Charlie Sheen and Jon Cryer Worked Together on 'Two and a Half Men'

Source: MEGACharlie Sheen and Jon Cryer costarred on 'Two and a Half Men' for eight seasons.

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."

Jon Cryer Viewed Charlie Sheen and Denise Richards' Divorce as a Turning Point

Source: MEGACharlie Sheen and Denise Richards finalized their divorce in 2006.

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."

Charlie Sheen Had an Infamous 2011 Meltdown Following a Rehab Stay

Source: MEGACharlie Sheen checked into a rehab in February 2010.

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.'"

Jon Cryer Revealed He Had Not Spoken to Charlie Sheen in Years

Source: MEGACharlie Sheen was fired from the show after eight seasons.

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.

Charlie Sheen Opened Up About His Firing From the SitcomSource: M