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You Can't Win
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Overview
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.
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Cast & Crew
![](https://image.tmdb.org/t/p/w92/fWR4Z1xk1ZMUMMnMeRADVh1s3DW.jpg)
Michael Pitt
Jack Black
![](https://image.tmdb.org/t/p/w92/zKk4vmDeUexdevtt6wm8WdMQ1TG.jpg)
Jeremy Allen White
Smiler
![](https://image.tmdb.org/t/p/w92/wPb71lRvduHn25WYJIuF7tK0fTt.jpg)
Hannah Marks
Julia
![](https://image.tmdb.org/t/p/w92/2vr8aJacajXz7m4lMc2WdVniCRZ.jpg)
Will Patton
Foot and a Half George
![](https://image.tmdb.org/t/p/w92/mhSoY1plaop5eufoHDP4fkIGUfh.jpg)
Charles Baker
Freemont Older
![](https://image.tmdb.org/t/p/w92/ud1RXbvW70J89iqeic7no8olxvb.jpg)
Julia Garner
Chicken
Genres
Drama