Denis Leary: Conan’s Comedy Cousin

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About this episode Dennis Leary discusses his enduring career, the transition of the Boston comedy scene, and his recent projects… AI summary

Dennis Leary discusses his enduring career, the transition of the Boston comedy scene, and his recent projects including 'Going Dutch' and 'Ice Age 6'. He shares personal anecdotes about quitting smoking due to genetic luck, his early struggles in stand-up, and industry insights regarding streaming vs. theatrical releases.

Key takeaways 5
  • The Boston comedy scene of the 80s/90s was characterized by a mix of 'angry' comedians (Leary, Bobcat Goldthwait) and unique styles (Stephen Wright, Paula Poundstone), often performed in rough venues like Lenny Clark's club.
  • Leary's comedic persona as an angry smoker was partly a character developed in college at Emerson University, which he later adopted for stand-up, though he quit smoking 4 years ago due to a sudden realization rather than a planned effort.
  • The film industry has shifted heavily toward streaming; Leary notes that low-budget films struggle in theaters against blockbusters and that tax incentives make locations like Ireland and Boston attractive for production compared to LA.
  • Leary experienced a rapid financial shift from having no money/credit cards to earning significant paychecks quickly after his role in 'The Sandlot' led to opportunities with Disney/Touchstone and films like 'The Ref' and 'Demolition Man'.
  • Leary attributes his good health despite a history of heavy smoking to genetic luck, citing his mother's longevity (died at 98) versus his father's early death (60) despite smoking.
Notable quotes 4 AI-generated: wording and quote attribution may be wrong. Use the play link to verify.
  • “I got my mother's insides and my dad's outsides, I think.”
    ▶ 20:23 Leary explaining his genetic luck regarding health and aging, contrasting his mother who never smoked/drank with his father who smoked heavily.
  • “I just finished the cigarette and I thought that's it. And I thought that's weird that I said that to myself and I had a full pack. So I'm like I'm going to smoke again tomorrow. I woke up in the morning. I threw that pack away. [__] never smoked again.”
    Leary describing the sudden moment he quit smoking after 52 years, contrasting it with his planned quitting of alcohol.
  • “Those [__] ripped you off. They rap me. Can you say [__]? Yeah, you can say anything. Don't No, but you can say rap. Drive me nuts.”
    ▶ 0:42 Leary joking about his low pay for voice acting in Disney's 'The Emperor's New Groove' compared to the massive profits the film made.
  • “I was fresh off the [__] tree... I go to first day on Demolition Man... Sly is in his demolition man outfit... driving both [__] slicing again... He's like, 'Hey, Dennis... You wanna hit some balls? Get some lessons? This guy's with me all the time.'”
    Leary recounting meeting Sylvester Stallone on the set of 'Demolition Man', highlighting Stallone's dedication to golf even during filming.

Chapters & Sections (45)

0:00 New Season of Scrubs and Denis Leary's Career chapter 3
0:00 New Season of the TV Show Scrubs Announced
1:17 Comedian Denis Leary's Career and Projects
2:38 Home Studio Setup and Remote Work Challenges
4:54 Boston Comedy Scene in the 80s chapter 2
4:54 Boston Comedy Scene in the 80s
7:14 Comedy Career and Influences Discussed
9:10 The Challenges of Performing in Massachusetts chapter 3
9:10 Kennedy Family Politics in Massachusetts
10:51 Overcoming Stage Fright and Performance Anxiety
12:03 Early Days of Standup Comedy Experience
13:53 Comedy Origins and Early Career Development chapter 3
13:53 Development of Stand-up Comedy Style
15:39 Scrubs Revival and New Season Details
17:10 The Art of Smoking as a Comedic Device
19:43 Genetic Luck and Aging Perception chapter 3
19:43 Genetic Luck and Aging Perception
21:20 Maintaining a Long-Term Career in Comedy
22:36 Family Ties and Physical Characteristics
24:17 The Evolution of Podcast Consumption Habits chapter 2
24:17 The Art of Podcast Consumption and Engagement
26:01 Saturday Night Live and Standup Comedy
28:33 Redoing Scripts and Animation in Movies chapter 4
28:33 Redone Scripts and Animation in Movies
30:22 Film Negotiations and Production Deals
31:42 The Decline of Traditional Movie Theaters
33:33 The Decline of Movie Theater Experience
36:11 Alternative Awards Show Commentary Concept chapter 3
36:11 Alternative Awards Show Commentary Concept
37:53 Licensing and Clearing TV Shows for Streaming
39:40 The Evolution of Podcasting as a Comedy Format
41:23 New Season of the TV Show Scrubs Announced chapter 2
41:23 New Season of the TV Show Scrubs Announced
44:14 Benefits of Online Shopping for Home Goods
45:48 Comedy Sketch about Bizarre Negotiation Tactics chapter 3
45:48 Comedy Sketch about Negotiation and Escalation
47:43 Filming in Ireland vs. the Netherlands
49:10 Film Production Costs and Tax Incentives
50:58 Early Career Experiences in Hollywood chapter 6
50:58 Career Reflections on Early Film Reviews
52:42 Behind the Scenes of Demolition Man Filming
55:37 Comedy Sketch Writing and Improvisation Techniques
57:10 Breaking into Hollywood with Early Success
58:32 Working with Comedy Heroes and Improvisation
1:00:01 Favorite Comedy Moments and Collaborations

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