Jon Cryer sheds more light on her troubled relationship with her ex Two and a Half Men the costar Charlie Sheen.
It appears Watching On Friday, May 1, Cryer, 61, reflected on her “complicated” work with Sheen as she talked about taking part in the 2025 Netflix documentary, Charlie Sheen.
“It was fun,” Cryer said of the performance Watching. “I had a lot of mixed feelings about being a part of that because he's obviously a weird guy and we had a complicated relationship.”
Cryer explained that she had issues with Sheen, 60, as he “went off track” during his battle with addiction, but then realized that he was too frustrated with the public to cheer for the troubled actor's downfall. (Sheen was eventually fired from the sitcom in 2011 after a series of public meltdowns and was replaced by Ashton Kutcher for the remaining seasons.)
“Most of the time I realized I wasn't angry anymore; I was still angry at America,” Cryer explained of his decision to be a part of Sheen's documentary.
He continued, “I knew him as a friend, as a colleague, so it was really painful to see all that and see that madness and see so many people enjoying it.
In a documentary released in September 2025, Cryer was candid when talking about his experience working on it. Two and a Half Men and Sheen while i Platoon The best biographical dramas began to dominate 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 middle of breaking up every way I can think of and negotiating his contract for another year of the show I'm supposed to be on. Apparently they had sold a few more seasons of the show. It was worth spending this amount of money on Charlie,” Cryer recalled in the documentary.
I She's pretty in Pink the star added, “[Charlie’s] conversations were off the charts because his life was falling apart. I, who was well off at the time, got a third of that.”
Emma McIntyre/Getty Images; Amanda Edwards/Getty Images Two and a Half Men creator Chuck Lorre and Charlie Sheen's longtime feud is finally over. In a Wednesday, November 1, interview with Variety, Lorre, 71, recalled reaching out to Sheen's lawyer after “thinking. [Sheen was] in a good place” and “arriving at this place there [the feud is] the old one […]
Responding to Cryer's comments in the documentary, Sheen praised his costaar for his “insight” and “compassion.”
“It was really nice to hear his perspective. He was in the line of fire with all this stupid stuff that was going on, and it was affecting him and his family and his career and all that. I'm not going to argue with anything he said,” Sheen said. People in September 2025.
The actor added, “He nailed that, and I'm so glad you opened that door, because it gave me a chance to start thinking about that. He said, 'He's a man who doesn't believe he deserves the things he has, or that he's earned it,' and I said, 'Wow.'
