Jon Cryer

Le Batard & Friends - South Beach Sessions

Dan Le Batard, Stugotz

Sports, Society & Culture, Tv & Film, Comedy Interviews, Comedy

4.9 • 15K Ratings

🗓️ 28 August 2025

⏱️ 64 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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0:00.0	You're listening to Draft Kings Network.
0:11.0	Look, every football game is a grind, and if you're like Dan and the crew, you know there's no such thing as one size fits all.
0:17.9	Your sleep should be just as custom as coach's game plan. That's where sleep number
0:22.4	comes in. You get to call your own plays. Softer, firmer, cooler, cooler, warmer, your side, your comfort,
0:27.6	change it whenever you want. No more feeling stuck like a busted play. And for all the late night
0:32.4	fights over the thermostat, climate series cools up 20 times faster than the competition.
0:37.4	True temp betting kicks heat
0:38.7	and humidity to the sidelines so you can actually stay chill all night long. Bottom line,
0:44.0	sleep number is like having a sleep coach in your corner, adjusting to you all night because
0:48.2	your best game starts with the right rest. Why choose a sleep number smart bed? So you can sleep
0:52.8	just the way that you like.
0:58.6	The only bed that lets you make each side firmer or softer whenever you like.
1:00.0	Your sleep number setting.
1:02.5	Sleep number's biggest sale of the year is here.
1:03.6	All beds on sale.
1:06.5	Up to 50% off the limited edition smart bed.
1:07.5	Limited time.
1:10.0	Exclusively at a sleep number store near you.
1:13.0	Sleep number, official sleep and wellness partner of the NFL.
1:15.7	See store or sleepnumber.com for details. Thank you. Welcome to South Beach Sessions.
1:34.4	We're out on the West Coast, and we are with someone who's been a TV sitcom star.
1:40.4	You were a bit of a child prodigy, practically born on off-Broadway, right? Born off-Broadway?
	...

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