'10 Things I Hate About You' Turns 20. NYT has an interview with the cast looking back

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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 on March 31, 1999, and made instant stars out of Stiles, Gordon-Levitt and Ledger.

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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 naïve or stuck-up 17-year-old.

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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, “O.K., 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, “O.K. 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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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.

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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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