Still Hilarious: 12 Cringeworthy Comedies That Stand the Test of Time

In the world of comedy, there are countless subgenres within the category. One movie watcher was looking for suggestions on a film forum that fit the bill of cringe comedy — a movie that is hilarious because of its painfully awkward moments, much like The 40-Year-Old Virgin. According to viewers, these 12 films are the best to choose from if you’re looking for a good cringe comedy.

1. There’s Something About Mary (1998)

There's Something About Mary - Cameron Diaz
Image Credit:Twentieth Century Fox.

This romantic comedy features Ben Stiller as a man who hires a private detective to find his high school crush, Mary, played by Cameron Diaz. The humor in this movie comes from the awkward situations and misunderstandings that arise as the characters navigate their relationships with each other. Despite its cringe-worthy moments, Something About Mary is still a beloved comedy that is still a fan favorite more than 25 years later.

2. Movie 43 (2013)

Movie 43 Hugh Jackman
Image Credit: K.C. Bailey

This anthology movie features a star-studded cast, including Hugh Jackman, Kate Winslet, and Halle Berry, among others. The humor in this movie comes from the absurdity of each segment, which ranges from a woman who has a sentient leprechaun attached to her private parts to a basketball coach who curses out his players in Mandarin. The humor in Movie 43 is so cringe-inducing some viewers claim they can’t bring themselves to finish it.

3. Borat (2006)

Borat bear in ice cream truck Sacha Baron Cohen
Source: Twentieth Century Fox.

Sacha Baron Cohen stars in this mockumentary-style movie as Borat Sagdiyev, a journalist from Kazakhstan who travels to America to learn about its culture. The humor in Borat comes from the outrageous situations that Borat finds himself in, as well as his inappropriate behavior and offensive remarks. Borat is known for its controversial and offensive humor, but that’s what makes it such a cult classic as an outrageous satire.

4. Not Another Teen Movie (2001)

Not Another Teen Movie
Image Credit: Columbia Pictures.

This parody movie pokes fun at all the tropes and clichés of teen movies. The humor in Not Another Teen Movie comes from the exaggerated and over-the-top characters and the references to other teen movies like The Breakfast Club and She’s All That. The movie is intentionally cringe-worthy in its portrayal of high school stereotypes, making it both hilarious and unbearable to watch.

5. Superbad (2007)

Superbad Columbia
Image Credit: Columbia

This comedy follows two high school seniors as they try to score alcohol for a party and win over their crushes. The humor in Superbad comes from the characters’ awkwardness and insecurities, as well as the raunchy and vulgar jokes throughout the movie. Jonah Hill, Michael Cera, and Christopher Mintz-Plasse are the three musketeers of Awkward. 

6. Meet the Parents (2000)

Meet the Parents
Image Credit: Universal Pictures

This comedy stars Ben Stiller as a man who travels to meet his girlfriend’s parents, played by Robert De Niro and Blythe Danner. The humor in Meet the Parents comes from the awkward and uncomfortable situations that Stiller’s character finds himself in and De Niro’s overbearing and intimidating behavior. The cringe-worthy portrayal of family tensions is extremely funny and relatable.

7. Forgetting Sarah Marshall (2008)

Mila Kunis Jason Segel in Forgetting Sarah Marshall
Source: Universal Pictures.

This romantic comedy follows Peter, played by Jason Segel, as he tries to move on from his ex-girlfriend, played by Kristen Bell, by taking a vacation in Hawaii. Peter finds himself in increasingly cringe-inducing situations with eccentric characters that he meets while on vacation as he tries to mend his broken heart and move on.

This movie has an underlying sweetness to it while also being hilarious. Sometimes you must lean into your cringe to be great, like Peter with his Dracula musical. It’s absurd, and that’s why it’s great.

8. How to Lose Friends & Alienate People (2008)

How to Lose Friends & Alienate People - Kirsten Dunst & Simon Pegg
Image Credit: Metro-Goldwyn-Mayer Studios

In How to Lose Friends and Alienate People, Simon Pegg plays a socially awkward journalist who moves to New York to work for a prestigious magazine. The movie humorously satirizes the celebrity and media culture as the character navigates through the glitz and glamour of the industry with his inappropriate behavior.

9. Grown Ups (2010)

Adam Sandler, Chris Rock, Rob Schneider, David Spade, and Kevin James in Grown Ups
Image Credit: Tracy Bennett, Columbia TriStar Marketing Group

Grown Ups features a star-studded cast, including Adam Sandler, Chris Rock, Kevin James, David Spade, and Rob Schneider, who play childhood friends brought together after the death of their basketball coach. The movie delivers laughs through the characters’ juvenile behavior and immature antics, tapping into the nostalgia for the carefree days of their youth.

10. Napolean Dynamite (2004)

Napolean Dynamite - Napolean and Pedro
Image Credit: Twentieth Century Fox.

Napoleon Dynamite is an indie comedy that follows the life of Jon Heder’s character, an awkward and socially isolated young man living in a small Idaho town. The movie offers laughs through its cast of quirky and offbeat characters and the absurd situations they encounter. This iconic film gave us so many memorable quotes, t-shirt slogans, and dances.

11. Jackass: The Movie (2002)

Jackass: The Movie Jason "Wee Man" Acuna, Bam Margera, Ryan Dunn, Steve-O, Chris Pontius, and Johnny Knoxville, Dave England, Ehren McGhehey
Image Credit: Paramount Pictures

Jackass is a documentary-style movie that chronicles the wild antics of a group of friends known as the Jackass Crew. The movie is filled with shock value stunts and pranks, and the humor comes from the reactions of the people around them. Although the portrayal of dangerous and reckless behavior might be cringe-worthy, the movie remains a popular comedy that people find amusing.

12. Zoolander (2001)

Will Ferrell Zoolander
Photo Credit: Paramount Pictures

Zoolander is a comedy featuring Ben Stiller as Derek Zoolander, a clueless male model caught up in a conspiracy to assassinate the Prime Minister of Malaysia. The movie delivers laughs through its exaggerated satire of the fashion industry and larger-than-life characters. Although the portrayal of shallow and superficial behavior might be cringe-worthy, the movie still manages to entertain with its humor, leaving audiences in fits of laughter.

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This article was produced and syndicated by Wealth of Geeks.

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