Charlie Sheen Leads Buzzy Group of Guest Stars in Hilariously Jam-Packed Bookie Season 2 Trailer: Watch! (Exclusive)

Mar. 15, 2025

Bookieis back and better than ever!

In PEOPLE’s exclusive first look at the highly anticipated second season of the Max original,Charlie Sheenleads a pack of hilariously funny guest stars.

Per the series logline, the new season follows Los Angeles bookie Danny (Sebastian Maniscalco), his best friend Ray (Omar J. Dorsey), his side-hustling sister Lorraine (Vanessa Ferlito), and reformed drug dealer Hector (Jorge Garcia) as they contend with Danny’s increasingly unstable clients.

While attempting to settle their debts, Danny makes “plenty of risky bets of his own,” the synposis continues, “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.”

‘Bookie’ season 2 key art.Warner Bros. Television

Warner Bros. Television

“We have business with El Condor,” Hector says after he, Danny and Ray drive up to armed gang members. “We’re bookmakers.”

When Hector breathes, “so far so good,” as the men give him the all clear, Danny asks incredulously, “So far so good? Are you high?”

“A little bit, yeah,” he answers honestly.

As the trio navigates business and other personal affairs, they meet several interesting characters along the way.

Zach Braff on ‘Bookie’.Warner Bros. Television

“Sell the wife, sell the house and put every penny you have on Loco Rocco’s game of the year!” Zach Braff, who seemingly plays a sports betting influencer, exclaims in front of a green screen.

“What do you think,” he asks to which Ray replies, “I think you owe us 42 grand.”

Eventually, the duo meet with Brad Garrett, who is a fictionalized version of himself.

“I know what you do, and I could be of immense help,” he says before breaking into an eerie high-pitched laugh. After exchanging glances and a heavy sigh, Danny tells Ray, “I wouldn’t trust this guy around a preschool, yet somehow I trust him with our money.”

A still from season 2 of the Max original series Bookie.Warner Bros. Television

The trailer continues and teases how Danny and Ray will face their fair share of blows. In one scene, Danny hilariously fights a tow truck driver with a hook for a hand.

The teaser only offers a brief glimpse of his appearance, but Sheen also returns as a fictionalized version of himself. TheTwo and a Half Menalum made cameos in two episodes in season 1.

Charlie Sheen in season 2 of Bookie.Warner Bros. Television

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Bookieseason two premieres Thursday, Dec. 12 on Max.

source: people.com