8 Hilarious Dark Comedies Worth Watching

Almost all great comedy is founded upon misery — by putting characters through hell and seeing the unexpected ways in which they react. There are plenty of old adages that illustrate this point, including the cliche that tragedy plus time equals comedy. Dark comedies are the films that remove time from the equation and still find ways in which to make tragedy hilarious. These particular dark comedies are some of the darkest of the dark, confronting us with shocking realities by forcing us to laugh at them and at ourselves.

1. Cheap Thrills

Cheap Thrills has plenty to say on economic issues, but it’s fascinating and funny for other reasons as well. It does, after all, involve a pair of old high-school friends fallen on hard times, and a rich couple that preys upon their weaknesses for their own entertainment, paying them to commit senseless crimes and do things that conflict with their moral compasses. Dave Koechner of Anchorman fame plays the rich husband, skillfully playing a darkened version of his normal persona. The old friendship quickly dissolves as the rich couple pits the pair against each other repeatedly, all for the sake of a few hundred dollars. The film hilariously pushes this premise as far as it will go, before ending with a brilliant final shot that puts the whole film into perspective.

2. Four Lions

Who deserves to be made fun of more than terrorists? Four Lions tackles that touchy issue head-on, focusing on a group of wannabe jihadists living in Britain who consistently bungle their ignorant attempts at terrorism with their own ineptitude. This consistently hilarious film walks a tightrope in more ways than one, as it focuses on characters trying to do despicable things that aren’t entirely unsympathetic. Deep down, they’re really just idiots looking for a purpose, but the purpose they find guides them to a thrilling climax wherein one character must stop a terror attack he helped to plan. By exposing the idiocy and hypocrisy of modern day terrorism, director Christopher Morris creates a film that’s laugh-out-loud funny throughout, regardless of its difficult political context.

3. Man Bites Dog

This Belgian mockumentary filmed in grainy black-and-white centers on a camera crew diligently recording the everyday life and times of prolific serial killer Benoit. Unlike most onscreen killers, Benoit is charismatic and friendly, even funny, and makes no secret out of his horrific doings, even describing with expertise the proper way to weigh down the body of a midget versus a child when throwing it into the river. The horrific becomes hilariously mundane. As the film goes on, Benoit’s insanity is matched by the camera crew’s as the wannabe documentarians are drawn increasingly into his violent world, making for a surreal but apt satire on the nature of documentary and reality television.

4. Super

What if Dwight Schrute and Juno teamed up to solve crimes? Super, a dark satire of comic book culture from director James Gunn who later made Guardians of the Galaxy, finds Rainn Wilson’s poorly adjusted hero Frank donning a cape and mask in order to save his wife from the drug-dealing strip club owner (Kevin Bacon) she leaves him for. Like a more grounded version of Kick-Ass, Super explores the horrifying reality of what it might actually be like to emulate comic book heroes in a world where death is far more permanent and pain is far more real. Things only become more horrifyingly hilarious as the manic pixie dream girl Libby (Ellen Page) eagerly becomes his sidekick and proves herself far more insane than Frank.

5. Happiness

Despite its title, Todd Solondz’s 1998 dark comedy Happiness features very few happy characters. The film follows three sisters and the people on the fringes of their lives, including a horribly depressed office drone (Philip Seymour Hoffman) who can only express his affection for the earnest Helen Jordan (Lara Flynn-Boyle). Elsewhere in the mostly plotless film, a man commits suicide after a breakup, and a psychiatrist pedophile is unable to resist the temptation to rape his son’s friends. The film doesn’t make light of such a serious subject so much as it surrounds it with a mundane world of tragically hilarious misunderstandings and awkward, often heartbreaking interactions that makes the horror of this plot line feel that much more real.

6. Very Bad Things

A Las Vegas bachelor party goes horribly wrong, and a group of inept friends, led by a put-upon Jon Favreau and a pure evil Christian Slater, must deal with the consequences of their accidental killing of a stripper, one step at a time. Very Bad Things is a ruthless film concerning the deception and outright murder lurking beneath the surface of a supposedly happy marriage. As things spin out of control and the body count continues to rise, Cameron Diaz eventually steals the show, playing a bride whose monomaniacal commitment to having the perfect wedding day eventually outpaces the crimes of her groom and his panicky friends.

7. World’s Greatest Dad

Robin Williams stars in this film from his friend, comedian-director Bobcat Goldthwait, which has only become more prescient since the beloved actor’s death. Williams plays a high school poetry teacher raising a son, who is the sort of snot-nosed, world-hating teenager only his father could love — and even he has a hard time with it. After his son dies by auto-erotic asphyxiation, Williams frames it as a suicide, penning a world-weary suicide note for him that makes the entire town romanticize a child they shunned during his life. Meanwhile, failed writer Williams begins to use his son’s suicide to further his own lust for success, writing an entire journal to be published. The film satirizes our romanticized treatment of our dearly departed while still creating a convincing portrait of a lonely father’s loss, personified through a tender anchoring performance from Williams.

8. After Hours

One of Martin Scorsese’s most underrated masterpieces, After Hours concerns a single hellish night in the life of word processor Paul Hackett, who becomes trapped in a bad part of New York after taking a taxi to see a woman he met at a cafe that same night. The woman turns out to be insane, or at least in the midst of some sort of breakdown, and Hackett soon leaves. He encounters many characters in his long quest to get home to get some rest before beginning another work day, though the locals are of little help. As the film goes on and the structure of his ordeals reveals itself, it begins to feel as if the universe is playing some sort of cosmic joke on poor Hackett, whose struggles become so difficult again and again one can’t help but laugh, even if they’d cry in his place.

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