If you walked into a movie theater in 1999, you probably didn't realize you were about to witness a blueprint. We’re talking about a decade where the "teen movie" was being cranked out of a factory. You had the slasher flicks, the gross-out comedies, and the occasional high-concept drama. But the 10 Things I Hate About You movie was different. It didn't just capture the late-90s aesthetic of platform flip-flops and Letters to Cleo; it actually respected its audience's intelligence.
It’s been over twenty-five years. Seriously.
Most movies from that era feel like dusty time capsules that make you cringe at the dialogue. Yet, for some reason, we’re all still obsessed with Kat Stratford’s prickly feminist energy and Patrick Verona’s chaotic charm. It wasn't just a "movie for kids." It was a clever, biting adaptation of William Shakespeare’s The Taming of the Shrew, and honestly, it’s probably the only version of that play that isn't deeply problematic by modern standards.
The Shakespearean DNA most people miss
You probably know it’s based on a play. Most people do. But the way screenwriters Karen McCullah and Kirsten Smith translated the 16th-century source material into Padua High School is basically a masterclass in adaptation. They didn't just swap out corsets for cargo pants. They kept the core conflict—a father decreeing that his younger, popular daughter cannot marry until his older, "shrewish" daughter does—and turned it into a relatable war of sibling rivalry and teenage rebellion.
Consider the names. It's not a coincidence. Patrick Verona is named after Petruchio, who hails from Verona in the play. The sisters’ last name, Stratford, is a direct nod to Shakespeare’s birthplace, Stratford-upon-Avon. Even the high school itself, Padua High, is named after the Italian city where the play is set.
But here’s the thing: the 10 Things I Hate About You movie actually fixes the play. In the original text, Petruchio basically gaslights Katherine into submission. It’s... dark. In the movie? Patrick and Kat actually have a connection. They’re both outcasts. He isn't "taming" her; he’s meeting her where she is. He buys her a Fender Stratocaster instead of demanding she call the sun the moon. That’s a huge distinction that gives the film its staying power.
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Why the casting was a lightning strike in a bottle
You can’t talk about this movie without talking about Heath Ledger. Before he was the Joker, before Brokeback Mountain, he was just this kid from Australia with a wild mane of curls and a smile that could dissolve a brick wall. The story goes that he beat out actors like Ashton Kutcher and Josh Hartnett for the role of Patrick. Thank god he did.
Ledger brought a weird, grounded vulnerability to the "bad boy" trope. When he sings "Can't Take My Eyes Off You" in the stadium—a scene he reportedly chose the song for himself—it isn't just a goofy stunt. It’s a moment of genuine, humiliating effort.
Then you have Julia Stiles.
Stiles played Kat Stratford with a level of intellectual ferocity that we just weren't seeing in teen leads back then. She wasn't the "cool girl" who just needed a makeover. She was angry. She read Sylvia Plath. She liked "angry girl music of the indie-rock persuasion." To a generation of girls who felt like they had to be easygoing to be liked, Kat was a revelation. She was difficult, and the movie argued that being difficult was actually fine.
The supporting cast was secretly stacked
- Joseph Gordon-Levitt: Before he was an indie darling, he was the sweet, slightly desperate Cameron James.
- Larisa Oleynik: Fresh off The Secret World of Alex Mack, she played Bianca with more depth than the typical "spoiled sister" archetype.
- Gabrielle Union: This was one of her first big roles, playing Chastity, the quintessential popular-best-friend.
- Allison Janney: Her portrayal of Ms. Perky, the erotic-novel-writing guidance counselor, is arguably the funniest part of the entire script.
The "10 Things" poem is a factual piece of film history
Everyone remembers the scene. Kat stands at the front of the class and reads her poem. It’s the emotional climax of the 10 Things I Hate About You movie. What people often get wrong is the idea that the scene was heavily rehearsed or faked.
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It wasn't.
Julia Stiles actually broke down in tears during the first take. It wasn't in the script for her to cry. That raw, shaky-voiced delivery was her reacting to the material in the moment. The director, Gil Junger, kept it because it was too real to cut. It’s the pivot point of the film—the moment Kat admits that despite all her defenses and her "shrewish" exterior, she’s just as vulnerable as anyone else.
The poem itself is actually based on a real-life heartbreak. One of the screenwriters, Karen McCullah, had kept a diary in high school about a guy named Anthony she used to date. She had written a list titled "Things I Hate About Anthony." When she and Smith were brainstorming the script, they pulled that list out. "I hate the way you talk to me, and the way you cut your hair..." That’s real teenage angst from a 1980s diary turned into a 1999 cinematic milestone.
The soundtrack: A love letter to the PNW
The film is set in Seattle (specifically Tacoma, at the stunning Stadium High School), and the music reflects that perfectly. In an era dominated by boy bands and Britney Spears, this movie leaned hard into power-pop and ska-punk.
Letters to Cleo became synonymous with the film. Seeing Kay Hanley perform on the roof of the high school during the end credits is peak 90s. The soundtrack featured The Mighty Mighty Bosstones, Save Ferris, and Semisonic. It gave the film an edge. It felt like the kind of music Kat would actually listen to, which helped the world-building immensely.
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Common misconceptions and weird facts
People always argue about where the movie was filmed. It looks like a set, but Stadium High School is a real place in Tacoma, Washington. It was originally built as a luxury hotel in the late 1800s before a fire gutted it, and it was eventually converted into a school. That massive, castle-like architecture is 100% authentic.
Another thing: the paint-ball scene.
That wasn't faked with CGI or clever editing. Ledger and Stiles actually spent a day pelted with paint. If they look like they’re having a blast, it’s because they were. There was a genuine chemistry between them that didn't feel manufactured by a studio. They briefly dated in real life during the production, which probably explains why the tension in the "I'm semi-transparent" scene feels so electric.
The legacy of Kat Stratford’s feminism
In the 2020s, we talk a lot about "strong female leads," but Kat was doing it when the phrase barely existed in the zeitgeist. She was an intersectional thinker before it was a buzzword. She called out the "patriarchal values" of her school and refused to conform to the dating rituals that her sister Bianca lived for.
What makes her great is that she isn't perfect. She’s judgmental. She’s often mean to her sister. She’s hypocritical. But the 10 Things I Hate About You movie treats those flaws as part of being a teenager. It doesn't punish her for having an opinion; it just asks her to be open to the idea that not everyone is out to get her.
Actionable insights for your next rewatch
If you’re planning to dive back into this classic, keep a few things in mind to truly appreciate the craft:
- Watch the background: The "Padua High" world is incredibly detailed. The posters on the walls, the cliques in the courtyard—it’s a very specific snapshot of 1999 subcultures.
- Track the Shakespeare references: See how many lines you can find that are direct lifts or paraphrases from The Taming of the Shrew. (Hint: Look at the scene where Patrick is trying to figure out how to "woo" Kat).
- Focus on the parents: Larry Miller’s performance as the overprotective, "pregnancy-suit" obsessed father is a masterclass in comedic timing. His character arc—learning to trust his daughters—is the secret heart of the movie.
- Notice the lack of technology: There are no cell phones. No social media. The "news" of the school travels through physical interaction and handwritten notes. It adds a layer of intimacy that modern teen movies often struggle to replicate.
The 10 Things I Hate About You movie succeeds because it doesn't talk down to its audience. It assumes you know who Sylvia Plath is. It assumes you can handle a plot that involves a complex web of bribery and deception. It’s a smart movie about people trying to be smart, and that’s why it’s still the one we keep coming back to when everything else feels a bit too "plastic."