You Can't Win (2026)

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 (48)CrewGenresDetailsReleasesMediaAwards

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

J

Jenni Bradstreet

Chinese Sleeper

J

Jim Chow

Chinese Sleeper

T

Tony Lao

Chinese Sleeper

D

David Leong

Chinese Sleeper

H

Hutch Stellick

Boy Jack

Ted Rooney

Jack's Father

Skyler Verity

Young Jack

Brandon E. Jackson

Prison Guard

C

Charles Baker

Fremont Older

Rusty Tennant

Depot Policeman

Chris LeBlanc

Corbett

R

Robert Zorn

Jungle Bum

W

William Warren Ward

Jungle Bum

E

Earl Alexander

Jungle Bum

R

Ron Lampman

Jungle Bum

R

Rob Finney

Jungle Bum

A

Art Hickman

Jungle Bum / Pharmacist

K

Ken Clark

Jungle Bum

T

Tim Henderson

Jungle Bum

Robert Blanche

Cy

H

Henry Mark

Chew Chee

A

Alex Terzieff

Work Crew Boss

T

Todd Lagestee

Work Crew Guard

Louisa Krause

Irish Annie

R

Ron Otis

Hotel Detective

John Paulsen

Junkie Husband

Kathy Hsieh

Junkie Wife

J

Jim Hamerlinck

Goldtooth

J

James Lapan

Station Agent

S

Stella Diaz

Station Agent's Wife

M

Mark Fullerton

Canadian Constable

S

Scott

Murphey

Anatol Yusef

Dirty Dick

Anthony A. Kung

Opium Den Pickpocket

A

Alexis Scarff

Ghost Mother

W

Wesley Scarff

Baby Jack

K

Kori Ennis

Salon Patron

D

David Beck

Salon Patron

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