10 Things I Hate About You is as fresh as ever, even 20 years later

On March 31, 1999, the teen comedy 10 Things I Hate About You hit theaters, and the world has never quite been the same. It boasts a cast on the cusp of stardom — Julia Stiles, Joseph Gordon-Levitt, and Heath Ledger among them, plus Allison Janney as the erotica-writing guidance counselor, just months before The West Wing debuted.

The film is remembered for more than serving as a breeding ground for a new generation of stars. It’s a pitch-perfect comedy, too. Based loosely on Shakespeare’s play The Taming of the Shrew, the movie told the story of two sisters in Seattle, Kat (Stiles) and Bianca (Larissa Oleynik), whose overbearing doctor father forbade them from dating in the fear that they’d come home knocked up. With her best friend Chastity (Gabrielle Union), Bianca is the school’s queen bee and the locus of attention for the guys, and she desperately wants to date; both greasy-haired hot rod Joey Donner (Andrew Keegan) and sweet new guy Cameron James (Joseph Gordon-Levitt) want to be the lucky guy.

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But Bianca isn’t allowed to date till Kat does. So Cameron and his nerdy new friend Michael (David Krumholtz) hatch a plan to get Joey to hire Patrick Verona (Ledger) to take Kat out. The trouble is that Patrick is the kind of guy who smokes cigarettes in class and is rumored to have eaten a duck alive, beak to tail. And Kat is an angry feminist who would rather do anything than go out with him.

The film holds up wonderfully, 20 years after its debut, not least because it managed to subvert some of the seamier, culture-bound aspects of The Taming of the Shrew — a story about a man badgering his high-spirited wife into submission — and turn them into something contemporary and sharp, without losing the romance.

To commemorate the 20th anniversary of one of the greatest teen comedies ever made, Vox’s culture staff decided to talk through what makes it endure so well. Joining the conversation are associate culture editor Allegra Frank and culture reporters Aja Romano, Constance Grady, and Alissa Wilkinson.

Kat, the teenaged feminist

Alissa Wilkinson: For whatever reason, this is one of the few films I distinctly remember watching in college — probably via a pirated file, R.I.P. turn of the century easy file-sharing networks — and yet I think it took me years to realize it’s a Shakespeare adaptation, even though Taming of the Shrew was of course a play I’d read in high school.

Rewatching it recently, I was struck by how odd that is. It’s not like it’s hiding it in any way, or even that it’s very subtle (even Clueless, I think, tips its hand less about its source material, Jane Austen’s Emma). I could write it off by blaming my own inattention to obvious detail, of course.

But I think part of what made me miss the archetype was that 10 Things I Hate About You feels so much like a movie of its moment, of 1999. I suppose you could say that of any movie, but the quips, the clothing, and especially the music make it feel extremely of that year, when I was in high school.

Not only that, but I think that, rhythm-wise, this one’s hard to beat. Sometimes it’s fast-paced; sometimes it’s slow and reflective; sometimes it’s outright sappy. But it hits every beat in a way that feels perfectly tuned for a teen romantic comedy. I won’t say it’s Shakespearean, obviously. But it lands its jokes and repartee, as well as its more tender moments, in ways that feel a tad reminiscent of the Bard.

It’s quite a movie to rewatch. It’s been a few years. And now the movie is turning 20. So when you look back on it, what do you think about?

Aja Romano: I have a lot of thoughts about Julia Stiles, but before I get to them, I’d like to touch on your point about 10 Things as an adaptation, because I think one of the most remarkable things about this film — which is honestly remarkable in so may ways — is the way in which it deftly balances a deep awareness of its source material with an energetic rejection of that source. The comparison to Clueless is significant here not just because of how contemporary both films feel (Clueless almost feels like an alternate reality), but because of the ways they grapple with their contentious forebearers. The Taming of the Shrew and Emma both crucially pivot around their heroine’s absolute mortification at the hands of her romantic foil, A Man Who Teaches Her A Lesson About Herself — but where Clueless chooses to embrace and massage this moral by making everyone involved ridiculous, 10 Things decides to turn the anger of Shakespeare’s heroine inward in order to grapple with his misogyny head-on.

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The most amazing thing about Kat to me is that she’s not just a ’90s feminist who’s ready to personally combat all the injustices women have been battling for centuries; she is herself an updated version of a character who’s personally born that injustice. Kate the Curst is the quintessential example — the trope-namer, if you will — of a female character who’s managed to overcome a misogynistic framing as the Shrill Woman, by enduring through the centuries as a stealth symbol of women’s independence and unconquerable fire.

And even knowing this, nothing prepared me, the first time I saw 10 Things 20 years ago, for how electrifying I found Julia Stiles’s Kat viciously asserting her right to be a bitch in a world that was prepared to demonize her no matter what. That she was still just a teenager made it even more radical to me at the time that she was both so fully conscious of the social rules she operated within and so fully prepared to reject them. The ease with which she repudiated both centuries of Shakespearean dogma and decades of high school rom-com tropes continues to feel like something of a miracle. There’s just no other heroine like her.

Constance Grady: 10 Things is one of the only successful adaptations of Taming of the Shrew that I know of, and plenty of people have tried to adapt it. It’s an impossible play. It’s brutally misogynistic: In Shakespeare’s original, Petrucchio deprives Katherine of food, sleep, and clothing until she agrees with whatever he says, essentially brainwashing her with abuse. But it also has so much force and fire, and the courtship battle between Katherine and Petrucchio seems so sexy at the beginning, that you understand exactly why so many directors and adaptors have tried to keep this play around. Isn’t there some way, you can hear them thinking, to make this story fun? After all, a heroine as fierce and funny as Katherine deserves nothing less.

Katherine wants so ferociously, and as a result puns so viciously, that she became one of Shakespeare’s most indelible heroines apparently against Shakespeare’s will. If his later heroines Rosalind and Beatrice and Viola are Katherine’s descendants — and there’s a solid argument to be made that they are — then in the long run, Katherine was the one who tamed her male author, not the other way around.

What makes 10 Things work is that it starts from the premise that Kat is correct to be angry. Her world is gross and misogynistic, and Kat has the tragic Joey “Eat Me” Donner backstory to prove it. Her anger is more than justified, and what makes Patrick worthy of her is that he respects her for her rage instead of trying to tame it out of her.

The only case in which Kat is shown to be wrong, in fact, is when she treats Bianca with disdain rather than sympathy, and lies to her rather than tell her the truth about the world. Their eventual rapprochement becomes one of the movie’s loveliest grace notes, and it’s part of what makes the movie’s feminism hold up. As far as 10 Things is concerned, Kat is right about everything except for the internalized misogyny that makes her despise her girly-girl little sister. Feminists are right to be angry, is the idea, but also girls should support other girls. We could do way worse with our teen movie lessons in 2019.

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Allegra Frank: Constance, your read on Kat — that she is angry, and rightfully so, and not denigrated for it — is something that’s only resonated with me as I’ve grown up and out of my own angry young person phase.

When I was much younger, watching 10 Things I Hate About You all chopped up on cable TV, Kat’s relentless pessimism felt like a parody of the emotion that I felt so intensely. And I came into the story without that Shakespearean context, aside from a meager understanding that this was one of those modern, Shakespearean riffs common in the 1990s. So instead, I took 10 Things I Hate About You as another sardonic, untruthful teen movie: where the teen girls are just SO, SO MAD, and HATE BOYS, and then FALL FOR THE BOYS THEY HATE. It rang hollow.

But now that I can better see the forest for the trees, I find her discomfort, her frustration, her distrust of basic high school society to be, if not completely relatable, empathetic. Now that I am a woman who can maturely support other women instead of sneering at their lack of bratty bona fides, relationships like Kat’s with Bianca and with, well, most people in general is something that I appreciate, not judge.

But the one thing I instantly loved and always will? That scene where Heath Ledger sings and dances to “Can’t Take My Eyes Off of You.” Please tell me I’m not alone in thinking this is the best part of the movie.

A cast on the cusp of stardom

Alissa: I do think you’re right, Allegra, that there’s at least a hint of the parody of Kat’s anger lurking around in the movie. There’s that scene where her black English teacher, Mr. Morgan (played by Daryl Mitchell) sardonically rags on her for her rich white girl problems, while he can’t get anyone to teach a novel by a black author. (The presence of the white kids who want to be Rastafarians sort of underlines the point.) She’s very angry, but also privileged and wealthy and not totally aware of it, being, you know, a teenager. But that doesn’t really undercut what she’s angry about, and I think that’s why it works so well.

I am with you on the “Can’t Take My Eyes Off of You” scene from the film, especially since my understanding is that Heath Ledger basically improvised a bunch of it (which may explain how genuinely Julia Stiles seems to be laughing). I’ve also always been personally fond of the party scene where she dances on the table; it is shot and blocked very well, and also, it’s the first time you get to see what a decent guy Patrick actually is, when he takes care of her when she’s drunk. Someone noted on Twitter recently that it cuts through some of the BS about teenaged guys not understanding consent; she’s drunk, he’s not, and so he doesn’t kiss her. And in the last century!

I think we all have a lot of thoughts about Julia Stiles. What are yours?

Aja: On one level, Kat is very obviously meant to subvert the rom-com trope of the “serious” girl who learns to let her hair down and reveal a wild side that only her romantic paramour gets to see. In this story, Kat has a very good reason for keeping herself and her emotions tightly under wraps. But Julia Stiles is so fully embodied as Kat that she almost entirely subverts the whole trope long before we find out that there’s a plot reason for Kat’s uptight persona. She does such a tremendous job balancing Kat’s complicated personality, all her spirit and fire, with her charm and wit and abrasive likability, and above all her insistence on her own autonomy.

In every scene, she exudes complexity and a range of nuanced emotion that make her impossible to pigeonhole into any of those typical rom-com tropes: she’s not the shy wallflower turned bold party girl, she’s not the frigid bitch turned unexpectedly relaxed and mellow, she’s not the serious student who takes off her glasses to reveal a surprise hottie. She’s a fully realized teenage girl, and she’s not here to be the subject of a male-gaze-based fantasy; she completely undoes the shaky logic of all these tropes with a single shoulder shrug.

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Julia Stiles’s independence as Kat also largely undermines the wager Patrick makes about her, because the movie makes it clear that she’s so conscious about her own choices that she’s well past the life stage of being manipulated by the ruse of a dumb bet. Heath Ledger’s Patrick clearly realizes this early on, and every scene in which she chooses to let him past her emotional walls reads like a victory, not for him, but for her, because she’s so consciously choosing to be vulnerable with him. That’s why the scene when she reads the poem is, in my opinion, so powerful — because Julia Stiles manages to make Kat fully in command of even her rawest emotions. Even when she learns about the bet, she’s never ashamed of having fallen for Patrick; instead she turns her emotional honesty into a final Hail Mary move to get what she wants.

(I feel really unqualified to talk about Kat as a fashion icon, but also I just really want to mention that as a genderqueer person, Kat’s wardrobe made entirely of dressed-down solid colors and subtly androgynous styles felt like a revelation to me at the time, and even though she finds her way into a shirt that has a subtle pattern in the final moments because she’s learned to get in touch with her feelings, she still lives for me as the no-bullshit ponytailed girl in the army fatigues, and I’m deeply grateful for her.)

Constance: Julia Stiles has a beautiful deadpan rage in this role, and she gives Kat an incredible sense of ambition: You really get the sense that this girl can’t wait to get the hell out of high school and move on somewhere that matters. Stiles made the role her own, so much so that I found myself offended by the very idea when I read recently that the director wanted to cast Katie Holmes as Kat instead. (I mean. Can you even imagine???)

But if we’re going to talk about the acting in 10 Things, we have to talk about the Heath Ledger of it all. Right? This movie was Ledger’s first major American role, his star-making turn, and he just exudes charisma in every frame. Julia Stiles, who I adore, has a tendency to go a little wooden at times, but Ledger’s presence is so loose-limbed and easy that he lets the audience skate right over any awkwardness that might have ensued.

He is so charismatic, in fact, that it took me many many years to realize that Patrick agreeing to try to manipulate a girl for money is objectively a kind of shitty thing to do. Who’s going to care about such petty concerns when Heath Ledger is doing that crinkly-jawed smile?

For me, it’s the combination of Kat’s take-no-bullshit personality and Ledger’s charisma, and the way they combine to preserve the playful eroticism of the source material while excising the misogyny, that makes 10 Things a classic. Well, that and the impeccable soundtrack. What about you?

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Allegra: For me, this film is 100 percent Heath Ledger’s. I will concede to all of your points that Julia Stiles is maybe not the one-note, infuriating presence I found her to be in my own teen years, now that I am grown-ish enough to remove my own blinders.

But Australian man Heath Ledger somehow managed to completely assume the role of American teen dreamboat. Ledger is the embodiment of charm here, in ways that feel hard-won and not born of privilege or ulterior motives. That “Can’t Take My Eyes Off of You” scene is still one of my favorites in history because of how it locks in amber the raw, rare talent that Ledger had — to be as silly as he was suave, as moving as he was able to move. It’s a gorgeously funny, vulnerable performance that is the stuff of lifelong crushes. And that never feels forced, or wrong, or frustrating; instead, I wish I could point to more teen movies of the era that had such an easy pair for us to root for.

“Can you ever just be whelmed?”

Alissa: We’ve mentioned some of the most memorable scenes and quotes — this movie is endlessly quotable. (Much, I daresay, like the Bard.) To wrap things up, then: What do you think makes this film so quotable? And which quote do you return to as your favorite?

Aja: This is a really interesting question because obviously film magic is often down to the power of a good screenplay, and this one has a great screenplay by frequent collaborators Karen McCullah and Kirsten Smith, who went on to adapt Legally Blonde and contribute to She’s the Man. They clearly had their fingertips on the pulse of ’90s pop feminism — and on the intrinsically hilarious, poignant nature of teen girlhood. (McCullah based the film title on a diary she kept about her own high school boyfriend. Awwww.)

But they’re also helped out tremendously by the power of a great ensemble cast. Every line Allison Janney utters as the oversexed, over-her-job guidance counselor is pure gold, and we’ve already discussed Daryl Mitchell’s exasperated English teacher. Larisa Oleynik and Joseph Gordon-Levitt are adorably over-earnest as the B romance in a sea of teen actors all playing their parts to the hilt. (Shoutout to Joey’s model poses.) And even with all that, the line that gets me every time is David Leisure as Mr. Chapin stealing detention Cheetos for himself with a simple, “This too.” His line delivery here is perfection.

Constance: I have to give a shoutout to the oft-overlooked pop philosopher Bianca, as well as the immortal Gabrielle Union as her best friend Chastity. Michael sneers at their philosophical discussions (Bianca: “There’s a difference between like and love. Like, I like my Sketchers, but I love my Prada backpack”), but Michael’s the dude who thinks you should wear a tie to a house party so what does he know? My personal favorite is their discussion of English’s endlessly confusing etymology: “I know you can be overwhelmed, and you can be underwhelmed,” Chastity muses, “but can you ever just be whelmed?” “I think you can be in Europe!” Bianca chirps.

Incidentally, Bianca is right. You can be whelmed in Europe, or at least you could a few decades ago. (“Whelmed” used to mean exactly the same thing as “overwhelmed,” but it fell out of favor around the 1950s when the antonym “underwhelmed” started to pop up.)

Allegra: I’m going to be a sap here and throw out what may be the most memorable speech in a film full of so many great turns of phrase. I always failed to connect with Kat — until her big, emotional moment, where she reads the poem that lists off the 10 things she hates about Patrick. And that 10th thing gets me sniffling every time. Ah, to be young and in love and only slightly ashamed to admit it.

Alissa: I’ve always chuckled over the scene where Bianca tells Cameron that Kat’s black lingerie means she wants to have sex someday, and wondered how many teenagers scribbled mental notes about it.

But I’m the tiniest bit of a romantic, and so I also love that exchange between Patrick and Kat on the steps, where she tells him that she doesn’t like to live up to other people’s expectations instead of her own. “So you disappoint them from the start and then you’re covered, right?” he asks, and she agrees. “Then you screwed up,” he says. “You never disappointed me.” Awwwwwww. That’s the whole movie, right there.

10 Things I Hate About You turns 20 on Sunday, March 31. It’s available to digitally rent or purchase on iTunes, Amazon, YouTube, Vudu, and Google Play.