Based on “The Taming of the Shrew,” the film centered on the Stratford girls, whose strict father won’t allow Bianca (Larisa Oleynik) to date until her older sister, Kat (Julia Stiles), does. The problem: Kat has no use for boys; she’s got her sights set on college. Hoping to go out with Bianca, new student Cameron James (Joseph Gordon-Levitt) hatches a convoluted plan to get Patrick Verona (Heath Ledger) to date the prickly Kat. Of course, drama, romance and a lot of awkward moments ensue.
What stands out 20 years later is the movie’s continued relevance — its Seattle teenagers debate sexual politics — as well as its status as a beloved teen comedy. Made for $11.2 million, “10 Things I Hate About You” was released March 31, 1999, and made instant stars out of Stiles, Gordon-Levitt and Ledger.
But things could have turned out differently because several actors you know could have ended up as the leads.
I recently spoke with the stars (including Gabrielle Union and David Krumholtz), director Gil Junger and others about casting near-misses, face-drawing and their memories of Ledger, who died of an accidental prescription-drug overdose in 2008. Here are edited excerpts from the conversations.
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KirstenSmith and Karen McCullah wrote the script at a time when teen rom-coms based on the classics were trending in Hollywood.
KIRSTEN SMITH: There was such a big teen movie explosion at the time. We were young writers who had never sold a script before, and it was very unusual you would get your first script made, let alone greenlit six months after it was optioned. It had this feeling all around of firsts.
JULIA STILES: I remember thinking (the screenplay) was so cool and I just loved the heart of Kat so much. I was dying to get the role. I had been reading “The Taming of the Shrew” in school, and it was the first time I had read a romantic comedy (script) that captured teenage angst in such a clever way.
LARISA OLEYNIK: I remember being pretty smitten with it right away. The script was unabashedly feminist and really of the riot grrrl era of the Pacific Northwest.
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Katie Holmes and Kate Hudson were among several performers up for leading roles. Even some of the final cast members originally wanted different parts.
MARCIA ROSS: (casting director) We screen-tested Josh Hartnett, Eliza Dushku, Heath and Julia. But Julia and Heath just had the best chemistry together. I loved Katie Holmes. She was about to get “Dawson’s Creek,” and we had to make a decision really fast. The other person I loved was Kate Hudson. But her mom (Goldie Hawn) didn’t like the script for her, so she passed.
JOSEPH GORDON-LEVITT: If I’m really honest, I didn’t want to do a high school romantic comedy. I wanted to do Sundance movies. I’m very lucky that five years later, I got to do that. The truth is, I was a naive or stuck-up 17-year-old.
OLEYNIK: I auditioned for both Kat and Bianca pretty much up until the very end, and I really wanted Kat. I think I was so obsessed with wanting to prove to them that that’s who I was, that by the time I’d get to the Bianca stuff, I’d be like, “Oh, yeah, sure, whatever.” And I’m sure that’s why it worked, because I was super-relaxed about it.
DAVID KRUMHOLTZ: (who played Michael, Cameron’s neurotic best friend) I wanted to play Cameron, but I had worked with Gil on a couple of TV projects, and he knew I could do Michael in my sleep, in the sense that you play a neurotic Jewish kid. I know that Joe wanted to play Michael.
GORDON-LEVITT: I auditioned both for Krumholtz’s part and my part, because I thought (Krumholtz’s part) was funny. Then (Gil) wanted me to play Cameron.
GABRIELLE UNION: (Chastity, Bianca’s pal) I was over 10 years older than my younger cast members, some of whom were still in high school. So, it was kind of like, how close is this to my high school years? Do I look crazy playing a 15-year-old? Don’t mention Earth Wind & Fire or give away your age.
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Heath Ledger thought he bombed his audition, but his star power was undeniable to everyone.
SMITH: (On) his audition tape, he wore a white suit with a black button-down shirt. He was really dressed up, very John Travolta “Saturday Night Fever.” It was a look that was rumpled and rock, but way more dressed up than anyone else was, which was badass because he could pull that off.
GIL JUNGER: Heath walked in, and I thought to myself, if this guy can read, I’m going to cast him. There was an energy to him, a sexuality that was palpable. When Heath was done, literally, with the first page, I said, “OK, you can put down the script. You’re doing great. I want to do a little improv with you.” I just wanted to see how fast his mind would adapt, comedically. After 35 seconds, I said, “OK. Fantastic.” But I could tell he was nervous that he blew it, because the audition was so quick, and I said, “No, no. you’re a very talented guy, and I really appreciate you coming in.” The instant the door closed, I turned to the women in the room and said, “Ladies, I have never wanted to sleep with a man, but if I had to sleep with a man, that would be the man. Please cast him immediately.”
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Ledger took creative control of the scene in which he woos Kat by singing “Can’t Take My Eyes Off You” from the bleachers at her soccer practice.
McCULLAH: The first song we had in the script was “I Think I Love You.” Then we decided on “I Touch Myself,” and I think Heath decided that that wasn’t romantic enough, so he chose the Frankie Valli song, which was a much better call.
JUNGER: I said to Heath, “Just run around the steps when the guards start to chase you.” Right after the first take, the nurse on set ran up to one of the guards. They were fearful he might have pushed himself almost to a heart attack. Heath was running with such joy that it physically exhausted the guards.
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Kat’s drunk table-dancing in a party scene would have career ramifications for Stiles.
STILES: I hadn’t ever really been drunk before in real life. I mean, I was 17, so I remember Heath — because he was older — giving me tips on what being drunk looks and feels like.
JUNGER: I was good friends with Paula Abdul, and I mentioned to Julia that I was going to have a big choreographer work with her and Julia said, “That’s fine, but I can dance.” I went against my normal instincts and trusted her.
STILES: I would never have the guts to do that now. I’m glad somebody got that on film. I mean I love dancing, but sort of provocatively on the table? I was pretty guileless at that point. I also have heard that that is what got me the part in “Save the Last Dance.” The director said to me that he had seen that scene, then realized that I could do hip-hop, not just ballet.
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Andrew Keegan, who played the wealthy bully, needed help for a scene involving an obscene drawing.
MCCULLAH: That scene came from a friend of mine from college. He passed out and his roommates drew a (penis) on his face, and then he got up and walked across the street to a 7-Eleven without knowing.
ANDREW KEEGAN: Quite frankly, I did not know how to draw (a penis) on someone’s face, and I believe David was the one that helped creatively with that.
KRUMHOLTZ: I had to teach Andrew. I sat him down and we rehearsed. In a way, I kind of conducted my own penis-drawing on my face.
KEEGAN: I have heard about that scene for my whole adult life, so I think I did a pretty good job.
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During the most heartfelt scene in the movie, in which Kat reads the titular poem to Patrick, Stiles went off-script and cried.
STILES: It had been such an emotional role and such a wonderful experience that I was overjoyed, and probably sad it was coming to an end, but I also was just in a very raw place.
JUNGER: Basically, the whole speech was one shot.
STILES: I remember Heath, when they turned around to do his reaction shot, he said something like, “I don’t need to do anything because this isn’t about me.” A lot of times you get one actor crying in a scene and the other actor feels like they have to cry, and he knew to be sort of restrained. I thought that was really cool.
JUNGER: I did everything I could to cover my mouth and nose because I was crying so hard. It was such an amazing performance. That take (in the film) is the first take. I think I jumped up and just hugged her for the longest time.
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In the final scene, Letters to Cleo performs on the rooftop of Padua High School, but the crew didn’t have permission to shoot there.
JUNGER: Disney said they loved the work I was doing but couldn’t justify spending that much money for one shot. And then when the line producer said to me, “What did they say?” I don’t know what the hell it was, but some instinct in me said, “They said yes. Shoot it.”
ANDREW LAZAR: (producer) It was so complicated, and we had a helicopter.
JUNGER: I was flying in the helicopter, and I said to the pilot, “Charge ’em.” And he flew right over (Letters to Cleo).
KAY HANLEY: (Letters to Cleo lead singer) We’re all arranged on top of this postage-stamp-sized roof with chicken wire the only thing protecting us from toppling to our deaths into the Puget Sound. The music starts playing (and) we start pretending we’re in a music video. We hear the whir of a chopper right above us, and then it divebombs us. We did two takes, and it was pretty much assumed that this shot wasn’t going to work, and Gil would never work in Hollywood again because he had just blown through half a million dollars doing this shot he was forbidden to do. And it ended up being a pretty iconic scene.
JUNGER:Kay was (exhilarated). She said, “Do you have any idea how scared I was?”
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The cast recalls the shoot as one of the best times of their lives, but they wish Ledger was here to celebrate the anniversary.
OLEYNIK: It’s projecting a fantasy of a high school experience, but it’s also grounded in what most 17-year-olds are still feeling, what I’m still feeling as a 37-year-old.
GORDON-LEVITT: I feel like the sheer closeness that we all had that summer is a big part of why people like that movie, because it wasn’t fake. I spent all summer laughing at (Krumholtz) and slowly starting to talk like him. By the end of that summer, everybody talked like an old Jewish man from Queens because of Krumholtz.
KRUMHOLTZ: You know, people still say, “I have a (penis) on my face, don’t I?” And I have to be like hey, you got me. It’s haunted me for the rest of my life. It’s wonderful.
STILES: It was a really fun summer. There wasn’t a mean person in the bunch. I remember (Heath) played the didgeridoo, which was the first time I had even been introduced to that.
KRUMHOLTZ: It always makes me swallow hard when I know that something I say about Heath is going to be put out there. My clique was Heath and his lovely assistant and best friend, Trevor (DiCarlo). I loved Heath. As I get older, and as the movie takes on greater relevance with new audiences, it’s harder to wrap my head around the idea that Heath passed on the way he did. I would’ve very much loved him to be part of this article, to feel appreciated for his work in the film, because he worked really hard on “10 Things I Hate About You.”
UNION: Heath had the ability to look at you, and (make) you feel like Princess Diana. In a very crowded Hollywood landscape, he could make you feel special and seen. That’s a pretty special gift, and I don’t think it’s talked about enough.
KRUMHOLTZ:Toward the end of his life I reunited with him, at a time when we were both quite vulnerable and trying to recover from some stuff that was haunting us. I had an opportunity to tell Heath how much I loved him and to sort of try to help Heath. He had become so famous, and his life had become so crazy, that in the moment when I could’ve said something, I didn’t, even though I thought it. It’s a big regret I have. To fans, he’s a movie star that died. To me, he was flesh and bone, soulful, sweet, and I know for a fact he was in recovery prior to his death. He was trying to get healthy.
I just want people to know there was a suffering individual there, who couldn’t have been a lovelier human being. I prefer to remember Heath as a 20-year-old kid doing his first American lead with a big giant Cheshire grin smile on his face, taking charge as the leader of the group like any good ensemble leader should.
This article originally appeared in The New York Times.