From crop tops to Disney remakes, ’90s nostalgia is everywhere right now. Perhaps the biggest pop culture trend of this beloved decade is the teen comedy flick. These films were a departure from the bubbly, rose-colored glasses John Hughes fare that defined the 1980s. Rather, the ’90s teen film genre was brimming with self-aware snarkiness. But underneath their slick cynicism, the characters still wanted the same things as any teen, past or present: acceptance, confidence, and maybe even a date for the prom.
This genre was so popular that there are far too many movies to remember. But what cements the classics are its legendary characters. Some were cringey, some were funny, and others made us tremble in our platforms. Here are The 10 Most Memorable Characters From Your Favorite ‘90s Teen Comedies.
10 Courtney Shayne – Jawbreaker
There can’t be a more ’90s way to kill somebody than choking them to death with a jawbreaker. To Courtney Shayne (Rose McGowan), all’s fair in love and popularity. Killing her Molly Ringwald-esque frenemy may have been an accident, but remorse is, like, so over. The mean girl has always been a teen movie archetype, but few have actually taken a human life, making Courtney as noteworthy as she is deadly.
Jawbreaker is considered to be the Heathers for the flip phone generation. However, if film criticism is high school, no critic was letting Jawbreaker sit at their lunch table. The film was universally panned. But despite its negative reception, Jawbreaker would go on to become a cult classic, thanks in large part to Courtney Shayne. Deal with it.
9 Sidney Prescott – Scream Franchise
The final girl of the ’90s. What can’t Sidney Prescott (Neve Campbell) survive? She may look like a meek girl next door, but Sidney’s got some serious survival skills. One would think that after four movies, masked killers of the world would just give up and leave her in peace… or as much peace as one can achieve after all their loved ones have been butchered.
Teens have been getting sliced and diced onscreen for decades, but Scream stands a severed head above the rest. It’s a witty, meta pastiche of the slasher genre, artfully mixing satire into its blood and guts. If there’s any character that deserves to be the face of this celebrated franchise, it’s Sidney Prescott.
8 Michelle Flaherty – American Pie franchise
The female characters of this franchise are about as deep as a tin foil pie plate. Really, their only function is to serve as Barbie-shaped trophies for the drooling teenage boys who objectify them. But then there’s Michelle Flaherty (Alyson Hannigan). As quirky as she is, Michelle is the closest American Pie character to resembling a real person. She’s comfortable in her own skin and proves that teen girls can be just as horny as their male classmates.
American Pie takes gross-out humor to gutter-low levels. There’s not a dessert, beverage, or sock that Jim (Jason Biggs) and his friends don’t defile. And yet there is no line more iconic or filthy than Michelle’s, “This one time at band camp…”
7 Patrick Verona – 10 Things I Hate About You
Heath Ledger’s death remains one of Hollywood’s greatest tragedies. There’s no disputing that the Joker is the role that defines his legacy. However, those who grew up in the ’90s will always remember him as Patrick Verona, the brooding loner in 10 Things I Hate About You.
This modern retelling of The Taming of the Shrew features a smorgasbord of ’90s teen celebrities including Julia Stiles and Joseph Gordon Levitt. Everyone pulls their weight, but it’s Ledger who steals the show. There isn’t a scene in the film more memorable than Patrick singing his heart out on the bleachers. He woos Kat (Stiles) right along with the viewer.
6 Kathryn Merteuil – Cruel Intentions
Cruel Intentions may have been released as a steamy teen drama, but it’s more known as a camp comedy classic. It recently celebrated its 20-year anniversary and if there’s one character the audience remembers, it’s the wicked Kathryn Merteuil (Sarah Michelle Gellar).
An update of Dangerous Liaisons and Les Liaisons dangereuses, Cruel Intentions is a luxurious bubble bath of ’90s teen nastiness. We know we should be rooting for sweetie-pie Annette Hargrove (Reese Witherspoon), but we can’t help cheer on Kathryn. She just has so much fun at being bad. Everyone she targets becomes a pawn and eventually a casualty. Her saliva-heavy kiss with Cecile Caldwell (Selma Blair) won an MTV Movie Award, the Oscars of the teen movie world.
5 Laney Boggs – She’s All That
Like many of its contemporaries, She’s All That is based on Pygmalion and My Fair Lady. But whereas films like 10 Things I Hate About You did its best to iron out the problems of its source material, She’s All That contains all the problems of the work it’s inspired from—just with a catchy soundtrack.
Laney Boggs (Rachael Leigh Cook) is the “updated” Eliza Doolittle, a quiet art student. She wears glasses, overalls, and sometimes—gasp!—her hair tied back. According to the loudmouth popular boys at school, this makes her ugly as dirt—though today she would pass for a garden-variety hipster. Meanwhile, the ’90s version of Henry Higgins high society is, no surprise, Freddie Prinze Jr.. He plays Zack Siler who is tasked with giving Laney a makeover. The film’s most famous scene is of the hottified Laney descending the stairs in slo-mo to romantic ballad “Kiss Me”. While we may love the 1990s, Laney’s transformation from unique individual to object of the male gaze reminds us of why the 21st century couldn’t get here fast enough.
4 Stifler – American Pie franchise
Stifler (Seann William Scott) was the bro-iest bro before the term even hit the pop culture lexicon. He’s creepy, crass, and obnoxious. So…why does the mere mention of his name never fail to bring a smile to our faces?
While the dude may have more flaws than hairs on his head, he is completely, unequivocally himself. Our teen years tend to be fraught with identity crises, yet Stifler knows exactly who he is, which is a hard-partying womanizer with the emotional maturity of a toddler. His character would never be accepted today, which makes him a total staple of the ’90s.
3 David Wooderson – Dazed and Confused
Alright, alright, alright. Most of us flee high school before our graduation caps even touch the ground. Not David Wooderson (Matthew McConaughey). Even though he’s in his early twenties, Wooderson prides himself on being a fixture at end-of-year high school parties. It doesn’t get more pathetic than this, yet somehow Wooderson comes off as Dazed and Confused‘s coolest character. He’s completely at peace with himself. This may be a result of all that dope-smoking frying his neurotic brain cells, but we still admire his joie-de-vivre.
McConaughey stands out among this A-list cast that includes a young Ben Affleck, Parker Posey, and Milla Jovovich, and his performance as Wooderson helped solidify the slacker archetype of the early ’90s. He’s may not be worldly or sophisticated, but Wooderson reminds to always keep l-i-v-i-n.
2 Tracy Flick – Election
Teen movies have seen their share of villains, yet none more conniving than Tracy Flick (Reese Witherspoon). She’s a wolf in a folksy sweater vest, who will kill you with kindness and a homemade cupcake. Election turns the good clean fun of a high school presidential race into merciless blood sport and nobody’s hands are dirtier than Tracy Flick’s.
What’s truly brilliant about this character isn’t her relentless ambition; it’s the fact that she dares you to like her. Tracy commits some truly heinous acts, but that’s because she refuses to play a game that’s rigged against her. Unlike rival candidate Paul Metzler (Chris Klein), Tracy wasn’t born with a silver spoon in her mouth. Not that she wants one. Tracy prefers silver knives, thank you very much. In a genre looked down upon for its flat characters, Tracy Flick is both well-rounded and sharp.
1 Cher Horowitz – Clueless
’90s cynicism? Whatever! When you’re a teen dream living in the lap of Beverly Hills luxury, what’s there to be cynical about? Cher Horowitz (Alicia Silverstone) lives in the now, and her now is decidedly ’90s. She’s based on the titular protagonist of Jane Austen’s Emma and both characters fancy themselves benevolent benefactresses to the lonely and unfashionable.
While we could all do with a dose of Cher’s positivity, the film is called Clueless for a reason. Cher truly doesn’t understand how frivolous and small her world really is. Her path to self discovery makes for one of the most profound character arcs of the entire genre. Cher learns that a person can have depth and still love shopping. Could we really rank her any place but #1? As if!
NEXT: 16 Best ’90s Teen Movies, Ranked