20 Sad Movies That Men Are Allowed to Cry At

Midnight Cowboy (1969)
Director: John Schlesinger.Stars: Dustin Hoffman, Jon Voight, Sylvia Miles, John McGive. Traditionally, the “buddy film” operates on an accessible, pleasant, and warm-hearted playing field—look no further than 50/50 as an example. But director John Schlesinger’s classic Midnight Cowboy is a special case, depicting a close friendship between two men against a seedy New York City backdrop full of prostitutes and drugs. The characters themselves aren’t exactly likeable on paper. Jon Voight plays a cold-hearted gigolo, while Dustin Hoffman one-ups him in ruthlessness as a jerky conman. It’s an unlikely camaraderie, but the two guys form a strong bond, telling each other about their dark childhoods. Eventually, though, Hoffman gets fatally sick, which causes Voight to rob and beat his sexually hungry customers in order to pay for his friend’s treatment. Midnight Cowboy’s final image, that of Voight’s arm around a dead Hoffman on a bus, corresponds with the film’s overall darkness, but it’s also more affecting than any other “buddy film.”