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You Can't Win
2026Directed by Robinson Devor2h 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.
- Western
Cast
- Michael Pitt as Jack Black
- Ivan Martin as The Sanctimonious Kid
- Will Patton as Foot and a Half George
- Jeremy Allen White as Smiler
- Hannah Marks as Julia
- Charles Baker as Freemont Older
- Julia Garner as Chicken
- James Hong as Old Chinese Man
- Rusty Schwimmer as Salt Chunk Mary
- Nina Arianda as Mrs. Alexander
- Jenni Bradstreet as Chinese Sleeper
- Jim Chow as Chinese Sleeper
- Tony Lao as Chinese Sleeper
- David Leong as Chinese Sleeper
- Hutch Stellick as Boy Jack
- Ted Rooney as Jack's Father
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