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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LumaFlicks Intelligence
Mood
Compelling • Engaging • Atmospheric
Best Time To Watch
Anytime
Perfect For
Movie Buffs
Fans Also Enjoyed
Inception, The Dark Knight, Fight Club
Watch With
Friends / Solo
You Can't Win offers an immersive story experience. Its combination of strong thematic elements, exceptional performances, and atmospheric direction makes it a standout choice.
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
Feb 17, 2026
2h 19m
English
United States of America
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