RE-RELEASE - Charlie Sheen
- Sep 16, 2026
- 56:26
- Full Episode
Dana and David welcome Charlie Sheen (and brother Emilio Estevez briefly). Charlie relives sitting shoulder-to-shoulder at Canelo vs. Crawford with David (and living to tell it), deconstructs the origin story of his most famous catchphrases, and shares what it was like growing up alongside Rob Lowe and Sean Penn. Charlie breaks down the legendary 10–90 deal where he bet on himself and WON, the blockbuster roles he passed on, his surprising memorabilia obsession, and the moment he was convinced Tom Cruise was Latin.
On Audacy’s Fly on the Wall, Saturday Night Live stars Dana Carvey and David Spade take listeners behind the scenes and reminisce about their favorite SNL moments, memories, and sketches with special guests.
Listen free: Apple: link.pscrb.fm/f0281/flyonthewallseriesapple-27cc3 Spotify: link.pscrb.fm/f0281/flyonthewallseriesspotify-e5650
Brief Summary
Charlie Sheen discusses his career, famous quotes, and relationships with actors in a humorous conversation with Dana Carvey and David Spade.
Key points
- Charlie Sheen's Comeback. Charlie Sheen reflects on his career and the chaos that followed his rise to fame.
- The Origin of Winning. Sheen reveals the unexpected source of his famous 'winning' catchphrase.
- A Surprising Collaboration. A potential show with Charlie Sheen fizzled out amidst chaos.
- Negotiating Fame. A candid discussion about the challenges of fame and negotiating contracts.
- The Moment of Wealth. A nostalgic recount of the first feeling of wealth after an acting paycheck.
- Turning Down Major Roles. Revealing the surprising films he turned down, including 'White Men Can't Jump'.
Episode highlights
- The Origin of WinningSheen reveals the unexpected source of his famous 'winning' catchphrase.“It was borrowed material, inserted into my brain.”9:53Sep 16, 2026
- A Surprising CollaborationA potential show with Charlie Sheen fizzled out amidst chaos.“Isn't Charlie a little bit in the dog house?”14:28Sep 16, 2026
- Negotiating FameA candid discussion about the challenges of fame and negotiating contracts.“I was trying to negotiate my way out of it.”18:45Sep 16, 2026
- The Moment of WealthA nostalgic recount of the first feeling of wealth after an acting paycheck.“In that moment, I felt, okay, all right, this is I'm feeling like a big shot.”22:26Sep 16, 2026
- Turning Down Major RolesRevealing the surprising films he turned down, including 'White Men Can't Jump'.“I turned down White Men Can't Jump.”27:38Sep 16, 2026
- The Influence of TalentReflecting on the exceptional talent of peers in the industry.“You become an audience member and then wait but you're in the scene.”31:36Sep 16, 2026
- Musical InspirationsDiscussing musical influences and preferences in rock and roll.“Who's your north star?”35:59Sep 16, 2026
- Elvis Auction MemoriesA nostalgic discussion about collectibles, including a famous Elvis green AMX.“Wow. I said, 'I think Charlie Sheen got it.'”37:50Sep 16, 2026





