You Can't Win poster
Where to stream

You Can't Win

4.920262h 19mMovieWestern

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.

DirectorRobinson Devor
WritersRobinson Devor·Barry Gifford

Where to watch

HooplaHooplaTubi TVTubi TV
Availability shown for Canada · rights vary by country

Cast · Directed by Robinson Devor

MPMichael Pitt
Michael Pitt
Jack Black
IMIvan Martin
Ivan Martin
The Sanctimonious Kid
WPWill Patton
Will Patton
Foot and a Half George
JWJeremy Allen White
Jeremy Allen White
Smiler
HMHannah Marks
Hannah Marks
Julia
CBCharles Baker
Charles Baker
Freemont Older
JGJulia Garner
Julia Garner
Chicken
JHJames Hong
James Hong
Old Chinese Man
RSRusty Schwimmer
Rusty Schwimmer
Salt Chunk Mary
NANina Arianda
Nina Arianda
Mrs. Alexander
JB
Jenni Bradstreet
Chinese Sleeper
JC
Jim Chow
Chinese Sleeper

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More from Ivan Martin · Co-star actor

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More from Robinson Devor · Director

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More like this

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You Can't Win — streaming FAQ

Which OTT platform streams You Can't Win?

You Can't Win is streaming on Hoopla and Tubi TV in Canada. It's not currently on Netflix.

Is You Can't Win on Netflix?

No, You Can't Win is not on Netflix in Canada as of October 2026. It's currently on Hoopla and Tubi TV.

Is You Can't Win on Amazon Prime Video?

No, You Can't Win isn't on Amazon Prime Video in Canada right now. It's on Hoopla and Tubi TV instead.

Where can I watch You Can't Win for free?

You Can't Win is available to stream free (with ads) on Hoopla and Tubi TV in Canada.

Is You Can't Win based on a true story?

Yes — You Can't Win is based on true events, dramatising real people and events (some details may be fictionalised for the screen).