25 Offensive Things You Forgot From Your Favorite '90s Teen Movies

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As Seen In: Empire Records (1995)
Director: Allan Moyle

The female characters in Empire Records are familiar Western character types. Just replace the token Native American woman with a token crazy chick on a Sinéad O'Connor kick, and you've jumped through fifty years of cinema history. We have the whore with the heart of gold (Renée Zellweger) and the chaste schoolmarm (Liv Tyler) that your grandfather knew on old West serials, just dressed in combat boots and mini-skirts.

While there are over half a dozen major male characters drawn with distinct characteristics, the women of Empire Records conform to stereotypes completely, down to the "surprise" skeletons hiding in their closets.

As Seen In: Singles (1992)
Director: Cameron Crowe

Singles is more of a twenty-something comedy than a teen comedy, and as such, rather than relying on broad stereotypes for laughs, the script digs deeper into the dating scene, deriving humor from its frank look at single life.

When Janet's (Bridget Fonda) boyfriend remarks that her breasts aren't big enough, she heads directly to the plastic surgeon for implants. Though we're sure she'll soon realize that beauty is more than skin-deep, the scene where her and the plastic surgeon debate the proper size for her new breasts begs the audience to take offense.

As Seen In: American Pie (1999)
Director: Paul Weitz

Stifler's mom (Jennifer Coolidge) has been the most enduring aspect of American Pie, well, just behind the pie-fucking. Coolidge brings humanity and hilarity to the role, and as such it's easy to forget just how problematic the portrayal of single mothers is in films like this.

Single dads are beleaguered career men, doing their best to raise their kids while fulfilling both sets of traditional gender roles. Cue the obligatory gag where dad burns something in the oven and the family has to have take-out for dinner again.

Single mothers, on the other hand, exist only as objects of lust for male characters. Why would widows and divorceés want anything more from life beyond a fully-stocked bar and a nerdy teen? Thank God for Match.com.

As Seen In: Jawbreaker (1999)
Director: Darren Stein

Heroines of '90s teen comedies are quick to remind you that despite their beautiful physically-trained Hollywood physiques, they aren't the ones with the eating disorder. When Courtney Shayne (Rose McGowan) insists that she doesn't suffer from anorexia nervosa, she points to a group of girls sharing a pack of raisins and refers to them as the "Karen Carpenter Table."

Karen Carpenter was a musician who died of complications relating to her eating disorder. Tasteful bit.

As Seen In: Dazed and Confused (1993)
Director: Richard Linklater

We're just as guilty as anyone else of quoting the line at parties. You know the one: "That's what I love about these high school girls, man. I get older, they stay the same age."

McConaughey's slacker drawl gave birth to the most quoted movie line in a pre-Austin Powers world. But let's take a second to break it down. The thing about high school girls is that as I grow older and progress further into adulthood, they are still nubile, naive, and very much underage.

That's what I love about statutory rape?

As Seen In: Jawbreaker (1999)
Director: Darren Stein

"They'll believe it because it's their worst nightmare: Elizabeth Purr, the very picture of teenage perfection, obliterated by perversion."

Oh, Courtney Shayne (Rose McGowan), how right you are. Just like in real life, the adults in Jawbreaker are ready to close the book on Liz's murder the moment they find out that she might have—GASP!—been having pre-marital sex. This is more a keen piece of social satire than a sexist toss-off on the part of the filmmakers, as Jawbreaker is dedicated to shredding the superficial veneer of high school sweetness.

The work that Jawbreaker tried to do obviously didn't help, as the "she acted like she wanted it" defense is still employed in the moral backwaters of America to this day.

As Seen In: Never Been Kissed (1999)
Director: Raja Gosnell

It's refreshing to see a powerful career woman depicted onscreen. Unfortunately, this isn't what happens in Never Been Kissed. Josie (Drew Barrymore) is the weakest person to enter a workplace since the dude with the stapler in Office Space. So, the first time that many young women were exposed to a woman with a male secretary, they got to watch a macho personal assistant walk all over his boss.

When was the last time you saw a secretary put finger quotes around the word "boss" in the presence of a superior? Have you ever seen a boss allow his underlings to talk loudly about their sexual exploits in their presence without reprimand? We much prefer the Peggy Olson school of dealing with your subordinates.

As Seen In: 10 Things I Hate About You (1999)
Director: Gil Junger

To be fair to 10 Things I Hate About You, the Bard made the sexist moves first. Thankfully, in adapting Shakespeare's play, the filmmakers took out the references to physical abuse, but the film is still about a strong, opinionated woman who needs to be "fixed."

The major examples of Kat's shrewish behavior are a) disagreeing with a teacher regarding literary analysis and b) identifying the high school social landscape as shrewish and vapid. These are bad things? There's enough charm in the film to make you forget that at the root, the premise is that women wouldn't buck the status quo so much if they had men to distract them.

As Seen In: Varsity Blues (1999)
Director: Brian Robbins

"It was never about love. It was about getting a better life. Lance and I were going to leave. Now I know's he's going to stay in West Canaan, be the manager of Wal-Mart and coach JV football."

There are only two options for you, as a young woman in a '90s teen comedy. Either you've secretly been studying hard despite your popularity and have been accepted into [insert Ivy League School the screenwriter went to here] or you've pinned all of your hopes for the future on your boyfriend.

We only chose Varsity Blues because we wanted to watch the infamous whipped cream bikini scene again, but this is a pervasive '90s movie trope. In these movies there is no such thing as trade school, community college, or even public universities. It's either Harvard or wifedom for you, ladies.

As Seen In: She's All That (1999)
Director: Robert Iscove

"Gay best friend" is an annoying and out-dated trope that needs to go away. Clueless, Drive Me Crazy, and several other films of the period offer numerous examples of this character, and all are carbon copies. Aren't we at a point where we can see more to straight female/gay male friendships onscreen than shopping and sassy quips?

In the very worst examples of this relationship, they don't even allow the character to be gay. Jesse (Elden Henson) fulfills every cliché responsibility of the gay best friend in She's All That, but at the eleventh hour they shoehorn in a relationship with Zack's sister (Anna Paquin). At least let your stereotype be a stereotype, damn.

As Seen In: Empire Records (1995)
Director: Allan Moyle

When Lucas (Rory Cochrane) busts Warren (Brendan Sexton III) for shoplifting, they take a minute to have a heart to heart in the manager's office before the fuzz arrives to take Warren downtown. Lucas rifles through the CDs (remember those?) that Warren stole and chastises him for stealing only rap and metal albums.

He's particularly miffed about the rap CDs because they feed the "criminal impulse." All right, entitled upper-class suburban pill-popping wrist-slitters, please tell us how more post-grunge is just what we need to put us back on the straight and narrow.

As Seen In: Cruel Intentions (1999)
Director: Roger Kumble

Drawing on the tone of its source material, Les Liaisons Dangereuses, Cruel Intentions set out to shock its way through the sex'n'power driven plot.

Often enough, these offensive moves are in service of the plot, but sometimes, they're just there to upset your mother. When Kathryn (Sarah Michelle Gellar) takes a bump of cocaine stored in her cross necklace, we got visions of our collective fundamentalist aunts shuffling out of the theatre in protest. You aren't offended though, right?

As Seen In: Clueless (1995)
Director: Amy Heckerling

We're just as much in love with Cher Horowitz's valley girl patois as the next person, but it surprising how much she uses the word "retarded." Clueless could be played in middle-school classes as a sensitivity PSA, as the beautiful, rich, vapid characters toss the word around like dresses in their walk-in closets.

So far as we can tell, the school lacks a special ed. department.

As Seen In: She's All That (1999)
Director: Robert Iscove

She's All That ins't exactly a victory for feminism. "This woman had no value until we realized that her glasses and ponytail were preventing her from being hot," isn't exactly a lesson anyone should have to stomach in 2013.

One of the most sexist moments in a film that has its fair share comes early on. Zack (Freddie Prinze Jr.) and Dean (Paul Walker) agree on their bet, but what girl are they going to bet on? To figure this out, they pick out over a half-dozen women, and discuss their flaws in-depth before siding on the bespectacled klutz, Laney Boggs (Rachel Leigh Cook). This scene is appropriately punctuated with the line, "Given the right look, the right boyfriend, in six months she could be prom queen."

Thanks, bros!

As Seen In: Cruel Intentions (1999)
Director: Roger Kumble

There are more homophobic slurs in the first ten minutes of Cruel Intentions than there are hurled at the visiting stands of an NFL game. There's one openly gay character (you can tell because he has bleached blonde hair, duh), but any credit this builds with GLAAD is quickly dispelled when, as usual, we see two women kissing. No, they're not gay, they just have sooo much sexual energy, they kiss other chicks for fun. (Spend time looking for the film that does this with two male characters and then you'll understand what the male gaze means.)

Then it's right back to the middle-school bus with anti-gay epithets tossed around as casually as sexual partners.

As Seen In: She's All That (1999)
Director: Robert Iscove

As New Yorkers, we see a lot of theater, much of it the kind that doesn't happen anywhere near Broadway. And if there's one thing Hollywood can't get right, it's any sort of visual or performance art. Demonstrating no knowledge, Hollywood suits see experimental art as an excuse to parade dwarfs alongside hot babes in black leotards. We aren't sure when experimental art scenes became an excuse to degrade the dwarf community, but rarely is such a scene so needlessly shoehorned into a film as it is here.

We'll take the landlord performance art scene from The Big Lebowski over this one any day.

As Seen In: Can't Hardly Wait (1998)
Director: Deborah Kaplan

There are no gay characters in Can't Hardly Wait. As a result, there is no one to react to the rampant homophobia, because, you know, calling other guys "f**" is just what sweet dudes in '90s movies do to let other dudes know they aren't very sweet.

The word is peppered throughout the film, but here is the most egregious instance. The end of the movie is the icing on the homophobic cake, as it's revealed that the nerds' big plan for getting back at uber-jock Mike Dexter (Peter Facinelli) is to make it look like he's gay, because, apparently, there's nothing worse than that.

As Seen In: Varsity Blues (1999)
Director: Brian Robbins

It's nice that Varsity Blues eventually gets around to paying lip service to Billy Bob's (Ron Lester) struggles with his body image. You'd better believe that, first things first, the filmmakers are going to get some serious comedic mileage out of his weight before they allow you to feel anything for the poor guy.

Despite the fact that a combination of football and a poor diet are literally killing Billy Bob from the beginning of the film, he is the film's clown. Nintey percent of the film's comedy is derived from Billy Bob making moves on women who would never date him and Billy Bob falling down. Oh, and there's also a joke about how he sweats a lot. The film really is a milestone in American comedy.

As Seen In: 10 Things I Hate About You (1999)
Director: Gil Junger

Sometimes a film will offend our music sensibilities, and that's bad enough. The teen movies of the Clinton years are full of terrible ska and pop punk covers of great songs. This cover of "Shout" isn't markedly better or worse than the other trombone-laden drivel that bounces viewers from prom to the after-party in these films, but to choose a song that's already so iconic in comedy is a serious misstep.

Madame, we have seen Otis Day and the Knights and you are no Otis Day and the Knights.

As Seen In: She's All That (1999)
Director: Robert Iscove

"I heard about this riot in Mogadishu, this represents the pain of that night."

Here's a tip for screenwriters of the future. If you want viewers to feel how deep and aware your upper-class suburban white character is, name-checking a brutal civil war is not the best route. We're sure that the people of Somalia were grateful that you dedicated some artwork to them, Laney Boggs. As they starved due to the complete destruction of their agricultural infrastructure, at least one of the citizens likely thought, "Damn, thanks for that abstract painting."

As Seen In: Varsity Blues (1999)
Director: Brian Robbins

Near the beginning of Varsity Blues there is a completely unnecessary scene where a hot teacher conducts a sex-ed class. In a '90s teen movie, an attractive, mature woman talking frankly about sex can only mean one thing—she's a stripper! And of course, her routine is set to "Hot for Teacher" and indulges every pleated-skirt and chalkboard fetish engendered by Britney Spears' debut single.

Rather than being appalled that her students have snuck into the strip club and seen her working her other job, she joins the under-aged football players for a drink. In fact, she is flattered that 17-year-olds find her attractive. And, wait for it—later on in the film, she makes a pass at one of them.

Well played, Varsity Blues, you squeezed every ounce of sexism you could out of this subplot.

Film: Never Been Kissed (1999)
Director: Raja Gosnell

The love story of Never Been Kissed involves a burgeoning romance between a high school teacher and his student. That student might secretly be 25, but Mr. Sam Coulson (Michael Vartan) doesn't know that when he puts the moves on her while riding the Ferris wheel at the town carnival.

If you can somehow forgive that, then don't forget Josie's (Drew Barrymore) brother Rob's (David Arquette) dalliance with an underage gymnast. Rob poses as a high school student to help out his sister who is also posing as a high school student. When a young woman approaches him and says, "I'm 16. I'm a gymnast. I don't have a boyfriend." we tread dangerously close to "movie of the week" territory.

As Seen In: Jawbreaker (1999)
Director: Darren Stein

How are the girls of Jawbreaker going to disguise the accidental murder of their friend? Stage a rape. The scene where the girls pull on rubber gloves and attempt to make their deceased friend look "raped" sets the stage for the darkly satirical tone of the film, and then goes a bit too far.

When the girls gleefully rip their dead friend's panties and shred her sheets, the film enters "tough to watch" territory. In 2013, this shit wouldn't fly.

As Seen In: American Pie (1999)
Director: Paul Weitz

Let's take a minute to revisit a scene than many of you rewound the hell out of back in the day. To break it down: A teenage boy has a crush on an exchange student. They set up a study date. Now, of course, because she's attractive, she doesn't want to actually study, she just wants to get naked.

While naked, she finds some porno mags. Of course, because she is an object of lust, she's going to pleasure herself for the boy's enjoyment. How do we know all of this? Well, the protagonists have set up a webcam to record her.

Nowadays, this plot would be more at home in a Lifetime Movie or a PSA about protecting your privacy, but 15 years ago, this was a humorous mishap. Because, hey, boys will be boys.

As Seen In: SMDH.
Director: Sigh.

You likely haven't forgotten the tokenism that ran rampant in '90s teen movies. Not Another Teen Movie called it out hard. Revisiting these films reminds you just how ridiculously similar the "token black guy" characters really were. They're always—and we mean always—either musicians or are in some way linked to hip-hop culture. The teacher in 10 Things I Hate About You raps Shakespeare; the only black guy in Cruel Intentions is a cello teacher; and the precious few black characters in Never Been Kissed are all present for the weird reggae bar scene.

Also, these characters are, as a rule played by either Donald Faison (of Scrubs fame) or Dulé Hill (from The West Wing and Psyche). If they weren't, this is because Faison and Hill were working other movies, in which case the producers hired poor-man's versions of these actors. The quota seems to have been one cool friend and/or one hip teacher per film, with a minimum of one rap verse or head-shake at the lameness of white people during their paltry screen time. If producers were feeling adventurous, there would also be one black female, whose defining characteristic is that she is dating the "token black guy."