10 Things I Love About 10 Things I Hate About You

When it comes to teen rom-coms, there’s no shortage of films that pay homage to one William Shakespeare. Romeo + Juliet, Get Over It, and She’s the Man are just a few movies using the Bard’s source material to appeal to a new generation. Arguably, the best of these adaptations is 10 Things I Hate About You, a reimagining of Shakespeare’s The Taming of the Shrew. 

Released in the spring of 1999, the film introduced audiences to a crop of emerging new talent — from its pair of talented screenwriters Karen McCullah and Kirsten Smith to stars Julia Stiles and Heath Ledger. While it’s no shock the movie proved to be a success, what is surprising is just how endearing it continues to be over two decades later. There’s so much to like about this film and for this very reason I compiled a list of the 10 Things I Love About 10 Things I Hate About You.

Starting with:

1. The Cast

A large part of why 10 Things works as well as it does can be attributed to the spot-on casting. Every actor here is perfectly suited in their role, and there isn’t a false note in any of the performances. From David Krumholtz’s übergeek Michael to Larissa Oleynik’s bubbly Bianca, every character makes a lasting impression thanks to the solid acting.

For their first time in starring roles, Julia Stiles and Heath Ledger give Kat and Patrick plenty of natural charisma to make them worth rooting for as a pair and as individuals. Played by Stiles, Kat’s contempt for her peers never feels unjustified. She’s matched well by Ledger, who appeals to her not with bad boy brooding, but with playfulness and a wry sense of humor.

Even the supporting cast of adult actors — often the most one-dimensional characters in the teen genre — elevate the film. Walter Stratford may be comically overprotective, but Larry Miller plays him just grounded enough to make him a believable father. Playing the two most eccentric staff members at Padua High, Daryl Mitchell (the no-nonsense Mr. Morgan) and Allison Janney (counselor-turned-erotic-novelist Ms. Perky) make the most of their limited screen time.

2. The Chemistry

Alchemy can make or break a film and in the case of 10 Things, the (movie) stars aligned. The characters truly feel like a group of genuine friends rather than a carefully assembled crew for a studio feature. The palpable camaraderie amongst the actors translates to the film and makes the story that much more enjoyable.

In a retrospective interview with Vulture, David Krumholtz spoke to how well the cast got along, calling the experience, “the best summer of our lives … it’s that beautiful coalition of actors that audiences respond to most when watching 10 Things I Hate About You.”

These feelings were echoed by Gabrielle Union, who shared a throwback post of the actors gathered together on location: “Just a bunch of kids having the time of our lives … The best/coolest/most generous group of people to share my 1st film experience.” What’s not to love about that?

3. The Setting

While it would’ve been a safe move to follow in Clueless’ platform shoes and base the movie in California, the filmmakers opted to go north to Tacoma, Washington.

The entire movie was filmed using real locations and no soundstages. It makes for some appealing backdrops as a result, whether it’s Kat and Patrick’s paddle boating on Lake Union, Cameron and Bianca visiting the famous Fremont Troll sculpture, the Stratford's cute coastal home, or even Stadium High itself. Despite shooting in a state famous for its clouds, it never casts a shadow over the film.

4. The Soundtrack

If you’re going to base a movie near Seattle during the ’90s, your soundtrack better deliver and thankfully 10 Things doesn’t disappoint. The music runs the gamut of classic rock to ska-punk to frothy teen pop. In keeping with the film’s theme of presenting a strong female perspective, the soundtrack features lots of female-fronted acts including Joan Jett, Save Ferris, and most prominently, Letters to Cleo.

Far and away the best music moment arrives at the film’s conclusion when Letters to Cleo appear one final time to perform their cover of Cheap Trick’s “I Want You to Want Me” atop Padua High. Like the movie itself, the song works as a great update to its source material — adding just enough new elements (crunchy guitars and spirited lead vocals) to send the movie out on a high.

5. The Serenade

One of the most iconic scenes in the movie, Patrick’s stadium serenade to Kat is reason alone to justify 10 Things’ place in the Teen Rom-Com Hall of Fame. Taking a cue from Jerry O’Connell’s love proclamation in Scream 2, 10 Things ups the ante by adding a marching band as Patrick sings “Can’t Take My Eyes Off You” while evading arrest.

It’s a perfect showcase of Ledger’s strengths: effortless charm and a light comedic touch that makes even a potentially saccharine scene work.

6. The Fashion

Like the music and filming location, the fashion of 10 Things places it in a very specific, very ’90s time period. This is a movie where characters unironically like their Skechers and where Patrick makes the grandest of club entrances rocking the following shiny trousers to woo Kat:

There’s no denying the clothing dates the film, yet you can’t help but enjoy the style for what it was at the time. Sure, the school nerds dress like they're in their 40s and chunky flip flops rule the day, but it nevertheless remains an amusing time capsule of trends around the new millennium.

Although Bianca’s midriff prom dress was and forever will be a sin against the fashion gods, I still maintain Kat’s dress is a serve to this day.

7. The Writing

First-time screenwriters Karen McCulah and Kirsten Smith pack enough wit, charm, and laughs into their adaptation that it makes it easy to get swept up in the fun. The writers are wise enough not to talk down to their teenage characters and instead invest them with realistic motivations. In a time when so many female characters were often portrayed as cheerfully accommodating, Kat’s uncompromising nature was a breath of fresh air and made her an admirable heroine.

The script isn’t without a few clunkers (“Remove head from sphincter, then drive!”) but luckily these are few and far between the rest of the movie’s many quotable lines.

8. The Poem

Next to Patrick’s song-and-dance number, this is 10 Things' other most memorable scene, and for good reason. Rather than a quick kiss and make-up at prom, Kat channels all of her inner turmoil into a sonnet aimed at Patrick in the film’s penultimate scene.

The poem is teen angst to a T and yet nothing about it feels contrived. It’s touching to watch the guarded Kat show a rare moment of vulnerability over her heartbreak, and Stiles’ tearful delivery (shot in the first take) makes the scene even more impactful.

9. The Director

It’s hard to believe that 10 Things is the work of a newbie, but first-time film director Gil Junger does a terrific job bringing every element together. Given the fantastic script and actors onboard, Junger already had two key ingredients to make a successful movie, but his nimble touch behind the camera adds to the film’s quality. Junger knows he’s making a comedy and as a result, he keeps the pace quick and tone light.

In the 10 Things retrospective featurette, it’s revealed that Junger cast himself as a teacher and romantic prospect for Ms. Perky. To avoid slowing down the film’s pace, he humbly excised all of his scenes and found a much more subtle way to appear in the film.

It’s a bit of a bummer that Junger didn’t stick with his film directing career long after the success of his first feature, but given how high he set the bar with his debut it’s understandable why a follow-up may have proved too daunting.

10. The Legacy

A modest hit at the box office upon release, 10 Things has since gone on to gain a wide audience who consider it one of the best teen comedies of the late ’90s. It cemented its stars as charismatic leads and the film’s supporting cast of then-unknown actors went on to star in major motion pictures and TV series, too. The movie even spawned a short-lived spin-off series on ABC Family (though the less said about it the better). For many viewers, 10 Things served as an introduction to the late Heath Ledger and it’s a shining example of just how bright a performer he was from the start.

It may be well over 20 years since that first trip to Padua High, but to this day I still maintain two things: 

1. Bobby Ridgeway kicked himself in the balls. 

And most importantly: 

2. When it comes to 10 Things I don’t hate it, not even close, not even a little bit, not even at all.