10 Most Cringe-Worthy Comedies Of All Time, Ranked

Comedy is one of the few film genres where the entire point is to elicit a reaction from its audience. If you watch a comedy without so much as smirking, then it must've done a pretty poor job. The idea of garnering a physical response from viewers gets taken to the next level with cringe comedy. Shows like "The Office" and "Curb Your Enthusiasm" aren't merely trying to get you to laugh; they also want you to squirm in your seat as you watch a character make a complete fool out of themselves out of some minor social faux pas.

To be clear, there's a difference in a cringe comedy that's specifically trying to make you feel awkward and a comedy that happens to be cringey by accident. There are plenty of films that'll make you cringe for all of the wrong reasons: You don't feel bad for the characters, or you feel bad for everyone who had to take part in making such a terribly embarrassing piece of cinema. We call that the "Movie 43 Effect."

On the other hand, these films are the best at what they do. They're the most cringe-worthy comedies of all time that figured out how to make audiences feel icky but still want to come back for more.

"There's Something About Mary," one of the best '90s comedies out there, sees Ben Stiller as a guy who seemingly can't do anything right. He plays Ted Stroehmann, who has had a crush on the titular Mary (Cameron Diaz) ever since they were in high school, but missed out on going to prom with her after getting a very sensitive area of his body stuck in his zipper. That sort of juvenile humor centered on people's body parts or bodily fluids (as is the case for the movie's most famous scene) is integral to the film, and you're either into that or you're not.

Ted might be one of the cringiest romantic comedy protagonists we've ever seen. He's pretty much a creep, and only looks good by comparison to the vile Pat Healy (Matt Dillon), a private investigator he hires to check up on Mary but falls in love with her himself. It basically becomes a cringe contest for the two to earn Mary's affection, leading to such awkward moments as Ted accidentally confessing to murder. Ted doesn't seem like a guy who would last long in the real world, but his antics are sure to still inspire plenty of laughter.

• Cast: Ben Stiller, Cameron Diaz, Matt Dillon
• Director: Peter and Bobby Farrelly
• Rating: R
• Runtime: 119 minutes
• Where to Watch: YouTube

It's rare for comedies to get theatrical releases anymore, let alone really penetrate the zeitgeist. But in 2004, a small indie film about a socially awkward outcast took the world by storm. "Napoleon Dynamite" was ripe with catchphrases, and anyone who could do a somewhat decent Napoleon (Jon Heder) impression would rule their cafeteria table. It's a relatively aloof film with not much in the way of plot. It's all kept afloat by Napoleon, who has more confidence than one might assume given his looks, trying to help out his new friend Pedro (Efren Ramirez) become class president.

Napoleon does things most of us wouldn't dream of because we're all afraid of coming off cringey. He'll try to impress a girl by giving her a very poorly-drawn picture of her. Honestly, that's probably the main reason why Napoleon Dynamite became such an icon. He exemplifies the kind of "don't care" attitude all of us should strive for. So many people wonder if something they do in public will be perceived poorly, but we should all strive to live as our authentic selves. You never know — it might even be accepted by others, like when Napoleon does a dance routine in front of the whole student body at the film's climax, and everyone applauds. It's a shame we'll probably never get a "Napoleon Dynamite" sequel, because it would be great to see if he's maintained that attitude into adulthood.

• Cast: Jon Heder, Efren Ramirez, Tina Majorino
• Director: Jared Hess
• Rating: PG
• Runtime: 96 minutes
• Where to Watch: Hulu

Ben Stiller's second entry on this list once again sees him as a good-natured guy who just can't seem to do anything right. At least his character, Greg Focker, has a girlfriend, Pam (Teri Polo), from the beginning this time. He only needs to get her parents' blessing to marry her. Greg is definitely a bit more competent compared to Ted in "There's Something About Mary," and that only allows the cringe to shine through more brightly. He's far more relatable because plenty of us can likely relate to wanting to impress a partner's family, but hopefully, we don't make all of the same mistakes Greg did.

It doesn't help that Pam's father, Jack (Robert De Niro), is a bit of a stickler. He puts Greg through the wringer, including a lie detector test. But "Meet the Parents" is a true comedy of errors, like flooding the backyard and accidentally injuring Pam's sister before her wedding. Stiller and De Niro make for a superb comedic duo, with Stiller's everyman energy contrasting beautifully with De Niro's natural tough guy persona he's showcased in films like "Raging Bull" and "The Untouchables." Greg's inability to do anything right becomes a self-fulfilling prophecy, and audiences can sit back and wait for things to finally turn around for him.

• Cast: Ben Stiller, Robert De Niro, Owen Wilson
• Director: Jay Roach
• Rating: PG-13
• Runtime: 108 minutes
• Where to Watch: Amazon Prime Video

Our review of "Shiva Baby" called it one of the most anxiety-inducing comedies in years, and that's an accurate summary. The film primarily takes place in one location — a shiva (a Jewish tradition of mourning) — that Danielle (Rachel Sennott) has to navigate. The problem is that Danielle's life is a mess. She's sleeping with a married man who's at the shiva, too, with his wife, and she generally appears to be adrift in life, not really having much going for her as opposed to her ex-girlfriend, Maya (Molly Gordon), who's going to law school.

Numerous stressors in Danielle's life collide, and it's made all the more terrifying by the fact she's confined to a single house. There's no escape, and no matter what room she goes to, there's someone there who wants to talk to her about something serious. We know Danielle wants to get out of all this awkward small talk, and her inner panic grows exponentially. "Shiva Baby" has plenty of comedic moments, but to all of the introverts out there, it almost plays like a horror film where Danielle's forced to confront her immaturity.

• Cast: Rachel Sennott, Molly Gordon, Fred Melamed
• Director: Emma Seligman
• Rating: Not Rated
• Runtime: 77 minutes
• Where to Watch: Netflix

There are plenty of great dark comedy movies you probably haven't seen, and if you've ever suffered from middle child syndrome, then "Welcome to the Dollhouse" is a must-watch. It follows Dawn Wiener (Heather Matarazzo), who's an exceptionally unpopular seventh-grader. Nothing ever goes her way, as she's bullied at school and typically ignored at home in favor of her younger sister, Missy (Daria Kalinina).

"Welcome to the Dollhouse" is a very uncomfortable watch. It plays through all of the beats of a typical coming-of-age story; but whereas many other films in that subgenre can have rose-tinted glasses about the joys of youth, there's really nothing here to give Dawn a break. Teachers punish her for other students' actions when she didn't do anything wrong, and she tries to get into a relationship with Brandon (Brendan Sexton III), who's bad news from the start. You have a little girl just trying to figure out where she belongs in life but can't seem to get anywhere. The comedy stems from how flippantly people are cruel to Dawn. Watching it, you want to think people wouldn't be that mean to a kid in junior high, but surely somewhere, this kind of thing has to happen.

• Cast: Heather Matarazzo, Matthew Faber, Angela Pietropinto
• Director: Todd Solondz
• Rating: R
• Runtime: 88 minutes
• Where to Watch: Tubi

The key to many of the most cringe-worthy movies ever made is that the main character is completely oblivious to the social contract. 2006's "Borat! Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan" is a mockumentary starring fake Kazakhstani Borat (Sacha Baron Cohen) learning about American culture. What makes the movie work so well (while also amplifying the cringey moments) is that even though Borat is a performance, most of the people he interviews aren't in on the bit. Borat says outrageous things, and it's fascinating to see how far people are willing to humor him when a camera's on them.

What separates "Borat" from being merely a good mockumentary to a great one is that the cringey moments highlight post-9/11 American ideas of exceptionalism. In one of the most notable scenes, Borat sings the Kazakh national anthem at a rodeo. But before singing, he exclaims, "May George Bush drink the blood of every man, woman, and child in Iraq" to wild aplomb from the crowd. So much uncomfortableness stems from the fact that we know Borat is joking about such fervent nationalism, but everyone in that crowd is dead serious. It's cringe comedy with a purpose that still feels excruciatingly relevant to this day.

• Cast: Sacha Baron Cohen, Ken Davitian, Pamela Anderson
• Director: Larry Charles
• Rating: R
• Runtime: 84 minutes
• Where to Watch: Hulu

Tim Robinson's best sketches on "I Think You Should Leave" typically involve a character who makes a minor faux pas only to go to extreme lengths to insist they didn't do anything weird. It's cringey, but fortunately, these sketches tend only to last a few minutes. "Friendship" basically involves taking one of Robinson's characters and following them for 100 minutes, watching him sink deeper into desperation. And all Craig Waterman (Robinson) is trying to do is make a friend.

Craig and Austin (Paul Rudd) seem like a great match, and when Austin invites his new buddy to hang out with his old friends, there are glimpses that things could work out. Even when Craig does something dumb at first, they're all able to laugh it off. But the incidents continue piling on until Austin doesn't want to hang out with Craig anymore. This sends Craig into a fervor because he doesn't have any other friends. It's excellent commentary on the male loneliness epidemic and how essential it is for guys to have someone they can pal around with. It's hilarious but touches on something profound, which is that we all need connection. Craig has a wife, Tami (Kate Mara), and son, Steven (Jack Dylan Grazer), but those don't quite fill the same role that he clearly needs.

• Cast: Tim Robinson, Paul Rudd, Kate Mara
• Director: Andrew DeYoung
• Rating: R
• Runtime: 100 minutes
• Where to Watch: HBO Max

In an alternate reality, there's a version of "The 40-Year-Old Virgin" that focuses solely on bawdy humor. The film's about Andy (Steve Carell) who lets slip that he's still a virgin at 40 years old, so his coworkers try to help him get laid. While all that's happening, he's organically starting a relationship with Trish (Catherine Keener), so he's caught between the desire to simply have sex or get into something deeper emotionally with her.

Obviously, "The 40-Year-Old Virgin" is filled with crude jokes and gross-out gags, including the memorable waxing scene where Steve Carell literally sheds blood for the role. It can be awkward watching Andy try to hit on women, but what grounds the film is that Andy's genuinely a sweet guy. He's not a creep, he just doesn't know how to interact with women. The film's cringey moments are therefore a lot more relatable, as many viewers can likely relate to saying something stupid to a woman you're trying to hit on. With this, "The 40-Year-Old Virgin" avoids being solely an exercise in making fun of virgins (there's nothing wrong with waiting a long time). It shows it's okay to be awkward, and there's hope yet for finding someone who thinks your foibles are charming.

• Cast: Steve Carell, Catherine Keener, Seth Rogen
• Director: Judd Apatow
• Rating: R
• Runtime: 133 minutes (for the unrated cut)
• Where to Watch: AMC+

When you think of the all-time great comedy directors, Martin Scorsese probably doesn't come to mind immediately. However, he's still responsible for one of the all-time great cringe comedies with the aptly named "The King of Comedy." Aspiring stand-up comedian Rupert Pupkin (Robert De Niro) wants to make it to the big-time, and he thinks he can do it by befriending talk show host Jerry Langford (Jerry Lewis) and appear on his program. The only problem is that Jerry (and most of society at large) wants nothing to do with Rupert, but he's not the kind of guy who understands social cues to find a new line of work.

It's too much of a stretch to say "The King of Comedy" invented the term "cringe comedy," as the work of Andy Kaufman undoubtedly helped bring a more surreal style of humor to the masses, but it's definitely an early ancestor of the format. Rupert doesn't know how to function in our world, not unlike one of Tim Robinson's many sketch characters or a guy like Napoleon Dynamite. But whereas we can find those characters endearing to various degrees, there's always a threat of violence lurking underneath the surface with Rupert where the laughs can stop at any second and get replaced with screams.

• Cast: Robert De Niro, Jerry Lewis, Sandra Bernhard
• Director: Martin Scorsese
• Rating: PG
• Runtime: 109 minutes
• Where to Watch: Amazon Prime Video

Christopher Guest mastered the art of the mockumentary with hilarious films like "Best in Show" and "A Mighty Wind," but "Waiting for Guffman" remains unmatched when it comes to cringe comedy. The 1996 film takes an eccentric community theater director, Corky St. Clair (Guest), who's putting on a 4th of July show for a small town. But the performers all come to believe that if the show is good enough, they could take it to Broadway; however, once you see all of them actually perform, it's clear that none of them really have talent.

That's the single cringey mission statement of "Waiting for Guffman." It's 84 minutes of people becoming delusional and thinking their small town play is something transcendent. There's a dramatic irony persistent throughout the film, and yet, the story doesn't make fun of these characters. They're delusional in a charming way where it makes them only want to work harder to make this play as good as it can be. The improvisational style Guest employs in his movies is on full display here, which helps make the characters feel more grounded. And feeling like real people only makes the cringe feel more potent.

"Cringe" has become something of an easy insult, but to be cringe is to be human. We all act ridiculous, say the wrong things sometimes, and behave delusionally. "Waiting for Guffman" finds the joy in cringe comedy because it's better act like a fool than to just be boring out of fear of judgment.

• Cast: Christopher Guest, Eugene Levy, Parker Posey
• Director: Christopher Guest
• Rating: R
• Runtime: 84 minutes
• Where to Watch: Amazon Prime Video