“I guess, in this society, being male and an asshole makes you worthy of our time.” 

Kat Stratford (Julia Stiles) really hit the nail on the head with that iconic quote, and I couldn’t have put it better myself. It’s lines like that one that makes 10 Things I Hate About You the quintessential 90s teen movie. Well, that and one of the best modern rock soundtracks to date. 

10 Things I Hate About You is a 1999 romantic comedy starring Julia Stiles and Heath Ledger, based off of the Shakespeare play The Taming of the Shrew. In the movie, Stiles plays Kat Stratford, an angsty high school senior who doesn’t care what anyone thinks and makes sure everyone knows it. Kat, usually clad in chunky flip flops and cargo pants, is a fiercely independent young woman who “likes Thai food, feminist prose, and angry girl music of the indie rock persuasion.” 

It’s Kat’s personal music taste that really creates and drives the soundtrack choices. We’re introduced to her character as she pulls up to her school blaring
“Bad Reputation” by Joan Jett and The Blackhearts from her car stereo as the opening credits roll. Features from Letters to Cleo, En Vogue & Salt-N-Pepa and The Cardigans are just some of the decade-defining songs used in the film. 

The soundtrack serves as the perfect sonic backdrop to the melodramatic love lives of four high school teens just trying to find their place in the world. With recurring features from hit 90s band Letters to Cleo, the track list is 90s alt-rock at its finest:

Kat’s younger sister Bianca (Larisa Oleynik), a sophomore social butterfly, is devastated when the girls’ father implements a strict rule pertaining to when his youngest daughter can date: Kat, who wants nothing to do with her male classmates, must date first. 

This compels the most popular kid in school, Joey Donner (Andrew Keegan), to offer mysterious bad-boy Patrick Verona (Heath Ledger) a sizable amount of cash to court Kat so that he can date her sister. To Kat’s chagrin, she can’t deny the feelings she has for Verona, and he finds himself falling for her as well.

Not only is the band Letters to Cleo featured multiple times in the soundtrack, but they also make cameos as Kat’s favorite band throughout the movie. First seen playing their songs “Come On” and “Co-Pilot” as Verona finds Kat at her favorite club, and again at their school’s prom, per his request. 

One of the more iconic scenes from the film occurs when a mob of high schoolers crash classmate Bogey Lowenstein’s (Kyle Cease) school club event, turning it quickly into a house party rager. Late into the party, Kat finds herself very drunk and ends up dancing on a table to Notorious BIG’s “Hypnotize” before hitting her head and falling into Verona’s waiting arms. 

As Kat and Patrick’s relationship progresses, another love story develops between Bianca and Cameron James (Joseph Gordon-Levitt), a new student who has become immediately infatuated with her. At Bogey Lowenstein’s party, Bianca realizes what a jerk Joey is and asks Cameron, whose feelings were made known earlier that evening, for a ride home. Another iconic 90s jam, “War” by The Cardigans, can be heard coming from the car radio. 

Finally, the fan-favorite scene of the movie features Heath Ledger singing “Can’t Take My Eyes Off Of You” with a full marching band. Need I say more? Ledger, as Verona, frolics to-and-fro, up and down the stairs of the high school’s stadium singing to Kat in front of her whole gym class. The performance is a very romantic gesture cut short by the police, as Patrick narrowly evades capture:

https://www.youtube.com/watch?v=S7N6kB11GpE

Whether you’re a fan of teen rom-coms or a lover of all things 90s rock, 10 Things I Hate About You is a must-watch every Valentine’s Day. Even for those who despise the holiday and everything to do with romance, the soundtrack alone makes up for every cheesy line. Underneath all of the obvious tropes, loud music and awkward kisses is a story of two outcasts just trying to find out where they fit in each other’s lives—and if that place is somewhere they dare venture. 

Happy Valentine’s day to all my romantics, nostalgics and melomaniacs everywhere. I hope your day was as lovely as Heath Ledger’s hair <3