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.

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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.

Related 10 Best Dark Comedies Of The 1990s

The 1990s produced some of the best dark comedies of all time, with filmmakers injecting bleak humor into a wide range of different genres.

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11 Webcam Scene

American Pie (1999)

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American Pie is a raucous teen comedy and the film that launched a revival of the genre. It follows a group of high school friends determined to lose their virginity before graduation and delves into the misadventures of the four boys as they navigate the complexities of relationships, peer pressure, and parental mishaps. You’ll never look at warm apple pie the same again.

Director Paul Weitz , Chris Weitz Release Date July 9, 1999 Cast Jason Biggs , Chris Klein , Thomas Ian Nicholas , Alyson Hannigan , Shannon Elizabeth , Tara Reid Runtime 95 minutes Writers Adam Herz Main Genre Comedy Expand

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 4

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There’s Something About Mary is a 1998 romantic comedy directed by Peter and Bobby Farrelly. The film stars Cameron Diaz as Mary, the object of affection for multiple men, including Ben Stiller’s character Ted. The story blends humor and romance as Ted attempts to reconnect with his high school crush, leading to a series of outlandish and comedic events. Matt Dillon also stars as a private investigator entangled in the pursuit.

Director Peter Farrelly , Bobby Farrelly Release Date July 15, 1998 Cast Cameron Diaz , Matt Dillon , Ben Stiller , Lee Evans , Chris Elliott Runtime 119 Minutes Distributor(s) 20th Century Fox Writers Ed Decter , John J. Strauss , Peter Farrelly , Bobby Farrelly Main Genre Comedy Expand

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)

Ace Ventura: Pet Detective 1

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Jim Carrey stars in Ace Ventura: Pet Detective as the titular character, who investigates the disappearance of the Miami Dolphins’ mascot. Courteney Cox, Sean Young, and Tone Loc star in this 1994 comedy, which cemented Carrey as a movie star alongside The Mask and Dumb and Dumber.

Director Tom Shadyac Release Date February 4, 1994 Cast Jim Carrey , Courteney Cox , Sean Young , Tone Loc , Dan Marino , Noble Willingham Runtime 86minutes Studio(s) Warner Bros. Pictures Distributor(s) Warner Bros. Pictures Writers Jack Bernstein , Tom Shadyac , Jim Carrey Expand

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.

Related Why Ace Ventura Hasn’t Aged Well

Jim Carrey’s breakthrough role came in 1994’s Ace Ventura: Pet Detective, but the film itself hasn’t aged well when it comes to certain social issues.

8 Austin Powers’ Strip Tease

Austin Powers: International Man Of Mystery (1997)

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Austin Powers: International Man of Mystery is the first film in Mike Myers’ James Bond parody series. Myers plays both Austin Powers and Dr. Evil, arch-enemies who are frozen in time and brought back in the ’90s. The film was followed by two sequels in 1999 and 2002, with a fourth film stuck in development hell.

Director Jay Roach Release Date May 2, 1997 Cast Mike Myers , Elizabeth Hurley , Michael York , Mimi Rogers , Robert Wagner , Seth Green , Fabiana Udenio , Mindy Sterling Runtime 89 Minutes Studio(s) New Line Cinema , Capella International , Moving Pictures , KC Medien , Eric’s Boy Distributor(s) New Line Cinema Writers Mike Myers Main Genre Comedy Expand

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)

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Directed by Tamra Davis and co-written by Tim Herlihy and Adam Sandler, Billy Madison is a Comedy film from 1995 that stars Adam Sandler in the title role. In order to prove himself a competent heir to a multi-million dollar fortune, Billy must return to grade school as an adult and navigate all 12 grades as quickly as possible.

Director Tamra Davis Release Date February 10, 1995 Cast Bradley Whitford , Adam Sandler , Chris Farley , Darren McGavin , Steve Buscemi , Bridgette Wilson-Sampras Runtime 89 minutes Studio(s) Universal Pictures Distributor(s) Universal Pictures Writers Tim Herlihy , Adam Sandler Expand

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)

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A modern reimagining of Jane Austen’s 1815 novel Emma, the iconic teen comedy Clueless stars Alicia Silverstone as Cher Horowitz, a rich and popular high schooler who takes a transfer student under her wing. Between making over her friends and trying to play matchmaker for her teachers, Cher finds herself increasingly unlucky in love – only to find it much closer to home than she would have thought. Brittany Murphy, Paul Rudd, and Donald Faison also star.

Director Amy Heckerling Release Date July 19, 1995 Cast Alicia Silverstone , Stacey Dash , Brittany Murphy , Paul Rudd , Donald Faison , Elisa Donovan Budget $12 million Studio(s) Paramount Pictures Distributor(s) Paramount Pictures Writers Amy Heckerling Runtime 97 minutes Expand

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 (1999) 0

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Never Been Kissed follows Josie Geller, played by Drew Barrymore, a copy editor who goes undercover as a high school student for an investigative report. Directed by Raja Gosnell, the film explores themes of adolescence and personal growth as Josie navigates her second chance at high school life. Supporting cast includes David Arquette, Michael Vartan, and Molly Shannon.

See more : Bungo Stray Dogs Season 5 Episode 3 Release Date and Time, Countdown, When Is It Coming Out?

Director Raja Gosnell Release Date April 9, 1999 Cast Drew Barrymore , David Arquette , Michael Vartan , Leelee Sobieski , Jeremy Jordan , Molly Shannon , Garry Marshall , John C. Reilly Runtime 107 Minutes Studio(s) Fox 2000 Pictures , Flower Films , Bushwood Pictures , Never Been Kissed Productions Distributor(s) 20th Century Fox Writers Abby Kohn , Marc Silverstein Main Genre Comedy Expand

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)

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The Nutty Professor features Eddie Murphy as Sherman Klump, a kind-hearted but obese professor who invents a miraculous weight-loss potion. Struggling with his weight and social insecurities, Klump transforms into the slim, charismatic, and arrogant Buddy Love. However, the consequences of his drastic transformation reveal deeper personal and ethical dilemmas. Directed by Tom Shadyac, the film blends comedy with a poignant exploration of self-acceptance.

Director Tom Shadyac Release Date June 28, 1996 Writers Jerry Lewis , Bill Richmond , David Sheffield Cast Eddie Murphy , Jada Pinkett Smith , James Coburn , Larry Miller , Dave Chapelle , john ales , Patricia Wilson , Jamal Mixon Runtime 95 minutes

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)

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Trainspotting is a darkly comedic drama based on the novel by Irvine Welsh. The film follows Mark Renton and his friends, a group of Scottish heroin addicts who journey outside of Edinburgh to find where the grass is greener. Renton attempts to clean up his act as he and his friends find themselves in increasingly absurd situations as they try to find the bright side of life.

Director Danny Boyle Release Date August 9, 1996 Cast Ewen Bremner , Ewan McGregor , Jonny Lee Miller , Kevin McKidd , Robert Carlyle , Kelly Macdonald Runtime 93 minutes Studio(s) MiraMax Writers John Hodge Expand

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)

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From the minds of Trey Parker and Matt Stone, South Park: Bigger, Longer & Uncut is an adult animated comedy film released in 1999. All hell breaks loose when Stan, Kyle, Cartman, and Kenny sneak into an R-rated film that features their favorite Canadian comedic duo, leading their parents (and the U.S. Military) to declare war against Canada to censor their naughty language.

Director Trey Parker Release Date June 30, 1999 Cast Trey Parker , Matt Stone , Mary Kay Bergman , Isaac Hayes , George Clooney , Brent Spiner , Minnie Driver , Dave Foley Runtime 81 Minutes Studio(s) Comedy Central Films , Scott Rudin Productions Distributor(s) Paramount Pictures Writers Trey Parker , Matt Stone , Pam Brady Main Genre Animation Expand

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.

1 Fatphobic Remarks

Romy And Michele’s High School Reunion (1997)

Romy and Michele’s High School Reunion 1

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Romy and Michele’s High School Reunion is a 1997 comedy film directed by David Mirkin. Starring Mira Sorvino and Lisa Kudrow, it follows two quirky best friends who reinvent their lives in a bid to impress former classmates at their high school reunion. The film explores themes of friendship and societal expectations with a humorous and light-hearted tone.

Director David Mirkin Release Date April 25, 1997 Cast Mira Sorvino , Lisa Kudrow , Janeane Garofalo , Alan Cumming , Julia Campbell , Mia Cottet , Kristin Bauer , Elaine Hendrix Runtime 92 Minutes

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.

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