Jon Cryer and Charlie Sheen were costars on Two and a Half Men for eight seasons until Sheen was fired from the hit sitcom in 2011.
“In the early years, the life with Charlie Sheen was great,” Cryer told Entertainment Tonight in June 2022.
The Platoon actor also mocked Alcoholics Anonymous, calling it “a bootleg cult” with “a 5 percent success rate.” The following month, Sheen was fired from his top-rated series.
Scroll through for a timeline of Cryer and Sheen’s ups and downs:
Things Started Out 'So Smoothly'
Two and a Half Men premiered on CBS in September 2003. “For those first couple of years, it was, you know, an incredible joy,” Cryer told Entertainment Tonight in 2022. “[Sheen] 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 Noticed There Was 'Trouble Brewing'
Cryer has said that he started to notice a change in Sheen after his 2006 divorce. “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,” he told ET in 2022.
He continued, "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."
Sheen Slammed Lorre on the Radio
In February 2011, Sheen called the creator of Two and a Half Men a “charlatan” and a “clown” during a live Alex Jones radio show.
Sheen Was Fired From 'Two and a Half Men'
The Arrival actor was fired from his CBS sitcom in March 2011. Ashton Kutcher was hired to join the cast the following season to fill the void.
“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,’” Cryer told ET in 2022
Two and a Half Men' Ended in 2015
After 12 seasons, eight of which Sheen appeared in, Two and a Half Men came to an end in February 2015.
In the series finale, Sheen’s character, played by a body double whose face is never shown, returns to his former home only to be crushed by a falling piano.
Sheen Reflected On the Events That Led to His Firing
In February 2021, the Golden Globe winner reflected on the behavior that led to his firing from Two and a Half Men.
“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 told Yahoo! Entertainment.
Cryer Joked About a Reunion With Sheen
Although Sheen called his former costar a “traitor” and a “troll” after he was fired from their CBS series, Cryer doesn’t have any hard feelings.
In June 2022, the Arrow alum tweeted, “Just Saw Top Gun: Maverick. Think it’s time to reunite with Sheen for Hot Shots: Part Tres.”
Not Ruling Out a Reboot
“I’m not going to rule anything out,” Cryer said of a Two and a Half Men reboot with Sheen during a December 2023 interview with Entertainment Tonight. "I have not spoken to Charlie. I don't know that he knows my number anymore. But anything could happen."
The actor also reacted to Lorre and Sheen ending their feud.
“I’m really glad they made up,” Cryer told the outlet. “I can only [speak] for Chuck, clearly. He has the enormous relief of somebody who's been able to rekindle a friendship that was really meaningful to him."
Sheen appeared as a version of himself in Lorre’s Max series Bookie, which premiered in November 2023. Ahead of the show’s premiere, Lorre told Variety that his first conversation with Sheen about the project was “healing” for him.
“Almost as soon as we started talking, I remembered, we were friends once,” he said. “And that friendship just suddenly seemed to be there again. I don’t want to be too mawkish about it, but it was healing. And he was also totally game to make fun of himself.”
