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15 of the Cringiest Scenes in Comedy History

cringe comedy moments

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15 of the Cringiest Scenes in Comedy History

Cringe comedy may be one of the most painful forms of comedy to watch, but if it’s done right, it can also be the most downright hilarious form, too. Humor theorist Noël Carroll explains the way in which humor that makes us cringe at social awkwardness can also make us laugh like this: “Imagine the cutlery laid out for a formal dinner. Suppose that the salad fork is in the wrong place. If you are the sort of person who is disturbed by such deviations from the norm, you will not be capable of finding this amusing. On the other hand, if you are more easy-going about such matters and also aware of the incongruity, it may elicit a chuckle. That is, you may find the error amusing or not. But if you find it genuinely amusing, you cannot find it annoying.” That’s a long way of saying that if you notice that a character in a movie or a TV show is deviating from the norms of society and you recognize that this is not the way to do things, you’ll find it funny, because of how wrong or impolite or simply awkward it is. Here are the 15 greatest examples of this being done.

15. Jen doesn’t know what IT stands for in The IT Crowd

The IT Crowd never really distinguished itself purely as a cringe comedy in the way that the likes of Peep Show and The Inbetweeners did. The IT Crowd was more of a workplace comedy about the culture clash of nerds and normies. But that doesn’t mean that Graham Linehan didn’t write in some painfully cringy scenes over the years. One example is when Jen – the only employee in the IT department who doesn’t know anything about IT (and also the head of the department) – is interviewing for an IT position at another company. Purely out of interest, the interviewer asks Jen what the letters “IT” stand for, before the interview has even started. But already, Jen is left stumped, because she has no idea! So, she drags it out as long as she can before revealing that she doesn’t know, and it’s painful and hysterical to watch.

14. The funeral in I’m Alan Partridge

In the series 1 finale of I’m Alan Partridge, Alan’s longstanding enemy, Tony Hayers, the chief commissioning editor of BBC Television, dies – and Alan is over the moon about it. He goes to the funeral wearing a Castrol jacket (surely he had another black item of clothing in his wardrobe) in order to network for business purposes. He schmoozes with Tony’s replacement to secure himself a new TV deal (which would eventually go south when he died, too). The height of the awkwardness of Alan’s character comes when he speaks to Tony’s widow, who tells him that Tony would’ve turned 41 next week had he lived, and Alan replies, “All those people who go around saying life begins at 40 – they’re notable by their absence. The nerve!” And then he asks this poor woman, the wife of the deceased, “Were you close?”

13. Will thinks he’s in there in a London nightclub in The Inbetweeners

In the episode of The Inbetweeners where the lads go out to a nightclub in London, Will thinks he’s got a thing going with a girl called Rachel, just because they were talking for a second in school and then in the line outside the club. He didn’t pick up on the signals that she was mostly ignoring him, and at one point, wanted to turn away from him so that people wouldn’t think they were together. So, thinking he’s totally in there, when he finally gets in the club and sees that she’s talking to a guy, he misreads the situation and tries to let the guy down gently, when really, he’s got it mixed up the other way around. It’s excruciating to watch.

12. Larry fires Paula in The Larry Sanders Show

The Larry Sanders Show was a forerunner to the likes of 30 Rock and Curb Your Enthusiasm as a self-aware satire of show business, and it’s about what a talk show host is like when he’s off camera. Janeane Garofalo had played Paula, the talent booker for the fictional talk show, for five seasons before she was written off, and she was written out of the show in the most hysterical and awkward fashion. Larry never liked confrontation, and when he was faced with having to sit Paula down and fire her, he awkwardly combines it with telling her that he likes her. He ends up asking her on a date to have dinner within the same minute as firing her.

11. George breaks up with a girl because she beat him at chess in Seinfeld

You could always count on Larry David surrogate George Costanza to provide the cringiest moments in Seinfeld. In the opening scene of the season 7 premiere episode “The Engagement,” George is playing chess with his girlfriend. He makes what he believes to be the winning move and says, “Well, you got no place to go. I’ll tell you what your problem is – you brought your queen out too fast. What do you think? She’s one of these feminists looking to get out of the house? No, the queen is old fashioned, likes to stay home, cook, take care of her man, make sure he feels good.” Then the girlfriend makes her move and says, “Checkmate.” Then George examines the board, sees that he’s been beaten, and says, “I don’t think we should see each other anymore.”

10. Jez peeing his pants at Mark’s wedding in Peep Show

“The Wedding” is widely regarded by the fan base of Peep Show to be the series’ finest episode, but it’s also the most difficult to watch, because there are so many moments that make you cringe. It was never going to go well, because Mark didn’t want to marry Sophie, so it was doomed from the start, but on top of that, there are so many cringeworthy moments. For starters, both Mark’s hat and shoes get covered in Super Hans’ vomit, then after Mark has finished washing them in the coffee shop bathroom, he proposes to a barista he’s never met, and then he tries to get hit by a car and has an awkward conversation with the man driving it. But the worst moment is when Mark and Jez are hiding up on the top floor of the church while he comes up with a plan to ditch Sophie. Jez desperately has to pee, Mark tells him he’ll have to pee in his pants, and he instantly starts doing it. And then it seeps through the floorboards and starts dripping down on Mark’s guests’ heads.

9. Gareth propositions Rachel in front of Tim in The Office

Throughout the second season of the original UK version of The Office, Tim and Gareth both fall for the same girl, but of course, only Tim has a chance, since he’s the only one of the two that’s a normal guy. But Gareth does not realize this, so when he catches Tim and Rachel kissing, he’s shocked. What he proceeds to say to them is stunningly awkward. He tells Tim, “I can’t believe you’d get off with a bird I fancy.” Then he tries to convince Rachel that Tim is the less attractive of the pair: “Look at his hair. He looks like a Fisher Price man. Look at his rubbish clothes.” Then he straight-up propositions Rachel right in front of Tim: “I’ll ask you straight. Can anything happen between us two while this is going on?” Curious, Rachel asks, “Like what?” and Gareth replies, “Specifically? Handjob. Don’t answer. Think about it.” And then he saunters off.

8. Larry heckles Sammi in Curb Your Enthusiasm

Larry David is the king of cringe comedy. He laced Seinfeld with it for seven years (he quit after season 7), and now, he’s been coming in with can’t-look-away humor in full force with his own show Curb Your Enthusiasm for nine seasons. It’s clearly working, since Rolling Stone magazine named the series the 19th greatest television series ever made. One cringy moment came when Larry’s friends Jeff and Susie have gotten their daughter Sammi to sing a song as a birthday present for Ted Danson. Larry sees this as a copout gift and thinks that Sammi is an awful singer, so he does what everyone else wants him to do and steps in to stop her halfway through the song. But no one really wants him to do it and he comes off looking like a jerk. Oh, Larry.

7. Mark diarrheas during Jez’s shroom party in Peep Show

In the series 3 episode “Shrooming,” Jeremy is planning to win back his ex Big Suze with an awesome magic mushroom party at the flat, while Mark is away on a business trip to Frankfurt. But his plans go awry when Mark turns up with a delayed flight and a terrible illness. He objects to Jez’s party taking place in his flat and Jez worries that if anyone sees Mark being sick, it’ll give them a bad vibe and ruin the trip, so he poisons Mark by giving him a high dose of medicine, putting him to sleep, and then locks him in his room. Eventually Mark is saved from his “false imprisonment” by his boss, Alan Johnson, and he rushes to take a diarrhea dump in the bathroom, out in the open, since Super Hans kicked the door out of its frame.

6. Dennis and Charlie are caught lying to the police in It’s Always Sunny

It’s Always Sunny in Philadelphia is rife with moments that are dark, savage, satirical, chilling – and cringeworthy. The cringiest moment of the entire series has to be when Dennis and Charlie have gone to a police station to describe a man who shushed them to the sketch artist, to give them a better chance of finding him and exacting their revenge. A detective comes in and asks them about the details of the case, and they sit there and try to lie just enough to get the sketch finished and in their hands, but not enough that they could be incriminated for providing the police with false information, and given that we know exactly what’s going on (and the cop probably does, too), it’s a terribly cringy situation to watch play out. The outtakes for that season are mostly this scene, because the actors just couldn’t get through it.

5. Roy pretends to be disabled in The IT Crowd

Widely regarded by many fans to be the best episode of The IT Crowd, the season 2 premiere “The Work Outing” – in which the IT department head to the theater to watch Gay: A Gay Musical – has many hilarious and cringeworthy moments, from Moss blagging his way into a bartending job to Jen confronting her co-worker about his sexuality. But there’s nothing cringier in the episode than the moment where Roy pulls the emergency cord in the disabled bathroom, thinking it is the flusher, only to have to pretend he is disabled when the staff break the door down. They give him a spare wheelchair after he tells them his was stolen (and his description gets some innocent person arrested by the police). Then he and other disabled guests are taken backstage to meet the cast of the play, after which he is loaded onto a bus and taken to Manchester.

4. Simon almost loses his virginity in The Inbetweeners

In The Inbetweeners – since it’s a show about four horny teenage boys going through high school and puberty – the main characters talk about sex and the prospect of having it constantly. Everything they do is an endeavor to eventually end up in bed with a girl. And that’s why Simon was so thrilled when he finally got a girlfriend who wanted to have sex with him. And it’s also why he was so furious when they got into bed, got ready to do it, and he couldn’t get an erection. Cue the most cringeworthy rant as Simon yells at his flaccid penis and starts slapping it, terrifying his girlfriend to the point that she kicks him out of the house (even though he’s completely naked).

3. The water bottle in Larry’s pants in Curb Your Enthusiasm

There’s a strong case to be made that season 2’s “The Doll” is the greatest episode of Larry David’s HBO sitcom Curb Your Enthusiasm. It’s a perfect example of Curb storytelling, with a back and forth to keep two parties happy – first, he cuts the President of ABC’s daughter’s doll’s hair, then he steals Sammi’s doll to give to the daughter because he has a new deal with ABC to preserve, then he brings back the short-haired doll for Sammi, until eventually everyone seems to be happy and the ABC deal is still on. That is, until Larry bumps into the girl whose doll’s hair he cut in the first place – the daughter of his new business partner – and she hugs him, mistaking the water bottle in his pocket for an erect penis. Yikes!

2. Jez brings Mummy’s corpse onto the boat in Peep Show

In the Peep Show episode where Jez takes Mark on a canal barge for his stag party, they meet a pair of girls and end up becoming close friends with their family during the holiday. Their dog’s name is Mummy, and of course, Jez ends up running over the dog with a car. Before the dog’s owner comes back, he quickly puts the corpse in his bag and then helps her find the dog, which she thinks is just missing. He tries to put it in the trash can on the boat, and then he and Mark try to burn it in the woods. Eventually, Jez is left still carrying around the charred remains of this dog in his bag, and through circumstances, ends up taking it on the boat where its owners are. They go rooting through his bag, mistaking it for barbecue meat (so then Jez, naturally, eats some of it), until they find the “Mummy” collar and it’s all over. Just agonizing to watch – but so funny.

1. David Brent’s charity dance in The Office

This moment stands as one of the greatest moments in comedy history. It’s from the episode “Charity” of the original British version of The Office, which many critics consider to be the show’s finest episode. It’s Red Nose Day and everyone’s doing different things for charity. The Brent-upstaging new guy Neil and Tim’s new, Dawn-upstaging love interest Rachel do a dance for charity that everyone loves and gives money for. David, feeling jealous that someone else is getting all of the attention (especially given that it’s Neil), decides to do his own, impromptu dance. At first, everyone’s all for it as they sing and clap along for him, but then they slowly lose enthusiasm and the whole thing becomes painfully awkward – and it’s comic gold.

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