There's a fine line between a movie that makes you laugh and one that makes you squirm in your seat. When a film intentionally leans into awkwardness, it can be a powerful tool for comedy or drama. But when it's done well, it's an art form. These are the films that have perfected the cringe, leaving audiences both delighted and deeply uncomfortable.
10. There's Something About Mary (1998)
This classic comedy is a masterclass in pushing boundaries while staying wildly entertaining. It's a rom-com with a twisted sense of humor, featuring scenes that are as memorable as they are mortifying. From a disastrous prom night to a hair-gel mix-up that's impossible to unsee, the film earns its spot with sheer audacity. It's a crowd-pleaser that knows exactly how to make you wince and laugh at the same time.
9. Wild Tales (2014)
This Argentine anthology is a wild ride through six tales of revenge and chaos. Each story spirals from a mundane situation into an explosive, darkly comic disaster. It's a film that keeps you on edge, blending suspense with humor in a way that's both thrilling and deeply uncomfortable. The unpredictability is part of the charm, making it a standout in the cringe genre.
8. Brazil (1985)
Terry Gilliam's dystopian nightmare is a surreal blend of dark comedy and political satire. The film follows a low-level bureaucrat in a totalitarian society, and his journey is as absurd as it is harrowing. The constant barrage of bureaucratic madness and surreal imagery creates a sense of unease that's both fascinating and exhausting. It's a film that's as brilliant as it is difficult to watch.
7. Krisha (2015)
This is the only film on this list that isn't a comedy. It's a raw, unflinching family drama that follows a woman's return to her estranged family for Thanksgiving. The tension is palpable from the start, and the film's realism makes the discomfort almost unbearable. It's a powerful piece of cinema that's hard to watch but impossible to forget.
6. Borat (2006)
Sacha Baron Cohen's mockumentary is a boundary-pushing satire that's as offensive as it is hilarious. The film's use of real people who aren't in on the joke adds a layer of danger and discomfort that's unique to this style of comedy. It's a film that's both lowbrow and intellectually sharp, making it a must-watch for fans of cringe comedy.
5. Shiva Baby (2020)
This modern indie gem is a pressure cooker of social anxiety. A college student attends a shiva with her parents, only to run into her sugar daddy and her ex-girlfriend. The film's claustrophobic setting and constant awkward encounters make it a masterclass in cringe. It's a sharp, uncomfortable comedy that's as relatable as it is excruciating.
4. The King of Comedy (1982)
Martin Scorsese's dark comedy is a chilling portrait of a wannabe comedian who takes obsession to a dangerous level. Robert De Niro's performance is both hilarious and terrifying, and the film's uncomfortable humor is as relevant today as it was in the 80s. It's a film that makes you laugh while also making you question your own morality.
3. Happiness (1998)
This film is a brutal exploration of human misery, and it's not for the faint of heart. It follows a group of interconnected characters, each dealing with their own dark desires and failures. The film's unflinching look at taboo subjects makes it one of the most uncomfortable viewing experiences you'll ever have. It's a masterpiece of discomfort that's both brilliant and deeply unsettling.
2. Curb Your Enthusiasm (2000-2024)
While technically a TV show, this series is the gold standard for cringe comedy. Larry David's character constantly finds himself in awkward social situations, and his inability to let things go makes for some of the most uncomfortable moments in television history. It's a show that's as hilarious as it is painful to watch.
1. The Office (UK) (2001-2003)
Ricky Gervais's original version of this mockumentary is the ultimate cringe comedy. David Brent's desperate attempts to be liked are so painfully awkward that they're almost unwatchable. The show's genius lies in its ability to make you laugh while also feeling secondhand embarrassment for its characters. It's a landmark in the genre and a must-watch for any fan of awkward humor.
These films and shows are not for everyone, but for those who appreciate the art of discomfort, they're essential viewing. They remind us that sometimes the most memorable moments in entertainment are the ones that make us cringe.
