Jon Cryer Says Early Years with Charlie Sheen on Two and a Half Men Were a 'Joy' Before 'Going Off the Rails'

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Jon Cryer still has fond memories of working alongside Charlie Sheen on Two and a Half Men.

"In the early years, the life with Charlie Sheen was great," Cryer, 57, told Entertainment Tonight. "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."

At the time, Cryer was also "struck by how great Charlie Sheen was at performing in front of an audience."

"He just had it straight out of the box like it was genetically programmed into his body. That was fun and very self-assured," he said. "For those first couple of years, it was, you know, an incredible joy."

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But the tables turned in the later years of the show as Sheen began to battle a series of personal struggles.

"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. But you could tell that there was some trouble brewing," Cryer said.

Related video: Jon Cryer reflects on working with Charlie Sheen in 'Two and a Half Men'

"He started to have issues with the writing and sometimes issues with the writing that I didn't understand," he continued. "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."

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Things grew increasingly worse amid Sheen's unpredictable behavior, which included a series of problematic statements and an unexpected feud with Two and a Half Men co-creator Chuck Lorre. According to Cryer, he had discussions with Lorre, 69, about ending the show altogether.

"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.'"

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Sheen, 56, was fired from the sitcom in 2011 after eight seasons. He was then replaced by Ashton Kutcher, and the series concluded in 2015 after 11 seasons.

Ten years after his departure, Sheen said he regretted the way in which he behaved back then.

"There was 55 different ways for me to handle that situation, and I chose number 56," he told Yahoo! Entertainment in February 2021. "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 explains. "And it was desperately juvenile."

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Addressing what caused him to behave in such a way, Sheen said, "I think it was drugs or the residual effects of drugs … and it was also an ocean of stress and a volcano of disdain. It was all self-generated, you know."

He added, "All I had to do was take a step back and say, 'Okay, let's make a list. Let's list, like, everything that's cool in my life that's going on right now. Let's make a list of what's not cool.' You know what I'm saying?" he added. "And the cool list was really full. The not cool list was, like, two things that could've been easily dismissed. I was getting loaded and my brain wasn't working right."

If you or someone you know is struggling with substance abuse, please contact the SAMHSA helpline at 1-800-662-HELP.