10 Most Unsettling Dark Comedies of All Time

10 Most Unsettling Dark Comedies of All Time

There’s something about modern life that calls for dark humor. It seems appropriate that, in the face of adversities, the best form of defense is to poke fun at those very adversities through the time-honored American tradition of celebrating the macabre, the unsettling and the downright twisted.

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Here we decided to put together a list of the ten black comedies that made us feel the most genuinely uncomfortable; menacingly comic cinematic milestones that managed to be by turns — or at once — both funny and disturbing. So get your cringe muscles tensed, and we’ll begin!

1. Fargo

Ethan and Joel Coen are moviemakers renowned for their discreetly humorous dialogue and excellent use of atmosphere, and their 1996 offering Fargo is arguably the ultimate testament to this. The movie tells the “true” story of a kidnapping gone horribly wrong and several murders out in the sticks of Minnesota and North Dakota. Through all its exciting, gory detail, it still retains a sense of humor so delicate it remains ambiguous. Whether it’s the violent introduction of Steve Buscemi to a woodchipper, or the sing-song accent of the movie’s various regional extras — not to mention the superb Frances McDormand — the atmosphere remains truly thrilling, unbearably tense, and constantly amusing.

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2. The War of the Roses

To some, Michael Douglas may be a washed-up star nowadays, but he’s the only actor to have starred in two films in our top ten list, and he resolutely stole the show in both. The War of The Roses is a great, if underrated, comedy of the darkest kind. The tale begins when two lovers meet (the female protagonist played by the excellent Kathleen Turner), fall in love, get married, improve their careers and become wealthy. Then it all goes horribly wrong. Brilliantly narrated by their divorce lawyer (Danny DeVito), the movie chronicles how the couple’s squabbles eventually escalate into a messy, violent climax, as they inflict despicable levels of vengeance upon each another. If you’ve ever been through a break-up, you’ll squirm throughout this movie, laughing uncontrollably at the same time. Look out for a brief cameo from Dan “Homer Simpson” Castellaneta.

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3. Addams Family Values

Perhaps not the most disturbing of films on this list, Barry Sonnenfeld’s Addams Family Values, which came out in 1993, is nonetheless a movie that conveys a constant and unnerving feeling of uncertainty. Perhaps it’s simply the more Gothic nature of the second Addams installment, the family’s impermeable relationship with death, or the darker and more serious use of the macabre juxtaposed with the normal American world around them. One way or another, it’s a black-as-night comedy with a true air of dis-ease. If you haven’t seen it since the fifth grade, take another look. The performances from Raúl Juliá, Anjelica Huston, Christopher Lloyd and Christina Ricci are tantamount to genius!

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4. Delicatessen

Whilst 1991′s Delicatessen is certainly not considered a prequel to Amélie — director Jean-Pierre Jeunet’s “other” movie — it could well be described as its (very) messed-up older sister. The story revolves around a Parisian apartment building above a shady butcher’s shop in a post-apocalyptic France. The butcher lures waifs in with the promise of a vacancy, and then promptly dispatches them in order to sell their meat to the tenants above. This scheme is only foiled by the arrival of a plucky circus performer who becomes the butcher’s next target, and by a team of vegetarian troglodyte terrorists. What makes the film so creepy is its grimy, dirty aesthetic — one totally removed from the twee croissant-a-thon of Amélie. Macabre comic brilliance.

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5. About Schmidt

What is it about a movie that addresses the inherent futility of life that makes it so depressing to watch? Oh yeah, the inherent futility of life. The darkly comic About Schmidt, released in 2002, concerns a widower, played by Jack Nicholson, whose relationship with his late wife had deteriorated before her death to the point of bitter hatred. Upon discovering evidence in the closet that his wife had been having an affair with a friend, Schmidt takes to the wheel of their oversized retirement plan — a Winnebago — and hits the road in order to try and dissuade his daughter from marrying an unsuitable fiancée. The movie is at times so dismal it’s hard to watch (but not in a bad way; it’s a good film), but great dialogue and expert performances from Nicholson and Kathy Bates make for a tongue-firmly-in-cheek satire of growing old and amounting to nothing.

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6. Falling Down

Falling Down isn’t one of Michael Douglas’ better known films, but it’s certainly one of his best performances. The 1993 Joel Schumacher directed shoot-a-thon focuses on Douglas’ character, William “D-Fens” Foster, an ex-defense engineer who develops homicidal tendencies following a traffic jam. The movie is non-stop action, with Douglas exhibiting an increasingly dangerous, yet understandable, level of violent rage over everyday problems. The most notable — and coincidentally, the funniest — of these moments is the scene in which he fires an machine pistol into the ceiling of a fast food restaurant for refusing to serve him a breakfast meal three minutes after the menu changed to lunch. Disturbingly comedic and startlingly easy to identify with, Falling Down is the perfect ad for therapy.

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7. American Psycho

Not exactly a movie to sit and watch with Junior, 2000’s American Psycho was a great movie inspired by a great book. In the movie, Christian Bale stars as Patrick Bateman, a late ’80s Manhattan yuppie with a penchant for luxury, and butchering hookers. The film is, at times, one of the most disturbingly humorous soirées into the mind of a high class killer ever produced; at other times, just completely twisted. A memorable scene involves Bateman being pushed over the edge upon realizing that an associate’s business card is better than his, leading to attempted murder in a restroom (an attack that is hilariously mistaken as something else by the victim…). “Oh my God, it even has a watermark.” Get the machete.

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8. Being John Malkovich

Written and directed by the winning team of Charlie Kaufman and Spike Jonze, 1999′s Being John Malkovich is a postmodern masterpiece of gallows humor. In true Kaufman style, this batty picture charts the tumultuous occurrences that follow the accidental discovery of a portal into the brain of actor John Malkovich. Whilst the comedy is subtle, the creepiness and melancholy atmosphere of the movie are not. Resplendent with unnerving puppets, Cameron Diaz at her absolute aesthetic worst, and a restaurant scene from hell, this movie represents Jonze and Kaufman at their very best; blending the incredulously comedic with the darkest of weirdnesses.

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9. After Hours

The nightmarish plot of 1985′s After Hours — one of Martin Scorsese’s lesser lauded movies — is an allegorical masterpiece entirely devoted to the concept of rotten luck. Perhaps this is what makes us feel so uncomfortable watching it. The story begins and ends at work; but the between time documents one man (the worker) confronting an increasingly ill-fated chain of events — from having insufficient money to ride the subway, to the suicide of a young woman, to being pursued by a murderous mob. The seemingly cyclical, claustrophobic nature of the situations in which the protagonist (played by Griffin Dunne) finds himself is way less comfortable than any movie starring Cheech and Chong should ever be (they both appear as burglars), but just as funny. In these times, though, it’s hard to watch the film without musing on how the contemporary ATM card might have negated its entire premise.

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10. Grosse Pointe Blank

The 1997 George Armitage movie Grosse Pointe Blanke is something of a cult classic. This truly dark comedy portrays the existential crisis of a professional assassin returning to his hometown for a high school reunion. This movie has it all: guns, death, more death, and the non-ironic use of comedic one-liners. But it’s something much deeper that gives this film its unsettling edge. The believability of John Cusack’s hitman gives the lead character a personality that is easy to relate to. We find ourselves recoiling in discomfort at the recognizable mental traumas he faces regarding his morally ambiguous career choice. Like someone who works at McDonald’s.

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