What puts a film in the Dark Comedy category? Well, it should have death (or the imminent threat therein) or dismemberment. It should be funny, though not necessarily in an LOL way. Ever find yourself chuckling in a film when no one else is? It may be you have a unique appreciation for one of my favorite twisted subgenres, the Dark Comedy. Here are, in no particular order, the 50 Best Dark Comedies ever.

Deathtrap (1982). What would you do to be famous again? Sydney Bruhl asks himself this in Neil Simon’s fantastic play-turned-movie that also features Dyan Cannon and the great Christopher Reeve.

The Last Supper (1996). Will murdering the right people make the world a better place? That’s what a group of sassy liberals think in this delightfully-twisted film that features my hero: Bill Paxton.

Dr. Strangelove (1964). What’s left to be said about How I Learned to Stop Worrying and Love the Bomb that hasn’t already been said? It’s satire, which is funny, biting, and poignant. Also, a guy rides a bomb, which you can see here.

House of Yes (1997). This movie gets a lot of love despite being nominated for a Razzie (I’m looking at you, Tori Spelling). This one makes the list mainly because I love movies about crazy people, and “Jackie O” certainly qualifies.

The Ruling Class (1972). A guy who thinks he’s Jesus Christ inherits a f*ckton of money, and hilarious hijinks ensue. What’s not to like? This one has been called “A comedy with tragic relief.” Makes sense. You can watch the whole thing here:

Heathers (1988). I was a senior in high school when this movie was released, so it holds a special place in my heart. Croquette, suicide, gun play, and Winona Ryder can all be enjoyed in this classic dark comedy.

The Trouble with Harry (1955). Few people know that Alfred Hitchcock actually had a wicked sense of humor. If you don’t know what a MacGuffin is, this movie is a great place to find out. Watch for an appearance by little Jerry Mathers.

Fargo (1996). If you don’t know about Steve Buscemi’s thrilling outcome in Fargo, it’s high time you saw this film. William H. Macy is the most ineffectual criminal ever, and this murderous romp is a ton of fun.

Clay Pigeons (1998). Vince Vaughn as a cowboy serial killer? Janeane Garafalo as an FBI agent; and Hershel from Walking Dead as a sheriff. Oh, and Joaquin Phoenix is in there, too. I love this movie, the soundtrack, and Vaughn in that cowboy hat.

Birdman (2014). Also called The Unexpected Virtue of Ignorance, this remarkable dark comedy features stunning camera work, intensely-real performances, and a premise that will leave you scratching your head. I think it won some awards too. *wink*

Very Bad Things (1998). Bachelor parties are not always murderous laugh fests, but as this movie demonstrates: sometimes they are.

Eating Raoul (1982). Cash for corpses might sound like a new kind of stimulus plan, but it’s actually the plot of this witty movie that’s almost a comedy of manners as well. Watch for Buck Henry. I love that guy.

Gremlins 2: The New Batch (1990). Can a sequel really be a different genre than its predecessor? Yep. This sequel is hilarious, satirical, and offers the best Lincoln’s birthday story you’ve ever heard.

Cornetto Trilogy (2004-2013). This series of 3 films is already considered classic comedy, though it’s also full of death, ice cream, Simon Pegg, and questions about whether or not dogs can look up. Containing Shaun of the Dead, Hot Fuzz, and The World’s End, this whole trilogy should be in your collection.

Arsenic and Old Lace (1944). This insane film is full of heavy-hitting actors chewing the scenery under the direction of the great Frank Capra. It’s also the best reason I can think of to never accept a glass of elderberry wine.

Death to Smoochy (2002). This is another movie that takes a lot of crap from critics (including Jon Stewart, whose hair is the only bad thing about this movie), but I adore it. Ed Norton, Robin Williams, Catherine Keener, and Danny DeVito are in perfect sync in this hilarious satirical dark comedy.

Mystery Men (1999). I saw this movie on a date with a guy I later decided to marry. Heroes die, evil doers commit dreadful deeds, and William H. Macy kicks ass with a shovel. What’s not to love (except Cassanova Frankenstein)?

Tucker and Dale versus Evil (2011). I laughed so hard at this movie, I might have hurt myself. Two kindly redneck types are presumed to be serial killers by some vacationing teens. A great twist on a standard trope—and Steve the Pirate to boot.

Harold & Maude (1970). Probably the gold standard of black comedies, Bud Cort and Ruth Gordon enjoy a sweet romance despite a 50+ year age difference. Includes suicide, anti-war protest, and a soundtrack that reminds us all of a time before Cat Stevens became Yusuf Islam.

Zombieland (2009). Possibly the best cast of any zombie movie ever (sorry, Brad Pitt), this one keeps getting laughs despite how many people die in it. Bill Murray is comedy gold and Woody Harrelson should have gotten free Twinkies for this performance.

Ravenous (1999). Guy Pierce and Robert Carlyle star in this exceptionally-witty tale of mystic cannibalism set in Civil War times. Jeffrey Jones, David Arquette, and John Spencer also appear. Bloody good stuff!

Clerks: Director’s Cut (1994). If you’ve seen both the theatrical and director’s cut of this movie, you know why only one is considered a dark comedy. A funny, daring pic full of filthy dialogue and a guy named Silent Bob—this movie will make you laugh every time you hear the number 37…for the rest of your life.

Who’s Afraid of Virginia Woolf? (1966). Elizabeth Taylor and Richard Burton shred each other in this delightfully-grating movie version of Edward Albee’s noted stage play. You’ll laugh, you’ll cringe, you’ll wish you were as drunk as the characters.

Cable Guy (1996). One of the most misunderstood films ever, Jim Carrey is fantastic as a disturbed man who lives vicariously through TV characters as he tries to ruin the life of Matthew Broderick for reasons only a sociopath would understand. Ben Stiller directed this brilliant movie. If you already love it, please enjoy these outtakes. If you don’t, please give it another chance.

Happiness (1998). A dark comedy featuring suicide, molestation, dismemberment, prank phone calls, infidelity, and folk-singing. What more do you need to know?

Neighbors (1981). Easily the weirdest film starring Belushi and Akroyd, this one must be seen to be believed as it asks the haunting question: “Do you know how long it takes to pork someone?”

Clue (1985). Many remember this movie as making people see it three different times (because there were three different endings). But it’s so much more. Funny, full of death, and boasting an absurdly-good cast, this is must-see for dark comedy fans.

American Psycho (1999). I waited more than a decade between reading this book and the movie being released. So worth it! This dark satire will make you laugh more than you think it should. And Christian Bale is transcendent as lead murderer Pat Bateman. Now that those Joker pics are out, nobody feels sad because of this scene anymore.

The Dinner Game (1998). Screw the American remake with Steve Carell. This original film is where it’s at. Funny, sad, and just a bit infuriating, the guy who finds idiots to take to dinner parties learns that being smart doesn’t have to mean being a condescending jag. And yeah, it’s in French.

Welcome to the Dollhouse (1995). A movie where rape threats are funny and misery is a source of amusement? Oddly enough, yes. Spectacular performances and an overtly-ordinary premise come together for a surprisingly-witty and memorable film.

Monty Python’s Life of Brian (1979). Beetle George Harrison funded this brilliant and damn funny spoof on religious dogma. It does get a little dark, what with all the torture and crucifixion. Rather than show you a scene, here’s John Cleese and Michael Palin defending the film to some crotchety religious types.

Addams Family/Addams Family Values (1991-1993). Were it not for the death of Raul Julia, we’d likely have had many more of these movies based on Chaz Addams wonderfully-twisted New Yorker comics. It’s one of the rare franchises where the sequel surpasses the original.

Pulp Fiction (1994). The movie everyone you know quotes lines from. This is part dark comedy, part action movie, part drug-fueled crime fest. Any way you slice it, this is a fantastic film full of dark humor and watches being kept in unlikely places.

Jawbreaker (1999). More than just Heathers ten years later—this one is pretty funny despite a goodly amount of crime and murder.

Murder by Death (1976). This spoof of Agatha Christie mysteries features a surreal cast including Maggie Smith, Peter Falk, Nancy Walker, Alec Guiness, and Elsa Lanchester to name a few. Funny, murder-filled, and still relevant even after all these years.

Delicatessen (1991). The French know how to take something uncomfortable and make it uncomfortably funny—as evidenced by this bizarre and character-driven romp. I love ensemble films, and this is a great one.

Man Bites Dog (1992). If you haven’t seen this one, you might just want to watch the scene everyone talks about. Or you might want to experience this crime mockumentary with a twist unlike anything you’ve ever seen before.

Fight Club (1999). Brad Pitt and Ed Norton star in this insane and incredible movie about a thing that we’re never supposed to talk about. Seriously, don’t. Do NOT talk about…dammit.

Kickass (2010). If you think you can handle a movie where little girls use the F-word, kids are in danger of being murdered, and one of the most hated actors of our lifetime dies horribly—this is the dark comedy for you.

Misery (1990). What makes a thriller like Misery into a dark comedy? Is it Mike Nichols’ flair for comic timing, Barry Sonnenfeld’s awesome camera work? Or Kathy Bates fervent use of the word “Cockadoodie?” It doesn’t matter. This is a tense, witty, evocative film that will make you cry for a small-town sheriff.

An American Werewolf in London (1981). This is a sexy, funny, gory film featuring a tiny cameo from Rik Mayall and a hilarious turn from Griffin Dunne. Made in a time of practical special effects, the highlight may well be Rick Baker’s incredible transformation scene—one that hasn’t ever been surpassed IMO.

The Raven (1963). Vincent Price and Peter Lorre aren’t always dangerously disturbed. Sometimes, they’re pretty funny, as in this satirical spoofing of their previous work.

To Die For (1995). What do you get when you throw Nicole Kidman, Joaquin Phoenix, Casey Affleck, Matt Dillon, and Wayne Knight in the same movie? You get a fun thriller full of horrible people doing terrible things. Well, one in particular. This film has great style, superb performances, fantastic outfits, and a dog named Walter.

Go (1999). A movie dealing with a wild night that sports a killer cast of now-famous actors and a plot that will have you cringing and fearing for the lives of these people. If you’re not into drug stuff, recklessness, attempted murder, or random crime, this is not the film for you.

Adaptation (2002). One has to wonder about Susan Orlean’s reaction to taking her non-fiction book about orchids and turning it into this incredible piece of brilliant insanity. Chris Cooper, Meryl Streep, and (gag) Nicholas Coppola star in this enjoyable foray into flower theft and gator husbandry.

In Bruges (2008). Putting Colin Farrell, Brendan Gleeson, and Ralph Feinnes in the same movie is already a work of genius. But this dark comedy comes together so beautifully you might think you’re watching something that cost far more than $15 million to make.

Stranger than Fiction (2006). In addition to this movie showing the world that Will Ferrell had some major acting chops, Stranger than Fiction is a beautiful love story and an affirmation of all that’s good inside us. I love it. But it also features good people in peril, and presents writers as being unstable, overly emotional, and prone to procrastination. If you can get past that bit of fiction, you’ll love it

Serial Mom (1994). A John Waters film where Kathleen Turner gains 30 pound to play a suburban housewife turned multiple murderess? Yes! Dear God, YES! Also featuring Rikki Lake, Matthew Lillard, Sam Waterston, and Traci Lords, you’ll laugh even as you cringe at the deeds of Beverly Sutphin.

Ed and His Dead Mother (1993). Is there anything more awesome than a young Steve Buscemi? Possibly, but this movie is still one of the greatest dark comedies of all time. With a supporting cast that includes Ned Beatty and John Glover, this is an awesomely-cringeworthy time.

The Perfect Host (2010). Been wondering what David Hyde Pierce has been up to since Frasier went off the air? Lots of things—the greatest and most unexpected of which is this odd and bizarre little film. Is “The Perfect Host” a murder story? A long con? Who actually is in mortal peril here? You’ll just have to watch to find out.

 Did I miss your favorite dark comedy? Did I undersell one of your faves? Tell me all about it in the comments. It’s the only way I’ll learn!

Featured Image Credit: FrenchToastSunday

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