Posted in: CBS, TV | Tagged: Bill Maher, Club Random, jon cryer, Two And A Half Men

Two and a Half Men: Cryer, Sheen "Don't Have a Relationship Anymore"

Two and a Half Men star Jon Cryer on what led to Charlie Sheen's firing, Sheen's reboot pitch, and the chances of working together again.

No one can ever deny Jon Cryer's longevity in Hollywood, but despite his lasting cultural impact as Ducky in the John Hughes classic Pretty in Pink, Lenny in Superman IV: The Quest for Peace (1987), Arrowverse's Lex Luthor, his latest series Extended Family or the 70+ other titles he's been in, the question always lurks with his Hot Shots! (1991) and Two and a Half Men co-star Charlie Sheen. While promoting his podcast, The Man Who Calculated Death, the actor appeared on Bill Maher's self-described non-political podcast, Club Random, to break down his life and career, especially their disagreements about what went wrong in the 2024 election.

Two and a Half Men Star Jon Cryer on What Led to Charlie Sheen's Exit

The discussion begins at the one hour, 15-minute mark when Maher bluntly asks, "What's your relationship with Charlie now?" Cryer responded with, "I don't know. We don't have a relationship anymore" while acknowledging that Two and a Half Men creator Chuck Lorre and Sheen have since reconciled with the actor's appearances on his Max sports comedy series Bookie.

Cryer said that Sheen's meltdown was primarily linked to him breaking his sobriety as an addict, which in part was due to his failing marriage. "Yeah and he was proud of his sobriety, incredibly charming, smart, and great at what he does. He's absolutely a wonderful comedian, gifted with his timing. I loved working with him. We had a great time. You know, after his marriage went south with Denise [Richards], clearly he was using again. On the show, he was still very professional, he was good to work with, but what happened was: that he started to have these things happen. He got arrested at the Plaza Hotel for trashing the room. He got arrested in Colorado for fighting with his wife. I don't know what happened."

Cryer affirmed Sheen's sobriety during TAAHM's early seasons when the Real Time host pressed him. Maher admitted he was shocked that Sheen was still getting offers like the Super Bowl ad during his series meltdown. "Because oddly, [Charlie] has a brand. He has the brand that's him, and that's one of the reasons why Trump gets away with what he gets away with…with Charlie, what happened with the show was he fell off the wagon, and they were doing all these kinds of things to sort work around it," Cryer explained. "He was missing days on the set. He would still show up on Friday night; he knew his lines, he was ready to go, and he could do the show, but he was barely functioning. Chuck, who's been very upfront about his own struggles with alcohol, was confronting him and saying, 'You need help. You have to do something.' Charlie said, 'No, I don't.'"

When Maher asked if Cryer sees himself reuniting with Sheen, the actor recalled the awkward time when Sheen pitched A Two and a Half Men reboot after the original series run wrapped with Ashton Kutcher. When Cryer turned Sheen's offer down, that was when Sheen summarily threw his co-star under the bus on social media, which dissolved their friendship. "I wish him nothing but the best; I won't do anything regularly with him. If it was a one-off, sure." Maher is convinced the "magic will come back" and things will be back to normal like Lorre patched things with Sheen since money would be the driving force. For more, you can check out the interview below.

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