You Can't Win

4.9/ 10 8 votes 2026-02-17 2h 19m 5 popularity

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.

Director: Robinson Devor

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Cast

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Michael Pitt

Jack Black

Ivan Martin

The Sanctimonious Kid

Will Patton

Foot and a Half George

Jeremy Allen White

Smiler

Hannah Marks

Julia

Charles Baker

Freemont Older

Julia Garner

Chicken

James Hong

Old Chinese Man

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