10 Things I Hate About You takes The Taming of the Shrew, drops it into a Seattle high school, and trusts a teenager to carry Shakespeare's meanest jokes. Kat Stratford (Julia Stiles) is smart, furious, and done with everyone, and the plot only works because a boy gets paid to win her over. Heath Ledger's grin and a stadium serenade did the rest. It's a rom-com that lets its heroine be genuinely difficult, and it likes her more for it.
The films below run on the same recipe: a sharp young woman and dialogue that actually earns its laughs, with real feeling under the wit. There is a rebellious, music-loving streak in the mix too, the side of Kat that reads Sylvia Plath and refuses the school's script. The list runs from the 80s films that wrote the template through the heirs still sharpening it today, and ends after graduation, once the hallways are gone.

The Breakfast Club

John Hughes locks five students in Saturday detention (a jock, a princess, a brain, a criminal, a basket case) and lets them talk until the labels stop fitting. It's the film that taught teen movies to take a teenager's inner life seriously.
This is where Kat's whole stance comes from: a refusal to be flattened into a high-school category. 10 Things inherits the belief that the smart, angry kid on the outside is usually the one seeing clearly, and that a hallway's opinion of you is not the same thing as the truth.
Say Anything...

Cameron Crowe's debut sends an unguarded, decent kid named Lloyd Dobler (John Cusack) after the class valedictorian, armed with nothing but complete sincerity and a trench coat. It gave the world one of cinema's great romantic images: a boy holding a boombox over his head outside her window.
That gesture is the direct ancestor of Patrick's stadium serenade in 10 Things. Both films are built around a boy willing to make a fool of himself in public for a girl who is smarter than he is, and both believe that kind of open-hearted grand gesture is the most romantic thing a teen movie can offer.
Pretty in Pink

John Hughes writes another outsider heroine: Andie (Molly Ringwald) is a working-class girl who builds her whole identity out of thrift-store clothes she remakes herself and the records she loves, and who falls for a rich kid whose friends will never accept her. The class line runs right through the middle of it.
It bridges the 80s rebellion and the rom-com formula 10 Things would later perfect: a girl who refuses to change herself for a boy or a clique. Both films hand their heroine real taste and a real spine, and both know that what you wear and what you listen to can be a way of saying who you are.
Clueless

Amy Heckerling did to Jane Austen's Emma what 10 Things did to Shakespeare: dropped the plot into a rich American high school and let it fizz. Cher Horowitz (Alicia Silverstone) is a matchmaker who is sure she has everyone figured out, right up until she doesn't.
Like Kat, Cher is smarter than the film ever lets her feel superior about, and the writing keeps pace with her. Both movies take a classic text, trust their teenage heroine completely, and turn a book you were assigned into two hours you actually want.
Empire Records

A day in the life of an independent record store fighting to stay independent, with a scruffy staff of misfits who treat their taste in music as the most important thing about them. It flopped and then became a VHS-era cult exactly because it belonged to the kids who felt like outsiders.
This is Kat Stratford's natural habitat: a place where knowing the right bands and reading the right books works like armor. 10 Things and Empire Records both understand a certain kind of teenager, the one who builds an identity out of what they love and isn't afraid of anyone calling it uncool.
She's All That

The most popular boy in school bets he can turn the art-freak nobody (Rachael Leigh Cook) into prom queen, and of course the bet turns into something real. It's 1999 teen-movie formula executed with total sincerity.
The plot is 10 Things looked at in a mirror: a wager over a girl who was never going to play along quietly, and a boy who has to actually see her before anything works. Both films come from the exact same year and the same instinct, that the setup only matters because of who the girl turns out to be.
Easy A

One invented rumor turns Olive (Emma Stone) into her high school's most talked-about girl, and she decides to run the story herself instead of drowning in it. The film hangs a whole comedy on The Scarlet Letter and a webcam confession.
Emma Stone narrates with the same dry, quick wit that made Kat such good company, and the movie is just as fond of a heroine who's three steps ahead of everyone gossiping about her. Both take a literary assignment and make it the most quotable thing in your week.
The Edge of Seventeen

Nadine (Hailee Steinfeld) is a sharp, miserable seventeen-year-old whose best friend starts dating her older brother, sending her into a spiral of brilliant, self-sabotaging sarcasm. Kelly Fremon Craig writes her as funny and genuinely hard to be around, and loves her anyway.
This is the closest modern heir to Kat Stratford: a teenage girl who wields wit as armor over a lot of real confusion and fear. Both films let their heroine be prickly and wrong and still completely worth rooting for, and both understand that the meanest kid in the room is often the one hurting most.
Whip It

Drew Barrymore's directing debut follows a small-town teenager (Elliot Page) who ditches her mother's beauty-pageant dreams for a roller derby league in Austin, finding a loud, bruised, all-female world where she finally fits. It runs on great music and even better misfits.
Like 10 Things, it is about a girl carving out an identity against the version everyone expects of her, trading the beauty-queen script for something she chooses herself. Both films find their heroine through rebellion and a subculture, and both are on her side the whole way.
Ghost World

Terry Zwigoff's adaptation of Daniel Clowes follows two sardonic best friends the summer after high school, drifting apart as one of them latches onto a lonely older record collector out of boredom and something like tenderness. It is deadpan and quietly sad.
This is the epilogue to the whole list: the sharp, ironic teenage girl a few years later, when the armor that got her through school starts to isolate her instead. Kat Stratford could grow up into Enid, and Ghost World asks the honest question the teen comedies leave out, which is what happens to that wit once the hallways are gone.
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