The series was originally announced under the title 'How to Be a Bookie' when HBO Max gave it a straight-to-series order for eight episodes on October 4, 2022, created by Chuck Lorre and Nick Bakay.

Charlie Sheen, who previously starred in Chuck Lorre's 'Two and a Half Men', joined the cast of Bookie in a recurring role announced on April 17, 2023, appearing as himself.

Several other alumni from Chuck Lorre's earlier shows also make guest appearances as themselves or in small roles, including Angus T. Jones, Eugene Byrd, and Eddie Gorodetsky.

Bookie was filmed on location in Los Angeles County, California, with the Champs Sports Pub in Burbank used as a recurring shooting location across several episodes.

On Rotten Tomatoes, 90% of 10 critics' reviews for the first season were positive, with the consensus praising the blend of Chuck Lorre's classic sitcom sensibilities with Sebastian Maniscalco's comedic style.

Despite being renewed for a second season on January 5, 2024, which premiered on December 12, 2024, the series was ultimately canceled in February 2025 after just two seasons.