Top 10 Most Awkward Comedy Movies Ever

For obvious reasons, this won’t be the last high school movie on the list — we can’t imagine more awkward fertile ground to start ourselves off on. Do we really need to say more than ‘four dorky high schoolers attempt, with varying degrees of success, to lose their virginity before the end of the school year’? Paul and Chris Weitz’s uber-raunchy comedy covers every time-honored teen movie trope you’d expect it to, and still manages to throw its audience some nerve-wracking curveballs along the way. An unexpected smash hit at the time of its release, “American Pie” broke new ground in painfully relatable cringe comedy. And, uh… baking. Sorta.

Director Frank Oz’s lethally funny dark comedy serves to remind us that we shouldn’t take each other for granted. It is also a reminder of why you shouldn’t pop mysterious pills at your fiancée’s uncle’s funeral. Or do anything to arouse the ire of that same uncle’s secret lover. Assembling an all-star cast that includes Matthew Macfadyen, Ewen Bremner, Peter Dinklage, and Alan Tudyk, Oz deftly maneuvers potentially jarring tonal shifts to great effect. Above all, the film’s setting lends itself beautifully to generating cringeworthy cinema: is there any worse place for drama to erupt?

Clearly North America doesn’t have a monopoly on awkwardness. While vacationing at a ski resort, married couple Tomas and Ebba are forced to confront the cracks in their family after a false brush with death. “Force Majeure” examines modern-day infidelity, parenthood, and the toll of secrets we keep from each other. The whole deliciously tense story illustrates Swedish writer-director Ruben Östlund’s greatest strength: the use of comedy to reveal profound truths about human nature. His 2022 film “Triangle of Sadness” builds on this, using a more extreme approach to explore themes of class warfare and elitism. His efforts were rewarded with Academy Award nominations for Best Director and Best Original Screenplay.

By now, it’s probably pretty clear that awkward comedies are most effective when they’re based on mundane, everyday situations — and Meet the Parents goes a long way in proving that. Attempting to make a good impression on his girlfriend’s uptight parents before he proposes, a neurotic nurse played by Ben Stiller quickly finds himself teetering on the edge of the circle of trust. Did we mention that his potential father-in-law — Robert De Niro as the poster boy for being stern — is ex-CIA? No pressure at all. While the film’s circumstances are excruciating by default, the real fun for the viewer is in watching Stiller and De Niro push each other’s buttons.

Seth Rogen and Evan Goldberg mined their own high school experiences in writing “Superbad”, and their embarrassment is our gain. Like the American Pie gang before them, Jonah Hill and Michael Cera play teens looking to close out their senior year with a bang… literally. What begins as a coming-of-age tale spirals into a night-long odyssey involving a less-than-convincing fake ID, numbskull cops, and an impromptu musical performance. Above all, Superbad never loses sight of the film’s heart: the bromance between Hill and Cera’s characters. Director Greg Mottola’s timeless comedy reminds us as viewers that nothing compares to rooting for the underdog — especially if the underdog in question brings to mind memories we’d rather forget.

We’ve probably all fantasized about laughing it up on a talk show host’s couch. Robert De Niro’s unstable, clout-chasing Rupert Pupkin takes things a step further to pursue his dream of being a famous comedian. A chance encounter with fictional late night legend Jerry Langford fuels Rupert’s delusions of grandeur, leading him to violate the unspoken rules of polite society in a variety of creative and deeply cringeworthy ways. A chilling, eerily prescient take on parasocial relationships, Martin Scorsese’s pitch-dark comedy is an emotional rollercoaster. Rupert is seemingly incapable of taking “no” for an answer: you’ll feel sorry for him in one scene, and in utter disbelief at his lack of self-awareness in the next.

Awkwardness is clearly passed down from generation to generation — “Little Miss Sunshine” is proof of this. Each member of the beleaguered Hoover clan struggles with their own personal battle, whether it’s grandfather Edwin’s substance use disorder, or youngest Olive’s desire to compete in the titular beauty pageant. Crammed into a stuffy van on a cross-country trek to the pageant in question, the Hoovers’ Volkswagen serves as a pressure cooker for cringe. As personality types clash and personal revelations abound, the family’s bond perseveres, despite countless obstacles that threaten to derail their journey. Winning the Oscars for Best Original Screenplay and Best Supporting Actor for Alan Arkin’s performance, “Little Miss Sunshine” proves that embarrassment and the warm ‘n’ fuzzies go hand in hand.

It’s virtually impossible to talk about gross-out comedy without bringing up Peter and Bobby Farrelly. Just ask Ted, the protagonist of “Mary,” who finds himself in a, erm, compromising position right from the beginning. The Farrelly Brothers are so committed to pushing the boundaries of awkwardness that we can’t even show you what’s debatably the movie’s cringiest moment. So… we’ll just have Ben Stiller and Chris Elliott explain it. Although “Mary” definitely tests the audience’s tolerance for intolerable characters in hard-to-stomach situations, it more than makes up for it with sheer laughs. And, hey, how can we complain about a movie that casts Jonathan Richman as its narrator — and then does that with him?

Let’s face it: learning about the “birds and the bees” is awkward. It’s probably exponentially more awkward if you need to have that conversation at age 40. This is the problem Steve Carell’s Andy faces once his friends and coworkers discover that he has never had sex. Their efforts to help him, while well-intentioned, pretty much only serve to land Andy in uncomfortable situations. Surrounded by comedy heavy hitters like Paul Rudd and Jane Lynch, Carell’s sweetness, naivete, and razor-sharp comedic chops are what make Andy’s predicament believable in a role that made him a household name. At the very least, you’ll never think of Kelly Clarkson the same way again.

Before we unveil our top pick, here are a few honorable mentions.

“Napoleon Dynamite” (2004)
An Instant Cult Classic of Cringe

“Shiva Baby” (2021)
An Impressively Stressful Dramedy Starring a Pitch-Perfect Rachel Sennott

“World’s Greatest Dad” (2009)
This Underrated Satire Explores the Difficulty of Doing the Right Thing

“Waiting for Guffman” (1996)
A Gut-Busting, Improvised Mockumentary About a Quirky Regional Theater Troupe

“Tim and Eric’s Billion Dollar Movie” (2012)
Stars Heidecker & Wareheim Bring Their Absurdist Antics From TV to the Big Screen

If you thought that fictional cringe was too much for you to handle, you may not be ready for “Borat’s” real-life awkwardness. Disguised as a clueless, mustachioed reporter sent to learn about American society by the government of Kazakhstan, Sacha Baron Cohen won a Golden Globe for his chameleonic performance. In addition, he was nominated for an Oscar for the film’s screenplay. Ignorant, inappropriate, and imbecilic, Cohen’s Borat has a masterful gift for saying the wrong thing at precisely the wrong time, generating unprecedented levels of discomfort and somehow managing to offend pretty much everyone. Who ever said awkwardness doesn’t pay?

Did we miss your favorite awkward movie? Post it in the comments! Or… don’t, if it’d be too awkward for you?