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IMDb 4.7 HD

You Can't Win

2026 2 h 19 min Drama

A 1920s drifter's life of crime and unlikely friendship anchors this biographical drama.

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United States 5 services Free 3 services Rental 2 services Purchase 2 services
Kanopy Free — —
Amazon Video — Rental Purchase
Hoopla Free — —
Tubi TV Free with ads — —
Fandango At Home — Rental Purchase

Availability data by JustWatch

About the film

What it’s about

Jack Black, a legendary outlaw, navigates the criminal underworld of the 1920s. His memoir, published in 1926, becomes an unexpected bestseller.

What hooks you

Michael Pitt plays Jack Black, the real-life hobo and thief whose 1926 memoir became a bestseller and influenced counter-cultural writing. Robinson Devor directs, with James Hong as an old Chinese man and Will Patton as Foot and a Half George. The film is based on Black's own book.

Who it’s for

It will appeal to those who like biographical dramas rooted in true crime and literary history, and to anyone drawn to stories of outsiders and the American underworld.

Technical details
Country
United States
Year
2026
Genre
Drama
Running time
2h 19min
World premiere
Feb 17, 2026

Ratings

MOVIE․ONE · 120 votes
5.0 /10
IMDb
4.784
Your rating —
— /10
1 · Didn't land 10 · Masterpiece

Creative team

All 15
Director Robinson Devor
Starring
  1. 01 Michael Pitt Jack Black
  2. 02 James Hong Old Chinese Man
  3. 03 Ivan Martin The Sanctimonious Kid
  4. 04 Will Patton Foot and a Half George
  5. 05 Hannah Marks Julia
  6. 06 Jenni Bradstreet Chinese Sleeper
  7. 07 Jeremy Allen White Smiler
  8. 08 Jim Chow Chinese Sleeper
  9. 09 Tony Lao Chinese Sleeper
  10. 10 Charles Baker Freemont Older
  11. 11 Hutch Stellick Boy Jack
  12. 12 Julia Garner Chicken
  13. 13 Ted Rooney Jack's Father
  14. 14 Robert Blanche Actor

Trivia

  1. Based on the novel by Jack Black.

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