The Sentimental Message Charlie Sheen Sent Two And A Half Men Co-Star Jon Cryer For Appearing In His Netflix Documentary

Charlie Harper (Charlie Sheen) and Alan Harper (Jon Cryer) talk in bed on Two and a Half Men
(Image credit: Two and a Half Men)

Charlie Sheen has been reflective as of late, and he’s baring all in a documentary, which is a major release on Netflix’s 2025 release schedule. Directed by Andrew Renzi, the two-part aka Charlie Sheen sees the titular star discussing his professional and personal highs and lows, and it features interviews from major stars. Two and a Half Men co-lead, Jon Cryer, is even featured in the doc, and Sheen just revealed the warm message he sent his former co-star after he participated in the project.

For eight years, Charlie Sheen and Jon Cryer entertained the masses as brothers Charlie and Alan Harper on Chuck Lorre’s hit CBS sitcom Two and a Half Men. The two actors’ relationship took a serious turn, however, due to Sheen’s downward spiral in 2011. Sheen has been candid about the damage that’s been done to his relationship with Cryer, expressing regrets for how the situation played out. While discussing his doc and memoir with People, Sheen recalled reaching out to Cryer after watching him in the doc:

The only person I didn't call personally to participate in the doc was Jon. And the only reason I didn't call him was because I didn't have the right number for him, so the director reached out to him. But when I saw everything that Jon spoke about, so honestly and very compassionately, I wrote to him and I said, 'Hey, thank you for your contributions, and I'm sorry we didn't connect personally. I hope to see you around the campus.'

Charlie Sheen’s message is major, considering the drama that unfolded in 2011. Amid his issues with alcohol and drugs, Sheen made disparaging remarks against Chuck Lorre. Jon Cryer didn’t publicly comment on the situation, leading to Sheen calling him out and referring to him as a “a turncoat, a traitor, a troll” while speaking to E! News at the time. Sheen later changed his tune, as he spoke highly of Cryer as a collaborator. During his recent interview, Sheen reflected on that tumultuous time in his life and how Cryer was impacted:

It was really cool to hear from his perspective. He was in the line of fire with all that stupid shit going on, and it was affecting him and his family and his career and all that. I can't debate anything that he said.

Even before appearing in his colleague’s Netflix documentary, Jon Cryer discussed his relationship with Charlie Sheen on a few occasions over the years. Cryer revealed that he and Sheen had a solid working relationship on Two and a Half Men (which is streamable with a Peacock subscription) and hung out occasionally off set. However, they “split off’ a bit due to Sheen’s growing drug habit. Now, Sheen is clean and sober, though, and it sounds like he wouldn’t mind hearing from Cryer:

I'm thinking I wrote to the wrong number. It's not like Jon did not respond. He's super responsible like that. So if you're reading this, Jon, DM me your new number!

Jon Cryer previously discussed the possibility of once again working with Charlie Sheen and Chuck Lorre, who mended fences while working on the show Bookie. On the whole, Cryer didn’t seem to totally shut down the possibility of joining forces with his Men collaborators again, but he also said he was unsure as to how Sheen was doing from a personal standpoint. Even if they don’t work together again, as it stands, there still seems to be a solid level of respect between Sheen and Cryer.

Fans can see Jon Cryer – along with Denise Richards, Chuck Lorre, Chris Tucker and more – get candid on aka Charlie Sheen, which will be available for Netflix subscription holders starting on September 10.

Erik Swann
Senior Content Producer

Erik Swann is a Senior Content Producer at CinemaBlend. He began working with the publication in 2020 when he was hired as Weekend Editor. Today, he continues to write, edit and handle social media responsibilities over the weekend. On weekdays, he also writes TV and movie-related news and helps out with editing and social media as needed. He graduated from the University of Maryland, where he received a degree in Broadcast Journalism. After shifting into multi-platform journalism, he started working as a freelance writer and editor before joining CB. Covers superheroes, sci-fi, comedy, and almost anything else in film and TV. He eats more pizza than the Teenage Mutant Ninja Turtles.

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