Charlie Sheen Explains Why He Didn’t Call Jon Cryer Directly
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Charlie Sheen has been making headlines again, this time for his new Netflix documentary, aka Charlie Sheen . While the film dives into his rollercoaster of a career and personal struggles, one detail caught people’s attention: Jon Cryer, Sheen’s long-time co-star on Two and a Half Men , appeared in the documentary, but Sheen himself admitted he never actually called Cryer to invite him.
Sheen explained that the only reason he didn’t reach out personally was because he simply didn’t have Jon’s current phone number. Instead, the documentary’s director, Andrew Renzi, was the one who contacted Cryer. After seeing what Cryer shared in the film—comments that Sheen described as both “honest” and “compassionate”—Sheen said he wrote to him afterward to express his gratitude and apologize for not making the connection directly. The catch? Sheen suspects that even that message might have been sent to the wrong number. He joked that if Jon happened to be reading the coverage, he should “DM his new number.”
What makes this story resonate is the history between the two actors. On-screen, they played brothers—Charlie Harper and Alan Harper—on one of the most successful sitcoms of the 2000s. Off-screen, though, things became more complicated. Sheen’s very public battles with addiction, along with clashes with CBS, Warner Bros., and co-creator Chuck Lorre, led to his firing from the show in 2011. Ashton Kutcher was eventually brought in as a replacement, but by then the series had already been reshaped by the fallout.
In the documentary, Cryer reflected on what those years were like and suggested that Sheen’s struggles may have been fueled by deep self-doubt and a lack of confidence. Surprisingly, Sheen didn’t push back against that assessment. Instead, he praised Cryer’s perspective, calling it “really insightful” and admitting it made him stop and think. He even described the experience as if he’d suddenly found himself in a therapy session with his former co-star.
Sheen went on to open up about how he had always carried a sense of not fully deserving his success. With no formal education or training—he didn’t even finish high school—he found himself suddenly thrust into stardom. That rapid rise left him feeling like it could all vanish at any moment, which added to the self-destructive voice inside his head.
Hearing Cryer articulate that struggle out loud seems to have hit a nerve. For Sheen, it was a reminder not just of their time working side by side, but of how his actions affected those around him—friends, colleagues, even family. Whether this will lead to a genuine reconnection between the two remains to be seen, but it’s clear Sheen values Cryer’s contribution, both to the show that defined much of their careers and to this new chapter of reflection.
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