Two and a Half Men: Why Jon Cryer Called His Charlie Sheen Relationship “Complicated”

Jon Cryer is opening up about his relationship with former Two and a Half Men co-star Charlie Sheen. During a May 2026 appearance on The View, Cryer spoke about being part of Sheen’s 2025 Netflix documentary, aka Charlie Sheen, and admitted their bond has never been simple.

“It was interesting. I had a lot of mixed feelings about being a part of it because, obviously, he’s a very complicated guy and we had a complicated relationship,” he said.

Cryer also shared that his feelings toward Sheen have changed over the years. He explained that he no longer feels angry at his former co-star despite their past issues.

His comments came shortly after Sheen revealed that the two have not reconnected since the documentary’s release. “Every time this comes up, I say I’m going to [reach out to him], and I never do,” Sheen told People, while also describing Cryer as a lovely and talented man.

What Happened Between Jon Cryer and Charlie Sheen?

Jon Cryer and Charlie Sheen became fan favorites while playing brothers Alan and Charlie Harper on Two and a Half Men for eight seasons. But their off-screen relationship later turned difficult after Sheen’s controversial departure from the hit sitcom.

Sheen was fired from the show in 2011 after publicly criticizing creator Chuck Lorre. Soon after, he also targeted Cryer, calling him a “troll” and “turncoat.”

“When I’m starring in multimillion-dollar films and he’s begging me for a supporting role I’ll say, ‘You left me out in the cold with all of your guilt and stupidity,‘” Sheen told E! News.

Despite the harsh comments, Cryer later said he was more worried about Sheen’s health than the insults. “Mostly I was worried that Charlie was going to die. That was the big fear for me,” he shared during an appearance on The Ellen DeGeneres Show (via TODAY). He added,

I will accept an apology both public and private. But again, it was in the heat of the moment I imagine when he said… so I did not put a whole lot of credence in it at the time.

In 2024, Cryer admitted on The View that he still cares about Sheen but is unsure about working closely with him again. Meanwhile, Sheen has repaired his relationship with Chuck Lorre and even appeared briefly in Lorre’s HBO series Bookie.

Jon Cryer Denies Any Feud With Charlie Sheen

Jon Cryer has denied reports that he is still feuding with former Two and a Half Men co-star Charlie Sheen. During his appearance on The View, Cryer explained that he no longer has any personal issues with Sheen and also criticized the way the media handled Sheen’s public struggles.

“I was still kind of mad at America,” he explained, adding, “Because when he went off the rails and went crazy, a lot of people seemed to enjoy that.”

The Extended Family actor admitted it was difficult watching his friend go through such a public downfall. “So that’s part of why I kind of wanted to, obviously, say my side of the story,” he said while discussing his decision to appear in Sheen’s documentary.

Cryer also made it clear that he is open to reconnecting with Sheen in the future. “I mean, it’s funny because every now and then an article comes out that we’re arguing and it’s just not the case,” he clarified, suggesting that both actors have largely moved on from their past disagreements.

What do you think of Charlie Sheen and Jon Cryer’s relationship? Share your thoughts with us in the comments below.

Two and a Half Men is streaming on Peacock.