Top 10 Comedy Movie Scenes That Make You Cringe
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Top 10 Comedy Movie Scenes That Make You Cringe

VOICE OVER: Ryan Wild WRITTEN BY: Nick Lester
These moments had us laughing our butts off … AND squirming in our seats. For this list, we're looking at most awkward yet hilarious scenes. Our countdown includes “Little Miss Sunshine”, "Borat", “There's Something About Mary”, and more!
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Top 10 Cringiest Comedy Movie Scenes


These moments had us laughing our butts off … AND squirming in our seats. Welcome to WatchMojo, and today we’ll be counting down our picks for the Top 10 Cringiest Comedy Movie Scenes.

For this list, we’re looking at most awkward yet hilarious scenes. We’ll be excluding cringey scenes from serious dramas, like that first date scene from Taxi Driver. If tragedy and comedy are linked, these clips prove why: sometimes all you can do is cringe and laugh at the same time. As always, please beware of spoilers ahead.

#10: Death & Defecation

“Death at a Funeral” (2010)
Fair warning: if you’re eating while watching, you may want to put down the food now. Taking our tenth spot we have legends Danny Glover and Tracey Morgan getting themselves into a hot mess… literally. And just when you think it can’t get more cringe than getting your hand stuck in a toilet while an old man is... occupying it, think again. Bodily functions are a surefire way to up the cringe factor, especially when the setting is a funeral - a time usually reserved for somber reflection, quiet, and respect. This scene has none of those things, and instead we watch as Morgan’s character gets himself deeper and deeper into … Well we won’t finish that sentence.

#9: Super Freak

“Little Miss Sunshine” (2006)
In a movie filled with unexpected moments both awkward and wonderful, the final dance number in “Little Miss Sunshine” stands out as a scene that’s as cringy as it is cute. Abigail Breslin owns the character of Olive, who unfortunately has to learn the hard way that she’s not ‘Little Miss Sunshine’ material. That doesn’t mean she doesn’t give it her all though! As she showcases moves that shock judges and spectators for all the wrong reasons, the scene plays off as weird and endearing at the same time. Weird or not, it had us all dying of laughter, and cheering when her family supportively joined in.

#8: Mike Yanagita

“Fargo” (1996)
For most of us, asking someone out on a date can make for an awkward encounter. But hopefully we never seem as cringy as Mike Yanagita in the Coens’ 1996 masterpiece, “Fargo”. Sure, the movie centers around a botched crime and involves a person being murdered in a wood-chipper, but the hardest scene to watch probably comes when Mike makes a pass at Marge following the death of his wife. From his dopey smile at the start of the scene, to his puppy dog tears at the end, the four-minute encounter in a Raddison’s plays like a slow-moving train wreck. All we can do is sympathize with Marge as she sips her diet coke and waits for this cringe-fest to be over with.

#7: Dinner Party

“Borat” (2006)
Where do we even begin with this one? “Borat” was a cultural phenomenon that produced some of the funniest unscripted moments in modern cinema. Played by Sacha Baron Cohen (SAW-sha), the titular character is a tornado of poor manners, bad taste, and raunchy, cringy encounters, and the dinner scene epitomizes all of these. From carrying a bag of his own… excrements to the dinner table, to awkwardly musing about how his countrymen would go crazy over one man’s wife and not another’s, the scene is as hilarious as it is hard to stomach.

#6: Like Warm Apple Pie

“American Pie” (1999)
This star-making scene turned Jason Biggs from a relative unknown into the poster-boy for cringe comedy. It’s one thing to experiment and think outside the box, but an apple pie? Of course, the crowning moment in this scene comes when Jim’s dad, played marvellously by Eugene Levy (LEVV-EE, not lee-vee), walks in on him in this compromising position. Jim’s naiveté, and his total lack of common sense (why do this right there in the kitchen?) makes his character that much more loveable and relatable. But it certainly doesn’t make the scene any easier to watch!

#5: Voicemail Fail

“Swingers” (1996)
In a brilliant and underrated movie, this scene still manages to set itself apart. Struggling to get over his ex, Jon Favreau’s character Mike Peters calls up a girl he just met, and just cannot stop leaving voice messages. What makes this monologue so cringe-worthy is how unbelievably long it lasts. Watching it, we ALL wish we could bust into that dingy apartment and pry the phone from Favreau’s shaky, clammy hands. But as the stuttering and awkwardness mounts, we’re left to cover our faces and thank our lucky stars that we’re not the ones leaving the message. This movie is money!

#4: Bag of Sand

“The 40-Year-Old Virgin” (2005)
Have you ever gotten so deep into a lie that the only way out was to just keep on lying? That’s how Andy must feel about ten seconds into the poker scene. Not wanting to reveal that he’s a virgin, Andy is forced to improvise a sexual encounter that never happened, and in doing so he all but confirms to the other guys at the table that he’s never really been with a woman. If there’s ever a movie to avoid watching with mom and dad, it’s this one, as there is basically nothing more cringy than Carrell’s loveable character trying to convince his buddies of his sexual prowess by describing a woman’s breast as a “bag of sand.”

#3: Dress Shopping

“Bridesmaids” (2011)
From the first stomach rumbles, this scene had us squirming. Little did we know just how far it would go. When bride-to-be Maya Rudolph’s Lillian and her bridesmaids head to a high-end bridal boutique, their visit is cut short by a serious case of food poisoning. What follows are some of the most memorable, hilarious, and cringiest moments in cinema history - with Melissa McCarthy desperately relieving herself in a swanky bathroom sink. Is it weird that this scene is as hard to watch as it is to look away from? And to think that this comedy hit boasts more than one mega-cringe scene.

#2: Cat Milking

“Meet the Parents” (2000)
Let’s be real here for a second, what can be more cringe-inducing than Robert DeNiro saying: [broll: “I’ve got nipples, Greg, can you milk me?”] Let us answer that question by showing Ben Stiller’s character miming in close-up the way he once milked his imaginary cat on a farm in Detroit. “Meet the Parents” will go down as one of the great fish-out-of-water comedies of all time, and so much of its humor is derived from Ben Stiller’s Greg embarrassing himself in front of his stuck-up in-laws. The look on his soon-to-be-wife’s face in the scene tells us all we need to know. This is cringe-comedy at its finest.

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

Nickname Fail, “I Love You, Man” (2009)
What IS a Jobin? (JOH-bin)

Text Mishap, “The Edge of Seventeen” (2016)
Regretting a Text is Even Worse When It’s Read Out Loud by Someone Else

Breakup, “Happiness” (1998)
It’s Not Me, It’s You

Cleanup, “Game Night” (2018)
Just Spreading Around the Mess

Licking Dog Poop, “Step Brothers” (2008)
These Bullies Mean Business

#1: The Zipper

“There’s Something About Mary” (1998)
If there’s one actor who’s mastered the art of cringe, it’s Ben Stiller. The guy is just hilarious when his back is against the wall, and the zipper scene in the criminally-good “There’s Something About Mary” is all the proof anyone needs. We won’t go into the details of the scene for fear of being banished by YouTube, but suffice it to say that you’ll have a hard time watching it through to the end. Heck, it’s one thing to get yourself in a bind, but another thing entirely when everyone, including the town priest, is brought in to have a look. This scene changed the way folks zip up their flies like Jaws changed the way we swim in the ocean.
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