While conventional comedies tend to lift your spirits, dark comedies have a knack for unsettling your mood. They deliver laughter, but they’re also designed to shock, horrify, offend, and even disgust you. Here are five comedies that promise humor that will make you squirm.

‘Dr. Strangelove’ (1964)

Dr. Strangelove, officially titled Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb, originally started as a serious drama. However, as Stanley Kubrick developed the screenplay, the absurdity of nuclear weapons and mutually assured destruction struck him as inherently comedic.

The movie delivers unforgettable comedic performances while capturing the intense anxiety of the Cold War era. It has since become the benchmark for dark comedies.

When screenwriter Charlie Kaufman set out to adapt Susan Orleans’ nonfiction work The Orchid Thief, he faced a severe case of writer’s block. He overcame this hurdle by weaving Orleans’ narrative into a story about his own creative struggle, and in the process, he invented a fictional twin brother.

‘Adaptation’ (2002)

While attempting to adapt a screenplay based on Susan Orleans’ nonfiction book The Orchid Thief, writer Charlie Kaufman struggled with writer’s block. He was eventually able to do it by folding Orleans’ story into one about his writer’s block, and inventing a twin brother along the way.

In Adaptation, Nicholas Cage plays Kaufman, a frumpy screenwriter well past his deadline on a film script. He turns to his twin brother Donald (also played by Cage) for help and is dismayed when Donald’s own contrived script is successful. Meanwhile, Orleans (Meryl Streep) enters into a secret romance with an orchid thief. 

The film is a twisting romp that features jealousy, looming deadlines, public embarrassment, and a deadly chase through a swamp.

‘Triangle of Sadness’ (2022)

Ruben Östlund’s Triangle of Sadness follows a model named Carl and his influencer girlfriend, Yaya, on a luxury cruise. While their journey begins in moneyed splendor, it takes a violent turn, leaving passengers stranded on an island.

Triangle of Sadness is a satire of the rich and powerful that is just as funny as it is violent and disgusting. It won the Palme d’Or at the Cannes Film Festival and received nominations for Best Picture, Best Director, and Best Original Screenplay at the Academy Awards.

‘In Bruges’ (2008)

Martin McDonagh’s In Bruges stars Colin Farrell and Brendan Gleeson as Irish hitmen hiding out in Bruges, Belgium. Farrell’s character has accidentally killed a young altar boy, and, unbeknownst to him, Gleeson’s character has been ordered to kill him for it.

In the film’s production notes, McDonagh explained that the idea for the film came to him while walking around the picturesque city of Bruges. As a result, the city becomes a character in the film, with its darker elements coming through as the story progresses. The film is thrilling and full of pitch black comedy. It also brought Farrell and Gleeson together on screen for the first time; they’d reunite years later in The Banshees of Inisherin. 

‘Parasite’ (2019)

Bong Joon-ho’s Parasite became the first non-English-speaking film to win Best Picture at the Oscars for good reason. The film follows a financially struggling family in Seoul who infiltrate the lives of the wealthy family that employs them. 

Parasite is a comedic, nerve-jangling, and at times horrific look at the chasm between the rich and poor. It’s nearly impossible to anticipate the direction the story will take, and it’s sure to stick with viewers long after the credits roll.