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You Can't Win

You Can't Win
★ 4.9/10•2026•2h 19m•Western

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.

Barry Gifford · Screenplay

Robinson Devor · Director

Robinson Devor · Screenplay

Michael Pitt · Screenplay

StatusReleased
Runtime2h 19m
LanguageEN
Release DateFeb 17, 2026

Actors

Michael Pitt

Michael Pitt

Jack Black

Ivan Martin

Ivan Martin

The Sanctimonious Kid

Will Patton

Will Patton

Foot and a Half George

Jeremy Allen White

Jeremy Allen White

Smiler

Hannah Marks

Hannah Marks

Julia

Charles Baker

Charles Baker

Freemont Older

Julia Garner

Julia Garner

Chicken

James Hong

James Hong

Old Chinese Man

Rusty Schwimmer

Rusty Schwimmer

Salt Chunk Mary

Nina Arianda

Nina Arianda

Mrs. Alexander

Jenni Bradstreet

Chinese Sleeper

Jim Chow

Chinese Sleeper

Tony Lao

Chinese Sleeper

David Leong

Chinese Sleeper

Hutch Stellick

Boy Jack

Ted Rooney

Ted Rooney

Jack's Father

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