You Can't Win(2026)
movie - first aired/released 2026-02-17 - 139 min - audience 4.9
Western
Directed by Robinson Devor
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 PittJack Black
Ivan MartinThe Sanctimonious Kid
Will PattonFoot and a Half George
Jeremy Allen WhiteSmiler
Hannah MarksJulia
Charles BakerFreemont Older
Julia GarnerChicken
James HongOld Chinese Man
Rusty SchwimmerSalt Chunk Mary
Nina AriandaMrs. Alexander- Jenni BradstreetChinese Sleeper
- Jim ChowChinese Sleeper
- Tony LaoChinese Sleeper
- David LeongChinese Sleeper
- Hutch StellickBoy Jack
Ted RooneyJack's Father
Skyler VerityYoung Jack
Brandon E. JacksonPrison Guard
Show all 48 cast members
- Charles BakerFremont Older
Rusty TennantDepot Policeman
Chris LeBlancCorbett- Robert ZornJungle Bum
- William Warren WardJungle Bum
- Earl AlexanderJungle Bum
- Ron LampmanJungle Bum
- Rob FinneyJungle Bum
- Art HickmanJungle Bum / Pharmacist
- Ken ClarkJungle Bum
- Tim HendersonJungle Bum
Robert BlancheCy- Henry MarkChew Chee
- Alex TerzieffWork Crew Boss
- Todd LagesteeWork Crew Guard
Louisa KrauseIrish Annie- Ron OtisHotel Detective
John PaulsenJunkie Husband
Kathy HsiehJunkie Wife- Jim HamerlinckGoldtooth
- James LapanStation Agent
- Stella DiazStation Agent's Wife
- Mark FullertonCanadian Constable
- ScottMurphey
Anatol YusefDirty Dick
Anthony A. KungOpium Den Pickpocket- Alexis ScarffGhost Mother
- Wesley ScarffBaby Jack
- Kori EnnisSalon Patron
- David BeckSalon Patron
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