Denis Leary - Conan O’Brien Needs A Friend

Denis Leary

Mon Feb 23 2026

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.

Transcript

Conan O'Brien (0:02)

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Dennis Leary (0:25)

Fools. Yeah. Fools.

Conan O'Brien (0:27)

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 (1:22)

Hi, my name is Dennis Leary, and I feel like I could give a fuck about being Conan o'.

Conan O'Brien (1:31)

Brie.

Dennis Leary (1:32)

Cause I'm already his fucking cousin.

Conan O'Brien (1:35)

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 (1:43)

Yeah.

Conan O'Brien (1:46)

Folly's here. Hear the yell back to school. Ring the bell Brand new shoes Walking

Dennis Leary (1:53)

loose Climb the fence Books and pens

Sonam Vaidya (1:57)

I can tell that we are gonna

Conan O'Brien (1:59)

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?

Summary

Podcast Summary

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

Episode Overview

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.

Key Discussion Points and Insights

1. Paper Chronicles & Podcast Rituals

Conan starts by riffing on the podcast ritual where guests announce their feelings about being Conan’s friend, noting how paper notes distract guests and even his team.
[03:03] The saga of noisy paper: Conan shares a mishap where, despite moving scripts to digital screens, Matt Gourley made distracting noise with his script during an interview with Kevin Nealon.
- "When I hear crinkle, crinkle, crinkle... And I look over and there’s Matt Verley. Crinkle." — Conan O'Brien [06:03]
Sona admits her own notes were mostly drawings of “dicks and butts.” [08:36]
The team jokingly recounts old podcast mishaps, poking fun at each other’s quirks.

2. Denis Leary on Podcast Fandom and Friendship

[10:22] Denis admits he doesn’t really listen to podcasts, but became a genuine fan because the show aired on the radio during his New York commutes.
- “I don’t really fucking listen to podcasts, okay?... 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.” — Denis Leary [11:13]
He delights in how much Sona and Matt roast Conan.

3. Boston, Family, and Irishness

[12:10] Both share battle stories of growing up “deathly pale” in Irish Catholic families in Worcester, MA.
- “We’re not just white. You are a deathly pallor, and I think I’m whiter than you. …We are literally walking lamps.” — Conan O'Brien [13:01–13:12]
Both compare Massachusetts’ unique flavor of Irishness, including “lace curtain” vs. “triple decker” Irish, and retell stories of their families’ absurd pride in local culture and sports.

4. Comics Come Home & Charity

[17:31] Denis highlights Conan’s appearance at his “Comics Come Home” charity event, raising funds for Cam Neely Foundation.
- “We knew he was gonna be funny on stage... He was so fucking nice to everybody... and then he was a complete asshole later on.” — Denis Leary [17:45]
- Conan sheepishly admits he managed to be nice for “like, nine minutes.” [18:16]

5. Worcester Life & Misadventures

The two reminisce about their Worcester upbringing: the local armory museum (“a hoarder’s attic of armor”), heroin epidemics, and the pride in having a minor league baseball team [25:57–27:03].
“It took us 150 years. The mill closed in like 1902.” — Conan O'Brien [26:59]

6. Family Dynamics: Cousins and Connections

[25:04] They trace their family trees, discovering tangled connections and the Worcester-centric worldview that shapes ambitions and expectations.

7. Food: The Horror of Irish-American Cuisine

[36:40] Both detail the notorious blandness of Irish food, tales of over-boiled vegetables, and fried ground beef as “spaghetti sauce.”
- “I keep waiting for the surgeon general to say, you know, fried ham with butter... lengthens your life—‘cause then I’d be in great shape.” — Conan O'Brien [36:53]
- Leary’s family used ketchup on pasta [39:15]; Conan recounts how his dietary rage peaked when he found no bacon at a California resort, leading him to “kick a tree outside.” [41:02]

8. Irish Drinking, Denial, and Catholic School

The segment is rich with memories of normalized Irish drinking culture (beer doesn’t “count”), endless family meals washed down with Guinness, and the distinct trauma of Catholic nuns wielding physical discipline.
- “He had 35 beers. He’s okay. He’s driving a school bus in the morning. He’ll be all right.” — Conan O'Brien [46:45]
Leary describes being consigned to his Aunt Betty (godmother) one summer—a childless, pious woman who forced daily Mass and Bible study, all while his siblings enjoyed freedom. [33:13]
Both recall Catholic school violence and the outrageous lengths of old-school nuns:
- “This nun had torn this girl’s earrings out of her ear. So she’s bleeding... And gave her detention.” — Denis Leary [63:27]

9. Boston Comedy, Emerson College, and Monty Python

[54:25] Conan and Denis discuss their comedy roots, with influences ranging from Monty Python (the “atomic bomb” of their comedic worldview) to George Carlin and SNL.
- “Monty Python just fucking made our heads explode.” — Denis Leary [55:31]
Leary details starting the Emerson College Comedy Workshop, which spawned many future comedy stars, and the surviving “abrasive” tone of Boston comics.

10. Show Business Now: 'Going Dutch' and Father-Son Dynamics

[64:19] Denis is currently starring in Going Dutch (shot in Ireland, “standing in” for the Netherlands), a unique show developed by his son, Jack Leary, who now serves as his boss.
- “My son has a great sense of humor... He’ll just come in like anybody else and go, ‘Dad, that sucked.’” — Denis Leary [65:41]

Notable Quotes & Memorable Moments

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]

Important Segments / Timestamps

[03:03] Conan’s vendetta against paper in the studio
[10:22] Denis confesses his podcast listening habits
[12:10] Discovery of Irish skin cancer and pale skin rivalry
[17:31] Comics Come Home charity—Conan’s charity gig recap
[25:04] Family roots and the shock of being related
[36:40] Deep dives into dire Irish-American cuisine and food culture
[46:28] Generational alcoholism: beer doesn’t count
[54:25] Boston comedy’s DNA; influence of Python, Carlin, SNL
[64:19] Leary discusses his show, 'Going Dutch', and working with his son

Tone and Style

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.

Final Notes

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.