and he’s about to play his most serious role yet in the Safdie brothers’ thriller, Uncut Gems.

The actor, 53, notably known for his comedies including Billy Madison, 50 First Dates and his recent Netflix hit, Murder Mystery, now stars as Howard Ratner, a New York City jeweler who takes risks bigger than he might be able to handle.

The A24 film, which premiered to strong reviews at the Telluride Film Festival in August, dropped the first look Tuesday at Sandler’s gripping role coming from the filmmaker brothers who brought dramas like, Good Time and Heaven Knows What.

The movie followers go-getter, Ratner, as he puts his family, career and own life on the line in a series of bets, some of which include working with NBA star, Kevin Garnett and artist the Weeknd, who stars as himself in the film.

“I made a crazy risk, a gamble and it’s about to pay off,” Sandler says in the trailer, describing one of his largest bets yet.

Frozen’s Idina Menzel stars as Sandler’s wife, Dinah, and the movie’s supporting cast includes Lakeith Stanfield, Judd Hirsch, and Julia Fox.

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“This is me, this is how I win,” Sandler grins at the end of the teaser.

Outside of the film, Sandler could score his own win as Uncut Gems has already generated Oscar buzz for the actor’s unlikely performance — which would mark Sandler’s first Academy Awards nomination.

Uncut Gems is set to open in theaters on Dec. 13.