You Can't Win
5.2
6 Reviews
2026
2h 19min
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.
Storyline
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.
Released
17 February 2026
Runtime
2h 19min
Director
Genre
Status
Released
Language
English
Production
Photus Films
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
Jenni Bradstreet
Chinese Sleeper
Jim Chow
Chinese Sleeper
Tony Lao
Chinese Sleeper
David Leong
Chinese Sleeper
Hutch Stellick
Boy Jack
Ted Rooney
Jack's Father
Skyler Verity
Young Jack
Brandon E. Jackson
Prison Guard
Charles Baker
Fremont Older
Rusty Tennant
Depot Policeman
Chris LeBlanc
Corbett
Robert Zorn
Jungle Bum
William Warren Ward
Jungle Bum
Earl Alexander
Jungle Bum
Ron Lampman
Jungle Bum
Rob Finney
Jungle Bum
Art Hickman
Jungle Bum / Pharmacist
Ken Clark
Jungle Bum
Tim Henderson
Jungle Bum
Robert Blanche
Cy
Henry Mark
Chew Chee
Alex Terzieff
Work Crew Boss
Todd Lagestee
Work Crew Guard
Louisa Krause
Irish Annie
Ron Otis
Hotel Detective
John Paulsen
Junkie Husband
Kathy Hsieh
Junkie Wife
Jim Hamerlinck
Goldtooth
James Lapan
Station Agent
Stella Diaz
Station Agent's Wife
Mark Fullerton
Canadian Constable
Scott
Murphey
Anatol Yusef
Dirty Dick
Anthony A. Kung
Opium Den Pickpocket
Alexis Scarff
Ghost Mother
Wesley Scarff
Baby Jack
Kori Ennis
Salon Patron
David Beck
Salon Patron
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