South Beach Sessions - Jon Cryer

The Dan Le Batard Show with Stugotz

Meadowlark Media

Sports

4.7 • 32.4K Ratings

🗓️ 28 August 2025

⏱️ 66 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

"You're always sure that another shoe's gonna drop and this is all gonna go away..." A teenage icon turned struggling actor to Emmy Award-winning sitcom star, Jon Cryer has seen every side of Hollywood and made an impact most couldn't even dream of. Jon tells Dan what it was like growing up in a showbiz family and how he experienced fame early in his career with "Pretty in Pink", being associated with the Brat Pack, and performing on Broadway as a teenager. He also explains the unique disappointment that comes with working on a failing TV show or a movie that bombs... to the then life-altering popularity of "Two and a Half Men", how he's moved on since it ended, and why he's still not ready to reconnect with Charlie Sheen. Listen to the true crime podcast, "The Man Who Calculated Death", available on the Wondery app or wherever you get your podcasts. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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	...

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