11 Most Cringe Moments From ’90s Comedies

Warning: This article discusses topics of transphobia, fatphobia, and inappropriate conversations.

The 1990s were a fantastic era for comedy movies, but some moments were so unbelievably cringey that they either aged awfully or were simply uncomfortable. While there were plenty of 1990s comedies that barely anyone remembered, other titles were iconic and a staple of cinema. Regardless of whether the film was a big hitter or not, many ‘90s movies were guilty of including truly cringeworthy moments.

These moments were labeled as such for a range of reasons. Some were darkly inappropriate, whereas others deserved the sound of crickets in the background. Unfortunately, many cult classic movies from the ‘90s aged poorly because of scenes like this. From the painfully unfunny to the creepily unusual, these moments from ‘90s comedies were quickly established as being completely cringe.

11 Webcam Scene

American Pie (1999)

Every American Pie movie included plenty of cringey moments, but the first installment of the franchise contained the absolute worst. The webcam scene in American Pie was cringey for several reasons, and the levels of discomfort only rose upon revaluation. It was weird enough that Jim and the boys were so desperate for a peek at a woman that they watched Nadia get changed via webcam, but it was even more bizarre that they felt it was fine to do so without her knowing.

What’s so stupid about this moment was that, later on, Nadia allowed Jim to make a move on her, so it wasn’t as if she had no interest in him. It was absurd that an unknowing Nadia was shamed and mocked for the livestream, shared around their school for everyone to see, and then sent back to the Czech Republic. Jim was celebrated for what was essentially sexual harassment, yet Nadia was made out to have done something wrong.

10 Hiring A Creep

There’s Something About Mary (1998)

There’s Something About Mary was a typical ‘90s rom-com, but the journey that Ted embarked upon to woo his former high school crush was just plain odd. His stalking of the titular character throughout the film was a strange choice, but it was disappointing that Ted was painted as the only main character in There’s Something About Mary who pursued her and wasn’t a creep. In reality, Ted was the worst of the bunch because he literally hired a private investigator to track Mary down.

PI Pat Healy was also disturbing, and it was simply cringey that he fell in love with Mary after observing her for a few hours. Pat’s lies and attempts to deceive the several other men chasing after Mary’s affections made no sense, and poor Mary deserved to be left alone. The ending of There’s Something About Mary was completely nonsensical, however, and if Mary had any common sense, she would’ve changed her name and moved far away.

9 Transphobic Jokes

Ace Ventura: Pet Detective (1994)

There were so many hilarious quotes from Ace Ventura, Jim Carrey’s iconic movie character from the ‘90s, but certain lines of dialogue from Ace Ventura: Pet Detective aged awfully. Lieutenant Lois Einhorn worked alongside the titular character, and she was later revealed to be the main villain of the film. However, the explanation behind this was far from appropriate. Einhorn and Ventura shared a kiss, but when the detective later learned that she was actually former kicker Ray Finkle, he violently vomited.

Finkle was dismissed from the Miami Dolphins for costing the team a win at the Super Bowl, and he was institutionalized for mental health reasons. He then went under sex reassignment surgery and took the identity of a missing female hiker. Every Ace Ventura movie included a ridiculous reaction from Ventura, but the titular character’s response to Einhorn being a man was disgusting because he focused on his romantic interactions with him rather than the problem at hand. Plus, it was shocking that the movie thought that using a transgender person’s identity as justification for antagonism was just uncalled for.

8 Austin Powers’ Strip Tease

Austin Powers: International Man Of Mystery (1997)

Austin Powers’ interactions with the sexy Fembots in the 1997 release Austin Powers: International Man of Mystery were overly absurd from start to finish. Every moment of the scene was painfully cringey. His attempts to not be enticed by referencing his turn-offs were wild, and although the film was a comedy, it was odd that attractive, robotic women were that much of a distraction from Austin saving the world. However, the strip tease was by far the most awkward moment.

Austin started to groove and sway along to “I Touch Myself” by Divinyls, but the fact that his seduction worked made the moment even more terribly cringey. Austin’s Union Jack underwear, him smoking several cigarettes in his mouth with a lighter gun, and his comments about it being “cold” when one Fembot released a cloud of gas from her breasts were all completely bonkers. Although one of the harsh realities of the Austin Powers movies was that the titular character was designed to be a caricature of an oversexed super spy, this scene took the concept too far.

7 The Graduation Parties

Billy Madison (1995)

Billy Madison featured several of the funniest quotes from Adam Sandler’s movies. While there were many hilarious moments throughout the film, Billy’s multiple graduation parties were just uncomfortable. Firstly, Eric Gordon shouting at a child during a three-legged race at the first-grade celebration and dragging them along the grass by their ankle was shocking and unnecessary. Gordon wasn’t a big fan of Billy, granted, but it was simply embarrassing that a grown man and business executive felt that it was okay to treat a kid that way.

However, the third-grade party was the most cringeworthy. Billy’s attempts to seduce Veronica, his teacher, in his garden tent were honestly quite skin-crawling. There were so many things about this scene to unpack: Billy’s collection of sexually explicit material that was accompanied by sound, his brag about understanding nine words in “A Tale of Two Cities,” and Veronica’s acknowledgment that he had her alone was all like the beginning of a bad pornography film. All of this, paired with the fact that a fully grown man was at school again, was unbearable to watch.

6 Josh and Cher’s Relationship

Clueless (1995)

Josh and Cher’s relationship in Clueless was shockingly controversial. The step-siblings, who spend most of the film at each other’s throats, end up as a couple at the climax of Clueless. However, Cher and Josh’s ages in Clueless also posed a problem. Josh was a college student, and Cher was in high school, so the age gap between the pair was uncomfortable enough anyway. While love affairs between step-siblings were often fetishized, in reality, the two wouldn’t dream of having a physical relationship.

Clueless was a movie adaptation of Jane Austin’s novel Emma, but the modern retelling didn’t hit in the same way. Cher and Josh’s kiss scene on the staircase of their home was cringey, especially as Cher only realized her feelings for her step-brother because her friend took an interest in him. Neither took their former familial connection seriously and at one point, Cher’s father even joked about Josh being his “son-in-law.” Josh’s awkward compliments about Cher before their kiss were weird, and their romance felt forced overall.

5 Not One, But Two Inappropriate Relationships At Prom

Never Been Kissed (1999)

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Never Been Kissed was an unforgettable ‘90s teen romance movie, but the main relationships were wildly inappropriate. Although Sam and Josie’s supposed love story wasn’t illegal, it was still creepy that the teacher thought it was fine to develop feelings for his student. Even though Josie was an undercover reporter, Sam didn’t know otherwise. Sam and Josie’s fight at prom was an iconic rom-com movie scene that didn’t age well, mainly because Sam failed to recognize that he was being controversial and was instead furious at Josie for lying.

However, Josie’s brother, Rob, was just as problematic. Realistically, he only joined high school again to ignite a second baseball career, but he claimed to be assisting his sister. Rob dated a sophomore student, but it was never highlighted properly and swept under the rug. Rob’s behavior at the prom was baffling, and he thankfully avoided the 16-year-old girl trying to have sex with him, but his screeching reaction to being nominated as Prom King was a little pathetic.

4 Sherman’s Weight Loss Reaction

The Nutty Professor (1996)

The Nutty Professor’s protagonist, Sherman Klump, was Eddie Murphy’s favorite performance, but one scene failed to have the same appeal years later. The 1996 remake of the 1963 title of the same name starred Murphy as the oversized Klump, who created a miracle drug that helped him lose an unachievable amount of weight in mere seconds. While his initial reaction to his new body was played for laughs, upon rewatching it years later, the moment wasn’t as funny.

Klump acted as if his size was the only thing that mattered. Although this was the premise of The Nutty Professor, Klump’s over-the-top cheers and obnoxious opinions about his former self left behind a bad taste. His motivation, which was to pursue women by being thin, became increasingly cringey when he boasted that he didn’t have breasts anymore and that he was able to see his penis again. The Nutty Professor might have been one of Eddie Murphy’s best movies, but Klump quickly became an unlikable character after this scene.

3 Francis Begbie’s Hook-Up Scene

Trainspotting (1996)

Trainspotting was another ‘90s movie guilty of transphobia. Although it relied on dark comedy in a gritty and suspenseful tale, and it was a movie where every character was actually horrible, Francis Begbie’s hook-up scene was rather unfair. After he met a beautiful young woman at a club, Begbie started making out with her in a car in an alleyway. However, when he slipped his hand under her skirt, he was shocked to feel a bulge he wasn’t expecting to be there.

Begbie’s shout of “F*ck!” in a panic was unwarranted. Begbie was an awful character in the Trainspotting cast anyway, but the look of disgust he offered the woman wasn’t as funny as the film’s writers hoped it would be. What was even more disappointing about this moment, however, was that Mark’s voiceover in the lead-up to this scene implied that nobody told Begbie about this ahead of time on purpose, which was not only a jerk move but also incredibly demoralizing to the woman. ​​​​​​​

2 Chef’s Advice To Stan

South Park: Bigger, Longer & Uncut (1999)

South Park: Bigger, Longer and Uncut was one of the best R-rated comedy movies from the 1990s and the first movie for the legendary animated franchise. While the film was generally a hilarious and engaging story, Chef’s advice to Stan was unbelievably hard to watch. Stan asked Chef the best way to woo Wendy, and the elementary school cook told the young boy that he needed to “find the clitoris.” Naturally, this was absolutely not something that a grown adult should have said to an eight-year-old.

Even though South Park’s best characters were famous because of their shocking language and out-of-the-box humor, this was a spectacular moment, and not in a good way. It was easy to laugh at this scene, undoubtedly, but the laughter often came from a place of discomfort. Chef was generally a great figure in South Park , but this was too cringeworthy, even for him. He immediately realized his mistake and tried to backtrack, but Stan’s incessant questions about what it was made it even more painful.

Romy And Michele’s High School Reunion (1997)

The 1997 film Romy and Michele’s High School Reunion uses fatphobic insults frequently, unfortunately. However, the remarks that were hurled during the titular reunion itself were unnecessary, cringey, and in reality, not really that funny. The entire concept of Romy and Michele’s High School Reunion was that the two main characters wanted to improve themselves so that their ex-classmates didn’t believe they were still losers, but the pair instead turned into the popular kids that they initially hated growing up.

When the two crossed paths with some of the girls who bullied them, Michele made a jab about their appearances and told them that they “were [not] the ones who got fat.” It was rather humiliating that she didn’t notice that they were pregnant. Regardless of whether they were with child or not, it was really cringey that after years of traumatic high school memories about these people, the only retort Michele came up with was a weak comment about their weight.