HomeMovies1999 Movie-versaries: 10 Things I Hate About You

1999 Movie-versaries: 10 Things I Hate About You

1999 was a big year for movies. It was the year that The Matrix‘s slow-motion bullet influenced action movies for years to come. It was the year American Beauty won Best Picture at the Academy Awards and Oscar fans have been arguing about it ever since. It was the year Pokémon jumped from Gameboys and TV to the big screen. And worst of all, it was the year that disappointed a generation of Star Wars fans with the release of The Phantom Menace.

To celebrate that landmark year in film’s 20th Anniversary, The Pop Break continues its year-long retrospective of 1999’s most influential (at least to us) films with staff writer Kat Manos reflecting on the best teen rom-com since Shakespeare: 10 Things I Hate About You.

No disrespect to John Hughes, but there was no greater time to love high school rom-coms in film history than in the ’90s. There were all the teenage sex romps, the transformation stories of ugly ducklings becoming beautiful swans, the strangely surreal musical dance numbers, secret bets, and everything hanging on attending one super-important party like the Prom.

And then there were movies like 10 Things I Hate About You, which managed to address all those teen comedy tropes and cleverly subvert them while still having the gall to evoke the writing of William Shakespeare. Looking back on the film’s 20th anniversary this year, it’s truly shocking not only how well the film still holds up, but how perfectly it encapsulated the charm of teen dramas in a pre-9/11 world.

Full disclosure: before I dive into why 10 Things I Hate About You is one of the greatest teen rom-coms ever made, it’s important to realize that I’m a bit biased. I’m also a Katarina who goes by Kat and probably made somebody cry today. Kat Stratford–played to perfection by Julia Stiles–and I have a lot more in common than even most people who know me would realize. I too grew up as a student athlete on the West Coast with a pretty overprotective father and always dreamed of going to New York for college (though I preferred NYU over Stratford’s choice of Sarah Lawrence).

I also had a sibling who was definitely a lot more popular than I was in school, and a rag-tag group of artsy friends obsessed with Shakespeare plays and all-girl punk bands. It would take a lot of convincing to talk me out of attending a concert or going on a tirade in English class about why “insert male author here” was actually a misogynist. Most importantly, I definitely would’ve killed for a white Fender Stratocaster.

My biases aside, there’s a lot more to be said about 10 Things I Hate About You than just my personal connection to it. Released just before the end of the millennium, the film was a breakout vehicle for three incredible actors we all still revere today: the aforementioned Stiles, Joseph Gordon Levitt, and of course, the late Oscar winner, Heath Ledger. Larisa Oleynik, Larry Miller, David Krumholtz, Gabrielle Union, Andrew Keegan, and even Allison Janney round out the phenomenal cast of characters recreating Taming of the Shrew for the 20th century.

At a time when Baz Luhrmann introduced his interpretation of Romeo + Juliet, Gus Van Sant’s My Private Idaho combined the Henry Shakespeare plays, Tim Blake Nelson took on Othello with O, and later, Amanda Bynes played a Twelfth Night Viola in She’s The Man, 10 Things I Hate About You translated Shakespeare a bit differently. While other movies either completely ignored the existence of the English playwright or perhaps gave him a wink-wink, nudge-nudge shoutout, 10 Things incorporated him into the story. Many first names are directly taken from the play; the surname Stratford references Shakespeare’s hometown of Stratford-upon Avon while Patrick Verona–played sublimely by Heath Ledger–obviously references the Italian city wherein most of his plays take place.

Here’s a shoutout to all the English teachers who showed this movie in class as justification that “we were all learning something.” Watching the film back two decades after its release, I actually do feel like there’s a lot to be learned from it. In a strange way, the film doesn’t completely reject the idea of young people having sex, but instead promotes staying safe and remembering to have sex for the right reasons. Likewise, the concept of consent is quite beautifully portrayed when Patrick (Ledger) refuses to kiss Kat because she’s drunk at a party—even though she asks him to and successfully wooing her is the very crux of earning money from the handsome but slimy Joey (Keegan).

10 Things–like many of Shakeapeare’s plays–also toys with the notion of identity. Namely, the importance of not quickly judging someone based upon their social status or supposed rumors swirling around. Classmates mischaracterize Patrick as a criminal thug and Kat as a shrewish, well “heinous bitch” as Allison Janney explains, but neither of them really have that identity. Bianca, played with deceptive brilliance by Oleynik, isn’t quite as shallow or naive as she seems either.

Without even thinking too hard about it, 10 Things I Hate About You holds up 20 years later not just because its source material pulls from Shakespeare, or its ability to quietly uphold seemingly woke tenets. The film remains enjoyable because it subverts so much of what we think about teen comedies. There’s more adult consent than sex romp antics. There’s less of teens changing who they are for their significant other, and more of teens being honest with themselves. Sure, there is a big song-and-dance number, but it involves Heath Ledger iconically singing Frankie Valli’s “Can’t Take My Eyes Off Of You” and that’s amazing, so we can’t knock that.

If you only have time for one throwback teenage rom-com to watch in 2019, choose 10 Things I Hate About You. Its memorable performances, gorgeous settings, and female-penned script are great enough to remind you that you can’t hate it—not even close, not even a little bit, not even at all.




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