Top 10 Darkest Comedy Movie Moments Ever

“The Cable Guy” (1996)
Directed by Ben Stiller, “The Cable Guy” didn’t perform well - at least when comparing it to other Jim Carrey films. Part of the reason why was its dark tone. While moviegoers in 1996 wanted another wacky Jim Carrey comedy, they instead got a black comedy-thriller about an obsessive and lonely cable guy stalking one of his customers, Steven. Things get so bad for the customer that he has a horrifying nightmare. During the sequence, the Cable Guy has creepy yellow-green eyes and an echoey voice. He chases and eventually corners Steven in a hallway. Following the nightmare, Steven receives a phone call from the real Cable Guy― who's sitting in the dark and allowing a spider to crawl across his face. We feel bad for anyone who watched this expecting another “Dumb and Dumber”.

“Bad Santa” (2003)
Most of “Bad Santa” can be placed on this list. Playing against typically warm and gooey Christmas movies, the film introduces us to Willie, a thief with a drinking problem. He poses as a department store Santa so he can case and eventually steal from stores. In one particularly dark scene, Willie shows up to work absolutely hammered. He rides an escalator while barely conscious, drunkenly strolls in front of waiting kids without his Santa beard, and carries a broken bottle. The children all leave horrified after he destroys a prop animal. While Willie is not a particularly likable character, he certainly makes for a memorable Christmas movie protagonist.

“Horrible Bosses” (2011)
In this dark comedy, three disillusioned working men decide to eliminate their bosses. Deep down, we know - or at least, think - that the protagonists won’t go through with it. But that doesn’t mean that everyone survives the movie. After Kurt steals his boss Bobby’s phone, he accidentally drops it in the house belonging to Nick’s boss, Harken. When Harken finds the phone, he thinks his wife is having an affair. So he gets in his car, grabs his gun, and takes Bobby’s life. Before this point, the plot seemed like an excuse for wacky hijinks. Harken himself seemed like nothing more than an overbearing boss. But this scene gave the movie real stakes and turned him into a dastardly villain. Talk about a jarring tonal shift.

“Super” (2011)
Written and directed by James Gunn, “Super” is a dark comedy that parodies superheroes and their heroic traits. Rainn Wilson stars as an unhinged man named Frank Darbo who fancies himself a superhero, donning a red suit and calling himself the Crimson Bolt. One of the first things he does as the Crimson Bolt is deliver some justice to a rude line-cutter. He strolls up to the man and hits him with a wrench. When the man’s friend intervenes, Crimson Bolt attacks her as well. We know that the line cutting man was certainly rude, but the brutal and realistic aftermath of his wrench injury was disturbing to see.

“Heathers” (1989)
This black comedy stars Winona Ryder as a popular and rich high school student named Veronica Sawyer. Veronica eventually grows close to a new and lonely kid named J.D. He commits a bunch of troubling acts throughout the film and Veronica eventually learns that J.D. has twisted intentions to utterly destroy the school. While Veronica successfully foils the plan and saves Westerburg High, she can’t stop him from taking his own life. J.D.’s plan and eventual fate are both extremely dark subjects for any movie, let alone a comedy.

“Shaun of the Dead” (2004)
Serving as the first entry in Edgar Wright’s Three Flavours Cornetto trilogy, “Shaun of the Dead” is both a satire of zombie movies and a beloved member of the genre. While the horror comedy is wickedly funny, the third act is particularly gruesome and tragic. After Shaun’s mother Barbara is bitten on the arm, he’s forced to say a quick goodbye. When she eventually turns, he takes it upon himself to end her reanimated existence. It’s a depressing moment that’s played to tragic perfection by the hilarious Simon Pegg. No one thought this funny apocalyptic comedy could produce such a tear-jerking moment.

“Borat Subsequent Moviefilm” (2020)
This surprise comedy sequel to the iconic 2006 original contained many references to the COVID outbreak and subsequent lockdowns. Not only does the plot show how Borat deals with the pandemic, but it also contains a rather shocking twist that no one saw coming. A fictionalized version of Kazakhstan’s former president, Nursultan Nazarbayev, claimed the first “Borat” movie made his country a laughingstock. So, they infected Borat with the coronavirus before he departed on his journey to the US. This turned him into patient zero. As Borat traveled across the globe, he unknowingly spread the virus. It’s safe to say that no one could expect a Borat movie to take such a dark turn.

“Parasite” (2019)
Serving as a unique blend between comedy, thriller, horror, and social satire, “Parasite” is hard to classify. While the movie can be very funny, it also contains a terrifying climactic sequence that takes place during a child’s birthday party. As the festivities continue, Geun-sae attacks Ki-woo. Geun-sae proceeds to fatally wound Ki-Jung in front of her parents and party guests. After her mother attacks him in retaliation, Ki-jung’s father, Ki-taek takes the life of his boss, Mr. Park. By the end of the birthday party, multiple characters have permanently fallen, one is severely injured, and another flees to evade the police. The Kim family never quite recovers from the tragic birthday party, a fact that leaves this hard-to-classify movie on a definitively somber note.

“Burn After Reading” (2008)
This dark Coen brothers comedy concerns two gym employees who come across the memoirs of an ex-CIA official named Osbourne Cox. One of the gym staff members is Brad Pitt’s dimwitted but easygoing and likable Chad, who mistakes the files and records on the CD for classified documentation. At one point, he snoops around the Cox house. But things get tense when a US Marshal named Harry shows up there, too. Chad decides to hide in a closet. But when he’s discovered, a panicked and scared Harry takes Chad’s life. The contrast between Chad’s goofy smile and his sudden demise is hilariously startling. It’s also one of the most unexpected moments in modern movie history. Leave it to the Coens to craft such a hilarious and dark demise.

“Fargo” (1996)
The Coen brothers are arguably the masters of black comedy. “Fargo” is their masterpiece in that regard, as it strikes the perfect balance between funny, warm, violent, and tragic. The ending is particularly disturbing. After Jean and Wade are taken out by Gaear and Carl, respectively, Gaear takes his ally Carl’s life. But that’s not all. When Marge eventually stumbles onto the scene, she finds Gaear using a wood chipper to get rid of any evidence of his crimes. This disturbing scene stands in sharp contrast to the weird and funny tone that carries through the bulk of the film. All the exaggerated Minnesotan mannerisms and “oh yeahs” can’t balance out the darkness of this scene.