Tied to the 20th anniversary of Bring It On, we hereby dub the next five days Teen Movie Week. Dig up your varsity jacket, pull up to your cafeteria table, and re-live your adolescence as we celebrate the best coming-of-age movies ever made.
There’s no denying where the power lies in teen movies. It’s not with the teachers (they’re frazzled and manipulated) or with the parents (they’re clueless). And, it’s definitely not with the popular boys. (Teen movie jocks are gormless sex pests, programmed to egg nerds and play sports.) It lies with the Plastics, the Heathers, the Six Chicks, the cheerleaders: the table of white, rich, and perfectly manicured mean girls who are invited to everything and are afraid of nothing.
These girls don’t exist in real life. I’m sure your school had bullies and popular cliques, but it most likely didn’t have a glamorous queen bee who could read fellow classmates with the finesse of a Drag Race finalist and destroy her enemies with the grace of Villanelle. The “mean girl” in your high school wouldn’t have stood a chance against Regina George or Courtney Alice Shayne. For that matter, neither would many mean girls from the teen movie universe.
That’s the purpose of today’s extremely serious investigation: to pit the mean girls of teen movies against each other to find out which one is the meanest of them all. The criteria we’re taking into account? The culture of fear they create, the quality and creativity of their remarks, whether they ever attempt physical violence, and most of all: whether their behavior makes you feel a bit sick, like you’re 13 and trying to fit in at school again. Basically, we’re asking: If the whole of the teen movie universe were condensed into one super-school, who would be sitting at the top table?
Tier 1: Disney-Level Antics
17. Amber, Clueless
You like her because you like the film. She’s not as mean as you think. That “whatever” with the “W” fingers? Pretty toothless. Also, you can’t really be mean while dressed halfway between Gwen Stefani and a young Marine.
16. Chris Hargensen, Carrie
Yes, she does that thing with the pig blood that leads to Carrie burning down the prom and killing most of the people there. Pfft. Big deal. Slaughtering loads of pigs for a prank suggests she may be a future serial killer, but she’s not a true mean girl.
15. Monique, She’s the Man
No self-respecting mean girl would mistake Amanda Bynes in drag for their actual boyfriend and allow Amanda Bynes to dump them in a packed bar, even if their boyfriend was an actor who was (almost certainly) cast only for looking like Amanda Bynes in drag.
14. Sharpay Evans, High School Musical
Sharpay has all the right ingredients: She looks like Paris Hilton; she’s thirsty for fame. There’s just one catch: She’s in a soft and fluffy Disney movie and never truly allowed the sabotage she was destined for. It’s so sad to see potential unfulfilled.
Tier 2: Will Probably Make You Cry
13. Rizzo, Grease
With all the singing in Grease it’s easy to get distracted from the fact that Rizzo is actually one of the coolest characters in the movie, and on this list. She chills in all-black looks (while her minions dash about in cutesy pink bombers), she literally kicks classmates off benches she wants to sit on, and she throws milkshakes on boys who’ve pissed her off. Her meanest moment though? After goading lovestruck Sandy into piercing her ears and smoking marijuana at a sleepover, she mocks the innocent Aussie while she’s out of the room. “Look at me I’m Sandra Dee, lousy with virginity,” she sings while hamming it up in a blond wig. Rizzo walked so the ’90s mean girls could run.
12. Gen, To All the Boys I’ve Loved Before
As many of the other mean girls on this list will tell you, nothing gives you a taste for revenge quite like a dweeb stealing your man. You didn’t put all that effort into being popular just to be toppled by a former best friend with zero social clout. And so, while To All the Boys I’ve Loved Before is one of the sweetest films on this list, Gen brings proper toxic acid. Her very modern power move? Filming Lara Jean and Peter making out in a hot tub to make it look like they’re having sex and then circulating it around the school. That’s pretty high-grade, borderline-illegal stuff.
11. Big Red, Bring It On
At the start of Bring It On we learn that the former captain of posh cheerleading team the Torros has the influence to convince her entire squad to do a cheer that’s just about her personality and hair color rather than school spirit. By the end we discover she’s been stealing all her routines from a Black, much less privileged squad. The former? Impressive. The latter? A pretty grotesque act. Putting her higher on this list would give her far more respect than she deserves for doing something that’s just plain immoral and unimaginative. Good try, but you’re out, Red.
10. Lucy Wyman, 13 Going on 30
Does 13 Going on 30 count as a teen film? We’re not sure. What we are sure of is that despite being potentially the worst-dressed mean girls on this list, the side-ponytailed Six Chicks and their leader, Lucy (the most side-ponytailed of them all), pull off two moves that are punch-in-the-stomach horrible to the movie’s heroine, Jenna Rink. First, Lucy is mean to Jenna’s lovely best mate Beaver—“I don’t need a play-by-play”—a move that is later copied by Jenna in an attempt to become the Seventh Chick. (He grows up to be Mark Ruffalo, you idiots!) But more than that: Lucy gets Jenna to do her homework in return for (1) the Six Chicks coming to Jenna’s birthday party and (2) bringing her crush with them. Then, at the party, she tricks Jenna (who is a little desperate, to be honest) into thinking they’re playing Seven Minutes in Heaven and runs off while she’s stuck in the cupboard. It cuts deep to watch.
Tier 3: High-Functioning Demons
9. Lana Thomas, Princess Diaries
This preppy snitch of a mean girl definitely doesn’t have the best chat in the game. “Mia, you are such a freak!” “What a frizz ball, look at her.” It’s hardly prickly stuff. In fact, compared to quite a number of the meanies on our list, Lana (Mandy Moore but blond) is actually a loser. She wears school uniforms, tattles on Mia for wearing a hat in class, and has friends with rhyming names (Anna and Fontana). In one scene we even see the three of them attend a beach party and, rather than getting wasted or hooking up with boys, they perform a wedding band cover of “Stupid Cupid” in midi skirts and cardies. (Regina George would never.) But Lana makes up for all of that with one simple, extremely mean act. After Mia’s been caught by paparazzi making out with a horrible, horrible popular boy in a shed at the beach party and is nervously getting changed out of her swimsuit in a tent, Lana knocks the shelter over so that the photographers can get their smutty “princess gone wild” photos for the local paper. It’s the teen movie equivalent of the queen forcing Princess Di out of the family and it almost means Mia has to denounce her right to the Genovian throne. And nobody wants to disappoint Julie Andrews.
8. Cady Heron, Mean Girls
You might think that Cady Heron (Lindsay Lohan) should rank higher on this list. Perhaps you’d argue that in many ways her journey from home-schooled new kid to high school queen bee is the canonical mean girl origin story: the true meaning of “living the American dream” for popularity-hungry high-schoolers. And it’s true that her descent into self-obsession and evil manipulation comes hard and fast. Within months she’s gone from a young person with healthy family relationships and earnest hobbies to a sabotage-happy, two-faced Plastic, lips constantly gloopy with gloss and mouth regularly spewing word vomit (and real vomit). But while Cady does make it to top-rank meanie, she doesn’t stay there long. Her reign comes crumbling down in just weeks thanks to her moral compass kicking in (and a pesky rumor that she pushed Regina George in front of a bus).
7. Darla Marks, Dazed and Confused
“AIR RAID!” While all the mean girls on this list have a gift for emotional torture, Darla Marks takes things to the next level. Played by Parker Posey, she’s a snarling, hair-flicking, flouncy cheerleader with a real talent for hazing juniors. “All right you little freshman bitches, all right. That was horrible, you little freshman sluts, get up …” is how she talks to the class of shivering kids she’s about to cover in ketchup and mustard. And as the film—which follows the last day of school in 1976—goes on, she gets drunker and more power-mad. In fact, while other mean girls are cruel for power’s sake, you get the sense that Darla couldn’t care less about popularity; she’s in the game for blood. But, hey, the ’70s were a different time, a lawless decade when mean girls could truly thrive.
6. Kathryn Merteuil, Cruel Intentions
While other mean girls rush about—land-grabbing popularity and attention in a frenzy—everything Kathryn Merteuil (Sarah Michelle Gellar) does is slow and considered. She’s rich: the richest at a private school of rich kids. She’s respected: a model student even though she’s constantly dabbing coke from a necklace with a hidden compartment. And she knows that real power doesn’t come from terrorizing juniors, it comes from sex, money, and revenge. Cruel Intentions follows this predator in brown lip liner as she uses the people around her like chess pieces in order to punish an ex. She takes his foolish new girlfriend Cecile under her wing with a sinister parental energy, guiding her to a humiliating demise. Meanwhile, she lures her sleazy stepbrother into doing her bidding with a bet that she promises—if she loses—will end with her having sex with him. (This makes her the only mean girl on the list who’s down with incest.) And yet, despite how smartly she thinks she’s played the system, her plan ends in painful disaster. Namely: her stepbrother’s death and her own subsequent exposure. We hate to say it, but if you’re looking for a rich, manipulative mean girl who’ll actually get the job done, call Gossip Girl’s Georgina Sparks instead.
Tier 4: Murder Isn’t Out of the Question
5. Courtney Alice Shayne, Jawbreaker
“The one in green, that’s Courtney. She was the leader. She was like Satan in heels.” That’s how the narrator introduces the most terrifying teen to walk Reagan High’s corridors. With eyebrows thinner than her patience, more pastel cardigans than your grandmother, and an unsettling lack of moral compass, the leader of clique the Flawless Four (Rose McGowan) has the charisma to not just rule the school but carry what’s actually quite a bad movie. She’s so evil that this Heathers rip-off opens with her not just killing her best friend by choking her with a jawbreaker candy, but then covering it up with How to Get Away With Murder–level strategy. She sets up a crime scene to make the death look like a rape. She trades nerdy witness Fern Mayo (Judy Greer) the gift of popularity for her silence. And she does it all while lashing her minions with Grade A sass: stuff like, “I killed the teen dream. Deal with it,” and, “Life’s a bitch, and then you die.” She’d make top three if the movie were better.
4. Jennifer, Jennifer’s Body
There’s some contention about whether Megan Fox’s character from this comedy-horror should rank so high on this list. That largely comes down to what you think makes a person a person: If a body is possessed by another thing’s spirit, do its crimes belong to the body or the spirit squatting in it?
Since we’re not here to debate the meaning of life, what I can say is that Jennifer has pretty stellar mean girl cred before she gets a demon soul; not top-ranking but middle-of-the-board. She’s a hyper-hot cheerleader who’s constantly shitting all over her dowdy friend Needy (Amanda Seyfried), getting her to ditch her boyfriend and head out with her to dive bars. And thanks to Diablo Cody (Juno) writing the film, she’s also got one of the sharpest tongues on the list. See: “My skin is breaking out and my hair is dull and lifeless. I feel like one of the normal girls.”
That said, she’d be nowhere near the top of the leaderboard if it weren’t for her being mistaken for a virgin by a local indie band, sacrificed to the devil in exchange for fame, and turned into a demon with an unquenchable hunger for blood. It’s at this point she starts killing and eating boys around town. And, you know, cannibalism does rank quite highly in terms of meanness. Especially when you combine it with disses like, “I’m going to rip out your heart, eat it … and shit it out!” Jennifer places fourth, but only so we don’t have to talk about philosophy for hours.
3. Regina George, Mean Girls
“Shut up. Shut up.” There is no denying that out of all the horrible teenagers on this list, Regina George (Rachel McAdams) is the only one with a CV strong enough to get her an interview for leader of a dictatorship. While some mean girls rule teen movie schools with violence and others rule with sassy put-downs, George leads with fear. This is a queen who will prank-call an enemy’s mom pretending to be Planned Parenthood, who’ll make it look like a book of bitchy comments she made about every girl at school was actually a targeted attack on her by someone else.
And the mind games don’t stop once you’re in her clique. She sets the rules (no hoop earrings, on Wednesdays we wear pink), tells your crush his hair looks sexy pushed back right in front of you, tries to catch you out with a three-way call. (The real phone-hacking scandal of the ’00s.) And let’s not forget the performative whispers, gaslighting, backstabbing, and “Oh my god I love your bracelet.”
Regina is a monster in a pink slogan tee and pastel eye shadow. It’s no wonder that half the school feels personally victimized by her. And yet, she’s not Number One Mean Girl material. Because, like many egomaniacs, she falls for her own spin. She’s tricked into bulking up on Kalteen bars. She lets Cady Heron steal her man. She doesn’t even look both ways before crossing the road. A true force of mean girl nature would have crushed Janis Ian and Damian’s plan quicker than you can say “fetch.”
2. Heather Chandler, Heathers
Whether you think the leader of the shoulder-padded clique the Heathers should rank higher on this list largely depends on how you interpret the croquet scene right at the beginning of the movie. That’s the one where we see Heather (Kim Walker) hit a ball at Veronica (Winona Ryder)’s head while she’s buried up to her chin. Dream sequence or some kind of twisted punishment? The fact we even have to question that must mean she’s an awful, awful girl.
This ’80s queen bee was an early adopter of the teen movie mean girl trope, a groundbreaker in spiky put-downs and canteen power play. She might have had to settle with a distinctly unsassy wardrobe of primary-colored twin sets and scrunchies, but no one on the planet can wield a put-down like her: “No one at Westerberg is going to let you play their reindeer games”; “Grow up, Heather, bulimia’s so ’87”; “Veronica needs something to write on, Heather, bend over.”
Heather’s so mean, in fact, that the film follows Veronica as she gangs up with hot sociopath Jason Dean (Christian Slater) to murder both her and her gang of cronies (which conveniently includes two other girls called Heather). That’s what gains Chandler her ranking (with or without the croquet violence). While other meanies on this list were stopped by pranks or humiliation, death can’t even finish this monster. She gets the last word from the grave: “God, Veronica. My afterlife is so boring. If I have to sing Kumbaya one more time …”
1. Taylor Vaughan, She’s All That
And here we have it: the perfect mean girl. I’m sure you were expecting Regina or Heather. Maybe you think I’m just being contrary. But while others on this list might be manipulative or power hungry, none has the chaotic dominance of Taylor Vaughan (Jodi Lyn O’Keefe). She is mean to everyone: her jock ex-boyfriend, her reality star current boyfriend, the popular kids, the nerds, the teachers. … She’s the meanest person in a movie with an extremely mean plot. And unlike a lot of the other girls on this list, she still wins prom queen.
She’s All That opens with her dumping football captain Zack Siler (Freddie Prinze Jr.) after falling for a Real World reality star on spring break. “Don’t worry, Zack, I’ll still go to the prom with you,” she says, checking her nails, speaking loudly enough for the whole school to hear. “Did you honestly think I was going to leave for college still dating you? Oh, you did? That’s so sweet.” And that’s just the start of Taylor’s narcissistic storm through the movie. As Zack takes up a friend’s bet and tries to turn awkward art geek Laney Boggs into prom queen material, Taylor consistently delivers burns as hot as the sunbed she gets her deep ’90s tan on. And she serves them up masterfully with the cutesie intonation of a suburban mom commenting on a Facebook photo (“honey,” “sweetie,” “oopsie”).
But there’s one particular moment when Taylor proves that she is the meanest girl to rule them all: About halfway through the film, Zack convinces Laney to get a makeover (shorter hair, red mini dress, no glasses) and go to a popular-kid party. She’s actually kind of having a nice time: falling in love, making friends, looking cute. Then Taylor walks up to her, pours a whole glass of red wine down her dress, and delivers a one-two punch of pure bile. First, the sassy one-liner: “Oopsie—you really should be more careful with silk.” Second, a monologue that hits you with the force of every humiliating moment from your teenage life at once: “Honey, look around you. To everyone here you’re vapor, you’re spam, a waste of perfectly good yearbook space. Nothing’s going to change that.” That speech makes me want to hide in a toilet cubicle for the rest of the year. All hail our queen and her iconic collection of pink boob tubes.
Kate Lloyd is an award-winning journalist from London who writes about both pop culture and real life—often at the same time.
