Notably grim and gritty for an early sound film, 20,000 Years in Sing Sing focuses on Spencer Tracy as gangster Tommy Connors, who gets sentenced to the titular prison for armed robbery and winds up dealing with a whole lot more. Based on a book by the actual warden of Sing Sing, the movie explores prison life in detail and doesn't flinch from the deadly consequences (on both sides) of an escape attempt. At first belligerent and hostile, Tommy soon comes to respect the warden (Arthur Byron), so much so that he gets to become part of a program that allowed inmates to temporarily leave the prison with nothing more than a promise to return.
That's where Bette Davis comes in, playing Tommy's girlfriend Fay. She finds herself in over her head with Tommy's former associates, and he gets out in order to help her. Redemption isn't quite in the cards for Tommy, though, and the movie ends on a bleak note in which no one really wins. It's refreshingly pessimistic, although the plot can be a little disjointed, and some of Tommy's fellow inmates seem to be important characters only to fade in and out of the story. Davis, too, comes and goes, although Tommy's love for Fay is ultimately what keeps the story going. It's not much of a part for Davis, and she's mostly crying about Tommy's fate or professing her love for him. She does get to do a pseudo-deathbed scene, which she milks for all it's worth, and she looks glamorous in her gangster's-moll outfit in her first appearance. But this is Tracy's movie, and he carries it with intensity and vulnerability.
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