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When Romance Met ComedyWhen Romance Met ComedyWith When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

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.)

10 Things I Hate About You was the first screenplay produced by screenwriting duo Karen McCullah and Kirsten Smith, who would go on to write other sneakily subversive female-led comedies like Legally Blonde, She’s The Man, and The House Bunny. While it’s easy enough to say that 10 Things succeeds thanks to its talented leads, memorable one-liners, and absolutely flawless soundtrack, I actually think there’s an impressive level of structural craft on display too, both in the script and the imagery. That’s especially apparent when you compare it to She’s All That, which is an endearing but far more simplistic take on very similar material. (Not only did these two bet-centric high school movies come out just months apart, they also both feature soccer-playing protagonists and Gabrielle Union in a thankless best-friend role.) The “I can make any girl prom queen” bet in She’s All That just kind of happens, but McCullah and Smith weave welcome complexity into the ensemble-focused plot mechanics of 10 Things I Hate About You. They’re also careful to ensure that all of their characters have clear, consistent, often multi-layered motivations, which seems like it should just be a basic tenet of storytelling but too often isn’t in studio comedies.

In The Taming Of The Shrew, Bianca can’t marry until her older sister is wed. McCullah and Smith update that idea into a house rule that says the overeager Bianca can’t date until her anti-social sister does. Though Kat and Patrick eventually become the film’s central couple, our initial point-of-view character is new kid in school Cameron (Joseph Gordon-Levitt), who instantly falls for Bianca and realizes the only way he stands a chance of dating her is if he finds someone to take out Kat. His nerdy friend Michael (David Krumholtz) suggests they get a backer (“Someone with money who’s stupid”) to handle the dirty work for them. So rich, entitled model Joey Donner (Andrew Keegan) provides a hissable central antagonist to handle the more dubious aspects of the plot. Meanwhile, the other characters are allowed to swirl around each other in all sorts of different combinations—like a really sweet friendship that develops between Patrick and Cameron as they pursue their parallel romantic quests.

Tying Bianca’s social life to Kat’s also allows the movie to be as much a story of sisterhood as it is romance. In classic teen rom-com fashion, 10 Things features both a raucous house party and a climactic prom. In both cases, however, Kat makes the decision to attend specifically so that Bianca will be allowed to go too. Her romance with Patrick is really just a bonus to her arc about loosening up her overprotective older-sister instincts and opening up to Bianca about her own negative experience with the peer pressure of popularity. It’s a really lovely throughline that adds depth to Kat’s character, and showcases the female-centric storytelling that’s so often part and parcel of the best romantic comedies.

10 Things is structured like a relay race, with the four central characters and their various sidekicks gracefully passing the baton from scene to scene. The opening 10 minutes, in particular, are a masterclass in storytelling efficiency and economy. The film jumps from Kat to Cameron to Patrick to Bianca back to Kat, while also introducing oddball adults like guidance counselor/aspiring erotic novelist Ms. Perky (Allison Janney) and no-nonsense English teacher Mr. Morgan (Daryl Mitchell), who challenges Kat’s anti-patriarchal views by pointing out her privileged white feminism. Within just a handful of scenes, we’ve met all of our main characters, understand their relationships to one another, and grasp the larger dynamics of Padua High School.

All of that makes Padua feel like a real place with characters who exist beyond what we see of them on screen, and that’s echoed in the visuals as well. The film was shot on-location at real high schools and homes in Washington, and director Gil Junger favors long takes that emphasize geography and spatial relationships. One of Junger’s most effective visual choices is to regularly place his leads deep in the background of shots. When Michael first enlists Joey’s help, Joseph Gordon-Levitt is seated a couple of tables away, out of focus but eagerly watching the action unfold. The camera never highlights the fact that he’s there or cuts to close-ups of his reaction. His placement just adds subtle depth and realism to the world of Padua. The film’s most overtly impressive image is a final helicopter shot of a rooftop Letters To Cleo performance, but Junger’s less showy camerawork is equally thoughtful and purposeful.

10 Things I Hate About You was Junger’s feature film debut after a long career directing TV comedies, and there are a couple moments where he pushes his sitcom instincts a little too far, like a rather superfluous scooter accident sequence. For the most part, however, Junger succeeds at packing the film with subtler visual gags. One of my personal favorites is the lead-in to the film’s big house party sequence—the classic teen movie scenario where a small gathering has unknowingly been co-opted into a school-wide bacchanal. When the doorbell rings, hoity Bogey Lowenstein cheerfully announces, “That must be Nigel with the brie” only to be met by a wave of unwanted party guests instead. If you watch carefully, however, the first person through the door really is Nigel with the brie.

10 Things I Hate About You is the sort of film that rewards multiple viewings. There’s a lot to dig into in the film, which clocks in at a relatively brisk 99 minutes and barely wastes any of them. The film combines the complex plotting of Shakespeare, the empathetic emotions of John Hughes, and some unapologetically angry turn-of-the-millennium feminism into a teen rom-com package that feels wholly original. 10 Things I Hate About You may be 20 years old, but like the best romantic comedies, it still feels timeless.

Next time: From one teen rom-com anniversary to another. Say Anything turns 30.

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About the author

Caroline Siede

Contributor, The A.V. Club. Caroline Siede is a pop culture critic in Chicago, where the cold never bothers her anyway. Her interests include superhero movies, feminist theory, and Jane Austen novels.