20 years ago in the shadow of Y2K anxiety, an unassuming movie set at a high school in Tacoma, Washington opened the same day as “The Matrix.” This was an era before e-mail, when alt-rock was a thing, riot grrls haunted record stores and, pace John Hughes, getting into college was more important than getting a prom date. The film’s rookie screenwriters—one in Los Angeles, the other in Denver—collaborated via snail mail on a feminist refresh of a Shakespeare play considered problematic for its misogyny.
Inspired by The Taming of the Shrew, “10 Things I Hate About You” featured an ensemble of mostly teen-age actors. It was the big-screen breakthrough for TV stars Joseph Gordon-Levitt, Larisa Oleynik, and Gabrielle Union, not to mention relative newcomer Julia Stiles and relative unknown Australian TV actor Heath Ledger. The dialogue was fresh as their faces, likewise the soundtrack featuring Semisonic, Letters to Cleo and Ledger’s rendition of Frankie Valli’s “Can’t Take My Eyes Off You” backed by a high-school marching band. The film had edge, but also heart.
This story about two sisters (Stiles, Oleynik) and two transfer students (Ledger, Gordon-Levitt), boasted fully realized conformist and nonconformist characters rather than the preppy versus punk archetypes then in currency. Given its gender balance and story, the film couldn’t be pigeonholed as a chick flick or bro-pic. It struck a nerve and the funnybone of a broad spectrum of moviegoers, from 13-year-old teens to tenured literature professors to theater parodists currently performing an unauthorized tribute in LA.
Kirsten Smith, screenwriter: In 1996 I was in Los Angeles working at CineTel, reading scripts and query letters. I answered a query from Karen McCullah, requesting sample scripts.
Karen McCullah, screenwriter: I was in Denver, writing scripts and working as a freelance publicist for an environmental nonprofit. I came out to LA and had drinks with Kirsten. We started writing an unproduced screenplay on cocktail napkins. We were both fans of Amy Heckerling’s "Clueless," based on Jane Austen’s Emma.
Smith: We wanted to find a fairytale or fable or novel on which we could base a modern story. Someone suggested The Taming of the Shrew. In our version, of course, the shrew wouldn’t be tamed, she was too shrewd. We considered a gender-reversal, making the male lead the shrew before we concluded that all high school guys are shrews. We sent each other drafts by mail. It took about a year. We wrote Kat as the kind of character we wanted to see, an indie rock riot grrl. I was into that at the time.
We went to Sundance in 1997 and circulated the script, but it didn’t take flight.
McCullah: It landed at Disney, which wanted to make one teen movie that year. Its choice was between "10 Things" and a script called "School Slut." We did another rewrite, then they greenlit the movie. Still, Disney asked why Kat was so angry.
Smith: All teenagers are angry.
Gil Junger Emmy-nominated TV director who made his feature debut with "10 Things": I was very much taken with the script. Its tone was smart, uniquely intelligent and funny. Casting wasn’t an easy process.
Andrew Keegan, star of "Camp Nowhere" and TV’s "Party of Five," cast as Joey: As a young actor, I was so thrilled by the prospect of playing Shakespeare! I remember Joseph Gordon-Levitt (star of NBC’s "Third Rock from the Sun") and I were among the first people cast.
Julia Stiles, Kat: I had been reading The Taming of the Shrew in exactly that year. So, yes, the adaptation really appealed to me. "10 Things" was my first big role. After a few years of auditioning but always being told I was too serious, getting hired to play Kat was a thrilling affirmation that maybe my seriousness was okay.
Larisa Oleynik, Bianca: There were many rounds of auditioning. I really wanted the part of Kat. Then I was asked to do a “chemistry” audition as Bianca opposite Julia Stiles’ Kat. Something felt right about it.
Junger: Most of the girls came in to audition wearing sexy clothes. Julia came in wearing baggy pants and a t-shirt, hair up in a bun. She wasn’t working the ‘look-how-pretty-I-am’ angle. When she shook my hand and looked into my eyes, I was struck by a depth and maturity. This, combined with her poise, was formidable.
Stiles: Kat was the first role I had read for a young woman that was so refreshingly feisty. I loved the script, especially because it had a healthy bite to it. For a romantic comedy to have a cynical sense of humor, but also be truly romantic, stood out at the time.
The director was close to the start of shoot and still didn’t have a male lead.
Junger: Marcia Ross, our casting guru, and her associates looked at about a thousand candidates. But I wasn’t going to cast the guy until I saw the guy. There were five casting women and me in the room when the next one walked in. It was Heath Ledger [then 18], and I felt as soon as he walked in, ‘If this guy can speak English I’ll cast him.’ Already he had the energy and that soulful sexuality of a movie star. I wanted to see how nimble he could be if I asked him to change tone with a few lines from the script. He was great. When he walked out the instant the door closed, we all knew.
By the time the magnificent seven arrived in Seattle in the summer of 1998, Gabrielle Union and David Krumholtz, respectively 25 and 20, eased into the roles of big sister and brother of the group; Ledger and Keegan were 19; Gordon-Levitt, Oleynik and Stiles were all 17, between their high school junior and senior years.
Junger: My mantra was, I’m not gonna to shoot a high school movie. I’m gonna shoot a movie about people in relationships who happen to be in high school.
Smith: Heath arrived a little later than the rest of the principal cast. When he did, he instantly became the group’s galvanizing leader.
Keegan: When Keith arrived at the hotel he was carrying a didgeridoo. Classic Australian.
Oleynik: The group had begun to gel by the time Heath came and became our ringleader. We didn’t want to be apart. It was like art camp. We were together both as a group and one-on-one. Julia was so cool and confident. David and Joey (Gordon-Levitt) got close right away. Joey, Julia and I talked about college. On lazy Saturdays I would go to Gabrielle’s room and we’d watch music videos. Andrew and I knew each other from the teen actor beat.
Keegan: It’s interesting to look back on this time before social media. We just hung out together. What happened on "10 Things" set, carried over to our off-screen relationships. You could talk to Heath about anything: He was wise beyond his years. David, Joey and Julia were all crazy Beastie Boys fans. Gabrielle was just the coolest. David and Joseph supplied the comic relief. Larisa was a delight. It sounds corny, but it was a magical experience.
Stiles: It was such a special summer and we were all so open-hearted. Each actor was excited to be there and not jaded or closed-off.
McCullah: Andrew Keegan had all these eight-year olds who knew him from TV, begging for his autograph.
Junger: When I shot the scene with David and Heath in the cafeteria, Heath fluffed a line. I took him aside and asked him if he was getting wasted. He replied, 'No. It’s just that they come knocking at the door at two in the morning." "Who?," I asked. “You know. Girls.” I’m telling you, there was a magnet in that kid. Another time, I said to him, you don’t know what’s going to hit you when this is released. He said, "Let’s not talk about that. Let’s talk about how I could be my best self today."
While many moviegoers might point to the moment at the prom when Bianca protects her date, Cameron (Gordon-Levitt), decking the conceited Joey with a wicked right hook before kneeing him in the crotch as a high point, the actress who played Bianca begs to disagree.
Oleynik: The best day on set had to be Heath singing “I Can’t Take My Eyes Off You” while dancing in the stadium bleachers. It could have been so cheesy, but it was sincere. I think all of us knew then that we had something special.
Junger: A high point was Julia’s recitation of the “10 Things” sonnet in front of her English class. She delivered it with such depth and pain—in just one take.
There are many reasons that "10 Things" enjoys such a robust afterlife. One is that it’s a coming-of-age movie in which not only the characters but also the actors playing them seem to be coming of age before our eyes. Another is that many high school and college professors use the film as a tool to better understand the Bard. Some say the movie eliminates the misogyny of the play.
Junger: It has aged well, largely because the script hits the truth of human emotions. Like Shakespeare.
Oleynik: These Shakespeare updates give students a way into the story.
Rebecca Munson, Shakespeare scholar, Project Manager for Princeton Center for Digital Humanities: The underlying question—can an independent-minded woman still pursue her own path if she’s romantically engaged—remains vital to today’s students. The tension between ambition and assertiveness, on the one hand, and the compromises required by romantic engagement, on the other, still apply, regardless of gender.
Katherine’s speech closing the Shakespeare play advocates, often with a wink, that wives obey husbands. Kat’s sonnet in the movie says, “I like you in spite of myself,” which isn’t incompatible with her pursuing her own goals and desires.