You Can't Win

Directed by Robinson Devor
2026    2h 19m[Drama](/on-demand/category/drama), [Western](/on-demand/category/western)
4.55.2
The true-crime story of Jack Black, whose 1926 memoir became an unlikely bestseller upon its release and later inspired generations of counter-cultural writing.

Where to Watch You Can't Win

Cast of You Can't Win

  • Michael PittJack Black / Screenplay
  • 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
  • Charles BakerFremont Older
  • Rusty TennantDepot Policeman

 

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