Charlie Sheen Shares Update on His Relationship With Jon Cryer After ‘Two and a Half Men’ Breakdown

Charlie Sheen has opened up about where things currently stand between him and his former co-star Jon Cryer after their time on Two and a Half Men.

In an interview with PEOPLE, published April 24, Sheen said he has not spoken to Cryer since the release of the 2025 documentary aka Charlie Sheen, even though Cryer appeared in it alongside other people from Sheen’s past.

Sheen explained that he has thought about reaching out, but has not followed through. “I don’t like to bother people,” he said. He added that he often tells himself he will contact Cryer, but never actually does.

Even so, Sheen said he believes Cryer would be open to reconnecting. He also spoke positively about his former co-star, describing him as talented and kind. “Jon’s a lovely man and a very talented guy,” Sheen said.

Sheen also expressed appreciation that Cryer took part in the documentary, along with other cast members and people from different parts of his life. He said he was thankful that so many people were willing to speak on camera rather than refuse to revisit the past.

However, their relationship has been strained for years. Cryer has said publicly that he and Sheen do not have a current relationship. In past interviews, Cryer explained that tensions grew after Sheen was fired from the sitcom in 2011.

At the time of Sheen’s exit, he publicly criticized Cryer during a difficult period in his life, which added to the fallout between them. The show continued for several more seasons without Sheen, with new cast changes introduced after his departure.

Cryer has since said he wishes Sheen well and has acknowledged hearing positive updates about his sobriety.

Despite the history between them, Sheen recently suggested there is no strong anger on his side today. He also joked during a panel discussion that Cryer still seems somewhat distant, even if he would like to reset things.

This is a classic case of a long-running Hollywood fallout where time has softened the tone, but not fully repaired the relationship. It sounds like there is no active conflict anymore, just distance. What do you think about this situation? Should former co-stars try to reconnect after so many years, or is it better to leave the past alone? Share your thoughts in the comments.