Charlie Sheen Bets On Himself And Keeps WINNING!

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October 2, 2025 • 60 mins

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. Prime Members, shop deals up to 40% off this Prime Big Deal Days, October 7th and 8th! To learn more about listener data and our privacy practices visit: https://www.audacyinc.com/privacy-policy Learn more about your ad choices. Visit https://podcastchoices.com/adchoices

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.css-14f5ked{margin:0;word-break:break-word;display:-webkit-box;-webkit-box-orient:vertical;box-orient:vertical;-webkit-line-clamp:2;overflow:hidden;}Charlie Sheen Bets On Himself And Keeps WINNING!