7 Takeaways From Jon Cryer’s Conversation on New Episode of ‘The Originals’ Podcast

A fresh episode of the LA Mag podcast is hosted by journalist Andrew Goldman each month
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The beloved star of Pretty In Pink and Two and a Half Men recently joined Andrew Goldman on Los Angeles’ podcast, “The Originals.” In the episode, titled, “Duckie’s straight, Molly! Sheen 2024?” the 56 year-old actor goes deep on Duckie, speculating about the character’s sexuality, his stalker-like tendencies, plus speculates on the reason co-stars Molly Ringwald and Andrew McCarthy were chilly to him on set. Plus, now ten years removed, Cryer looks back on the Charlie Sheen meltdown and discusses how it presaged the rise of Trump.

On his resemblance as a younger man to Pete Davidson. Yeah, we resemble each other quite a bit. That has been remarked upon in the past, actually by Pete Davidson himself. He told me when he first did stand up, he would come out on stage and say, ‘No, I’m not the gay guy from Two and a Half Men.’ He and I actually did a movie called Big Time Adolescence together, and he’s quite wonderful in it. But yeah, we’ve got a very similar vibe, but he’s taller than me and I don’t know that I have the famously big dick energy that he supposedly exudes.”

Cryer reacts to Andrew McCarthy once remarking that he was “just so needy” on the set of Pretty In Pink. Well, obviously he was needy. He was a guy with an alcohol problem at the time. And so we all need different things. But yeah, I could see people getting annoyed with me at the time. I was very out there, and I put it out there that I wanted to be friends with people and I wanted to socialize. I know that’s not cool for teenagers to do, or at least it wasn’t at the time. And it wasn’t where Andrew and Molly were.”

Neither Andrew McCarthy nor Molly Ringwald were particularly warm to Cryer on the set of Pretty In Pink. How Cryer’s life imitated Duckie’s on that set and has ever since. [On the set of Pretty In Pink] I do recall feeling like, ‘Wow, I’m making this movie. I’m one of the cool people.’ And then being there and going, ‘Oh, maybe I’m not one of the cool people.’ But that, by the way, that happens still. I still get gigs and I still have that moment in the lunch line where they fill my tray with food and then I look out and I go, ‘Where am I going to eat?’ I still have that. So that never goes away.

On the set of Two and a Half Men, Charlie Sheen would often show Cryer beaver shots of recent conquests. Cryer now regrets not responding differently. “Charlie would say, ‘I was out with a girl last night, let me show you a picture.’ And I expected a headshot, I did not expect the nether thing. And for God’s sake, I hope it was consensual, I hope she understood that she was giving a picture of that, because otherwise it was incredibly disgusting…In retrospect I should have said, ‘Hey man, not necessary. This is a workplace.’”

On his prediction in 2016 that electing Donald Trump president would be tantamount to electing Charlie Sheen. “Back when the Republicans still had a shot of picking somebody else, I went on a talk show and said, ‘Hey, it’s not a great idea to have a president who just says every stupid thing that comes into his head. Because I was just working with a guy who said every stupid thing that came into his head and it blew up in his face.’ And I stand by it. I called it back in the day.”

On how Charlie Sheen would have been a better president than Trump. “There’s zero doubt that Charlie Sheen would have been a better president than Donald Trump. Because Charlie does try to occasionally be internally consistent. Trump is a total narcissist who is situationally manipulative. He will go 180 degrees of whatever he’s saying if it suits him at the moment. Charlie, isn’t like that. Charlie is loyal, which Donald Trump clearly is not. Trump demands loyalty but gives none.”

On Charlie Sheen reaching out after the end of Two and a Half Men proposing to reunite on a new Harper brothers series. “Charlie gave kind of a perfunctory apology and said he wanted to start the show back again. And I said, ‘No.’ The problem with Charlie is that when things are going great, he blows it up. It’s a classic thing with people dealing with alcoholism. And so let’s say I did start doing the show with him again. God forbid it was successful.”

Jon Cryer can be seen playing Lex Luthor in Supergirl, which just wrapped. The entire series is available to stream on Netflix.

Listen to the new episode of The Originals podcast.