You Can't Win

You Can't Win

2026
2h 19m
5.2

5.2/10

6 votes • View on IMDb
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.

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Status: Released

Language: EN

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Production Information

Production Companies
Photus Films
Production Countries
United States of America
Spoken Languages
English

Keywords

literary adaptation hobo biographical drama

Quick Facts

Release Date February 17, 2026
Status Released
Language EN
IMDb ID tt1402593

Cast

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
Jenni Bradstreet

Chinese Sleeper

Jim Chow
Jim Chow

Chinese Sleeper

Key Crew

Barry Gifford
Screenplay
Robinson Devor
Director
Robinson Devor
Screenplay
Michael Pitt
Screenplay
Charles Mudede
Screenplay