Genre blending is a tricky art, and more often than not it results in a mixed bag of a film. Like the comedic horror film that forgets to bring the scares or forgets to tickle the funny bone. Thedarkcomedyisn’t quite the result of genre-blending, but it comes close. This subgenre has graced the comedy genre with some of its more offbeat classics.
These movies are funny, but they also contain something that will stay with the audience much longer than a punchline. There’s some level of analysis of the human condition or society that rings true, even if it can be tough to stomach (especially in a movie that just made you laugh moments ago).

20Risky Business (1983)
A major step on Tom Cruise’s ascent up the stardom ladder,Risky Business' sex work-driven narrative doesn’t hit the same way it did 10 years ago, much less 40. But it’s still one ofCruise’s best movies, and the romance scene with Tangerine Dream’sLove on a Real Trainplaying over it is one of the 1980s' best.
The concept of running a suburban brothel lends itself naturally to an R-rated comedy, butRisky Businessis less about sex and more about growth. Cruise’s Joel Goodsen needs to learn that love is more than flesh, and Rebecca De Mornay’s Lana is the one to educate him. As far as coming-of-age narratives go,Risky Businessis toward the top.

19Heathers (1988)
Heathersis a lot harder to watch in the age when school shootings are a seemingly accepted commonplace, but it’s still something special. The plot takes place at a somewhat stereotypical high school, populated with jocks, nerds, stoners, artists, and cheerleaders. Veronica Sawyer (Winona Ryder) may be a member of the friend group known as the ‘Heathers,’ but she’s more of a floater than a member of any particular clique.
And this is made all the more apparent when Jason ‘J.D.’ Dean (Christian Slater) enters the scene, adding a standoffish loner to the list of cliques. But Sawyer sees something in him, and they begin a mutual descent down a murderous rabbit hole that ultimately ends with J.D. and a bomb vest. But, Sawyer also finds out it’s not about cliques or any other such vapid nonsense, it’s about knowing who youreallyare and what you’rereallycapable of. And, of course, what kind of action you’re willing to stand in defiance of.

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18Fargo (1996)
One of the best movies the Coen brothers have ever gifted cinephiles,Fargois first and foremost a showcase for the talent of Frances McDormand. But it alsoreinvented murder mysteries for modern audiences, allowed William H. Macy to play a very particular type of villainous, and gave Steve Buscemi and Peter Stormare an incredible plot line. They play kidnappers, hired by a man to capture his own wife.
Unfortunately for Buscemi’s Carl Showalter, his plot line ends a bit earlier than Stormare’s Gaear Grimsrud (but not by much). The image of Grimsrud pushing down the last bit of Showalter is unforgettable, especially considering the audience has spent so much time with the character. It’s one of the most jarring scenes from a Coen brothers film, and it’s just one of many that helpsFargostand as a masterpiece.

17American Psycho (2000)
Based on Bret Easton Ellis' novel of the same name, Mary Harron’sAmerican Psychois an amazing showcase for Christian Bale. Playing Patrick Bateman, one of2000s cinema’s best villains, Bale physically and emotionally dives into his portrayal, not unlike he would forThe Machinist(and then immediatelyBatman Begins).
A satire of excess and vapid lifestyles, the titularAmerican Psychois just an exaggerated version of people out in the real world. Those who see a member of the homeless community and stuff their money further down their coat pockets. Bateman’s no different, he just also happens to have a butcher knife in one of those pockets.

16Death to Smoochy (2002)
WhileDeath to Smoochywasn’t much of a critical darling, it’s still anunder-seen Robin Williams dark comedy. Oddly enough,Death to Smoochycame out the same year as two other dark Williams movies:One Hour Photoand Christopher Nolan’sInsomnia.
Death to Smoochyis the least effective of the three, but it’s also the only one to attempt comedy. Attempt being the operative word because, more often than not, the overall sour tone of the film sinks the fun factor. With that said, even when the movie does score in the laugh department, it’s still pretty twisted, e.g. when Williams' former child entertainer character plants a penis cookie in the mid-show gift bag of his replacement.
15The Girl Next Door (2004)
MarketingThe Girl Next Dooras yet another sex-fueled romp did thesweet coming-of-age narrativea massive disservice.The Girl Next Dooris infinitely better than “similar” movies of its era e.g.Eurotrip, and even gives movies likeRoad TripandOld Schoola run for their money.
It’s actually far more in line with something likeRisky Business. And this similarity didn’t helpThe Girl Next Doorwith critics when released, but it’s hard to deny that it’s been integral in making the comedy stay endearing even 20 years later. Toss in a legitimately sinister performance from Timothy Olyphant, andThe Girl Next Dooris a movie well worth discovering or re-discovering, just don’t expect to laugh thewholetime.
14Little Miss Sunshine (2006)
Bolstered by outright great performances (particularly from Steve Carell),Little Miss Sunshineis both one of the aughts' best dramas, one of its best comedies, and one of its best independent movies as a whole. The cast is fully onboard with the film’s tone, and from Abigail Breslin as the titluarLittle Miss Sunshineto Carell, Paul Dano, Toni Collette, Greg Kinnear, and Alan Arkin, everyone is note-perfect in their role.
It’s a beautiful movie about recognizing the lack of importance of physical beauty, much less society’s obsession with it. Sadly, this extends to real-life child pageants, a creepy enterprise thatLittle Miss Sunshinestops short of directly satirizing or criticizing. Instead, it’s about family, and this family in particular is more troubled than hilarious.
Comedian Bobcat Goldthwait can get pretty dark, not unlike the few movies he’s directed. None, however, are as thought-provokingly grim asWorld’s Greatest Dad.
Robin Williams is devastating in the lead role of a single teacher who’s just lost his son to autoerotic asphyxiation and now has a media frenzy trying to essentially capitalize on his grief. But Williams' Lance Clayton wants to control the narrative a bit, so he stages his son’s death as a suicide via a note. From there, the note ostensibly written by the deceased younger Clayton gets passed around his (and his father’s) school and all of a sudden everyone has nice things to say about a young man they’d never once acknowledged. It’s rough stuff, but Williams is more than capable of leading a hefty narrative.
12Burn After Reading (2008)
If anyone had just watched the Coen brothers’Burn After Readingand were asked to name one thing about it they remember, there’s a more than great chance they’re going to say “The death of Brad Pitt’s Chad Feldheimer” or something comparable. This is partially becauseBurn After Readingis, as a whole, not one of the Coens' more memorable films.
But every scene with Pitt is a winner, as his goofy Feldheimer is a guy who’s fun to watch getting in over his head. Unfortunately, just as curiosity killed the cat, it killed the meathead.
11In Bruges (2008)
Martin McDonagh is one of the best directors working today. And, likeThe Banshees of InisherinandThree Billboards Outside Ebbing, Missouri,In Brugesproves it. Most of the narrative is spent with hitmen Ray (Colin Farrell) and Ken (Brendan Gleeson), the latter of whom has been given the task of taking out the former.
Why? Because Ray accidentally killed a kid during one of his missions. And, as his boss Harry Waters claims, this should only result in one taking their own life. And, in the third act, once it’s down to just Ray and Harry, history repeats itself, and Harry stays true to his word. The look of defeat in Fiennes' eyes as he raises the gun to his temple speaks volumes, yet when he pulls the trigger the viewer still jumps back a bit. It’s an action that was perfectly foreshadowed, but it plays out so brilliantly that it manages to surprise.