Fly on the Wall with Dana Carvey and David Spade

Episode: Denis Leary: Conan’s Comedy Cousin
Date: February 26, 2026
Guest: Denis Leary

Episode Overview

In this episode, Dana Carvey and David Spade are joined by legendary comedian, actor, and writer Denis Leary. The trio delves into Leary’s long-spanning career, the vibrant Boston comedy scene, their Irish roots (and how Denis is related to Conan O’Brien), stand-up rituals, showbiz changes, and memorable stories from sitcoms, movies, and voice work. The conversation is loose, hilarious, and full of old-school comedy camaraderie, giving listeners a "fly on the wall" viewpoint of how comedians see their journey, their influences, and the shifting state of the entertainment industry.

Key Discussion Points & Insights

1. Denis Leary’s Comedy Roots and Boston Scene

[06:38–11:42]

• Boston Comedy Influences: Denis and Dana reminisce on Boston’s comedy legacy—names like Stephen Wright (the “start of it all”), Paula Poundstone, and Bobcat Goldthwait, all representing a unique, sometimes “angry” style.
  • Denis: “There was a lot of anger in Bobcat’s act.” [08:35]
• Tough Beginnings: Denis describes being broke, starting out in Boston in the '80s, performing at clubs run by the Clark family, and bombing repeatedly before finding his comedic style.
• First Breakthrough Joke: Denis recalls the Emerson Comedy Workshop at college and creating a character—an “angry guy who smoked”—which became his onstage persona.
  • “If I could buy a pack of tits, I would.” [16:57] (his first big laugh)

2. The Showbiz Climb and Keeping It Going

[13:45–17:30 | 26:40–29:02]

• The hosts and Denis discuss the journey from beginner panic to career stability.
• Charity Performances: Denis talks about performing annually at large gig fundraisers, and managing nerves as a veteran.
  • “At the ages that we’re at...it’s not panic. It’s like, can’t wait to get up there.” [11:55]
• Longevity: The trio reflects on the privilege—and luck—of still working decades into their careers.
  • “How about that? All three of us are still working.” [26:30]

3. Smoking On and Off Stage

[21:06–25:02]

• Leary’s Smoking Habit: Denis confirms he was a heavy smoker for 52 years (“I just quit four years ago”), initially using the cigarette as a part of his stage act, eventually quitting both on and off stage.
  • David: “And you smoked on stage?” Denis: “Carnegie Hall, Mayor Bloomberg’s office...I smoked everywhere.” [21:33]
  • Denis on his health: “I don’t know what to say, but you have— it’s like you never smoked.” [24:20]
• Quitting Mechanism: Denis shares that both booze and cigarettes left his life in a similarly abrupt fashion: “I just have one of those addictive personalities that at a certain point, my brain goes, we don’t need these things anymore.” [24:01]

4. Family, Irish Heritage & the Conan Connection

[27:34–30:36]

• Related to Conan O’Brien: Denis confirms “Conan’s my cousin! Did you guys know that?” [27:37] and discusses the general height and look in his Irish family.
• Irish Stereotypes: Joking about the meaning of their last names in Gaelic (“Leary” means “calf keeper” [30:27], “Carvey” as “rough or rugged” [30:14]), and poking fun at their shared rugged roots.

5. Never Hosting SNL, and Career Choices

[31:00–33:07]

• Denis never auditioned or hosted SNL, even when asked in '92/'93 at the height of his fame: “I had too much respect for what you guys were doing…” [31:28]
  • He shares how grueling the host week is and why he turned it down.

6. Animation Experiences: From Bug’s Life to Ice Age

[33:30–36:06]

• Bug’s Life and Ice Age: Denis contrasts experiences with animation studios, comparing pay and workload. Announces “Ice Age 6 is coming out next year.” [34:05]
  • “We got bumps for all of them...they can see how much these movies are streamed now.” [34:31]

7. Streaming vs. Theaters: The New Hollywood

[36:06–41:16]

• They openly dissect the death of “mid-range” movies, threats and opportunities from streaming, and how even family comedies and character-driven dramas get squeezed by blockbusters.
  • Denis: “You want to be streaming...more people will see your movie on a Friday night than will see it if you ran it in theaters combined.” [37:14]
• Cultural Changes: How live sports dominate TV, and the timeless magic of the movie theater experience versus phones and multitasking at home.
• Pet Peeves: Denis rails against watching classics like ‘Goodfellas’ on an iPhone: “I mean, what are you wearing— Apocalypse Now on your iPad?!” [39:44]

8. TV and Shooting Abroad

[47:03–51:07]

• New Show – Going Dutch: Denis stars in “Going Dutch,” filmed in Ireland but set on a real U.S. military base in the Netherlands. The show’s premise blends absurd reality with comedy.
  • “It became a den…for illegal drugs—can’t blame them.” [50:04]
• Why Shoot in Ireland?: Cost, tax breaks, and a booming local film industry: “…hundreds of Americans fly to Ireland…and it’s still exponentially cheaper than Hollywood.” [51:19]

9. Adam Sandler’s Respect & Film Criticism

[52:16–53:41]

• The trio laments how critics underappreciated Adam Sandler and “Grown Ups” films despite fan popularity.
  • Denis: “Now...he’s turned into a great actor and he can make big funny movies.” [53:05]
• Denis also reflects on starting as a theater actor, then learning film acting “on the fly” alongside stars like Stallone.

10. Demolition Man & Hollywood Stories

[54:40–58:04]

• Demolition Man Anecdotes: Denis shares stories of working with Stallone and Sandra Bullock.
  • On Stallone: “He was the nicest guy...Sly, he was hitting golf balls so hard, he busted a net.” [55:49, 57:03]
  • “Three week vacation where I got paid because Stallone was trying to kill the golf ball.” [57:55]

11. On Success, Fame, and Phil Hartman

[58:55–62:51]

• Denis discusses the surreal moment he “made it”—going from broke to “0 to 60” when the scripts and deals came rolling in.
  • “We had a lot of money all of a sudden from having nothing.” [60:38]
• Phil Hartman Memories: Deep affection for Hartman on the set of Small Soldiers; “He was making me laugh so hard…the director would go, you guys have to leave and act to a tennis ball.” [61:33]
  • On Phil’s ‘Unfrozen Caveman Lawyer’: “Once I told him that was my favorite guy, he would just break that guy out on set.” [62:19]

Notable Quotes & Memorable Moments

• Denis Leary:
  • “Because he’s Irish and he’s my cousin. Did you guys know that?” (on Conan O'Brien, [27:37])
  • On smoking: “I smoked everywhere. I smoked in Mayor Bloomberg’s office in New York City while he was the mayor. He was the complete anti-smoking guy.” [21:33]
  • “I just gave up on the idea of quitting, so...I finished the cigarette. And I went, man, that’s it.” [23:46]
• Dana Carvey:
  • “You only are your digital copy…there’s no macro or truth of exactly how you look.” [25:21]
  • On the meaning of Irish surnames: “In Gaelic, O’Garbian means rough or rugged. That’s a miss. That fits.” [30:14]
• David Spade:
  • “All three of us are still working. How about that?” [26:40]
  • “Who’s gonna go to the theater? Who are they gonna go see? Tom Cruise, right? Still apparently. Fucking big Marvel movies, which are again…on the wane as well.” [37:40]
  • On podcast banter: “But if Dana is a good talker, hysterical, and then we just said, maybe we should try something like this…” [44:40]
• On Adam Sandler:
  • “Now the last laugh is on them because he’s turned into a great actor and can make big, funny movies.” (Denis, [53:05])
• On Phil Hartman:
  • “He made me laugh so hard as you guys do.” (Denis, [62:51])

Timestamps of Key Segments

• Boston Comedy Beginnings: [06:38–11:42]
• First Big Joke / Onstage Persona: [15:44–17:30]
• Smoking & Quitting: [21:06–25:02]
• Conan’s Cousin & Irish Heritage: [27:34–30:36]
• Animation (Bug’s Life, Ice Age): [33:30–36:06]
• Streaming vs Theaters: [36:06–41:16]
• Filming in Ireland (Going Dutch): [47:03–51:07]
• Adam Sandler & Grown Ups Cheer: [52:16–53:41]
• Demolition Man / Stallone Stories: [54:40–58:04]
• Success, Fame, and Phil Hartman: [58:55–62:51]

The Fly on the Wall Podcast Vibe

The episode is marked by quick-fire anecdotes, friendly teasing, and reflective humor on the absurd world of showbiz. The trio’s natural chemistry, shaped by decades on the comedy circuit, produces constant laughs and candid confessions. From sharing veteran advice about nerves and success to musing on movies, podcasting, and family, listeners are treated to not just stories, but also a genuine feel for the unpolished side of comedy life.