Jon Cryer recently addressed a potential reunion with his former Two and a Half Men co-star Charlie Sheen on live TV. The Emmy-winning actor was asked point-blank about the possibility of working with his former co-star again. Cryer, known for his role as the neurotic yet lovable Alan Harper, didn’t dodge it, offering a measured, gracious response.
Jon Cryer answers if he’ll work with Charlie Sheen again
Jon Cryer has opened up about the possibility of working with Charlie Sheen again.
The rift between Jon Cryer and Charlie Sheen started in 2011 after Sheen was dismissed from Two and a Half Men. Amid Sheen’s public struggles with drug addiction, he lashed out at Cryer, labeling him a “turncoat, traitor, and troll” for not contacting him. Cryer largely kept silent during the fallout, but the dispute ended both their professional partnership and personal friendship.
During his recent appearance on Live with Kelly & Mark on May 25, 2026, host Kelly Ripa raised the topic of Cryer’s appearance in the new Charlie Sheen documentary. That prompted her next question: “Have you spoken to him since?”
“No, we haven’t,” he replied, before adding, “There’s nothing contentious. There’s no ill will between him and me at all.”
Cryer noted that while he and Sheen haven’t spoken directly, the Red Dawn actor did reach out with a message thanking him for taking part in the Netflix documentary, aka CHARLIE SHEEN.
However, addressing the question fans have asked for years about whether he will ever reunite with Charlie Sheen, Cryer quipped, “You just have to think… how much Charlie Sheenness do you want in your life?”
Jon Cryer hinted that a long-term professional reunion is unlikely. “When things go great for him is when he burns it all down,” the 61-year-old hesitantly added. However, for a one-off, Cryer said he’d be open to working with Sheen again.
The Extended Family actor went on to clarify that there’s no lingering animosity. “I think the world of him,” he said. Cryer added that he’s genuinely happy to see Charlie Sheen making better choices and prioritizing his health.
Originally reported by Sibanee Gogoi on ComingSoon.
