The Saddest Comedies Ever Made

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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.

Sideways

Most video stores — remember those? — classified Alexander Payne’s 2004 Oscar-winner as a comedy, and yes, it is full of funny scenes (their sneak into the home of Jack’s hook-up) and witty dialogue (“You don’t understand my plight”). But when you get down to it, it chronicles the downward spiral of an alcoholic, elitist failure who can’t let his wife go, and who quite possibly loses a great woman in order to preserve the lies of his cheating friend. Not quite a laugh riot anymore, is it?

World’s Greatest Dad

Here’s one that looks like it should be dumb fun: Ever-wacky Robin Williams playing the dad to a horny teen, in a comedy written and directed by Police Academy regular Bobcat Goldthwait. But any illusions that World’s Greatest Dad was going to merge the sensibilities of Shakes the Clown and Mrs. Doubtfire were dispelled early in the film, when high school teacher Lancy Clayton (Williams) discovers his son’s dead body, the result of an autoerotic asphyxiation accident; for the rest of the film, Goldthwait (and Williams, who’s seldom been better) walk a delicate line between all-out grief-induced tragedy and gasping, oh-my-god-they’re-getting-away-with-this pitch-black comedy.

Margot at the Wedding

Woman and her son travel to her sister’s wedding. Woman is unimpressed with the sister’s choice of husband, tries to wreck the whole thing. Cast Kate Hudson, Katherine Hiegl, and Jack Black in this thing, have Garry Marshall direct, and you’ve got a big, dumb, studio rom-com. But cast Nicole Kidman, Jennifer Jason Leigh, and — surprisingly — Jack Black in this thing, have Noah Baumbach (Greenberg) direct, and you’ve got Margot at the Wedding, a toxic, funny, and ultimately tragic comedy/drama from 2007. In that broadly played alternate version, the sparring sisters and schlubby would-be brother-in-law would take their licks and learn their lessons; in Baumbach’s altogether more acidic universe, Kidman’s Margot is so poisonous and unlikable that no such happy endings are possible — or, frankly, believable.

The Informant!

Steven Soderbergh’s 2009 sports a giggly premise, a supporting cast loaded with comic greats past (The Smothers Brothers) and present (Patton Oswalt, Paul F. Tompkins, Tony Hale, Joel McHale), a jaunty Marvin Hamlisch score, and even a slammer on the title. But the film itself is a bit trickier than that; Soderbergh went off and made a sly anti-comedy, in which the surface elements, secondary players, and non-sequitur laced voice-over (“I don’t like wool on skin. Not even that merino wool they have at Marshall Field in Chicago. Ginger likes it because it’s formfitting, but she likes avocados. And who wants that texture in their mouth?”) misdirect our attention from the mentally unstable, wildly delusional protagonist at the story’s center.

Harold and Maude

Hal Ashby’s brilliant 1971 film — best known to later generations for its shout-out as “the greatest love story of our time” in There’s Something About Mary — is a wild and often uproarious black comedy, in which the many (many) mock suicides of its main character (Bud Cort) are played for big, dark laughs. And, initially, the incongruity of his romance with 79-year-old Maude (Ruth Gordon) is aimed at the funnybone as well, though director Ashby is careful to tell their story straight, and make everyone around them ridiculous. The picture doesn’t take the world seriously, but it takes Harold and Maude seriously, which is why its unexpected turn to tragedy in its final scenes works as beautifully as it does.

Grumpy Old Men

This 1993 comedy, which unexpectedly made Jack Lemmon and Walter Matthau bankable again (at 68 and 73, respectively), got most of its laughs from the frequently foul-mouthed banter of its stars, who played a pair of long-bickering Minnesota neighbors. But Matthau (lest we forget, an Academy Award winning actor) also lands a genuinely moving moment in the middle of all the Right Said Fred and smelly-fish gags, when he discovers Lemmon having a heart attack and takes him to a hospital. At the admittance desk, he’s asked whether he’s family or friend — and in his moment of response, he hints not only at his genuine love for his nemesis, but the loneliness within himself.

Planes, Trains, and Automobiles

On one level, John Hughes’ 1987 classic is the slapstick-tastic tale of two weary holiday travelers, bravely soldiering through a hilarious cross-country trip in which everything that can go wrong, will go wrong. And, on another level, it’s the story of a clinically depressed widower in fierce denial, clinging desperately to the human companionship he so desperately needs in order to preserve what remains of his shredded sanity.

Happy Thanksgiving, everybody!