10. The Third Man (1949)

directed by Carol ReedPerhaps one of the most cynical movies ever made, The Third Man features an inept protagonist whose breezy attitude allows him to be easily-manipulated by everybody around him, from the local cops to mysterious women to hardened crooks. His love of dimestore romanticism is challenged by the nihilistic worldview of postwar Vienna, where the criminal element thrives. Soon, our passive hero is thrust into the position to do The Right Thing. He does and is rewarded with rejection and loneliness. No matter. He’ll make it through this just like he has everything else: with a crooked smile and a laidback attitude. Seldom has an ending this bitter seemed so sweet.

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