You Can't Win
Plot.
A drama set in the 1920s hobo underworld and centered on the unusual friendship between an adventurer and a young prostitute alongside Black's life on the road, in prison and his various criminal capers in the American and Canadian west from the late 1880s to early 20th century.
Where to Watch.
No streaming offers found
Cast & Crew.

Michael Pitt
Jack Black / Screenplay

Jeremy Allen White
Smiler

Hannah Marks
Julia

Will Patton
Foot and a Half George

Charles Baker
Freemont Older

Julia Garner
Chicken

Rusty Schwimmer
Salt Chunk Mary

Barry Gifford
Screenplay

Louisa Krause
Irish Annie

Robinson Devor
Director / Screenplay

Anatol Yusef
Dirty Dick

Charles Mudede
Screenplay

Ted Rooney
Jack's Father

Robert Blanche
Cy

Ivan Martin
The Sanctimonious Kid

Sean Kirby
Cinematographer

Christopher Julian
Editor

Marco Perez
Editor

Adam Sekuler
Editor

Susan Shopmaker
CastingDirector
