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.”