You Can't Win (2026)

5.2/10 139 min Drama

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.

Cast

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

Rusty Schwimmer

Salt Chunk Mary

Nina Arianda

Mrs. Alexander

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