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You Can't Win
2026, Feb 17
2h 19m
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.
Directed by
Robinson Devor
Jeremy Allen White
Smiler
Will Patton
Foot and a Half George
Julia Garner
Chicken
James Hong
Old Chinese Man
Michael Pitt
Jack Black
Charles Baker
Freemont Older
Rusty Schwimmer
Salt Chunk Mary
Hannah Marks
Julia
Nina Arianda
Mrs. Alexander
Robert Blanche
Cy
Louisa Krause
Irish Annie
Ted Rooney
Jack's Father
Anatol Yusef
Dirty Dick
Ivan Martin
The Sanctimonious Kid
Chris LeBlanc
Corbett
John Paulsen
Junkie Husband
Rusty Tennant
Depot Policeman
Anthony A. Kung
Opium Den Pickpocket
Skyler Verity
Young Jack
Brandon E. Jackson
Prison Guard
Kathy Hsieh
Junkie Wife
Jenni Bradstreet
Chinese Sleeper
Jim Chow
Chinese Sleeper
Tony Lao
Chinese Sleeper
David Leong
Chinese Sleeper
Hutch Stellick
Boy Jack
Robert Zorn
Jungle Bum
William Warren Ward
Jungle Bum
Earl Alexander
Jungle Bum
Ron Lampman
Jungle Bum
Rob Finney
Jungle Bum
Ken Clark
Jungle Bum
Tim Henderson
Jungle Bum
Henry Mark
Chew Chee
Todd Lagestee
Work Crew Guard
Jim Hamerlinck
Goldtooth
James Lapan
Station Agent
Stella Diaz
Station Agent's Wife
Mark Fullerton
Canadian Constable
Scott
Murphey
Alexis Scarff
Ghost Mother
Wesley Scarff
Baby Jack
Kori Ennis
Salon Patron
David Beck
Salon Patron
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