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10 great dark comedies

Dark comedies are a nasty business.Not only do they deal with subjects that many people find offensive, but filmmakers who attempt them often find themselves caught between two frequently conflicting forces: the lure of the box-office and the lure of cult status. One can see that push and pull in “School for Scoundrels,” starring Billy Bob Thornton and Jon “Napoleon Dynamite” Heder, which
/ Source: contributor

Dark comedies are a nasty business.

Not only do they deal with subjects that many people find offensive, but filmmakers who attempt them often find themselves caught between two frequently conflicting forces: the lure of the box-office and the lure of cult status. One can see that push and pull in “School for Scoundrels,” starring Billy Bob Thornton and Jon “Napoleon Dynamite” Heder, which is a remake of a 1960 British comedy.

Staying true to the dark nature of a film’s soul can often mean box-office death; such films often alienate more sensitive audience members. On the other hand, dark comedies that drift away from their true nature find themselves wallowing in the abyss that is mediocre, uninspired comedy. They alienate their core audience while leaving the general audience unimpressed. Thus, it is a rare dark comedy that emerges as a complete success.

The difference between a comedy with dark humor and a true dark comedy can sometimes be nebulous. There are many comedies with bits of dark humor, but far fewer true dark comedies. When done right, the dark comedy is one of cinema’s most rewarding experiences. Here are the 10 best ever made.

10. Serial Mom (1994)

Dark premise: Serial killing is funny.

Turning convention on its head once again, director John (“Hairspray”) Waters takes the wholesome, perfect American mother and makes her a serial killer. In every way, Beverly Sutphin (Kathleen Turner) is the perfect mother. She’s caring, loving, and has raised two wonderful children. It just happens that she’s also a serial killer. From this premise, Waters creates one of his most subversive yet accessible films. “Serial Mom” lies somewhere between David Lynch’s “Blue Velvet” and the John Belushi film “Neighbors”.

Darkest/funniest/most twisted Moment: One of Beverly’s neighbors (Mink Stole) has been receiving disturbing crank calls. When we finally found out that Beverly is the culprit, her sweet demeanor blown, the ensuing call devolves into a spasm of profanity and hilarity.

Best line: “Chip, you know how I hate the brown word.”

9. Raising Arizona (1987)

Dark premise: Kidnapping babies is funny.

“Raising Arizona” is a mix of slapstick and dark humor that continues the Coens brothers’ penchant for putting simple people in complex situations. This is the story of a childless couple, ex-con H.I. (Nicolas Cage) and ex-police officer Edwina “Ed” McDunnough (Holley Hunter) who decide to steal one baby from a group of quintuplets since, as Ed concludes, the family has more than they can handle.

Darkest/funniest/most twisted Moment: The scene when escaped convicts Gale and Evelle (John Goodman, William Forsythe) realize they’ve left the baby on top of the car after robbing the bank is about as good a confluence of dark comedy as there is.

Best line: (old man in bank during a robbery) “Now, what’s it gonna be young feller? You want I should freeze or get down on the ground? ‘Cause if’n I freeze, I can’t rightly drop. And if’n I drop, I’m gonna be in motion.”

8. M*A*S*H (1970)

Dark premise:
War is funny.

“M*A*S*H” is largely a comedy of manners, throwing a trio of unorthodox doctors into a situation that should beat them down. Instead, they thrive. Set during the Korean War, the film instead becomes a commentary on Vietnam. “Hawkeye” Pierce (Donald Sutherland), “Trapper John” MacIntyre (Elliot Gould), and “Duke” Forrest (Tom Skerritt) essentially make the war theirs by drinking, gambling and cavorting whenever possible. Director Robert Altman captures the essential cultural conflicts of an era.

Darkest/funniest/most twisted moment: When the judgemental Major Frank Burns (Robert Duvall) and Major Margaret O’Houlihan (Sally Kellerman) end up in bed together, the hypocrisy is not lost on anyone, prompting Hawkeye and his mates to take full advantage, sending him out of the field hospital in a straight jacket after he cracks under the ridicule.

Best line: “Oh, Frank, my lips are hot. Kiss my hot lips.”

7. Swimming with Sharks (1994)

Dark premise:
On the job misery is funny.

While critics often consider Robert Altman’s “The Player” the cream of the crop of this type of Hollywood insider film, this film presents a much more darkly humorous portrait of the inner workings of Hollywood. A young, inexperienced man named Guy (Frank Whaley) takes a job as a producer’s assistant for Buddy Ackerman (Kevin Spacey). He quickly discovers that his boss is not only abusive, but revels in demeaning Guy at every opportunity. Director George Huang’s experience as a personal assistant obviously inspired the film.

Darkest/funniest/most twisted moment: During Guy’s first day, Buddy asks him for a packet of Sweet ‘n Low and Guy gives him Equal. Buddy rips Guy a new one, revealing just how difficult Guy’s professional life is about to become.

Best line: (Buddy to Guy) “You are nothing! If you were in my toilet I wouldn’t bother flushing it. My bathmat means more to me than you!”

6. Withnail & I (1987)

Dark premise:
Alcoholism and unemployment are funny.

Though it’s more of a cult classic in Britain, those who love this film anywhere quote lines verbatim. The film follows the escapades of two unemployed actors at the end of the 1960s. With little to do, Withnail (Richard E. Grant) and Marwood (Paul McGann) decide to take a vacation at the country house of Withnail’s gay uncle, Monty (Richard Griffiths). There’s lots of drinking, drugs, self-pity and theatrical self-denial. Most of the film’s humor comes from the contrast between Withnail’s aristocratic sensibilities and the utter pathetic condition of his situation.

Darkest/funniest/most twisted moment: From the moment the two arrive in Monty’s cabin, they realize that they are entirely unprepared for the experience. Their panic hits its apex when Withnail, finally at wit’s end, confronts a local farmer and exclaims, “We’ve gone on holiday by mistake!”

Best line: “I don’t advise a haircut, man. All hairdressers are in the employment of the government. Hairs are your aerials. They pick up signals from the cosmos, and transmit them directly into the brain. This is the reason bald-headed men are uptight.”

5. Harold and Maude (1971)

Dark premise:
An unorthodox relationship between a boy and a woman old enough to be his grandmother is funny.

Even if the relationship wasn’t between a teenage boy and a 79-year-old woman, the fact that they meet at a funeral because attending funerals is a hobby they both share would probably be enough to make it a dark comedy. Add to it that Harold (Bud Cort) is obsessed with suicide and regularly stages his own death and you have the basis for a very odd relationship. Maude (Ruth Gordon) is an artist who lives in a railroad car and spends her time freeing trees from the city and replanting them in the forest.

Darkest/funniest/most twisted moment: Harold’s suicide attempts are priceless, but none is better than the one where his mother, attempting to sign Harold up for a dating service, begins answering the questionnaire herself while Harold slowly loads a gun. As she asks and answers her own questions and does so oblivious to anything Harold is doing (or has done in his entire life), Harold first points the gun at her, then turns it on himself and fires, completing one of his most realistic stunts, though hardly getting any reaction from his self-absorbed mother.

Best line: “I would be remiss in my duty if I did not tell you that the idea of intercourse — the act of your firm, young body... commingling with... withered flesh... sagging breasts... and flabby buttocks... makes me want to vomit.”

4. Kind Hearts and Coronets (1949)

Dark premise:
Murder is funny.

“Kind Hearts and Coronets” has achieved greatness because it combines an aristocratic sensibility both in tone and subject with the murder of an entire family. Because the D’Ascoyne family wronged his mother when she married outside her class, Louis Mazzini (Dennis Price), an unrecognized descendant, plots to kill the entire family so that he may ascend to Duke and inherit the family’s wealth. All the roles of the D’Ascoyne family been played by the brilliant Alec Guinness, who is better known to modern movie fans as Obi-Wan Kenobi.

Darkest/Funniest/Most Twisted Moment: When Lady Agatha D’Ascoyne goes up in a balloon, conveniently close to Louis’ residence, he pulls out a bow and arrow and shoots her down. Watching Guinness as Lady Agatha, hair waving in the wind as the balloon sails over London, is hysterical.

Best line: “The Reverend Lord Henry was not one of those new-fangled parsons who carry the principles of their vocation uncomfortably into private life.”

3. Bad Santa (2003)

Dark premise
: A profane Santa Claus is funny.

If you regard Christmas and Santa Claus as sacred symbols, this is not the film for you. However, if you regard those same sacred symbols and events as being rife for comic attack, then “Bad Santa” will make you laugh until you cry. It follows the antics of the worst Santa Claus ever. Willie (Billy Bob Thornton) and his partner Marcus (Tony Cox) are really con men. Each year they pose as Santa and elf so they can rob department stores. This year, however, Willie gets tailed by an odd kid (Brett Kelly), who seems strangely unaffected by Santa’s offensive behavior. This Santa curses, drinks heavily, and sleeps with his customers if the opportunity arises.

Darkest/funniest/most twisted moment: When Willie meets a woman (Lauren Graham) with a Santa fetish and they get it on, it’s as over-the-top twisted and funny as a scene gets.

Best line: (Whatever it might be, it’s not printable here)

2. Heathers (1989)

Dark premise:
Teenage suicide is funny.

Where most teenage comedies skim the possibilities of dark humor, “Heathers” mines it with every possible pick. The three Heathers (Shannen Doherty, Lisanne Falk and Kim Walker), along with Veronica (Winona Ryder), form the most powerful clique in Westerberg High School. Even though she’s part of the group, Veronica loathes the Heathers and loathes high school in general. When she meets new kid J.D. (Christian Slater), they go on an “accidental” killing spree, that has the effect of making suicide seem cool.

Darkest/funniest/most twisted Moment:  The point where J.D. and Veronica plan the “phony” double suicide of jocks Kurt and Ram to the discovery by officers McCord and Milner (the last names of the lead actors from “Adam 12”) of their bodies and the mineral water that confirms their homosexuality is among the great comic sequences.

Best line: (J.D. to Veronica) “This is Ohio. If you don’t have a brewski in your hand you might as well be wearing a dress.”

1.   Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)

Dark premise
: Nuclear war is funny.

Director Stanley Kubrick followed the Cold War doctrine of “mutually assured destruction” to its logical, yet insane conclusion, and came up with this dark comedy, which begins with bombing orders being transmitted to Major Kong (Slim Pickens) from the nutty Brigadier General Jack D. Ripper (Sterling Hayden). The film basically shifts between three places: the plane, the war room and Ripper’s office. The brilliant Peter Sellers plays three different roles: the President of the United States, Group Captain Lionel Mandrake and Dr. Strangelove. Every scene that takes place in the war room is laugh-out-loud funny as the President tries to get General Buck Turgidson (George C. Scott) to explain how bombing orders were given without the President’s consent and then how to bring the bombers back. Sellers’ performance as Dr. Strangelove is one of pure comic genius.

Darkest/funniest/most twisted moment: Nothing is funnier than Group Captain Lionel Mandrake's reaction when he's confronted by the idiotic and slightly paranoid Colonel Bat Guano (Keenan Wynn) and prevented from calling in the recall codes that could save the world because the Colonel thinks Mandrake is a “prevert.”

Best Line: “Gentlemen, you can’t fight in here! This is the War Room!”

Jason Katzman is co-creator and writer for Shadowculture's Mr. Cranky. Jason Katzman can be reached at