This article contains mention of sexism and homophobia.
Summary
It’s expected that not every movie from decades past will age well, as the ideas surrounding what’s acceptable to say and do on film have changed a lot. There are some cult classic films from the 1990s that were hailed as great contributions to cinema at the time but should be reevaluated. More often than not,offensive depictions of people’s identities and ideologies are the red flags in these movies.As more diverse filmmakers and writers are given a voice in Hollywood, this is becoming less of an issue, but past films should still be viewed with a critical eye.
Some of the mostinfluential movie directors of the 1990sgot their start with projects that have earned cult classic status but haven’t aged the best by today’s standards. These movies and the creative teams behind them shouldn’t necessarily be forgotten or torn down, but it’s important to recognize the flaws in all pieces of media, even if they’re considered important and iconic. Art and filmmaking have evolved and become more complex with each generation becausenew artists are informed by the successes and failures of those who came before them.

10 Box Office Flops That Eventually Became Cult Classics
A movie’s financial success isn’t always an indicator of its quality, and some box office bombs have been still found passionate cult followings.
Cruel Intentions
Cast
With a screenplay and direction by Roger Kumble, Cruel Intentions is a Romance and Teen Drama film that stars Selma Blair, Sarah Michelle Gellar, Reese Witherspoon, and Ryan Phillippe. The plot revolves around a group of teens, with a man betting one of them that he can seduce a girl successfully.
What the adaptation of the classic French novelLes Liaisons Dangereuseslacks in complexity and class, it makes up for in pure, unadulterated scandal.

The explosive combination of Sarah Michelle Gellar, Ryan Phillippe, Reese Witherspoon, and Selma Blair is the highlight ofCruel Intentions. What the adaptation of the classic French novelLes Liaisons Dangereuseslacks in complexity and class, it makes up for in pure, unadulterated scandal. However,teenage sexuality and exploitation are at the forefront ofCruel Intentions,making it difficult to let loose and enjoy the horrible things the characters are doing to each other.
Additionally, the weaponization of sexuality and homophobia takes the viewer out of the experience of the movie and immediately dates the script. Gellar’s character, Kathryn, is depicted more harshly than Sebastian (Phillippe) because she’s the villain. However, this makes her character slightly one-dimensional and uplifts Sebastian. Part of this characterization is fair, as Sebastian does evolve and attempts to change, and his ending is even harsher than Kathryn’s. The original screen iteration of the book,the 1988Dangerous Liaisons, is a bit easier to watch because of its difference in place and period.

Ace Ventura: Pet Detective
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.
Jim Carrey’s talents are wasted inAce Ventura: Pet Detective.Though the character has some funny quirks, there’s too much wrong with the movie to watch it today without cringing. The movie falls victim to jokes and plot points that don’t reflect contemporary culture.Ace Venturauses Carrey’s signature facial expressions as the crux of every joke,making them grow stale within the first few minutes. Additionally, his character’s treatment of women and blatant homophobia makes it endlessly uncomfortable.

One of the worst parts ofAce Venturais how the trans character, Einhorn, is treated. Though the character is the villain, the story humiliates her by publicly outing her and making a joke about Ventura being attracted to her. This is a disrespectful and outdated portrayal of the LGBTQ+ community. The movie could have easily been just as effective without using trans identities as a plot twist. Thoughaspects ofAce Ventura: Pet Detectiveare nostalgic, the movie doesn’t have the star power of some of Carrey’s other work,making it easy to forget.
Dazed and Confused
Set during the last day of school in 1976, Dazed and Confused follows Texas teens, including student Randall Floyd, as they navigate the social dynamics of high school. Floyd, a star athlete and cannabis enthusiast, faces a dilemma when his football coach insists he sign a “no drugs” pledge.
Before Richard Linklater made history with theBefore TrilogyandBoyhood, he told a more traditional high school story throughDazed and Confused. ThoughDazed and Confusedcan be credited with launching the career of Matthew McConaughey and having some of the most iconic dialogue of the 1990s, there are still dated aspects of the film. Primarilythe hazing and violence the older high school boys use to terrorize the younger ones.While it’s clear that this is a terrible thing, it’s also played for laughs.

Overall, the successes ofDazed and Confusedoutweigh the issues, as the movie is regarded as one of the best of the 1990s and one of the more accurate portrayals of high school. Few films from this era can claim they didn’t glamorize violence and make sexism seem cool. However, it’s impossible to ignore thatthere are practically no female characters with development or substancepresent in the film, which is something no movie should get away with today.
She’s All That
When popular high school student Zack Siler breaks up with his girlfriend, he’s confident he can replace her with any girl in school. His best friend disagrees, leading to a bet in which Zack has six weeks to turn awkward and unpopular Laney into the school’s prom queen.
Today,She’s All Thatis remembered as a classic, but there areharsh realities of rewatching 1990s rom-coms. It’s also known for being one of the biggest perpetrators of sexist tropes that run rampant in the genre. There is a scene inShe’s All Thatin whichLaney (Rachael Leigh Cook) literally takes off her glasses and is then considered beautifulby the charming and handsome Zack (Freddy Prinze Jr.). This is the scene that sparked one thousand parodies, and rightly so, as Laney’s treatment throughout the movie is terrible.

She’s the butt of the joke to Zack and his friends until he finds himself attracted to her and suddenly realizes that she has value. Her interests and beliefs are played for laughs, and there’s little to no pushback on the concept that her makeover makes her a better and more fulfilled person, and Zack barely does anything to redeem himself in the eyes of the audience. Though it’s a harmless and fun movie, on the one hand,it teaches generations of youths all the wrong lessons about love and self-acceptance.
Buffalo ‘66
Billy Brown, freshly out of prison, kidnaps a tap dancer named Layla and forces her to pose as his wife to impress his estranged parents. As they navigate a series of bizarre and touching encounters, Billy’s facade begins to crumble, leading to unexpected bonds and revelations.
A young Christina Ricci stars inBuffalo ‘66alongside Vincent Gallo, who also directed the movie and contributed to the screenplay.

A young Christina Ricci stars inBuffalo ‘66alongside Vincent Gallo, who also directed the movie and contributed to the screenplay. Though technicallyBuffalo ‘66is a triumph of independent filmmaking, the story should be viewed through a critical lens, consideringit begins with Gallo’s character kidnapping Ricci’s character and ends with the pair of them falling in love.WhileBuffalo ‘66doesn’t condone this behavior and is commenting on it, there have been many instances in which the intentions of the film have been misinterpreted.
It’s not just the film itself that stirs up controversy so much as the offscreen dynamic. In the years since its release, Ricci has described the environment on set with Gallo as a difficult one, especially considering the actress was only 17 when the film was shot (viaHuff Post). To this day, Gallo is a controversial figure, and his behavior on set has been under intense scrutiny, withBuffalo ‘66being no exception. Additionally,Layla’s (Ricci) lack of agency throughout the narrative can be upsetting to viewers.

Reality Bites
Reality Bites, directed by Ben Stiller, explores the lives of four recent college graduates as they navigate the challenges of adulthood. Stars Winona Ryder, Ethan Hawke, and Janeane Garofalo portray friends struggling with employment, relationships, and personal identity in an early 1990s cultural landscape. The film captures the angst and disorientation of Generation X while providing a candid look at youth in transition.
It’s hard to imagine a more quintessential 1990s cast than that ofReality Bites. Featuring Winona Ryder, Ethan Hawke, and Ben Stiller in an ill-fated love triangle,it’s difficult to feel sympathy for the disaffected youths seen onscreen inReality Bites.The film is a precursor to the mumblecore genre and presents a slice-of-life narrative about a group of lost twenty-somethings in Texas. Stiller proved to be a solid director in his feature debut but has found greater success in his other work.

ThoughReality Bitesmight speak to young people feeling lost and uncertain, the film’s central problems aren’t as relevant because of how the world has changed. If anything, audiences might be jealous of the characters, as they don’t have the pressures of the internet or social media. Additionally,the romance between Lelaina (Ryder) and Troy (Hawke) is slightly one-dimensional,and neither character is overly likable. Though there’s nothing inherently wrong withReality Bites, its chief annoyance for audiences might be the self-indulgence of the characters and filmmaking.
Chasing Amy
Chasing Amy is a romantic comedy-drama film by writer-director Kevin Smith. Following the viewpoint of comic artist Holden McNeil (Ben Affleck), the movie focuses on his hopeless romantic attachment to a fellow comic artist who happens to be a lesbian - and his best friend’s attempts at voicing his disapproval. The film explores the complex layers of love and what forms it takes.
He plays Holden, a man who falls in love with Alyssa, played by Joey Lauren Adams, but discovers she’s a lesbian.

Ben Affleck stars inChasing Amy, which perpetuates the issues of homophobia that were common in the ’90s.He plays Holden, a man who falls in love with Alyssa, played by Joey Lauren Adams, but discovers she’s a lesbian. However,Chasing Amyhinges on the outdated idea that a straight man can win over a lesbian woman, using it as a subversion of the rom-com formula. More recently, the director, Kevin Smith, has opened up about how the movie has aged. This is a reminder that in 1997, sexuality wasn’t discussed openly, andChasing Amywas boundary-pushing (viaBuzzfeed).
Instead of taking a nuanced look at how sexuality is fluid and might change over time or that biphobia often prevents people from fully exploring their identities,Chasing Amypokes fun at the entire LGBTQ+ community.Chasing Amyis ultimately not about Alyssa but about Holden discovering that the world is bigger than he ever imagined. Being a product of its time and lacking context,Chasing Amyfails to unpack its full context. There are much better films from the New Queer Cinema moment of the time about identity, butChasing Amynever claimed to be part of that list.
Teenage Mutant Ninja Turtles (1990)
Visually,Teenage Mutant Ninja Turtlescan’t compete with any of the live-action movies of today, as the turtle suits have aged from slightly uncanny to downright unsettling. Compared to the 2014 iteration by Michael Bay, the ’90s movies are cult classics, but this is thanks to nostalgia rather than quality. Adapting an iconic comic book character is never easy, and there was enormous pressure onTeenage Mutant Ninja Turtlesto do justice to the source material. While it’s interesting to see how the studio imagines the turtles might look in the real world,the story works better in animation,
While it’s not completely fair to compare live-action to animation, the 1990 movie could have gone further in capturing the aesthetic and visual style of the comics. It’s undeniable that the film was a box office smash and that the following sequels cemented this adaptation as the definitive version for many years. However, there’s still room for a more cohesive and effective version within the canon, asthe movie lacked the stylized and campy sensibilities of other live-action comic book filmslike Tim Burton’sBatman.
Robin Hood: Men in Tights
Robin Hood: Men in Tights is a comedic reimagining of the classic Robin Hood legend, directed by Mel Brooks. Cary Elwes stars as Robin Hood, leading a group of merry men in a fight against the tyrannical Prince John and the Sheriff of Rottingham. This parody film combines humor and satire, featuring memorable performances and musical numbers that poke fun at the genre and various pop culture elements.
The best parts ofRobin Hood: Men in Tightsare the performances from the stellar cast of comedians that Brooks assembled.
Though some ofMel Brooks’ funniest movie scenestake place inRobin Hood: Men in Tights, it’s not his strongest film and hasn’t aged well in some aspects of its humor.It’s expected that comedy movies from decades past will have dated elements as expectations and standards have changed, but the depictions of female characters like Maid Marian (Amy Yasbeck) and Latrine (Tracey Ullman) center their sexuality and physical attractiveness as the most important parts of their roles. While this is played for laughs, it still fails to develop their characters.
Additionally, outside the social issues in the film, it’s just not on the same level as the classics from the director, gets off to a slow start, and relies on trope-based jokes to engage the audience. This comes through in the use of puns and sight gags like the Everlast chastity belt or whenRottingham hires a mafia boss to take out Robin during the archery competition.The best parts ofRobin Hood: Men in Tightsare the performances from the stellar cast of comedians that Brooks assembled. They makeRobin Hood: Men in Tightssharper through their work.
15 Best Cult Classics That Perfectly Capture The 1990s
These cult classic movies are the perfect visual representation of the 1990s, each one offering a unique and influential perspective of the era.
Last Action Hero
Last Action Hero follows young Danny Madigan, who magically enters the world of his favorite action film through a special ticket. Inside the movie, he teams up with action hero Jack Slater, played by Arnold Schwarzenegger, to battle cinematic villains. Directed by John McTiernan, the film blends reality and fiction, offering a whimsical take on action film tropes.
Last Action Herocame out after the action movie boom of the 1980sthat thrust Arnold Schwarzenegger to fame and created the buff and bulging action hero archetype. The movie attempted to interrogate the formula of these movies and poke fun at them through a satirical lens. However, for a variety of reasons, it bombed at the box office and only achieved cult classic status thanks to its availability on the internet many years later. It’s one of Schwarzenegger’s most poorly received movies to date.
In the years since its premiere,Last Action Herohas ebbed and flowed in popularity, as it didn’t deserve the vitriol it got in the ’90s,but still has plenty of issues. While Schwarzenegger’s career didn’t end after the movie, his reputation shifted slightly, and the film added a flop to his legacy. Certain problems have also come to light, like the lack of logic in the multiverse plotlines and the darkness of the premise, as Danny turns to movies in the wake of his father’s death. The original structural problems distracted audiences and critics from these aspects of the story, but they’ve become clearer with time.
53%
80%
47%
57%
Dazed And Confused (1993)
93%
90%
41%
55%
77%
88%
62%
74%
87%
83%
42%
81%
48%