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You Can't Win

  • 2026
  • 2h 19m
  • Drama

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

Jack Black

Jeremy Allen White

Smiler

Hannah Marks

Julia

Will Patton

Foot and a Half George

Charles Baker

Freemont Older

Julia Garner

Chicken

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