The premiere of “10 Things I Hate About You” on March 31, 1999, brought us Heath Ledger in one of his first movie roles, the phrase “Can you ever just be whelmed?” and one of the silliest teen comedies ever made. It was also one of the only major studio films to be shot in Seattle during the late 1990s. Seattle in 2019 is a vastly different place than it was in 1999, and with the rise of the digital era, being a teenager looks different, too. With that in mind, on the 20th anniversary of its release, we take a look back at “10 Things I Hate About You” — and the Seattle where it was filmed — to see how both have stood the test of time.

(Mark Nowlin / The Seattle Times)
(Mark Nowlin / The Seattle Times)

Not your average teen rom-com

Co-written by Karen McCullah and Kirsten Smith, and helmed by Gil Junger,  “10 Things I Hate About You” was conceived as a comedic adaptation of Shakespeare’s “The Taming of the Shrew” and it entered a crowded field of movies vying for the eyeballs of 13-year-olds.

1999 was a high point for teen-focused movies, with the release of movies like “She’s All That,” “Cruel Intentions,” “Election,” “Varsity Blues,” “American Pie,” and the only teen comedy about Watergate (really), the underrated Michelle Williams-Kirsten Dunst vehicle “Dick.” But, crucially, “10 Things I Hate About You” was the only one of these many teenage rom-coms filmed on location in Seattle. And if, like me, you were 11 years old in 1999 and lived in Seattle, that meant it was about to become your favorite movie.

If you haven’t seen it, the story is a classic marriage plot that holds up better than it perhaps deserves to: The Stratford sisters — Kat, angry, rebellious, and played by Julia Stiles; and Bianca, a popular and thirsty Larisa Oleynik — are forbidden to date by their overprotective OB/gyn father, who says that Bianca can date when Kat does, assuming this will never happen. This leads to a dating scam involving a cherubic, pining Joseph Gordon-Levitt; a young, smoldering Heath Ledger; and, somehow, David Krumholtz (aka Bernard in “The Santa Clause”). Because Shakespeare’s comedies end in marriage, you know where this is going, but then, you already did.

This movie’s strong suit is not its realism. This is a patently ridiculous film that takes place in a universe more like the one in “Art School Confidential” than anything John Hughes-adjacent. It’s set at an urban West Coast high school that boasts a vibrant cowboy community and a gang of sweater vest-clad future MBAs who go around casually saying things like, “That must be Nigel with the Brie.” (Maybe at Lakeside?)

I could go on. I won’t. Because, silliness aside, one element of “10 Things I Hate About You” that’s held up over time is its caustic protagonist: Julia Stiles’ Kat Stratford, an antiheroine long before Walter White, a girl who is moody and difficult and prone to feminist rants, who makes no apologies for who she is or what she feels, even when it’s inconvenient for someone else.

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Nerdy, flawed teenage boys are often the heroes of teen comedies — see everything Judd Apatow has ever touched — and in today’s content-choked golden age of television, smart girls are (blessedly) everywhere. But in 1999, even with the influx of movies about teenagers, they were not. Aside from the abruptly canceled “My So-Called Life,” “Daria” and maybe “Buffy the Vampire Slayer,” the media landscape of the ’90s and early ’00s wasn’t particularly interested in smart girls, instead zeroing in on blandly appealing girl-next-door types, without any messy opinions or feelings. With her copy of “The Bell Jar” and insistence on attending Sarah Lawrence, Kat Stratford was the exception to the rule.

A time capsule of pre-tech boom Seattle

And there’s another reason watching “10 Things I Hate About You” is also newly, surprisingly poignant in 2019. It was one thing to see my city on-screen when the movie first came out — my classmates and I sensed that Seattle, like the Velveteen Rabbit, had finally become real. It’s quite another to realize that the city captured in this movie is the Seattle where I grew up, and one that I didn’t think I would ever see again. If you spent any time at all in Seattle in the ’90s, you’ll see it in “10 Things I Hate About You.”

(Mark Nowlin / The Seattle Times)
(Mark Nowlin / The Seattle Times)

From the opening shot of downtown from Kerry Park that pans out to include the Seattle Parks Department’s signature rainbow amenities sign, the movie is like stepping into a perfectly preserved time capsule of Seattle in the late ’90s — one made all the more bittersweet for its inclusion of some dearly departed Old Seattle spots.

The “biker bar” visited by Ledger, Gordon-Levitt and Krumholtz is, of course, the now-shuttered Buckaroo Tavern, at North 42nd Street and Fremont Avenue North in Seattle. A family-owned watering hole on the border between Fremont and Phinney Ridge, the dive bar was known for its cheap beer and blinking neon cowboy sign. It closed in 2010. The space is now home to upscale bistro Le Coin.

Down the hill in the heart of Fremont, the bookstore where Stiles affectionately attacks Ledger with a copy of “The Feminine Mystique” is Fremont Place Book Co., a small, bright, well-stocked neighborhood bookshop that closed in 2011 after 23 years in business. “The Feminine Mystique” may not seem like much, but it reminded me of the many weekend afternoons I spent browsing the shelves there, a moment of nostalgia I did not expect from  a movie for teenagers released in 1999.

Seattle’s more obvious treasures are also used to beautiful effect, even if locals know the geography doesn’t quite line up. The Fremont Troll is employed as a casual meetup spot (I would never!), Gas Works Park becomes a paintball range (this has never happened), an absurdly glamorous prom venue combines both the Paramount Theatre and Century Ballroom (mine was at the train station).

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In a scene you could replicate today, Julia Stiles and Heath Ledger paddle-boat on Lake Union.
In a scene you could replicate today, Julia Stiles and Heath Ledger paddle-boat on Lake Union.

But the casually beautiful shot of the Aurora Bridge over Lake Union? That’s real. And, as one of my friends pointed out when I solicited memories of the movie, you really can go paddle-boating on Lake Union if you push off from the Center for Wooden Boats. All to say: We sort of do live in a romantic urban paradise. Of course they wanted to film here.

And they almost didn’t. At an anniversary screening in Los Angeles, producer Andrew Lazar said that the production had planned to film in Los Angeles, but when Lazar and director of photography Mark Irwin scouted Tacoma’s Stadium High School as a location, they decided to relocate the story to the Seattle area.

[Related | Why ‘10 Things I Hate About You’ holds a special place in the heart of this Stadium High School alum]

Watching the movie, it’s hard to imagine it set anywhere else, and that has as much to do with the soundtrack as the visuals. If locations like Buckaroo Tavern nudge the film toward nostalgia, the music is what pushes it over the edge.

Stiles’ character has a proclivity for “Thai food, feminist prose, and angry girl music of the indie rock persuasion,” and the soundtrack reflects this. It’s aged extremely well. “10 Things I Hate About You” features appearances from Letters to Cleo (one on the roof of Stadium High School!) and Save Ferris, the script references Bikini Kill and The Raincoats, and there’s a Gits poster in Stiles’ character’s bedroom.

As the bubble-gum pop of the late ’90s was just taking off (think: Britney Spears and boy bands), “10 Things I Hate About You” captured punk, the last moments of riotgrrrl, and the ska-inflected indie rock that followed. The movie even ends with a 17-year-old girl being given a guitar. It feels like a low-key love letter to the musical subcultures of the Pacific Northwest and their influences, and evidence of just how far into the mainstream the region’s reach really was.