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How Charlie Sheen leveraged sports-gambling habit to reunite with Chuck Lorre on ‘Bookie’

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Chuck Lorre and Charlie Sheen have history. And not the good kind.

More on that antagonistic saga in a moment. But the bottom line is, water is now flowing under the bridge.

Lorre is once again working with the actor, after a 12-year freeze after Sheen’s messy exit from Lorre’s hit CBS sitcom “Two and a Half Men.” Sheen plays a gambling-addicted version of himself in the new Max series “Bookie” (two episodes each Thursday through Dec. 21), starring comedian Sebastian Maniscalco.

“The timing couldn’t have been better,” says Lorre. “That whole thing was in my rear-view mirror.”

That “whole thing” was quite the thing. Rewind 20 years, and Sheen was cast as Charlie Harper in “Men” alongside Jon Cryer. The show, which Lorre co-created, is a hit and rumbles along for eight years.

But in early 2011, the train jumps the tracks. Sheen’s substance abuse problems cause him to lash out against Lorre. The insults mount, CBS fires Sheen and Lorre puts the show on hiatus.

Sheen files suit against producer Warner Bros. Television for $100 million and settles for an undisclosed sum that fall, just as Lorre brings on Ashton Kutcher as a replacement to continue the show (it wrapped in 2015).

Chuck Lorre was ready to re-engage with Charlie Sheen after shedding ‘that darkness’

Lorre tells USA TODAY he had not spoken to Sheen for “at least a decade” when his “Bookie” co-creator Nick Bakay suggested that the role of a real celebrity with a gambling problem go to Sheen.

“Nick said to me, ‘Can you do it?’ But the emotion and angst for me were gone, I could even watch old episodes of ‘Two and a Half Men’ and laugh,” says Lorre. “All that darkness wasn’t in my space anymore. So I told Nick, ‘Let’s see if he’ll do it.’”

By Lorre’s account, Sheen was very enthusiastic. “It was kind of joyful,” he says. “It’s wonderful to work together again.”Sheen told the New York Post that he had a “tsunami of anxiety” about the phone call.

“Chuck got on the phone and couldn’t have been more lovely or engaging,” Sheen said. “It was so healing … and it was so surreal when the little voice in your head keeps saying, ‘This can’t be happening.’

Lorre says casting Sheen wasn’t simply about healing old wounds. “Bookie” required at least “one real celebrity willing to play a version of themselves with a gambling issue, and Charlie knows that world well.

“When we were doing ‘Two and a Half Men,’ there was many a Monday morning when Charlie would come in and tell me about his journey on Sunday with all the NFL games he had bet on,” says Lorre. “I was always like, ‘Oh, he’s playing at a very high level here.’

“But the best thing was that for ‘Bookie,’ although asking an actor to play themselves is always a risky proposition, he was absolutely game to make fun of himself,” says Lorre. “And his acting chops and timing are all still there.”

Charlie Sheen was eager to make some fun of himself for his guest starring role in ‘Bookie’

Just how game Sheen was to poke fun at himself is apparent in one exchange during the premiere episode of “Bookie”? (He reappears in the season finale.)

Maniscalco is sent to collect $75,000 in lost bets from Sheen in the middle of an illicit card game he’s running at a rehab facility in Malibu. As the two face off over the money owed, there’s suddenly a lull in the conversation.

Maniscalco then says, “You ever talk to Jon Cryer?”

Sheen shoots him an arched eyebrow, then answers, not really.

“Oh,” says Maniscalco. “He was my favorite.”

Sheen’s deadpan response is sublime.

There are a few more interesting cameos in “Bookie.” One of the other people at the table in the gambling scene is Angus T. Jones, now 30, who played young Jack Harper (the “half”) on “the sitcom” on “Men.” While it’s a blink-and-you’ll-miss-him appearance, it’s a nice mini reunion.

‘Bookie’ star talks comedy: Sebastian Maniscalco talks new TV show ‘Bookie’ on Max, plus Chris Rock’s stand-up advice

Ray Romano appearance on ‘Bookie’ came down to a phone call from Sebastian Maniscalco

And then there’s Ray Romano (“Everybody Loves Raymond”), who turns up in the opening moments of the series as a beleaguered, badgered and woefully compulsive gambler who is being thrown out of his up-for-sale house by his wife.

Romano slouches away towards his car, and then immediately calls Danny (Maniscalco) to place a series of highly risky bets, doubling down on his fate.

Getting Romano was Lorre’s idea, and its execution came down to a phone call by Maniscalco.

“I played his brother in ‘Somewhere in Queens,’ so I called him up and said, ‘I’m doing this new thing and you’d be great for the opening scene.’ And he came in for a day and knocked it out,” he says. “I grew up watching him and Seinfeld (Maniscalco was a guest on “Comedians in Cars Getting Coffee”), guys with some of the biggest shows ever on TV.”

“It’s amazing to be working with them,” he says.

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