You Can't Win

Feb 17, 2026

2h 19m

★ 5.0

Overview

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.

Genres

Western

Production Companies

Photus Films

You Can't Win Trailers

Cast

Jack Black

Michael Pitt

The Sanctimonious Kid

Ivan Martin

Foot and a Half George

Will Patton

Smiler

Jeremy Allen White

Julia

Hannah Marks

Freemont Older

Charles Baker

Chicken

Julia Garner

Old Chinese Man

James Hong

Salt Chunk Mary

Rusty Schwimmer

Mrs. Alexander

Nina Arianda

Chinese Sleeper

Jenni Bradstreet

Chinese Sleeper

Jim Chow

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