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You can stream Hogtown (2014) on Philo with a subscription.

A man disappears on the same day he makes his fortune in this re-imagining of a true story, which is still unsolved. In this version of the disappearance of Ambrose Small, the setting has been changed from Toronto, 1919, to Chicago of the same year. Gorgeous cinematography in mostly black and white underscores the racial tensions of the time, while intentional anachronisms and Calgary-raised director Daniel Nearing’s postmodern vision give the film an otherworldly quality. While the investigation of Small’s case is a central device, Nearing’s real objective is to expose the characters of the time and stoke the flames of mystery.