Charlie Sheen Joins Cast of HBO Max Comedy, “How to Be a Bookie”

Charlie Sheen is returning to television in HBO Max’s upcoming bookmaking comedy, How to Be a Bookie (HTBAB). The rise of sports betting in the US – illegal in all states but Nevada until 2018 – may be sparking a similar interest in shows and movies on the subject. It would be a repeat of the flood of poker movies in the late 1990s and early 2000s when that game was experiencing its renaissance.

According to Deadline, Sheen is set to costar alongside headliner Sebastian Maniscalco in the eight-episode first season. HBO first announced the single-camera gambling-themed show last year, but interest was minimal due to a lack of star power at the time.

With Sheen’s addition, however, THBAB has become one of 2023’s most anticipated new TV series.

Appearing with Sheen and Manisculco are Omar J. Dorsey, Jorge Garcia, Andrea Anders, Vanessa Ferlito, and Maxim Swinton.

Lorre and Nick Bakay co-wrote, while Lorre and others, including Andy Tennant, will direct.

Gambling Sitcom First Lorre, Sheen Collab Since 2011’s Two and a Half Men

The show’s gambling-focused storyline follows Danny (Maniscalco), a “veteran bookie” struggling to survive US sports betting legalization.

Against that backdrop, according to IMDb, he navigates life with his family, coworkers, and “increasingly unstable clients.”

What role Sheen is stepping into has yet to be announced. But, Danny’s relationships will likely serve up the comedy gold, something Sheen and show co-creator Chuck Lorre have plenty of experience with.

HTBAB is the first time the duo has worked together since 2011.

At the time, a falling out saw Lorre replace Sheen with Ashton Kutcher on CBS’ Two and a Half Men. Sheen received four Emmy nominations for his work on the show before his ousting.

The pair’s eight-year collaboration on one of television’s most successful comedies came to a messy end in 2011. The fracture followed a very public mental breakdown that saw Sheen hurling insults at his longtime creative conspirator.

Lorre retaliated by killing off Sheen’s character, not once but twice (and ultimately, by dropping a piano on his head).

After being fired, Sheen responded with a $100 million lawsuit against Lorre and the show’s studio, Warner Bros. Television. According to CNN, that suit was later settled “to the parties’ mutual satisfaction.”

Since then, Sheen has reportedly regretted that exit and taken responsibility for his previous actions. It seems that made a difference in his relationship with Lorre as the pair are collaborating on HTBAB for WBTV.

It’s the first project for Lorre with HBO Max (soon to be renamed Max) as the distributor.

As yet, neither Max nor WBTV has commented on Sheen’s casting.

Bookmaking Comedy Marks Sheen’s Return to TV After Break

Sheen’s recurring role on HTBAB is part of a television renaissance for Sheen, who is also set to star in an episode of Doug Ellin’s dramedy Ramble On.

Notably, he’s been away from the small screen since appearing in two episodes of Typical Rick in 2017.

However, how long-running Sheen’s role proves to be may depend on the show’s popularity.

According to available details, he only appears in one of eight episodes. So, audiences will have to buy in enough that Max raises the ask on episodes.

It will be interesting to see how gambling, specifically illegal bookmaking, comes across in a mainstream sitcom.

Ideally, no pianos will be harmed.

How to Be a Bookie is currently in production. Max has yet to announce an air date.

About the Author

Robyn McNeil

Robyn McNeil

Robyn McNeil (she/they) is a Nova Scotia-based writer and editor, and a lead writer at Bonus. Here she focuses on news relevant to online casinos, while specializing in responsible gambling coverage, legislative developments, gambling regulations, and industry-related legal fights.
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