Screenshot: YouTube/Touchstone

When 10 Things I Hate About You first introduces Kat Stratford, she’s in a 1964 Dodge Dart GT, blasting Joan Jett’s “Bad Reputation” and staring down a car full of pretty girls. Kat (played by Julia Stiles) is a misfit, a rebel, a black-clad Bikini Kill fan who has no time for standard high school fluff, and she lets you know it the second she hits the screen.

Misfit girls were already well-trodden territory in teen films by the time 10 Things I Hate About You premiered on March 31, 1999. Pretty in Pink had Andie Walsh. Ally Sheedy was The Breakfast Club’s resident outcast. Only two months before we met Kat Stratford, played by the inimitable Julia Stiles, She’s All That’s Laney Boggs slunk through the halls of her fictional high school in glasses and (ugh) overalls.

But 10 Things I Hate About You—Shakespeare’s Taming of the Shrew, but at a modern-day Seattle high school—made the misfit cool. Unlike the aforementioned documented oddballs, Kat didn’t actually need to be tamed. She didn’t shake a head full of dandruff on a desk like Sheedy’s so-called basket case, or come from the literal wrong side of the tracks like Andie (Pretty in Pink, for the record, has not aged well). She wasn’t graceless and sexless like Laney Boggs.

Kat didn’t have to put on makeup or a dress, or date a rich dude, or go to the popular kids’ ill-fated pool party. Kat could shit on Hemingway in class without worrying her classmates would think she was lame for being smart, since she didn’t care what they thought in the first place. She could ram her car into the one belonging to the hottest boy in school, because she already fucking owned him.

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Kat stood out because she didn’t feel the need to fit in, not because her peers were telling her she couldn’t, and that meant there was nothing about her that needed to change. When Heath Ledger’s Patrick Verona showed up and eventually fell for her, she still got to stay mean and black-clad and listen to Bikini Kill all she wanted, right up to when the credits rolled.

This was revolutionary, or at least it felt revolutionary to me. I was too young to see 10 Things I Hate About You when it first came out, but a few years later, the summer before I started 7th grade, I made my parents rent it for me from Blockbuster. I watched it three times in a row before I had to return it. I was enamored with Heath Ledger and his t-shirts, obviously, but I was also enamored with Kat.

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I was familiar with the misfit predecessors and their Cinderella stories, but they seemed so lame in comparison to Kat, who wasn’t imprisoned by her Otherness but emboldened by it. “You don’t always have to be who they want you to be, you know?” she tells her younger sister Bianca, and though my tween brain yearned to be more like Bianca, i.e., cute, popular, and adored, I liked that Kat existed as an option. She was the first teen rom-com heroine I recognized was celebrated for being herself, which meant it was fine for the rest of us to be ourselves, too.

In real life, though, being a misfit wasn’t an option so much as an assignment. I didn’t realize at the time that I was only a few years away from becoming my own brand of oddball—not a Seattle grunge rebel like Kat, but a lonely hanger-on, an invisible sidekick to the movie’s heroine instead of the star of the show. I don’t know how or why that happened, but it did. Sometimes someone else just decides you don’t fit in, and it sticks. So I went to parties to watch my sort-of friends make out with the boys I liked, when really I wanted to be home with my Sims families, who would never make fun of me for my hair.

Unlike Kat, I was too self-conscious to be an outcast by choice (not to mention I didn’t look a thing like Julia Stiles, which was not in my favor), and unlike the John Hughes misfits and even the ever-sad Laney Boggs, there was nothing specifically wrong with me that a makeover montage could fix. And, though 10 Things I Hate About You was predicated on the idea that a hot teen misfit could find another hot teen misfit whose nonconformity fit her own, Heath Ledger did not appear to be coming my way. It turns out there isn’t always a well-suited social deviant available to make out with your face while Letters to Cleo blares in the background.

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10 Things I Hate About You helped make the teen girl outcast cool (but not too cool), but it didn’t quite make her real, at least not to me. Not that it had to, since it’s a romantic comedy, but it’s noteworthy that in the 20 (!!!) years since Kat rolled up in her beat-up Dodge, misfits have seen even further progression. The fall after 10 Things premiered, we met Freaks and Geeks’ Lindsay Weir, another celebrated misfit with a strong sense of self, though in no way capable of meeting her romantic misfit match. A dozen-plus years later, The Edge of Seventeen introduced Hailey Steinfeld’s Nadine, an outcast who sought comfort in self-isolation and pulled herself out of it, instead of relying on someone else to do it.

Earlier this month, I watched the great Pen15—a show coincidentally set around the same time and age-frame in which I first saw 10 Things I Hate About You—and was struck by how familiar main characters Maya and Anna felt in their uncoolness. Like me, they were uncool because that’s how the dice rolled, and they were awkward because, as a teenager, who isn’t. But as uncomfortable as it is to watch them flail in their awkwardness, it’s fun to see how much they are themselves, unburdened by the constraints of popularity, and, in many ways, unbothered by the fact that they haven’t managed to achieved it.

Granted, Pen15's misfits are several years younger than Kat and her contemporary teen outcasts, and it’s hard to know what they’d be like come high school. But for now, they too get to be celebrated for being themselves, Sylvanian Families figurines and all, without any romantic prospects on hand to validate or change them.

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So on the one hand, like so many of the teen misfits who predated her, in the end, Kat still got to be hot and get a hot guy. But she also helped changed the rules for nonconformists, making way for future heroines—fictional and nonfictional—to be increasingly genuine, no matter how uncool or awkward or unapologetically weird. Without Kat flashing her soccer coach, or smashing up Joey Donner’s car, or maintaining Bobby Conway kicked himself in the balls, we may never have gotten Maya Ishii-Peters’s impromptu drum solo, and the world would be a little less wonderfully odd.