You Can't Win
You Can't Win

You Can't Win

HD ★ 4.9 📅 2026 ⏱ 139 min
Western

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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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
Tony Lao
Tony Lao
Chinese Sleeper
David Leong
David Leong
Chinese Sleeper
Hutch Stellick
Hutch Stellick
Boy Jack
Ted Rooney
Ted Rooney
Jack's Father
Skyler Verity
Skyler Verity
Young Jack
Brandon E. Jackson
Brandon E. Jackson
Prison Guard
Charles Baker
Charles Baker
Fremont Older
Rusty Tennant
Rusty Tennant
Depot Policeman

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