If you close your eyes and think about 1999, you can probably hear it. That specific, crunchy guitar riff. The sound of a Fender Stratocaster plugged into a slightly-too-loud amp. It’s the sound of Kat Stratford pulling her beat-up car into a high school parking lot while Joan Jett’s "Bad Reputation" blares. Honestly, the 10 Things I Hate About You soundtrack didn't just provide background noise for a Shakespeare adaptation; it basically defined an entire subgenre of teen angst that felt... actually cool?
Most movie soundtracks from that era were just collections of radio hits thrown together to sell CDs at Sam Goody. This was different. It felt curated. It felt like someone actually looked at the character of Kat—a Sylvia Plath-reading, feminist-punk-loving teenager—and asked, "What would she actually listen to?"
The result? A weird, wonderful mix of ska, power pop, and classic rock that somehow still sounds fresh decades later.
The Letters to Cleo factor and the power of the cover song
You can't talk about this movie without talking about Letters to Cleo. They are the sonic backbone of the film. While most people remember Kay Hanley singing on the roof of the high school at the end, their influence starts much earlier.
Covering Cheap Trick is a bold move. It’s risky because Cheap Trick is perfect. But the version of "I Want You to Want Me" found on the 10 Things I Hate About You soundtrack captures that specific late-90s bubblegum-grunge crossover perfectly. It’s polished but still has enough grit to feel authentic to the Pacific Northwest setting of the film.
Then there’s "Cruel to be Kind." Originally a Nick Lowe track, the Letters to Cleo version turns it into a high-energy anthem that plays during the prom. It’s interesting how the film uses music to bridge generations. You have songs that parents would recognize, reimagined for kids wearing butterfly clips and cargo pants.
Kay Hanley actually spoke about this years later, mentioning how the band was basically "the house band" for the movie's universe. They weren't just a track on a disc; they were part of the story.
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Why "Bad Reputation" was the only way to start this movie
The opening of the film is iconic for a reason. We see the "popular" girls in their convertible listening to "One Week" by Barenaked Ladies. It’s light, it’s poppy, it’s safe. Then, the camera pans to Kat.
The immediate shift to Joan Jett’s "Bad Reputation" tells the audience everything they need to know about the protagonist without a single line of dialogue. It’s a masterclass in music supervision. While the 10 Things I Hate About You soundtrack leans heavily into the 90s, this nod to 1980s punk-rock rebellion anchors the film's feminist themes. It says Kat Stratford doesn't care about your social norms.
The ska influence nobody expected to age well
Let’s be real for a second. Ska is a polarizing genre. In 1999, it was everywhere. By 2005, it was a punchline. But on this soundtrack? It works.
Save Ferris and The Mighty Mighty Bosstones were the kings of this era. Including "I Know" by Save Ferris was a stroke of genius. It captures that frantic, horn-heavy energy of a high school party where everything feels like the end of the world but you still want to dance.
The soundtrack also features "The Wrong Thing to Do" by The Mudmays and "New World" by Leroy. These aren't household names now, but they fit the vibe of a movie set in Seattle—even if the movie feels more "Sun-drenched SoCal" than "Rainy Emerald City." It’s that specific brand of "Third Wave Ska" that felt like sunshine and teenage rebellion mixed together.
That Heath Ledger moment: "Can't Take My Eyes Off You"
Okay, it’s not technically on the official studio soundtrack album (which is a crime, frankly), but Heath Ledger’s performance of the Frankie Valli classic is the emotional core of the film’s musical identity.
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Why does it matter for the 10 Things I Hate About You soundtrack? Because it changed how we viewed the character of Patrick Verona. Before that scene, the music associated with him was dark, mysterious, and distant. By having him hijack the marching band to sing a brassy, pop-standard show tune, the movie uses music to strip away his "bad boy" armor.
It’s also a testament to Ledger’s charisma. He wasn't a singer. He was a kid with a microphone and a brass section, yet that moment is more memorable than almost any other musical beat in a 90s rom-com.
The deeper cuts: Semisonic and Air
Everyone knows Semisonic for "Closing Time." But the 10 Things I Hate About You soundtrack used "F.N.T." (Fascinating New Thing). It’s a much better song for a budding romance. It’s breezy. It’s hopeful. It lacks the overplayed melancholy of their bigger hit.
And then there's Air. Including "Sexy Boy" was a sophisticated move. Air is a French electronic duo. In 1999, they were the height of "cool-girl" music. Putting that in a teen movie gave the film a level of indie-cred that She's All That or Can't Hardly Wait didn't quite reach. It suggested that Kat and Patrick had tastes that went beyond what was playing on TRL.
A track-by-track look at the vibes
If you look at the tracklist, it’s a chaotic journey through the late 90s.
- "I Want You to Want Me" – Letters to Cleo: The high-energy opener.
- "F.N.T." – Semisonic: The "falling in love" montage song.
- "I Know" – Save Ferris: The sound of being 17 and confused.
- "Your Winter" – Sister Hazel: The obligatory acoustic ballad for when things go wrong.
- "Even Angels Fall" – Jessica Riddle: Pure 90s female-vocalist pop.
- "Breathless" – The Dan Band: A weirdly catchy addition.
- "Cruel to Be Kind" – Letters to Cleo: The prom climax.
- "War" – The Cardigans: A darker, trip-hop influenced track that showed the movie had teeth.
The Cardigans’ "War" is actually one of the most underrated parts of the whole experience. Most people know them for "Lovefool," but "War" is moody and strange. It fits the tension between Kat and her father, and her internal struggle with her own reputation.
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The legacy of the 10 Things I Hate About You soundtrack
Why do we still care? Honestly, it’s because this album represents the last gasp of the "Alternative" era before everything turned into the slick, over-produced pop of the early 2000s.
It was a time when a movie about a high school could have a soundtrack featuring Joan Jett, The Raincoats, and Salt-N-Pepa (even if the latter was just for a dance scene). It didn't try to be one thing. It was messy, just like high school.
The music supervisor, Karen Glaser, clearly understood that the audience wasn't a monolith. Some kids liked punk. Some liked ska. Some liked power pop. By mashing them all together, the 10 Things I Hate About You soundtrack became a time capsule.
How to experience it today
If you’re looking to revisit this, don't just stick to the Spotify playlist. You have to watch the movie to see how the songs are used as punctuation marks.
The way the music cuts out when Kat reads her poem. The way the brass section kicks in when Patrick starts running from the security guards. It’s a symbiotic relationship between image and sound.
If you want to dive deeper into this specific sound, here are a few actionable steps:
- Check out the "Sister" album by Letters to Cleo. If you liked their covers in the movie, their original 90s output is peak power pop.
- Look into the 90s Riot Grrrl scene. Kat mentions Bikini Kill and The Raincoats. These weren't just throwaway lines; they were the real-world inspiration for her character's defiance.
- Listen to the full "Moon Safari" album by Air. It provides the "chill" counterbalance to the frantic energy of the rest of the soundtrack.
- Track down the vinyl. There have been several anniversary reissues of the soundtrack on colored vinyl. It’s the best way to hear that 90s guitar crunch.
The 10 Things I Hate About You soundtrack isn't just nostalgia bait. It’s a well-constructed piece of musical storytelling that proved teen movies could have "good" taste. It didn't talk down to its audience. It invited them to listen to something a little louder, a little faster, and a little more honest.
Next Steps for the 90s Music Fan:
To truly capture the vibe of the era, look up the original 1979 Nick Lowe version of "Cruel to be Kind" and compare it to the Letters to Cleo version. You’ll see exactly how the producers updated the "Power Pop" sound for a new generation. Additionally, exploring the discography of Save Ferris will give you a better understanding of the ska-punk explosion that briefly took over American airwaves at the turn of the millennium. These sounds are the direct ancestors of the modern "indie-sleaze" revival we see today.