20 years later, 10 Things I Hate About You remains a model for how to do the teen rom-com right
One of the most prevalent of rom-com tropes is the random, unmotivated musical number. The “Say A Little Prayer” sequence in My Best Friend’s Wedding. The drunken karaoke in 27 Dresses. The elaborately choreographed dance routines in Something Borrowed, 13 Going On 30, and She’s All That. But when it comes time for 10 Things I Hate About You to deliver its own take on the convention, it puts a little more thought into it. Patrick Verona (Heath Ledger) has thoroughly embarrassed Kat Stratford (Julia Stiles) on their first date by awkwardly turning down her attempt to kiss him. She’s pissed. His young romantic allies advise him that the only way to get back into her good graces is to “sacrifice himself on the altar of dignity to even the score.”
So interrupting her soccer practice with his marching band-backed performance of Frankie Valli’s “Can’t Take My Eyes Off You” isn’t just a grand romantic gesture for the sake of one. It’s a public apology—one that doesn’t put her on the spot, but that does let her know the ball is in her court if she wants it. It moves the plot forward, deepens multiple character relationships, and allows Ledger to deliver a shot of charisma without losing his character’s bad boy vibe in the process. (The whole thing ends with him goofily dodging two security guards.) Those are small details, but they’re characteristic of the way 10 Things I Hate About You subtly elevates teen rom-com tropes with more thought and craft than they’re usually given. And that’s why the film still feels as fresh today as it did during its release 20 years ago.
10 Things isn’t the only teen movie turning 20 this year. 1999 was an absolutely bonkers year for the genre. Along with dark comedies like Election, Drop Dead Gorgeous, and Jawbreaker, there was Varsity Blues, American Pie, the Dangerous Liaisons update Cruel Intentions, Never Been Kissed, Drive Me Crazy, the Pygmalion-inspired She’s All That, and, of course, 10 Things I Hate About You, which updated the questionable gender politics of William Shakespeare’s The Taming Of The Shrew with a dose of late ’90s Riot Grrrl energy. Most of these films owe their existence to Amy Heckerling’s 1995 masterpiece Clueless, which updated Jane Austen’s Emma and revived the high school comedy genre after its lull in the early ’90s. It probably didn’t hurt either that Baz Luhrmann’s 1996 Romeo + Juliet had helped make Shakespearean verse sexy again.
If 10 Things I Hate About You isn’t quite as perfect as Clueless, it’s certainly the best of the 1999 teen romantic comedies. And it holds the distinction of being the year’s thinking person’s teen rom-com, largely thanks to the unconventional choice of its two romantic leads. Julia Stiles and Heath Ledger are weightier, more thoughtful actors than usually get cast in these kinds of roles. (The other people up for the Ledger part were Josh Harnett and Ashton Kutcher, charming actors who would’ve made this a very different movie.) Stiles and Ledger were both unknowns, and 10 Things was Ledger’s first American movie. Their naturalistic performances lend the otherwise fairly heightened film a realism akin to later, more grounded teen films like The Spectacular Now and The Edge Of Seventeen. That’s best exemplified by Stiles’ heart wrenching delivery of the poem that gives the film its title, which solidified her as an iconic talent for a microgeneration of teen fans.
Even more importantly, 10 Things lets Stiles and Ledger play appreciably off-kilter characters, which is something more rom-coms—high school or otherwise—could stand to do. Patrick is a mysterious longhaired Australian who at one point whips out a giant pocketknife to stab the frog he’s supposed to be dissecting and then runs his fingers through an open flame. Kat is an angry, anti-capitalist feminist whose first line in the movie is, “Romantic? Hemingway? He was an abusive, alcoholic misogynist who squandered half his life hanging around Picasso trying to nail his leftovers.” The film pokes fun at their more self-righteous ways. (When Kat argues that skipping prom will allow them to make a statement, her best friend sarcastically quips, “Oh goody, something new and different for us!”) But it doesn’t demand that either of them change to earn their happy endings either.
That’s especially welcome for Kat, who gets to eschew the messy “she got a makeover to be conventionally attractive, but she’s still her quirky self!” messaging that has served as a loophole for everything from Grease to Pretty Woman to The Princess Diaries to, most comparably, She’s All That. In this update, the “shrew” doesn’t need to be tamed at all. She just needs to find someone who appreciates her the way she is—bare faced, dressed down, and righteously angry. Making both Kat and Patrick outsiders allows their relationship to feel like one between equals who bring out the best in each other as they let down their loner guards and engage in some actual vulnerability for once. In fact, 10 Things feels far more like a low-key hangout rom-com than it does a teen coming-of-age story.
Kat’s girlish younger sister Bianca (Larisa Oleynik) gets the more conventional teen movie arc of learning that being popular isn’t all it’s cracked up to be. But even that happens without much melodramatic handwringing. It’s a realization she pretty quickly and quietly comes to over the course of one disappointing party. The character who actually has the biggest arc is probably Kat and Bianca’s hilariously overprotective single dad (Larry Miller), who comes to realize he should respect the agency and independence of his teenage daughters, rather than trying to control their every move. 10 Things I Hate About You has a lot of genuine affection and respect for teenagers, particularly angry teen girls, which is a big part of the reason it was such a formative movie for me in my own teen years. (The other big reason was Heath Ledger and that aforementioned flame scene.)