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. 

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Charlie Sheen Bets On Himself And Keeps WINNING!

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