RE-RELEASE - Charlie Sheen

Fly on the Wall with Dana Carvey and David Spade

  • 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'.

Tension

45/ 100Some tension

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