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You Can't Win

5.2 Rating 2026 139 min

Drama

The true-crime story of legendary outlaw Jack Black, whose 1926 memoir became an unlikely bestseller upon its release and later inspired generations of counter-cultural writing.

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Trailers & Extra Clips

You Can't Win - Trailer

Trailer

Cast & Crew

Michael Pitt

Jack Black

Ivan Martin

The Sanctimonious Kid

Will Patton

Foot and a Half George

Jeremy Allen White

Jeremy Allen White

Smiler

Hannah Marks

Julia

Charles Baker

Freemont Older

Julia Garner

Chicken

James Hong

Old Chinese Man

Rusty Schwimmer

Rusty Schwimmer

Salt Chunk Mary

Nina Arianda

Mrs. Alexander

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