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San Quentin (1937 film)
1937
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Just before Steve Jameson (Pat O'Brien) takes over as captain of the yard at San Quentin, he meets and falls for singer May Kennedy (Ann Sheridan). May's brother, "Red" (Humphrey Bogart), is arrested soon after and sentenced to San Quentin, where Steve is implementing reform. Believing Steve's methods too harsh, May breaks up with him. Meanwhile, Red slowly comes to appreciate... Wikipedia