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

Ted Rooney

Jack's Father

Skyler Verity

Young Jack

Brandon E. Jackson

Prison Guard

Rusty Tennant

Depot Policeman

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