In 2011, after eight seasons of starring as the lead character Charlie Harper in the popular television sitcom Two and a Half Men, Charlie Sheen was fired for making belittling comments about Chuck Lorre, who co-created the show and was one of its executive producers.

Now, 12 years later, Sheen and Lorre are reuniting on a new Max comedy series titled How To Be a Bookie, according to a Deadline report. The show, created by Lorre who co-wrote the script with Nick Bakay, will star Sheen as a yet-to-be-announced recurring character.

Sheen's shift on Two and a Half Men brought him much success, including four Emmy nominations and two Golden Globe nominations. When Sheen was fired, he was struggling with a recurring drug problem that saw him in rehabilitation three times in 12 months. In retaliation for his dismissal, he launched a $100 million lawsuit against Lorre and Warner Bros. TV, which was eventually settled. In 2021, Sheen stated he could have handled the situation differently and expressed regret over his past actions.

In the years since his exit from Two and a Half Men, Sheen has had lead roles in the FX sitcom Anger Management, which aired for two seasons and 100 episodes, and the 2017 ensemble film 9/11. He has also had a guest role in the ABC television sitcom The Goldbergs.