Charlie Sheen and Jon Cryer’s Ups and Downs: Inside the ‘Two and a Half Men’ Costars’ Complicated Friendship

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Charlie Sheen and Jon Cryer’s Ups and Downs: Inside the ‘Two and a Half Men’ Costars’ Complicated Friendship

A complicated history. 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. “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." The Pretty in Pink actor previously stated that he believes Sheen’s 2006 split from Denise Richards was what may have prompted him to start using drugs again that year. "At first he could handle it, and he was still incredibly professional — and still lovely, by the way, to everybody on set — but you could just see that stuff was wearing on him," Cryer told Entertainment Weekly in 2020. Production for Two and a Half Men was halted twice, first in 2010 and then again in 2011, while its star attended rehab. While reflecting on Sheen’s battle with addiction in 2022, Cryer told ET that he and Chuck Lorre, the show's creator, were deeply worried about the actor’s health. [jwplayer WqZpHiyZ-zhNYySv2] “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,'" the Emmy winner said. Less than a week before Sheen was slated to return to the sitcom after his 2011 stint in rehab, he called into the Alex Jones radio show to rant about Lorre, calling him a “charlatan” and a “clown.” The Platoon actor also mocked Alcoholics Anonymous, calling it “a bootleg cult” with “a 5 percent success rate.” The following month, the New York native was fired from his top-rated series. Ashton Kutcher later joined the cast as a billionaire who purchased Sheen's character's house after his untimely death. After being fired, the Three Musketeers actor had some harsh words for his former costar. “Jon has not called me,” Sheen claimed while speaking to E! News in March 2011. “He’s a turncoat, a traitor, a troll.” However, in February 2021, the Spin City alum told Yahoo! Entertainment that he had regrets about how he acted at the time. "There was 55 different ways for me to handle that situation, and I chose number 56," he said at the time. “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, and it was desperately juvenile." Scroll through for a timeline of Cryer and Sheen’s ups and downs: [podcast_block]

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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.”

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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."

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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.

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Sheen Was Fired From 'Two and a Half Men'

The Arrival actor was fired from his CBS sitcom in March 2011. 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.

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'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.

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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 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.

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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.”