Jon Cryer reflects on his 'painful' experience with 'Two and a Half Men' costar Charlie Sheen

Jon Cryer has broken his silence on his past relationship with his former Two and a Half Men co-star Charlie Sheen.

On the Friday, May 1 episode of The View, Cryer showed up to promote his role in the off-Broadway revival of The 25th Annual Putnam County Spelling Bee.

During the conversation, the 61-year-old American actor was asked to share his thoughts about Sheen’s documentary and the extent of his participation in it.

Sharing his thoughts about the project, he said, "It was interesting. 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. But mostly I realized that I wasn’t mad at him anymore: I was still kind of mad at America."

Cryer admitted that it was “painful” to see him going “off the rails” and “crazy,” as “a lot of people seemed to enjoy that.”

The Pretty in Pink star knows Sheen as a “friend, as a coworker,” and that is why he became part of his documentary. Also, he wanted to tell his side of the story.

“And everybody came out of the woodwork in that documentary to tell a lot of very truthful, tough things about Charlie. And I thought, ‘Well okay, if the time is to be honest, let’s be honest,’” Cryer noted.

He went on to sing praises of the team as they “did a great job,” trying to show "a lot of who he is.”

"He did text me afterward at one point to say ‘Thanks for doing it,'" Jon Cryer revealed.

It is pertinent to mention that aka Charlie Sheen, which was released on September 10, 2025, is available on Netflix.