Castle on the Hudson (1940) (Years Without Days)

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Mobster Tommy Gordon isn't worried about being sentenced to Sing Sing prison because his political pals have promised him a quick parole. A troublesome prisoner, he finally concedes that his friends have deserted him, and he makes an effort to reform. When his girlfriend Kay is injured in an accident, Warden Long gives Tommy a pass to go see her. But trouble erupts when Tommy encounters the man responsible for his imprisonment.