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You Can't Win
You Can't Win

You Can't Win

2026 139 min ⭐ 5.2 Drama

Viewers interested in modern Drama cinema often explore You Can't Win because of its cast, story direction, and audience popularity.

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.

You Can't Win
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Popular Cast

Michael Pitt

Michael Pitt

Jack Black
Ivan Martin

Ivan Martin

The Sanctimonious Kid
Will Patton

Will Patton

Foot and a Half George
Jeremy Allen White

Jeremy Allen White

Smiler
Hannah Marks

Hannah Marks

Julia
Charles Baker

Charles Baker

Freemont Older
Julia Garner

Julia Garner

Chicken
James Hong

James Hong

Old Chinese Man
Rusty Schwimmer

Rusty Schwimmer

Salt Chunk Mary
Nina Arianda

Nina Arianda

Mrs. Alexander

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