The 10 Best Dark Comedies of All Time

When you look at posters for the 1989 cult classic Heathers, you may assume it's a romantic comedy between '90s film icons Winona Ryder and Christian Slater. You'd be wrong. When the popular Veronica (Ryder) meets her new boyfriend, J.D. (Slater), they're committed to breaking up the toxic clique at their high school, the Heathers. When they accidentally poison the head of the Heathers and stage it to look like a suicide, Veronica realizes that J.D. is having a little too much fun with their little crime spree. Both intelligent and cynical, violent and satirical, Heathers started a legacy of dark comedies that have continued today.

Best quote: "Dear Diary: My teen angst bullshit now has a body count."

"What's your favorite scary movie?" These five words changed the horror genre in 1996 when Wes Craven released the original slasher comedy, Scream. The film became a cultural sensation in 1996 with stars like Drew Barrymore, Courtney Cox, Neve Campbell, David Arquette, and Skeet Ulrich. While faced with the genuine terror of a masked murderer coming after a tight-knit group of friends in the suburbs, characters also find the time to crack a few jokes and wink to the audience. "No, please don't kill me, Mr. Ghostface! I wanna be in the sequel," Rose McGowan mocks. Critics praised the self-aware horror flick for being a subversive take on what was becoming a dying genre, and the constant self-parody along with mounting tension left audiences satisfied. 

Best quote: "Now Sid, don't you blame the movies! Movies don't create psychos. Movies make psychos more creative!"

Perhaps the strangest film on this list, Sex and Death 101, begins with a fast-food executive, Roderick, who receives an email containing 101 names of everyone he has slept will ever sleep with. We also see a seductress, Death Nell, who's enacting revenge on men across the city. As Roderick excitedly crosses names off his list in a "conquest," and Nell continues to slaughter men in the act of vengeance, Roderick comes to realize that the only problem with his exciting escapades is that Nell is the last name on his list. Starring Simon Baker (The Devil Wears Prada) and Heather's star Ryder, this odd film is an exciting take on the phrase "be careful what you wish for."

Best quote: "My wounds are deeper than your desire."

In a twisted version of Groundhog Day, this 2017 black comedy slasher film focuses on college student Tree Gelbman (Jessica Rothe) as she continues to relive the day of her murder until she can finally figure out who has been after her. Dying in a unique, satirical way on her birthday every day, Tree (and the audience) grow infuriated by the jumpscares she can see coming and the killer she can't seem to unmask. The ending of this film is as satisfying as it is celebratory and is a fresh take on the time-loop concept.

Best quote: "Poisoning a cupcake? Really? We're Kappas. We don't eat cupcakes."

This Oscar-winning film leaves audiences questioning how far the main character Cassie (Carey Mulligan) is willing to go on her quest for vengeance. From the opening sequence to the final scene, viewers can expect a satisfying take on "every man's worst nightmare" of being falsely accused of sexual abuse. Cassie gives no opportunities for excuses ("If I hear [we were kids] one more time…"), using her cunning persona to lure men in and teach them a thing or two about consent. The all-star cast includes Bo Burnham, Jennifer Coolidge, Alison Brie, and Laverne Cox. 

Best quote: "You might be surprised to hear that gentlemen are sometimes the worst."

Everyone loves a good body swap and creepy town legend "The Butcher" is no exception. In this hilarious yet horrific film, 17-year-old Millie Kessler finds herself in the body of a murderer and has 24 hours to get back to her actual form. On the other hand, The Butcher is taking advantage of his petite blonde form to lure victims in maniacal ways. Starring comedic legend Vince Vaughn and Big Little Lies actress Kathryn Newton, this film will have you peeking through your fingers in fear while laughing simultaneously. 

Best quote: "Don't underestimate a straight white man's propensity for violence. I don't care how fucking old they are."

Sebastian Stan and Daisy Edgar-Jones star in this genuinely creepy yet comedic film about the hidden horrors of dating in the 21st century. "It starts out like a romantic comedy, and you're supposed to see that there's a potential between the main characters, but the truth is this guy is sort of obsessed with her," Stan says in his cover story with L'OFFICIEL USA. "We've been raised with this narrative that you're going to meet someone who will instantly open up and understand you, and then you'll be together for the rest of your lives. The movie's a little bit of a commentary on that—how you fall for somebody because you're starved for real connection, but is that person really who they say they are?" Stan and Edgar-Jones give standout performances in this dark comedy. 

Best quote: "Come on. Give me a smile."