Charlie Sheen and Jon Cryer: The Complex Bond of 'Two and a Half Men' Costars
Jon Cryer and Charlie Sheen's friendship took a rocky turn when Sheen was fired from 'Two and a Half Men' Discover the ups and downs that led to their complicated relationship in this intriguing article
Jon Cryer and Charlie Sheen co-starred on Two and a Half Men for eight seasons until Sheen's dismissal from the popular sitcom in 2011.
"In the beginning, working with Charlie Sheen was wonderful," Cryer shared with Entertainment Tonight in June 2022.
Production for Two and a Half Men was suspended twice, first in 2010 and then again in 2011, while the star was in rehab. Shortly before Sheen was expected to return to the show in 2011, he made critical remarks about Lorre during a radio show appearance, leading to his dismissal from the series the following month.
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Scroll through for a timeline of Cryer and Sheen’s ups and downs:
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Charlie Sheen and Jon Cryer’s Ups and Downs: Inside the ‘Two and a Half Men’ Costars’ Complicated Friendship
Jon Cryer and Charlie Sheen co-starred on Two and a Half Men for eight seasons until Sheen's departure from the hit sitcom in 2011.
"In the early years, working with Charlie Sheen was fantastic," Cryer said in an interview with Entertainment Tonight in June 2022.
Production for Two and a Half Men was paused twice, first in 2010 and then again in 2011, due to the star's attendance at rehab. Shortly before Sheen was scheduled to come back to the show after rehab in 2011, he called into the Alex Jones radio show to criticize Lorre, referring to him as a "charlatan" and a "clown."
Furthermore, the Platoon actor made fun of Alcoholics Anonymous, referring to it as "a bootleg cult" with "a 5 percent success rate." The next month, Sheen was dismissed from his top-rated series.
Scroll through for a timeline of Cryer and Sheen’s ups and downs:
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Things Started Out 'So Smoothly'
Two and a Half Men first aired on CBS in September 2003. "It was an amazing joy for those initial years," Cryer shared with Entertainment Tonight in 2022. "When we began the show, [Sheen] had been sober for two years, and maintaining his sobriety was very important to him. The show was also running very smoothly during those early years."
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Cryer Noticed There Was 'Trouble Brewing'
Cryer mentioned that he began to notice a shift in Sheen after his divorce in 2006. "He was still great to work with, punctual, and knew his lines, but you could sense that something was not right," he told ET in 2022.
He added, "He started to struggle with the writing and had issues that I couldn't comprehend. I would point out, 'This is the same type of joke you had no trouble with a year and a half ago, so why is it a problem now?' It was very subtle, but it took some time before things really started to unravel."
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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.
Credit: Warner Bros Tv/Chuck Lorre Prod/Kobal/Shutterstock
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.
Cryer told ET in 2022, "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.'"
Credit: Warner Bros Tv/Chuck Lorre Prod/Kobal/Shutterstock
'Two and a Half Men' Ended in 2015
After 12 seasons, with Sheen appearing in eight of them, Two and a Half Men concluded in February 2015. In the final episode, Sheen's character, portrayed by a body double without showing his face, comes back to his old home, only to meet his demise under a falling piano.
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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 believe it was the influence of drugs or the lingering impact of drug use … and it was also an overwhelming amount of stress and a deep well of negativity. It was all self-inflicted, you know,” he told Yahoo! Entertainment.
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Cryer Joked About a Reunion With Sheen
Despite Sheen's negative words about his former costar and being fired from their CBS series, Cryer harbors no resentment. He even tweeted in June 2022 about potentially reuniting with Sheen for another movie.
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Not Ruling Out a Reboot
"I'm keeping all options open," Cryer mentioned when asked about the possibility of a Two and a Half Men reboot with Sheen in a December 2023 interview with Entertainment Tonight. "I haven't had any communication with Charlie. I'm not even sure if he has my contact anymore. But you never know what the future holds."
The actor expressed his happiness about Lorre and Sheen reconciling their feud. "I'm really glad they made up," Cryer said. "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 made a guest appearance as a fictionalized version of himself in Lorre's Max series called Bookie, which debuted in November 2023. Prior to the show's premiere, Lorre revealed to Variety that his initial discussion with Sheen regarding the project was "therapeutic" for him.
"As soon as we started talking, it was like I suddenly remembered that we used to be friends," he explained. "That sense of friendship just rekindled right then and there. I don't want to get too sentimental, but it was really healing. And he was also completely willing to poke fun at himself."
