Image of Heath Ledger as Patrick and Julia Stiles as Kat in a scene from '10 Things I Hate About You.' They are both white teenagers sitting on steps staring into each others' eyes. Patrick has wavy, chin-length brown hair and is wearing a black tank top. His hair's pulled back into a short pony tail and there is green paint in his hairline. Kat has wavy blonde hair pulled up into a ponytail, and has various colors of paint in her hair. She's wearing a red shirt.

10 Things I Love About ’10 Things I Hate About You’ on Its 25th Anniversary

It’s been 25 years since 10 Things I Hate About You premiered on March 31, 1999. While teen movies can be hit or miss, 10 Things remains one of the best offerings in the genre, acting as a time capsule while also serving as a teen story that transcends generational boundaries.

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In honor of this 1999 teen classic starring Julia Stiles and Heath Ledger, here are 10 things I love about 10 Things I Hate About You.

10. It’s one of the best examples of a modern retelling of classic literature

In an era where there were high points like Clueless (a modern take on Jane Austen’s Emma) and low points like O (an Othello adaptation featuring Julia Stiles), 10 Things is a quality retelling that shows the relevance of The Taming of the Shrew to a young, modern audience.

People often treat The Taming of the Shrew as a challenge to feminism because of the way Katherine is “tamed” at the end. Theatrical productions often highlight this by having Katherine announce her own “taming” with a wink-wink, nudge-nudge.

However, that analysis is a disservice to the nuanced female character Shakespeare created. Shakespeare has written complicated roles before for female characters like Rosalind in As You Like It and Viola in Twelfth Night, and he gives Katherine a similarly complicated arc. Since women weren’t allowed to be on the stage, Shakespeare originally wrote these parts for men who expected meaty roles.

10 Things sees Kat Stratford (Stiles) finding the balance between being true to her values without putting up walls between herself and others. Patrick Verona (Ledger) finds this balance too, because vulnerability is something that all human beings should learn, no matter their gender. 10 Things captures something very close to what I think Shakespeare’s intended message was with The Taming of the Shrew in a way that is entertaining, funny, and poignant.

9. Julia Stiles’ performance

Julia Stiles reads 'The Bell Jar' in '10 Things I Hate About You'.
(image: Buena Vista Pictures)

Stiles’ Kat became an avatar for all the smart, socially-conscious girls out there seeking a balance between asserting themselves and learning how to human properly. Stiles’ amazing performance delivered the kind of teen girl who was equally believable reading Sylvia Plath as she was rocking out at a ska show and dancing drunkenly on a table to Notorious B.I.G. While other teen movies delivered cookie-cutter stock characters, 10 Things allowed Stiles to deliver a teen girl character who was both relatable to many real-world teen girls, and also aspirational, with the strength and wit that so many of us wish we had.

8. The Heath Ledger of it all

Image of Heath Ledger as Patrick in '10 Things I Hate About You.' Patrick is a white teenage boy with chin-length, wavy brown hair. He's wearing a blue t-shirt and staring soulfully off camera.
(image: Buena Vista Pictures)

10 Things I Hate About You was the film that established Heath Ledger in the U.S. and gave an entire generation a new crush. Even then, you could tell he wasn’t any ordinary teen actor or child star. He brought a mature, grounded quality to this performance that stood apart from most male teen actors at the time. It made sense that this actor, who seemed so completely secure in his skin and wise beyond his years, could believably play a young man unthreatened by an outspoken young woman. A character who is actually drawn to strong women. Not only was Ledger’s performance amazing, but his Patrick Verona filled many teens with the hope that they wouldn’t have to dampen down their intelligence or tone down their enthusiasm to find someone who’d appreciate exactly that about them.

7. Iconic Moment #1: Patrick Serenades Kat

Singing “Happy Birthday” aside (which is always excruciating for everyone), few can resist the charms of an earnest, well-performed serenade. And few movie serenades have the earnestness and the charm of Patrick singing “Can’t Take My Eyes Off of You” to Kat on the Padua High football field.

From selecting a classic song instead of a trendy jam to enthusiastically continuing the performance while being pursued by security guards, Patrick delivers a perfect expression of affection for an unconventional girl like Kat.

6. The star-studded young cast

Image of Gabrielle Union as Chastity, Joseph Gordon-Levitt as Cameron, and Larisa Oleynik as Bianca in '10 Things I Hate About You.' Chastity is a Black teenage girl with shoulder length straight hair wearing a patterned tank top and sunglasses on her head. Bianca is a white teenage girl with shoulder length red hair wearing a white sundress and holding a binder to her chest as they walk. Walking behind them, Cameron is a white teenage boy with short dark hair wearing an open green buttondown over a maroon t-shirt.
(image: Buena Vista Pictures)

The 10 Things cast was stacked with young actors who were Having a Moment, many of whom went on to have huge careers: Joseph Gordon-Levitt (Cameron), who became the go-to guy for directors doing weird genre stuff; Alex Mack herself, Larisa Oleynik (Bianca); Gabrielle Union (Chastity), who could probably still play teenagers in her 50s, if she wanted to; David Krumoltz (Michael), recently in Oppenheimer; and Andrew Keegan (Joey), who was the go-to guy for early Aughts Shakespearean adaptations, are some familiar faces who had one of their biggest hits with this movie.

5. The star-studded older supporting cast

Image of Allison Janney as Ms. Perky in '10 Things I Hate About You.' She is a white woman with curly brown hair sitting at a desk in her office wearing pearls, a pink knit suit, and holding a mug with a cat on it.
(image: Buena Vista Pictures)

Not only were the teen actors in the film great, but 10 Things made great use of some established comedic actors in the supporting adult roles. The most iconic, of course, was Allison Janney as Ms. Perky, the most inappropriate guidance counselor of all time who works on writing her romance novel during school hours. Larry Miller was both bonkers and loving as Kat and Bianca’s overprotective obstetrician dad, Walter. David Leisure and Daryl Mitchell rounded out the cast as two of Padua High’s teachers.

4. The women-penned script

Julia Stiles and Larissa Oleynik in '10 Things I Hate About You'.
(image: Buena Vista Pictures)

The Taming of the Shrew can be a complicated play to discuss in a feminist way. 10 Things screenwriters Karen McCullah and Kirsten Smith (Legally Blonde, She’s the Man) adapted the Shakespeare play in a way that treats teen girls with respect by giving them well-rounded personalities and opportunities for growth and change.

Meanwhile, the boys are written in a way that examines how boys and girls do interact and how they should interact. In Patrick, Cameron, and Michael, we see boys who genuinely like and respect their love interests, trying to meet them on their terms, even as their hormones rage and they make mistakes. It’s a marked difference from Joey, who is self-involved and treats girlfriends like accessories instead of people.

3. Gil Junger’s direction

Would I love to see a woman director’s take on this story? Sure. But Junger did an amazing job, and it’s clear from his extensive comedic resume (he directed episodes of Blossom, Living Single, Ellen, Dharma & Greg, and The Hughleys) that he’s comfortable with directing stories outside his personal experience with compassion and nuance.

2. The iconic soundtrack

10 Things has one of the best movie soundtracks ever, featuring beloved ’90s bands like Sister Hazel, Semisonic, Save Ferris, and two great covers by Letters to Cleo: “Cruel to be Kind” (in the video above) and “I Want You to Want Me.”

1. Iconic Moment #2: Kat’s Poem

Watching Kat not only be brave enough to write a poem expressing feelings she could barely admit to, but brave enough to read it out loud, was freaking epic and a perfect way to show that this “shrew” wasn’t “tamed.” She simply evolved.

Also, the end credits? Iconic.

10 Things I Hate About You is currently streaming on Hulu, and is available to rent and buy everywhere films are available.

(featured image: Buena Vista Pictures)


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Author
Teresa Jusino
Teresa Jusino (she/her) is a native New Yorker and a proud Puerto Rican, Jewish, bisexual woman with ADHD. She's been writing professionally since 2010 and was a former TMS assistant editor from 2015-18. Now, she's back as a contributing writer. When not writing about pop culture, she's writing screenplays and is the creator of your future favorite genre show. Teresa lives in L.A. with her brilliant wife. Her other great loves include: Star Trek, The Last of Us, anything by Brian K. Vaughan, and her Level 5 android Paladin named Lal.