Inside Charlie Sheen and Jon Cryer's Complicated Friendship: What Happened Between the Former 'Two and a Half Men' Costars?

Charlie Sheen and Jon Cryer's friendship has gone through a turbulent phase over the past years.

In 2003, Sheen and Cryer worked together on the hit sitcom Two and a Half Men, portraying brothers Charlie Harper and Alan Harper, respectively.

According to The Famous Teddy Z star, the early years with Sheen on the show were "great."

"We got along great, he had been sober for two years when we started the show, and it was really important to him to keep sober. And for those first few years, the show was also going so smoothly," Cryer recalled in a 2022 interview with Entertainment Tonight.

Cryer, who was "struck by how great Charlie Sheen was at performing in front of an audience," added, "He just had it straight out of the box like it was genetically programmed into his body. That was fun and very self-assured. For those first couple of years, it was, you know, an incredible joy."

Sheen married Denise Richards before working on Two and a Half Men, but their marriage ended when the mom-of-three filed for divorce in March 2005.

In the years after they finalized the paperwork in November 2006, Sheen began facing personal struggles that disrupted his performance on set.

"When we started noticing things were getting stranger for him, and his marriage fell apart, he was still lovely to work with, he still showed up on time and knew his lines and was doing the job," Cryer told Entertainment Tonight. "But you could tell that there was some trouble brewing."

He added, "He started to have issues with the writing and sometimes issues with the writing that I didn't understand. I would say, 'This is the kind of joke you had no problem with a year and a half ago, and suddenly now it's an issue?' So, you know, it was very subtle. It took a while before it started really going off the rails."

While working on Two and a Half Men, Sheen's life spiraled into chaos, plagued by substance abuse, personal issues, relationship setbacks and legal struggles.

In February 2010, Sheen's then-publicist, Stan Rosenfield, announced the Platoon actor had entered a rehabilitation facility "as a preventative measure."

"He will take some time off from his series Two and a Half Men. He has asked that his privacy be honored. No further statements are planned," he continued.

When Sheen entered rehab, Two and a Half Men also went on hiatus. His life still descended into chaos, marked by the infamous statements about drug usage as well as denouncing CBS and the sitcom's producer, Chuck Lorre.

One month after Sheen called Lorre a "charlatan" and a "clown" during a live radio show in February 2011, he was fired from the sitcom after starring in eight seasons. He was then replaced by Ashton Kutcher, who worked on the series until it concluded in 2015 after 12 seasons.

According to Cryer, he and Lorre thought about ending the show for good at one point.

"I think there was a moment where Chuck Lorre and I were looking at each other and we said, 'It's not worth this show going on if going on enables Charlie Sheen to kill himself. If giving him enough money to do whatever the thing is that ends his life, you know, we don't want to be a part of that,'" he said. "And I think, actually, when Charlie was let go from the show, the first thought amongst most of us was, 'OK, we're done. This has been a great thing, but we're done at this point.'"

Nearly a decade after Sheen's firing, Cryer opened up about the "great camaraderie" on set while also pointing out the things that took a toll on the show.

"It was crazy. It was way more craziness than I really was hoping for, honestly," he told Access Live in 2019.

"It was tough to watch a guy who I had seen… you know, when we started the show, Charlie had been sober for a while and was really in control of his life," Cryer continued. "And it was tough to see that go away. That was the hardest part of being involved in that process. But actually doing the shows was always great. There was never a time when it wasn't great."

Cryer revealed he had not spoken to Sheen "in a couple of years," adding that having Sheen in his life had been "kind of a rollercoaster."

"I just haven't decided to get back on that rollercoaster," he said.

Speaking in a February 2021 interview with Yahoo! Entertainment, Sheen expressed remorse for his past actions, saying there were "55 different ways for [him] to handle that situation, and [he] chose number 56."

"And so, you know, I think the growth for me post-meltdown or melt forward or melt somewhere — however you want to label it — it has to start with absolute ownership of my role in all of it," Sheen expressed. "And it was desperately juvenile."

As for what caused his past conduct, Sheen said it was either "drugs or the residual effects of drugs."

He shared, "And it was also an ocean of stress and a volcano of disdain. It was all self-generated, you know."

During an appearance on The View, Cryer said Sheen and Lorre's reconciliation was "really lovely."

However, Cryer admitted to feeling conflicted over doing a Two and a Half Men revival with his former costar.

"Oh gosh, I don't know how that happens," he said. "I mean, Charlie is doing a lot better now, which is wonderful. He and I have not spoken in a few years but he's doing a lot better, which obviously I am happy about."

While Sheen was the "highest paid actor in television, probably ever," Cryer said the father-of-four "blew it up" so he had no idea if he "wanted to get in business with [Sheen] for any length of time."

Still, Cryer suggested he might be open to a "one-off" project.

"To be clear, as many of the issues that Charlie faces, I do think he'd be a better president," Cryer said in an April episode of "The MeidasTouch Podcast," comparing The Arrival star to Donald Trump.

"The thing I was pointing out was that, at the time when I made that comment, Charlie was still just going off and saying whatever stupid tiger blood comments he was making," he added, referring to his comment about Trump being the "Charlie Sheen of politics."

Cryer continued, "And Trump has always been comfortable with saying whatever stupid thing he said because people wrote him off as harmless and didn't hold him responsible for those things."

The No Small Affair actor pointed out the president's "allure to the people who like him is that he just says whatever stupid thing he's thinking. They say, 'Well, that's him being authentic.'"

"But he's always been like that old guy at the end of the bar who thinks he knows how the world works, but he's really kind of a loser," Cryer shaded Trump.

Sheen's Netflix documentary, aka Charlie Sheen, featured people closest to him, including Cryer.

In Andrew Renzi's new two-part documentary, the Pretty in Pink star got candid about his time with Sheen on Two and a Half Men. At one point, he revealed he was worried "every day" about losing his costar due to his substance abuse.

"He goes in and out of being able to have a healthy way of dealing with that and then an incredibly destructive way of dealing with that, which is the drugs and the partying," Cryer said of Sheen.

He continued, "I could see his timing was off. He was clearly overcompensating for being loaded. ... That's when I was worried about Charlie every day. Every day I was like, 'Is this the day that we're going to lose him?'"

After aka Charlie Sheen premiered, Sheen confirmed he did not personally call Cryer to participate in the documentary.

He explained, "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 revealed he did not hear back from Cryer, which was reportedly unusual for his former costar.

"I'm thinking I wrote to the wrong number," he said. "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!"