Max has dropped the trailer for Bookie Season 2, and it’s shaping up to be an even wilder ride. Created by Chuck Lorre and Nick Bakay, the dark comedy series returns Thursday, December 12, with Sebastian Maniscalco reprising his role as Danny, a bookie scrambling to save his business from California’s looming legalization of sports gambling. Alongside Omar J. Dorsey as his best friend Ray, the duo navigates a world filled with hilarious and unpredictable characters—including some of Hollywood’s biggest comedic names.
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The eight-episode second season kicks off with Danny and Ray taking on new high-stakes challenges, including increasingly unstable clients and their own risky bets. Returning cast members include Vanessa Ferlito as Danny’s entrepreneurial sister Lorraine, Jorge Garcia as the reluctantly reformed drug dealer Hector, and Rob Corddry, now a series regular.
Max teases, “Full of relatable mishaps, Bookie chronicles one man’s journey to adapt to an ever-changing world as he attempts to charm and con his way to the top.”
The trailer reveals some big-name guest appearances, including Charlie Sheen (returning as himself), Ray Romano, Zach Braff, and Brad Garrett. Romano and Garrett bring some Everybody Loves Raymond energy, while Braff’s character finds himself interrupted mid-commercial shoot by Danny and Ray, who demand he clear his $42,000 gambling debt. Meanwhile, Sheen’s sparing but impactful appearances promise to inject even more chaos into the storyline.
Eagle-eyed viewers will spot Ghosts star Asher Grodman handing over a suspicious envelope of cash, and Romano appears as a mysterious figure whose advice might lead Danny and Ray into even deeper trouble.
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From fistfights with eccentric gamblers to confrontations with heavily armed men, the trailer teases a mix of comedy and chaos. One standout moment sees Danny squaring off against an aged brawler with a literal hook for a hand, while Ray takes a punch from his baby mama in another laugh-out-loud scene.
Between Danny’s offbeat sense of humor and the escalating stakes, the bookmakers seem destined for more trouble than ever—especially when they bet on Brad Garrett’s fictionalized version of himself as a supposed savior for their woes.
Bookie is produced by Warner Bros. Television and executive produced by Maniscalco, Lorre, Bakay, Judi Marmel, and Andy Tennant, who also directed multiple episodes.
Mark your calendars: Bookie Season 2 premieres Thursday, December 12, on Max, with new episodes dropping weekly through January 30, 2025.
Catch the trailer now and get ready for a season packed with laughs, risks, and one unforgettable cast.