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South Beach Sessions with Dan Le Batard

Jon Cryer

South Beach Sessions with Dan Le Batard

Meadowlark Media

Society & Culture, Sports, Comedy

4.915K Ratings

🗓️ 28 August 2025

⏱️ 65 minutes

🧾️ 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 D Beach Sessions.

0:29.0

We're out on the West Coast, and we are with someone who's been a TV sitcom star.

0:34.4

You were a bit of a child prodigy, practically born on off-Broadway, right? Born off-Broadway?

0:42.2

Now that you mention it, yes. I've rarely been referred to as a prodigy. I tend to think of like

0:46.7

Mozart. That's my level of prodigy. Not quite at Mozart just just yet. Fair enough. But knew you were

0:56.4

going to be on my way. John Pryor is what I should have said. I'm sorry, I haven't actually said

1:00.6

your name. There we go. Because you objected immediately the prodigy. But you were going to be

1:06.1

an actor from the very beginning. Yes. You had no choice. I had no choice. Yeah, no.

1:11.6

My parents were performers.

1:13.6

My mother's also a writer and composer.

1:16.6

And so I grew up kind of backstage and in it, you know.

1:20.6

I actually had a weird thing recently.

1:22.6

You're a paid professional.

1:23.6

I'm going to put the microphone in front of you.

1:26.6

Don't make love to the microphone.

1:28.3

Okay.

1:29.3

So I recently had an odd situation where a friend of mine recommended a memoir of an

1:38.3

kind of an avant-garde producer from the 60s, 70s, and 80s, a guy named Albert Poland.

1:45.0

It's called Stages is the memoir.

1:46.9

And he said, you've got to read this because your parents are all over it.

1:49.7

I was like, I'm sorry?

1:51.5

And it turns out my parents, obviously being very active in off-Broadway and some amount of avant-garde stuff at the time.

...

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