Charlie Sheen Bets On Himself And Keeps WINNING!

Fly on the Wall with Dana Carvey and David Spade

Dana Carvey, David Spade, & Audacy

Comedy, Comedy Interviews

4.7 • 11.6K Ratings

🗓️ 2 October 2025

⏱️ 60 minutes

🔗️ Recording | iTunes | RSS

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Summary

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

Transcript

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0:00.0	He came back talking about this guy named Tom Cruise.
0:03.7	Oh.
0:04.1	In my mind, I added a Z, and I thought he was Latin.
0:07.2	I thought he was a Mexican or Spaniard or something, right?
0:09.9	It was, it was, it was, it was, it was, it was, it was, warlock or bust.
0:13.4	Yeah.
0:14.7	And I said to Dave, I said, if that, if that breaks loose, we're clearly in the crush zone, right?
0:22.2	And I said, are you cool if I'm the last guy like on this planet that you interact with?
0:32.2	Charlie Sheen.
0:33.6	Charlie Sheen, the one and known.
0:35.1	Internationally known as God is my witness.
0:41.0	I don't know what that means.
0:42.3	You need a witness for that?
0:43.5	It's just a figure speech.
0:46.0	Charlie Sheen.
0:47.6	What a career.
0:49.3	Yeah.
0:51.2	Huge movies.
0:52.1	You were talking about his run of movies.
0:56.3	From 21 years old, I think he popped in into Ferris Bueller with a cameo, just a good-looking burnout dude. Did one scene and stood out.
1:04.2	Yeah. I think he stayed up all night for that to show that he was a guy that stayed up all night.
1:08.8	Yes. And when you're 19, you stay up all night.
	...

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