Your favorite classic teen movie says a lot about you. It’s a statement about your preferred aesthetics and your taste level. One single reference tells new friends and first dates everything they need to know, from how popular you were in high school to how likely you are to currently own a Cher Horowitz-style cropped plaid skirt suit. Clueless fans have a CliffsNotes understanding of the classics and a deep-seated belief in the transformative powers of a makeover (they love Queer Eye). Superbad aficionados think they’re a lot funnier than they are, and secretly wonder if #MeToo has gone too far. John Hughes diehards have unhealthy romantic relationships, The Craft enthusiasts live in Bushwick, and Cruel Intentions stans have FetLife accounts and ship Cersei and Jaime Lannister.
And then there’s 10 Things I Hate About You. Twenty years later, this movie is still by far the best classic teen flick to associate yourself with. It’s less basic than Mean Girls, more highbrow than Fast Times at Ridgemont High, and isn’t totally cringeworthy by 2019 standards (see: Grease, Sixteen Candles). Identifying with 10 Things I Hate About You tells the world that you also know who The Raincoats are, and that you can appreciate the rarified delights of a high school rom-com that culminates in a Shakespearean sonnet. Just don’t be that guy who feels the need to point out that Kat’s final homework assignment isn’t in iambic pentameter.
The iconic 1999 adaptation takes Shakespeare’s The Taming of the Shrew and gives it a riot grrrl twist. The clunky plot finds two Seattle sisters, Bianca Stratford (Larisa Oleynik) and Katarina Stratford (Julia Stiles), being wooed, respectively, by a very fresh-faced Joseph Gordon-Levitt and breakout star Heath Ledger. Kat is an outspoken feminist and literal ball-buster, which apparently makes her the most undateable senior at Padua High, despite the fact that she is literally Julia Stiles and a thousand times cooler than the “unwashed miscreants” she goes to school with. The Stratford sisters’ comically-overprotective dad (Larry Miller) decrees that the boy-crazy Bianca can only date when Kat does. Gordon-Levitt’s Cameron convinces the most popular and odious boy in school (Andrew Keegan) to pay Ledger’s Patrick Verona to take Kat out, at which point Cameron plans to swoop in and romance Bianca himself.
In his original review, Roger Ebert praised the film, “despite its exhausted wheeze of an ancient recycled plot idea (boy takes bribe to ask girl to prom, then discovers that he really likes her—but then she finds out about the bribe and hates him). I haven’t seen that idea in almost two months, since She’s All That.” As Ebert pointed out, 10 Things I Hate About You was released during a high school romance glut, making its longevity all the more impressive.
The film is far from perfect, with some jokes that refuse to stick, slang that was outdated even at the time, and a secondary romance that’s hard to get invested in (it’s impossible to understand why Gordon-Levitt is so obsessed with the casually cruel popular girl, let alone why we’re supposed to root for them). Also, sneaking in Shakespeare quotes isn’t as clever or as seamless as the screenwriter seems to think it is. But script-level issues cease to matter the second Ledger and Stiles team-up on screen.
In a new New York Times oral history celebrating 10 Things I Hate About You’s 20th anniversary, casting director Marcia Ross reveals that they looked at stars like Katie Holmes and Kate Hudson for the starring role, “But Julia and Heath just had the best chemistry together.” Director Gil Hunger recalls, “Heath walked in, and I thought to myself, if this guy can read, I’m going to cast him. There was an energy to him, a sexuality that was palpable…The instant the door closed, I turned to the women in the room and said, ‘Ladies, I have never wanted to sleep with a man, but if I had to sleep with a man, that would be the man. Please cast him immediately.’”
As Patrick Verona, Heath embodies a character who’s initially repugnant to Kat—not a “pretty guy” like Jared Leto, and a smoker to boot. But Patrick quickly goes about proving that he’s not like the other boys. He’s friends with the bartender at Club Skunk, a Pacific Northwest fever dream of a massive smoky club filled with girlfriends in crop tops writhing around to Letters to Cleo, where he impresses Kat by referencing The Raincoats and Bikini Kill. He doesn’t take advantage of Kat when she’s drunk at a party—granted, a low bar, but one that many teenage boys still trip over. He’s also willing to embarrass himself in front of the entire school for Kat, and uses his unnecessarily-complicated-plot-device savings to buy her a really nice guitar.
Kat and Patrick are rom-com role models: a female protagonist who doesn’t automatically lower her standards for someone just because he looks like Heath Ledger, and a male romantic lead who has actual interests, a moral compass, and genuinely wants to see his girlfriend succeed on her own terms. If anything, 10 Things I Hate About You made its audience a bunch of promises about teenage boys that it could not deliver on. Imagine all the misunderstood, Sylvia Plath-loving k.d. lang fans this movie convinced to wait around for their own Heath Ledger, when their beautiful, Shakespeare-obsessed best friend Mandella was right there all along! Then again, Kat is headed to Sarah Lawrence after graduation, so there’s still hope.
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Tragic heterosexuality aside, 10 Things I Hate About You still manages to transform a play called The Taming of the Shrew into something of a feminist text. Sure, Patrick Verona makes jokes about “beer-flavored nipples,” but he also spends an entire movie montage shopping for a copy of The Feminine Mystique. By fake ‘90s high school standards, that’s a male ally. The relatively evolved film rolls its eyes at rich white kids who dress like Rastafarians, and even pokes fun at Kat’s privileged crusades. The protagonist’s strident white feminism gets called out by Mr. Morgan (Daryl Mitchell), her black English teacher, who sarcastically applauds her for overcoming “all those years of upper middle class suburban oppression.” Still, the fact that there are only two major cast members of color—the other played by Gabrielle Union—casts considerable doubt on this seeming self-awareness.
10 Things I Hate About You isn’t as easily quotable as many of its teen-flick counterparts (although I’m personally partial to “I like my Sketchers, but I love my Prada backpack,”) but it’s passably funny, sartorially fascinating, and the soundtrack still slaps. Most importantly, even jaded teen romance critics won’t be able to watch Heath Ledger and Julia Stiles fall in love without feeling like it’s the very first time.
