Posted in: Casting, CBS, HBO, TV | Tagged: cbs, charlie sheen, chuck lorre, hbo max, How to Be a Bookie, max, Sebastian Maniscalco, Two And A Half Men

How to Be a Bookie: Charlie Sheen, Lorre Make Nice for Max Comedy

Charlie Sheen is set to reunite with Two and a Half Men creator Chuck Lorre for the Max comedy series How to Be a Bookie.

For those doing a double take on the headline, former Two and a Half Men star Charlie Sheen and his one-time mortal enemy series creator Chuck Lorre (with Lee Aronsohn) officially buried the hatchet on their issues to star on the latter's first Max (formerly HBO Max) comedy How to Be a Bookie. Sheen is set to have a recurring role in the single-camera comedy that will star Sebastian Maniscalco, according to Deadline Hollywood. The series, written by Lorre and Nick Bakay, follows a veteran bookie (Maniscalco) who struggles to survive the impending legalization of sports gambling, increasingly unstable clients, family, co-workers, and a lifestyle that bounces him around every corner of Los Angeles high and low.

Charlie Sheen from Two and a Half Men to How to Be a Bookie

Along with How to Be a Bookie, Sheen is also attached to star in the dramedy Ramble On from Doug Ellin, currently being shopped, which also features his father, Martin Sheen, Kimiko Glenn, Bre-Z, John C. McGinley, Jamie-Lynn Sigler, Zulay Henao, Mark Cuban, James Hiroyuki Liao, Harvey Guillén, Ana Ortiz, Sara Sanderson, Mikaela Hoover, and Adam Waheed. Sheen was in the popular CBS comedy opposite his Hot Shots! (1991) co-star Jon Cryer and Angus T. Jones for eight seasons. Appearing in 178 episodes, Sheen left after eight seasons after his aforementioned meltdown against Lorre and co-star Cryer in a series of incoherent rants that included him having "tiger's blood" and "winning."

Cryer is the only cast member to appear in all 262 episodes of the 12-season series (2003-2015) that garnered nine Emmys, including two for him as Outstanding Lead Actor in a Comedy Series. Sheen garnered four nominations. The series followed a hedonistic jingle writer Charlie (Sheen) has to deal with some life changes as his brother Alan (Cryer) and nephew Jake (Jones) move into his beach-front house. After Sheen's departure, Ashton Kutcher joined the cast playing a separate original character Walden Schmidt. Jones left the series after season 10 with one final appearance in the series finale. The series also starred Conchata Ferrell as Berta, appearing in 211 episodes.

There was a tease of Sheen's return for the finale never materialized as a piano fell on a lookalike ringing the doorbell at the beach house before revealing Lorre, who uttered his catchphrase, "Winning!" before another piano fell in probably one of the most bizarre displays in television history. While pride probably stopped Sheen from officially returning, it seems like his remorse is genuinely going out of his way to work with Lorre again. Despite the fallout, Sheen managed to star in another sitcom, FX's Anger Management, appearing in all 100 episodes and making an appearance on ABC's The Goldbergs.

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