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Charlie Sheen and Chuck Lorre’s Ups and Downs After ‘Two and a Half Men’ Firing, ‘How to Be a Bookie’ Reunion

Charlie Sheen and Chuck Lorre faced a series of ups and downs after the actor’s substance abuse issues began affecting his work on Two and a Half Men. Sheen portrayed Charlie Harper on the CBS series from 2003 to 2011, when he was fired after making a series of controversial statements about Lorre, the show’s cocreator. The Anger Management alum‘s character was killed off the show at the beginning of season 9 in fall 2011. Ashton Kutcher joined the cast to act alongside original star Jon Cryer until the series wrapped in 2015. Before the sitcom came to an end, Sheen told TV Guide that he was ready to make amends with Lorre. “He was doing his job, I was doing mine. At the end of the day, the guy’s a genius. Look at what he does,” he said. “I don’t have to spend time with him anymore for him to be brilliant.” Scroll down to see Sheen and Lorre’s ups and downs:

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January 2011

Two and a Half Men began a hiatus and halted production after Sheen was ordered to go to rehab to deal with his drug and alcohol struggles. The Ferris Bueller’s Day Off actor opted to do at-home treatment, later calling his house “Sober Valley Lodge.”

One month later, Sheen raised eyebrows for criticizing Lorre during multiple interviews. The New York native called the Mike & Molly creator a “clown” during an appearance on the Alex Jones Show. “I’ve spent, I think, at close to the last decade, I don’t know, effortlessly and magically converting your tin cans into pure gold,” he added.

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March 2011

The Major League star was fired from the Warner Bros. Television production after slamming Lorre publicly. “Your client has been engaged in dangerously self-destructive conduct and appears to be very ill,” read in a letter sent to Sheen’s lawyer by the studio outlining the reason for his termination.

The letter obtained by TMZ at the time alleged that Sheen had “difficulty remembering his lines” and that his “conduct and condition created substantial tensions on the set.”

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March 2011

Sheen filed a $100 million lawsuit against Lorre and Warner Bros. Television after being fired from the series. His filing was made in an attempt to receive compensation for the canceled season 8 episodes that resulted from the show’s hiatus.

The case was settled in September 2011 with TMZ reporting that the Spin City alum would receive an immediate payout of $25 million, which would eventually become $100 million in syndication profits for years to come.

“Warner Bros. Television, Chuck Lorre and Charlie Sheen have resolved their dispute to the parties’ mutual satisfaction,” read a statement from the studio at the time. “The pending lawsuit and arbitration will be dismissed as to all parties. The parties have agreed to maintain confidentiality over the terms of the settlement.”

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September 2011

When season 9 of Two and a Half Men premiered, Charlie Harper was seemingly killed off. Kutcher then joined the cast as Walden Schmidt. When the series came to an end in February 2015, Sheen’s character was revived by a body double — but he was later crushed by a falling piano.

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December 2011

Lorre opened up about his fears for Sheen during an interview with TV Guide. “I was so afraid my friend was going to die,” the showrunner said, referring to the star’s drug use at the time of his firing. “The [studio and the network] chose to make a moral decision as opposed to a financial one. This was not a game. This was drug addiction writ large.”

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September 2014

Sheen told TV Guide that he was interested in returning to Two and a Half Men ahead of its final season. “I’ve reached out to them and they’ve reached back,” he claimed.

While the Money Talks star was willing to go back to set, he noted that he wasn’t exactly on good terms with Lorre. “Ethereally we have, personally we have not,” Sheen said of whether he made peace with the producer, adding, “I wish him nothing but the best.”

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January 2015

Lorre played coy about Sheen making a cameo on the comedy’s finale — and insisted there was no beef between the pair. “I think we’re going to have a finale you’re going to be very pleased with and that’s all I’m going to say about it,” the show’s creator teased to reporters at the Television Critics Association’s winter press tour.

He later circled back to the Three Musketeers actor’s part on the sitcom, saying, “It would be inappropriate to not acknowledge the extraordinary success we had with Charlie and how grateful I am, we all are, to his contributions. And there’s nothing but great feelings for the eight-and-a-half years we worked together.”

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January 2017

The She Wants Me star confessed during an appearance on the Kyle & Jackie O show that he regretted how he treated Kutcher when he joined the Two and a Half Men cast. “I was stupidly mean to him because I overlooked the reality and difficulty of taking over a show,” Sheen told the radio hosts. “Which I did, I took over Spin City when Michael J. Fox was too sick to work, but no one ever put those two together. … So I should have been nicer.”

The Due Date actor slammed the That ‘70s Show alum via social media multiple times in the years after he joined the sitcom in 2011. In 2014, he tweeted that Kutcher was Cryer’s “lame sidekick.”

Sheen explained in January 2017 that he buried the hatchet with his fill-in while at a Dodgers game the previous November. “It was awkward, but I made it fine because I felt bad for him,” he recalled. “He thought he was going to catch a right cross, but I just wanted to give him a hug.”

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April 2023

Deadline reported that Sheen will reunite with Lorre for his Max comedy How to Be a Bookie. Variety confirmed the news as well, reporting that the actor will have a recurring role on the show, which stars Sebastian Maniscalco. Reps for Warner Bros. Television and HBO Max (which will become Max in May 2023) declined to comment.

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November 2023

During an interview with Variety, Lorre recalled reaching out to Sheen’s rep to make amends years after their feud began.

“Almost as soon as we started talking, I remembered, we were friends once,” Lorre 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.”

Lorre also shared what it was like to work with Sheen again on Bookie. “When he came to the table read of [the pilot] episode, I walked up, and we hugged. It was just great,” he said. “He proceeded to kill it at the table read. His chops were just so finely tuned, as if we had not missed a beat.”