Charlie Sheen Has a Message for His Former “Two and a Half Men” Costar Jon Cryer… (Exclusive)

NEED TO KNOW

  • Charlie Sheen says he still regrets how Two and a Half Men ended in 2011, amidst his spiraling addiction issues

  • He’s now telling all in a new memoir and documentary, and he told PEOPLE he hopes to get in touch with Jon Cryer someday

  • He notes that Cryer was incredibly compassionate and insightful in his reflections on Sheen

For eight years, between 2003 and 2011, the sitcom Two and a Half Men starring Charlie Sheen and Jon Cryer was one of the biggest shows on television — but production had to be halted in 2011 after Sheen’s drug addiction spiraled, and the network eventually decided to fire him. (He was replaced by Ashton Kutcher, and the show continued for three more seasons.)

Now, Sheen, who turned 60 on Sept. 3 and has been sober for eight years, is looking back at those tumultuous times in both a memoir (The Book of Sheen, out Sept. 9) and the Netflix documentary (aka Charlie Sheen, streaming Sept. 10). In the new PEOPLE cover story, he shares how grateful he is for Cryer’s compassion in the documentary.

E.J. Camp/CBS via Getty 'Two and a Half Men' stars (from left) Charlie Sheen, Angus T. Jones and Jon Cryer.

E.J. Camp/CBS via Getty

‘Two and a Half Men’ stars (from left) Charlie Sheen, Angus T. Jones and Jon Cryer.

“The only person I didn’t call personally to participate in the doc was Jon,” Sheen says. (The two-part series also features Sheen’s ex-wives Denise Richards and Brooke Mueller, and longtime friends Sean Penn and family members as well as Cryer and their Two and a Half Men creator Chuck Lorre.)

“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.’ “

Sheen says he hasn’t heard back, which isn’t like his former costar. “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!”

Cliff Watts Charlie Sheen reveals all in the latest PEOPLE cover story.

Cliff Watts

Charlie Sheen reveals all in the latest PEOPLE cover story.

Sheen says he understands that Cryer, 60, had reason to be upset with him for letting his past addiction issues derail the trajectory of their hit show.

“It was really cool to hear from his perspective,” Sheen says of everything Cryer talks about in the doc. “He was in the line of fire with all that stupid s— going on, and it was affecting him and his family and his career and all that. I can’t debate anything that he said.”

Warner Bros Tv/Chuck Lorre Prod/Kobal/Shutterstock Sheen (left) and Cryer on 'Two and a Half Men' in 2003.

Warner Bros Tv/Chuck Lorre Prod/Kobal/Shutterstock

Sheen (left) and Cryer on ‘Two and a Half Men’ in 2003.

Sheen was, however, surprised that Cryer suggested that Sheen’s addictions possibly stemmed from his inability to believe in himself.

“He nailed that, and I’m so glad he opened that door, because it gave me a chance to really start thinking about that,” Sheen says. “He said, ‘He’s a guy that doesn’t believe he deserves the things he has, or that it was he earned,’ and I was like, ‘Whoa.’ “

He continues, “Suddenly, I felt like I was on a couch in Jon’s therapy office, and he was dead on. That’s something that I’ve felt my whole life, because I had no formal training. I had no formal education, I didn’t even finish high school. And suddenly I’m working and traveling, I’m a star and all this stuff. It just happened. There was no plan. And there was always the voice of doubt there, telling me it’s only a matter of time before this all goes away, so to enjoy this as heartily as you can.”

“That was really insightful of Jon, really, and compassionate,” he adds.

Steve Granitz/WireImage Charlie Sheen and Jon Cryer at the 35th Annual People's Choice Awards in 2009.

Steve Granitz/WireImage

Charlie Sheen and Jon Cryer at the 35th Annual People’s Choice Awards in 2009.

As for fans begging for a Two and a Half Men reboot, in 2024 Cryer, said he didn’t think it would likely happen.

“When Two and a Half Men was happening, Charlie was, like, the highest-paid actor in television,” Cryer said on The View. “Yet, he blew it up, so you kind of have to think. I love him, I wish him the best, he should live in good health for the rest of his life, but I don’t know if I want to get in business with him for any length of time.”

While Sheen and Cryer have yet to publicly reconcile, Sheen has long since made amends with Two and a Half Men creator Chuck Lorre, with whom he worked again on the gambling drama Bookies. In 2011, Sheen publicly disparaged his former boss, something he says he still regrets to this day.

“We had a wonderful relationship for over eight years on Two and a Half Men. And then things happened,” Lorre told PEOPLE in 2024, referencing their public fallout and 12-year feud. “And so to find our way back to having that friendship again, and I’m a big admirer of his work, I always have been. It’s never been about the work. The work is impeccable.”

Now that he’s been sober for eight years, Sheen says his biggest remaining regret is how things ended the way they did on Two and a Half Men.

“I regret that specifically still,” he says. “I think if I hadn’t done what I had, I could be living a different life right now. All my problems wouldn’t be what they are. But you just don’t know that.”

One thing he does know is that he plans on remaining clean and sober. In the documentary, Cryer says he’s nervous to even talk about Sheen, in case things go sideways with him again.

“I think he’s justified to feel that way, because that’s kind of the historical pattern, but that’s not the case today,” Sheen says. He smiles and adds, “And I’m going to go out of my way to make him wrong every single day.”

Cliff Watts Charlie Sheen photographed at Image Locations house Beach 89 in Malibu, Calif., on Aug. 25, 2025.

Cliff Watts

Charlie Sheen photographed at Image Locations house Beach 89 in Malibu, Calif., on Aug. 25, 2025.

To read more about Charlie Sheen, pick up the latest issue of PEOPLE, on stands now.

Read the original article on People




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