your.
Conan O'Brien
See, I don't know. I've never quite figured out what our connection is. Is a Reardon. We're all related somehow.
Dennis Leary
Your mother was a Reardon.
Conan O'Brien
Right. We all come from that same green rock.
Dennis Leary
Yeah, we all look the same. Yeah, you guys look alike. I know. Look at my legs. Start here. But I think it was that there's dailies reardance on your mother's. Yeah, yeah. So I think there's dailies in the Reardon side. And those dailies came out of Cork, which is where the Larrys were, and went into Kerry, and one of them ended up in Killarney. So that's where I think it all connects up. So that Daily was involved.
Conan O'Brien
But some people think, oh, so you and Dennis used to see each other at Christmas and stuff growing up? It's like, no, we didn't find out the way. Sona and I are cousins. Yeah, please.
Sonam Vaidya
I know.
Conan O'Brien
I'm so armo. You have no idea.
Sonam Vaidya
Not a fiber.
Dennis Leary
Well, listen, you gotta just tell you something about purebreds like us.
Sonam Vaidya
Yeah, tell me.
Dennis Leary
Okay. We can't go out in the sun, right? And don't put too much spice in the spaghetti.
Conan O'Brien
Don't put any.
Dennis Leary
Don't put any. Don't put any.
Conan O'Brien
Don't put any.
Dennis Leary
You know what? Let us boil it.
Conan O'Brien
Yeah, we'll take care of it.
Dennis Leary
And we don't have drinking problems. No, we don't. We do not.
Sonam Vaidya
You just drink lots of beer.
Dennis Leary
We drink all this, which is. Beer is non alcoholic, non alcohol.
Conan O'Brien
There's no alcohol in beer.
Dennis Leary
There's no alcohol in beer or Guinness.
Conan O'Brien
Jesus.
Dennis Leary
What's wrong?
Conan O'Brien
Well, you gotta come back because this was really fun.
Dennis Leary
Yeah.
Conan O'Brien
And I had a like. Hey, watch the language. I'm trying to reach.
Dennis Leary
I didn't say motherfucker one fucking time.
Conan O'Brien
You know what?
Dennis Leary
God bless you and I didn't say cocksucker.
Conan O'Brien
Somewhere some dead nuns are very proud of you.
Dennis Leary
Murdered nuns?
Conan O'Brien
Yeah, ones that started their car at the wrong time.
Dennis Leary
Their car climbing out of the coffins.
Conan O'Brien
There's no way she's alive. Not after what I've done.
Dennis Leary
She can't be alive.
Conan O'Brien
All right, Dennis, Go with God. We'll see you later.
Matt Gourley
Conan o' Brien Needs a Friend With Conan o' Brien, Sonam of Session and Matt Gourley Produced by me, Matt Gourley Executive produced by Adam Sachs, Jeff Ross and Nick Leow. Theme song by the White Stripes Incidental music by Jimmy Vivian. Take it away, Jimmy. Our supervising producer is Aaron Blair and our associate talent producer is Jennifer. Samples, engineering and mixing by Eduardo Perez and Brendan Burns. Additional production support by Mars Melnick. Talent booking by Paula Davis, Gina Bautista and Brit Kahn. You can rate and review this show on Apple Podcasts and you might find your review read on a future episode. Got a question for Conan? Call the TeamCoco hotline at 669-587-2847 and leave a message. It too could be featured on a future episode. You can also get three free months of SiriusXM when you sign up@siriusxm.com Conan and if you haven't already, please subscribe to Conan O' Brien needs a friend wherever Fine podcasts are downloaded.
Conan O'Brien
Prime. One day delivery is fast.
Dennis Leary
How fast we talking?
Conan O'Brien
We're talking yoga mats and fitness trackers delivered so fast you can kick off your routine tomorrow. Fast. We're talking weights at your door without really waiting. Fast. Water bottles and hydration backpacks. Fast and fast. Resistance bands faster than you can say feel the burn. Fast.
Matt Gourley
More jump ropes.
Conan O'Brien
Just a hop, skip and a jump away.
Dennis Leary
AKA Fast. Whew.
Matt Gourley
That was actually, actually a good workout.
Dennis Leary
Fast.
Conan O'Brien
Fast. One day delivery for all things fitness. It's on Prime. Quick. Choose a meal deal with McValue. The $5 McChicken meal deal, the $6 McDouble meal deal, or the new $7 Daily Double meal deal, each with its own small fries, drink and Four Piece McNuggets. There's actually no rush. I'm just excited for McDonald's for a limited time only. Prices and participation may vary not by hypothetical.
Dennis Leary
McDelry.
Podcast: Conan O’Brien Needs A Friend
Episode: Denis Leary
Release Date: February 23, 2026
Host: Conan O'Brien
Guests: Denis Leary, Sona Movsesian, Matt Gourley
In this hilarious, boisterous episode, Conan welcomes comedian and actor Denis Leary—a self-proclaimed cousin, fellow Massachusetts native, and longtime fan. Their conversation dives into the peculiarities of Irish-American upbringing, the legendary Boston comedy scene, family dynamics, culinary nightmares, and the ongoing rituals of Catholic school survivors. The chemistry between Leary and Conan (with constant ribbing from Sona and Matt), turns nostalgic family stories and local color into rapid-fire, profane stand-up.
On being pale:
"We are not even white. ...It’s like translucent. ...People have used me in mines to get copper out." — Conan O'Brien [13:01–13:12]
On Irish food:
"My brother ended up marrying an Italian girl... She was Irish cook... I remember Don Gavin, the comedian from Boston... He was eating my mother’s food, and my brother turned to me and said, ‘This tastes like shit.’ I went, ‘You can taste it?’" — Denis Leary [37:59]
On charitable acts and authenticity:
"He was so nice to everybody. And then he was a complete asshole later on." — Denis Leary [17:45]
On Catholic school trauma:
"They were like a cult of angry fucking women who just hated fucking kids." — Denis Leary [63:04]
On generational comedy talent:
"In college, Stephen Wright was the shyest human being on the planet... when he started doing standup... [it] was one of the reasons I got into it." — Denis Leary [52:13]
The tone is candid, abrasive, and peppered with expletives, yet always affectionate. The banter is relentlessly self-mocking, much of it rooted in shared trauma (Catholic school), family foibles, and the strange pride of being Irish-American in Massachusetts. Denis and Conan’s rapport is unmistakable—interwoven with years of inside jokes, shared roots, and mutual roastings.
This episode is a must-listen (or read) for anyone nostalgic for 20th-century New England, Irish-American quirks, or the war stories of comedians who survived Boston’s legendary scene. The testimony to family, pain, food, humor, and generational confusion is both personal and universal—a freewheeling Irish wake with a laugh every minute.