The Saddest Comedies Ever Made

As we move into Thanksgiving week, DVD players and cable networks across the land will be cuing up our favorite turkey day movie, Planes, Trains, and Automobiles. One of its viewers may very well be Flavorwire favorite Emma Stone, who recently told Entertainment Weekly that Planes is the movie that made her want to be an actor — specifically, Steve Martin’s late-night motel “Chatty Cathy” tirade. Miss Stone explains, “You go from laughing hilariously at Steve Martin to your heart breaking for John Candy in that one scene, and that was, I think, the first time that I saw that you could do both.” Planes, Trains wasn’t the first movie to prove that you could “do both” — i.e., mesh the funny and the sad with equal effectiveness. But it’s one of the best, and after the jump, we’ll take a look at that and a few other very sad comedies.

The Kid

Writer/director/star Charlie Chaplin was never shy about mixing comedy and pathos — sometimes leaning too heavily on the latter. But when he got the mixture right it was golden: witness the Little Tramp’s crushing New Year’s Eve disappointment in The Gold Rush, the unabashedly sentimental and perfect closing scene of City Lights, or his first feature-length comedy, 1921′s The Kid. The film, whose opening titles promise “a picture with a smile — and perhaps, a tear,” finds Chaplin’s “little fellow” finding and raising an abandoned baby as his own, only to have the child taken by the authorities. And if the weeping of little Jackie Coogan (who later played Uncle Fester on The Addams Family) doesn’t mist you up during that climactic sequence, well friend, you have no soul.