Podcast Summary: Fly on the Wall with Dana Carvey and David Spade

Episode: Billy Crudup on Working with Adam Sandler & George Clooney + Theater Horror Stories
Date: December 4, 2025

Episode Overview

This episode features acclaimed actor Billy Crudup, known for his roles in The Morning Show, Without Limits, and the new film J. Kelly alongside Adam Sandler and George Clooney. With hosts Dana Carvey and David Spade, the conversation dives deep into Billy’s acting journey, behind-the-scenes stories from stage and screen, athletic movie roles, and the philosophical reflections on fame, mentorship, and the nature of showbiz. The episode also touches on Billy’s upcoming stage role in High Noon in London.

Key Discussion Points & Insights

1. The Origins and Oddities of Theater Life

• [03:00] Billy shares early theater experiences, including a panic-inducing moment where he forgot his lines during a one-man show:

  “I called for line and we didn’t have any system in place for line.” – Billy Crudup [10:43]

• The trio riff on the vulnerability and unpredictability of live performance, and why audiences remember debacles.

  “Audience would never forget it, though. I’d actually rather see a debacle.” – Dana Carvey [11:32]

• Billy discusses the physical and mental toll of theater, including naked stage appearances for little pay (“$225 a week” [08:04]) and the confusion of multi-role performances.

2. The Morning Show and Building a TV Character

• [19:38] Discussion pivots to The Morning Show; Billy describes the process of revisiting the same character season after season, which is rare in his career.

  “To return to this guy where they keep writing weird for me to do has been... really fun.” – Billy Crudup [19:48]

• The hosts praise Billy’s electrifying, “alpha male” performance:

  “We were reintroduced to you by that season and that arc and that character... you were just sort of in the pocket.” – Dana Carvey [20:35]

• Billy reflects on channeling “room readers” he observed at NYC galas for his role, delivering monologues that reflect real-life power dynamics:

  “It's just riddled with dudes who are room readers looking for the power. They talk fast, they think fast, they’re very proud of themselves. They’ve never failed before…” [21:23]

3. Fame, Ambition, and the American Dream in J. Kelly

• [36:54] Focus on J. Kelly (directed by Noah Baumbach), starring George Clooney and Adam Sandler.

  “There’s something just gorgeous about George playing that character... Adam is his agent in it and is absolutely spectacular.” – Billy Crudup [37:37]

• They discuss the film’s premise: a famous actor reflecting on the life he missed while chasing career ambitions, and American cultural ideas of success.

  “Most of the lives that people lead are normal and they are fine, but they're not gilded... while you’re waiting for your great life to start, you miss your life.” – Billy Crudup [39:02]

• The conversation highlights the contrast between real life and social media curation:

  “Everyone seems to be better looking than they are... Everyone's on a yacht and they're all curating their lives.” – Dana Carvey [41:24]

• Memorable scene: Clooney’s character has to confront whether anything he’s achieved professionally can make up for what he’s lost personally.

  “But all of this, everything that I've done, all these movies that I've made... it must be worth something. And she's like, ‘but what if it isn't?’" – Billy Crudup [42:49]

4. Sports, Athletic Roles & Without Limits

• [25:25] Dana, a self-described track and field nerd, is excited to discuss Without Limits, where Billy played legendary distance runner Steve Prefontaine.
• Billy explains his athletic upbringing, intense research, and physical training to portray Pre:

  “We spent about six weeks training out here. And the guy ran in a kind of specific way... He liked to run with guts.” [29:46] “Middle distance runners... are running like four minute mile pace. For anybody else, it’s a full sprint.” [30:19]

• The hosts acknowledge the movie’s enduring appeal among runners and sports fans.

5. Mentorship and Navigating Showbiz

• Adam Sandler’s mentorship is discussed, with Billy noting how crucial supportive figures are in an often competitive business:

  “Very few do you see, like, some mentorship... but tells the story of you to people who want to hire you.” [51:22]

• They reflect on how rare—and important—it is to find genuine support in entertainment.

6. Upcoming Stage Role: High Noon in London

• [54:10] Billy is gearing up to play the Gary Cooper role in a new stage adaptation of High Noon, written by Eric Roth. He shares the process of adapting film to stage, learning from classic Westerns, and building a physically and psychologically authentic sheriff.

  “I play the Gary Cooper part... watching a lot of Westerns now. They're actually great to revisit.” [56:39]

• Challenges include minimal dialogue and bringing a gunfight to the stage:

  “He’s known as a guy of few words on stage. That doesn't really translate, you know.” [58:03] “So what they've done... they've given him like an internal monologue where he gets to speak to the audience.” [59:14]

Notable Quotes & Memorable Moments

• On stage horror stories & vulnerability:

  “I started to have a full-blown panic attack. You get tunnel vision. My heart’s coming out of my chest... I called for line and we didn’t have any system in place.” – Billy Crudup [10:12]

• On the American myth of endless opportunity:

  “Most lives that people lead are normal and fine, but they’re not gilded. So while you’re waiting for your great life to start, you miss your life.” – Billy Crudup [39:02]

• On Clooney’s real-life persona:

  “Clooney is phenomenal. He has the most brilliant stories. He is incredibly generous, really gregarious... He talks about his career with a level of humility that is unusual.” – Billy Crudup [45:33, 46:42]

• On mentorship in the biz:

  “Very few do you see like some mentorship... not only makes you feel good about it, but tells the story of you to people who want to hire you.” – Billy Crudup [51:22]

• On the paradox of social media fame:

  “Everyone's a star... Everyone seems to be better looking than they are... Everyone's on a yacht and they're all curating their lives.” – Dana Carvey [41:24]

Timestamps for Important Segments

• 03:00-11:30 – Theater horror stories and line-forgetting disaster
• 19:38-24:54 – The Morning Show deep dive: Billy’s character, writing, and real-life inspirations
• 25:25-34:02 – Sports, Without Limits, and the Pre interview
• 36:54-43:03 – J. Kelly: working with Clooney & Sandler, American ambition
• 54:10-62:21 – New play: High Noon in London, blending film and live stage
• 45:33-47:58 – George Clooney stories: humility, longevity, and modesty

Final Thoughts

Billy Crudup proves to be a thoughtful, funny, and candid guest, giving listeners a behind-the-scenes look into both the highs and pitfalls of an actor’s journey—from stage fright to star turns with Hollywood royalty. The episode is a blend of sharp industry observations, affectionate ribbing, and nostalgia, complemented by Dana and David’s signature comic banter—a must-listen for fans of acting, comedy, and showbiz storytelling.