“How do I love thee? Let me count the ways.” The Class of 1999 continues with the 20th anniversary of 10 Things I Hate About You, arguably the class valedictorian of a slew of teen films released in 1999 that defined a generation and managed to sustain the test of time. There is no denying entertainment factor of films such as Varsity Blues, She’s All That or Cruel Intentions but 10 Things seems cut from the whip-smart cloth that has made 1995’s Clueless such an enduring hit. With top-notch writing and a compulsively likable ensemble cast, 10 Things I Hate About You represents the 90s teen comedy at its best. In honor of its 20th anniversary, I shall break down some fun facts about the film in the style of 10 Things with a very special 20 edition.

1. 10 Things I Hate About You is a loose modernization of William Shakespeare’s late-16th-century comedy The Taming of the Shrew, retold in a 1990s high school setting. The modern version 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.
2. The film made stars out of most of its cast, who were just breaking out at the time but some the lead roles nearly went to other performers. Katie Holmes and Kate Hudson were among several performers up for leading roles. Even some of the final cast members originally wanted different parts. Katie Holmes was about to get Dawson’s Creek at the time of casting according to casting director Marcia Ross and she personally loved her for a role but she was ultimately lost in the shuffle. Kate Hudson was also up for 10 Things but Ross says her mom, Goldie Hawn, told her not to do the movie. Eliza Dushku and Josh Hartnett also screen-tested for Kat and Patrick but it all came down to the chemistry between Julia Stiles and Heath Ledger, who popped right away together. Patrick wasn’t intended to be Australian but it was written in to accommodate Ledger and allow him to display his natural charisma. Joseph Gordon-Levitt had no interest in doing a teen rom-com, even at 17 because he described himself as “a naïve or stuck-up 17-year-old” and wanted to do Sundance movies. He has ultimately called the film one of the best experiences of his life. Larisa Oleynik auditioned for both Kat and Bianca, the latter role she ultimately received. She wanted to prove she could be a Kat but understands why her personality made her more suited for Bianca. David Krumholtz, who played Michael, auditioned for Cameron (the role that went to Gordon-Levitt) and Levitt actually wanted to play Michael at first because he thought the role was funnier. Krumholtz had worked with the director Gil Junger on a few TV projects before 10 Things and Junger thought Krumholtz was better for Michael.
3. Speaking of the cast, the eternally young Gabrielle Union, who plays Bianca’s friend Chastity, was 10 years older than most of her fellow cast members, in fact, some of them were still in high school themselves. Union felt weird at first being so much older than the cast, but everyone clicked so well that age wasn’t even a factor when the shooting began.
4. Kirsten Smith and Karen McCullah wrote the script at a time when teen rom-coms based on classics were trending in Hollywood. They described the writing and coming together of the project as a sort of perfect storm where timing was everything. They 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.
5. The late Heath Ledger thought he bombed his initial audition. Ledger wore a white suit with a black button-down shirt. He was really dressed up, very John Travolta in Saturday Night Fever. It was a look that was rumpled and rock, but way more dressed up than anyone else was according to Kirsten Smith. Director Gil Junger thought if this guy can read the part he’s going to get it because his natural charisma was undeniable. The audition was quick, with Ledger doing lines from the script and a bit of improv and then he was asked to leave. Ledger thought he bombed because he wasn’t in the room long. Gil Junger says “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.”
6. It’s often believed that Ledger looked down on the film after it was released because he never took on another role in a teen rom-com but this was simply not the case. Many of the cast members, who remained in contact with him until his untimely death, say Ledger was very appreciative of the film and the only reason he didn’t do another role like this because he was always evolving as an artist and simply didn’t want to repeat himself. 10 Things was his big break and he knew it was the vehicle that got him started in the industry.
7. Andrew Keegan, who played Joey Donner, needed some artistic help with a certain drawing that made it into the film. The scene in question is when Keegan draws a penis on Krumholtz’s face. The moment came from a real-life college experience for writer Karen McCullah. Her friend 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. Keegan didn’t know how to draw a penis on someone’s face so Krumholtz had to instruct him on the matter with several drawing rehearsals on a piece of paper before the actual take.
8. Heath 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. The original songs chosen were “I Think I Love You” or “I Touch Myself” but Ledger didn’t think they were romantic enough according to writer Karen McCullah. Ledger ultimately chose “Can’t Take My Eyes Off You” which proved to be the right choice.
9. Julia Stiles’ table dancing to “Hypnotize” by Biggie Smalls is what got her the role in Save The Last Dance. Stiles says that she didn’t know how to act or dance drunk since she was only 17 but since Ledger was older, she asked him for tips and a lot of his suggestions are what made it on screen. As for the dance, Gil Junger was going to bring in a choreographer but Stiles insisted she could move and Junger went against his judgment and trusted her and rightfully so because the moment was an iconic one for Stiles because it was all natural. The director of Save The Last Dance said he wanted her for that film after seeing that scene because she could dance to hip-hop.
10. During the most heartfelt scene in the movie, in which Kat reads the titular poem to Patrick, Stiles went off-script and cried. This is probably one of the signature scenes of the movie and while Stiles didn’t change any of the lines, she wasn’t directed to cry and it’s just something that happened, a moment the director went with. The scene was shot towards the end of filming and Stiles was just emotional that this great experience was coming to an end, which is why her emotions were so heightened by the time she got to it. The whole speech ended up being one shot and while they needed reaction shots from Ledger, he insisted the moment was about her and didn’t want to take away from it by also coming off too emotional.
11. The entire film was shot using real locations and no sets were used. The filmmakers wanted an authentic look for the atmosphere and the high school setting so it was decided to shoot using only real locations. The school used in the film is Stadium High School located in Tacoma, Washington. The house that was used in the film for Bianca, Kat and their father still stands in Tacoma, Washington. Both the interior and exterior of the house were used in the film.
12. 10 Things I Hate About You is a very creative title and it comes from a diary entry that writer Karen McCullah made in high school. She explained “I had a boyfriend named Anthony that I was frequently unhappy with. I made a list called Things I Hate About Anthony. When Kirsten Smith and I decided to write this, I went through all of my high school diaries to bone up on the angsty memories, and when I told her about that list, she was like, “That’s our title.” Anthony and McCullah are actually still friends and he’s proud that he helped influence the name of the movie.
13. Gil Junger initially didn’t want to direct the film. His agent gave him the script and he said he didn’t want to do a “typical teen movie.” He wanted to do a romantic love story but his agent pushed him to read it and he was surprised by how much he loved it and how grounded the script was.
14. 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. Disney loved the work that Junger was doing but couldn’t justify spending that much money for just one shot. Junger lied to the line producer and said they had permission to go ahead and shoot the scene. Letters to Cleo lead singer Kay Hanley says that they were arranged on top of a postage-stamp-sized roof with chicken wire the only thing protecting them from toppling to their deaths into the Puget Sound. The music starts playing and they start pretending they’re in a music video. They did it in two takes and while Junger though he would be blasted for doing the scene without proper permission, it has become an iconic part of the film that most fans remember fondly.
15. The film was released to better critical reception than most of its 1990’s teen movie counterparts. The film is 66% fresh on Rotten Tomatoes with a consensus that reads: “Julia Stiles and Heath Ledger add strong performances to an unexpectedly clever script, elevating 10 Things (slightly) above typical teen fare.” In the years since its release, Entertainment Weekly listed the film at #49 on its list of Best High School Movies.
16. The film was released on the same weekend as The Matrix on March 31, 1999. The film placed second behind The Matrix at the box office on its opening weekend with $8.3 million. The people behind the film joke that they wonder what people saw that weekend but were happy the film found an audience despite the competition. The film ultimately grossed $38.1 million at the domestic box office and $53.5 million worldwide off of an $11.2 million budget.
17. The cast went on to great success after 10 Things, working consistently in the industry since the film’s release. Julia Stiles went on to other box office hits such as Save The Last Dance and the Bourne films while Ledger achieved greatness in a short time before his death due to roles in Brokeback Mountain and The Dark Knight, the latter of which earned him a posthumous Oscar for Best Supporting Actor. Joseph Gordon-Levitt went on to star in such films as Inception, Looper, The Dark Knight Rises and (500) Days of Summer while Gabrielle Union went on to such projects as Bring It On, Bad Boys II and Think Like A Man. Larisa Oleynik, David Krumholtz, and Andrew Keegan have continued to work on various television projects.
18. Behind the scenes, writers Kirsten Smith and Karen McCullah went on to write Legally Blonde, The House Bunny, She’s The Man and The Ugly Truth. The duo continues to be writing partners still today.
19. The cast had remained very close over the years and say it’s one of the rare Hollywood experiences where everyone still feels like family although they wish that Heath Ledger could still be with them to celebrate 20 years later. Gordon-Levitt says “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 has added “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 experience, to feel appreciated for his work in the film because he worked really hard on 10 Things I Hate About You. At the end of the day, the whole cast and crew agree he was the ensemble letter of that cast.
20. The last fun fact comes from me. 10 Things I Hate About You stands up 20 years later not only because it’s funny and sweet but because it presents characters that are real and don’t talk down to the audience. The best teen films make their characters grounded in reality, where even the caricatures of the high school experience have a bit of depth. 10 Things was able to accomplish these feats and because of this, it broke into the pop culture landscape and has managed to entertain not only my generation but those who are currently in high school today. Like the John Hughes teen films of the 80s, 10 Things I Hate About You is as timeless as the Shakespeare play that inspired it.