How Charlie Sheen and Chuck Lorre Fell Out — Then Reunited for ‘Bookie’

Not so long ago, Chuck Lorre’s relationship with Charlie Sheen had soured so much the TV producer dropped a piano on Sheen’s character in the Two and a Half Men finale. But now, less than a decade later, Lorre and Sheen are collaborating again: The actor has a recurring part in Bookie, Lorre’s new Max comedy, debuting on Thursday, November 30.

“I was hopeful that Charlie was in a good place and up for it,” Lorre told Entertainment Tonight earlier this month. “I called his agent… they put me in touch with Charlie, and I said, ‘Here’s a funny idea.’”

Nothing was funny, however, about Sheen’s 2011 media blitz, in which the actor lobbed countless insults Lorre’s way after the Two and a Half Men co-creator called out Sheen’s substance abuse in a vanity card in one episode of the CBS sitcom.

E.J. Camp/CBS

In an interview on the Alex Jones Show (per The Hollywood Reporter), Sheen called Lorre a “clown” and a “charlatan” with an “un-evolved mind.” To TMZ, Sheen said he “violently hate[d]” Lorre, deeming the writer a “stupid, stupid little man and a p–sy punk.” And in an open letter posted online, he called Lorre a “contaminated little maggot.”

Production of Two and a Half Men’s eighth season was promptly shut down, and Sheen was later fired from the series and replaced by Ashton Kutcher. Sheen then filed a $100 million lawsuit against Lorre and Warner Bros. in the Los Angeles Superior Court, and in the resulting settlement, Sheen got a rumored $25 million payout from the studio, per THR.

In the series finale of Two and a Half Men in 2015, a body double filled in for Sheen as Charlie Harper returned home, only to be crushed by a falling piano on his stoop. Lorre then appeared as himself on camera, saying “Winning!” — a catchphrase from Sheen’s 2011 meltdown — before his onscreen alter-ego met the same death-by-piano fate.

Meanwhile, Sheen moved onto other projects, including the FX sitcom Anger Management and guest appearances on The Goldbergs and Typical Rick. And in a 2021 interview with Yahoo Entertainment, Sheen blamed his behavior in “an unfortunate sequence of public and insane events” on “drugs or the residual effects of drugs” as well as “an ocean of stress and a volcano of disdain.”

He added: “There [were] 55 different ways for me to handle that situation, and I chose number 56. 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.”

Now, however, bygones might be bygones with the upcoming premiere of Bookie, a comedy starring Sebastian Maniscalco as a Los Angeles sports betting bookie facing obsolescence. As Lorre developed the series with writer Nick Bakay, he thought that Sheen should play a high-rolling version of himself.

“I remember Charlie was very much engaged in sports betting, and he would tell me stories about it all the time,” Lorre told Variety. “You know, when things were good.”

Lorre said that he had gotten to the point where it wasn’t painful to watch Two and a Half Men episodes again — and that his and Sheen’s falling-out felt like old news.

“I loved working with Charlie on Two and a Half Men. We did 170 episodes together before it all fell apart,” he explained. “And more often than not, we had a good time. Assuming he’s in a good place, I’m in a good place.”

So Lorre reached out to Sheen, who was also ready to leave the feud in the past. “I was nervous, but almost as soon as we started talking, I remembered, we were friends once,” Lorre told Variety. “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 seeing Sheen again at the first Bookie table read felt like “just the most natural thing in the world,” Lorre told ET. “The two of us hugged,” he said. “It was closure. It was healing. And it was a big weight off my heart.”

Bookie, Series Premiere, Thursday, November 30, Max