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You Can't Win

2026 · Robinson Devor · 139 min

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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.

Michael PittJack Black

Ivan MartinThe Sanctimonious Kid

Will PattonFoot and a Half George

Jeremy Allen WhiteSmiler

Hannah MarksJulia

Charles BakerFreemont Older

Julia GarnerChicken

James HongOld Chinese Man

Rusty SchwimmerSalt Chunk Mary

Nina AriandaMrs. Alexander JJenni BradstreetChinese Sleeper JJim ChowChinese Sleeper TTony LaoChinese Sleeper DDavid LeongChinese Sleeper HHutch StellickBoy Jack

Cast

Michael PittJack Black

Ivan MartinThe Sanctimonious Kid

Will PattonFoot and a Half George

Jeremy Allen WhiteSmiler

Hannah MarksJulia

Charles BakerFreemont Older

Julia GarnerChicken

James HongOld Chinese Man

Rusty SchwimmerSalt Chunk Mary

Nina AriandaMrs. Alexander JJenni BradstreetChinese Sleeper JJim ChowChinese Sleeper TTony LaoChinese Sleeper DDavid LeongChinese Sleeper HHutch StellickBoy Jack

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