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Jon Cryer details ‘complicated’ past relationship with Charlie Sheen

May 1, 2026
in News
Jon Cryer details ‘complicated’ past relationship with Charlie Sheen

These days, Jon Cryer has somewhat of a winning relationship with his “Two and a Half Men” co-star Charlie Sheen.

Fourteen years after Sheen was fired from the beloved sitcom following severe addiction struggles, Cryer partook in the Netflix documentary “aka Charlie Sheen.”

“It was interesting,” the “Pretty in Pink” star mused about the September project while on “The View” Friday. “I had a lot of mixed feelings about being a part of that because obviously he’s a very complicated guy and we had a complicated relationship. But mostly I realized that I wasn’t mad at him anymore: I was still kind of mad at America.”

Sheen and Cryer starred on “Two and a Half Men” for eight seasons from 2003 to 2011.

Actor Jon Cryer discusses his
Jon Cryer (pictured here on Friday) called appearing in his “Two and a Half Men” co-star’s documentary, “aka Charlie Sheen, “interesting.” ABC/The View
Jon Cryer on The View.
Despite having “mixed feelings” about joining in on the project, the “Pretty in Pink” actor realized he wasn’t mad at Sheen anymore but was “kind of mad at America.” ABC/The View

At the time of the “Wall Street” star’s firing, Sheen suffered a series of public meltdowns and clashed with the show’s creator, Chuck Lorre.

Sheen also accused Cryer of being a “turncoat, a traitor, a troll”for not reaching out to him during his drug battle.

Ashton Kutcher replaced the “Major League” actor for the show’s final four seasons. The series ended in 2015.

However, Cryer now realizes that the public took pleasure when Sheen “went off the rails and went crazy.”

Charlie Sheen, Angus T. Jones, and Jon Cryer from the television show Two and a Half Men, posing in a promotional photo.
Cryer and Sheen starred on “Two and a Half Men” together for eight seasons from 2003 until the latter was fired in 2011 (as seen here on the show with co-star Angus T. Jones). CBS via Getty Images
Charlie Sheen (left) and Jon Cryer (right) sit on a couch in a scene from
Despite the show continuing without Sheen and instead with Ashton Kutcher, the Broadway performer realized that the public took pleasure when his former co-star (pictured here on the sitcom) “went off the rails and went crazy.” CBS via Getty Images

“I knew him as a friend, as a coworker, so it was really painful to see all that and see that craziness and see a lot of people enjoying it,” he continued while on the morning talk show. “So that’s part of why I kind of wanted to, obviously, say my side of the story.”

Cryer said that the documentary featured people sharing “a lot of very truthful, tough things about Charlie.”

“And I thought, ‘Well okay, if the time is to be honest, let’s be honest,’” he recalled, adding that the project showed “a lot of who he is.”

“aka Charlie Sheen” detailed the Hollywood icon’s career, romances and his infamous addiction struggles.

Jon Cryer on The View, with four female hosts, seated at a curved table with
The “No Small Affair” actor called it “really painful” to see the public enjoying Sheen’s struggles. ABC/The View
Jon Cryer sitting in a director's chair in a film set, wearing a black shirt and black pants, speaking to the camera.
Cryer (pictured here in the September documentary) said he partook in the project after thinking, ‘Well okay, if the time is to be honest, let’s be honest.’” Netflix

“He did text me afterward at one point to say ‘Thanks for doing it,’” Cryer expressed.

The “25th Annual Putnam County Spelling Bee” star also said he would be open to continuing to repair his relationship with Sheen.

“Yeah, I would,” Cyrer shared. “It’s funny because every now and then an article comes out that we’re arguing, and it’s just not the case.”

In the doc, the Broadway performer opened up about not earning nearly as much as Sheen did while on the show.

Jon Cryer and Charlie Sheen pose in the audience at the 35th Annual People's Choice Awards.
Cryer revealed that Sheen (pictured here together in 2009) did text him after the doc to thank him for participating. Kevin Winter
Charlie Sheen and Jon Cryer attending the
The former CBS star also said he’d be open to continuing to repair their relationship with his on-screen brother (pictured here together in 2003). FilmMagic

Sheen made close to two million dollars an episode during his final year on the sitcom.

Cryer was only earning about $550,000 per episode at that time. Once Sheen departed, however, Cyrer began earning $620,000 an episode.

Cryer claimed that Sheen’s contract negotiations “went off the charts because his life was falling apart.”

“The dictator of North Korea was a guy named Kim Jong-Il,” he explained. “He acted crazy all the time and thus got enormous amounts of aid from countries who were so scared of him that they would shovel money at him.

Charlie Sheen smiling and looking to the right.
Sheen (pictured here in the doc) praised Cryer for participating in “aka Charlie Sheen,” saying: “It was very sweet, very cool that everybody showed up like they did.” Courtesy of Netflix
Jon Cryer sitting in a director's chair in a film set, wearing a black shirt and black pants, speaking to the camera.
The Hollywood icon (pictured here with Cryer in 2009) said he also thinks “Jon would be open” to reconnecting, adding, “Jon’s a lovely man and a very talented guy.” Netflix

“Well, that’s what happened here. [Sheen’s] negotiations went off the charts because his life was falling apart. Me, whose life was pretty good at that time, I got a third of that.”

Meanwhile, last month, Sheen praised his on-screen brother for joining in on “aka Charlie Sheen.”

“It was very sweet, very cool that everybody showed up like they did, because they could have easily said, ‘Go f–k yourself. I’m not interested. I lived it. I don’t need to talk about it again,’” the former CBS star told People at the time. “And I would have been, ‘OK, that’s fine.’ But they didn’t, and they stepped up.”

As for if the pair have further connected, Sheen admitted, “I don’t like to bother people. But I think Jon would be open to that. Jon’s a lovely man and a very talented guy.”

The post Jon Cryer details ‘complicated’ past relationship with Charlie Sheen appeared first on Page Six.

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