Jon Cryer is shedding more light into his troubled relationship with his former Two and a Half Men costar Charlie Sheen.
Appearing on The View on Friday, May 1, Cryer, 61, reflected on his “complicated” dynamic with Sheen as he spoke about taking part in the 2025 Netflix documentary, aka Charlie Sheen.
“It was interesting,” Cryer said during his appearance on The View. “I had a lot of mixed feelings about being a part of that because obviously he’s a very complicated guy and we had a complicated relationship.”
Cryer explained that he had his issues with Sheen, 60, as he went “off the rails” during a highly publicized battle with addiction, but then realized he was more frustrated at the public for reveling in the troubled actor’s downfall. (Sheen was ultimately fired from the sitcom in 2011 after a series of public melt downs and replaced with Ashton Kutcher for the remaining seasons.)
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“Mostly I realized that I wasn’t mad at him anymore; I was still kind of mad at America,” Cryer explained of his decision to take part in Sheen’s documentary.
He continued, “I knew him as a friend, as a coworker, so it was really painful to see all that and see that craziness and see a lot of people enjoying it. So that’s part of why I kind of wanted to, obviously, say my side of the story.”
In the documentary released in September 2025, Cryer was incredibly candid while speaking about his experience working on Two and a Half Men with Sheen while the Platoon actor’s spiraling personal life dramas began to eclipse the show.
Charlie Sheen and Jon Cryer in Two and a Half Men. (Photo by Greg Gayne/CBS via Getty Images)“He’s in the midst of falling apart in every way I can imagine and he’s renegotiating his contract for another year of a show I am supposed to be on too. Apparently they had pre-sold a couple of extra seasons of the show. It was worth their while to spend this astonishing amount of money on Charlie,” Cryer recalled on the documentary.
The Pretty in Pink star added, “[Charlie’s] negotiations went off the charts because his life was falling apart. Me, whose life was pretty good at that time, I got a third of that.”
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In response to Cryer’s comments in the documentary, Sheen praised his costar for being “really insightful” and “compassionate.”
“It was really cool to hear from his perspective. He was in the line of fire with all that stupid s*** going on, and it was affecting him and his family and his career and all that. I can’t debate anything that he said,” Sheen told People in September 2025.
The actor added, “He nailed that, and I’m so glad he opened that door, because it gave me a chance to really start thinking about that. He said, ‘He’s a guy that doesn’t believe he deserves the things he has, or that it was he earned,’ and I was like, ‘Whoa.’”
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