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Debuting on March 31, 1999, the high school romantic comedy 10 Things I Hate About You graced theaters and garnered a worldwide box office total of $53.4 million. This film marked Heath Ledger's first major American role and propelled Julia Stiles into the spotlight. Inspired by Shakespeare’s The Taming of the Shrew, the story revolves around sisters Kat and Bianca as they navigate high school romance. Bianca (Larisa Oleynik) is forbidden to date unless her older sister Kat (Stiles) does, leading Joey Donner (Andrew Keegan) to hire Patrick Verona (Ledger) to woo Kat. Initially, Kat despises Patrick, but love blossoms between them. The screenplay, crafted by Karen McCullah and Kirsten Smith, who later wrote Legally Blonde and The House Bunny, was directed by Gil Junger. The soundtrack featured tracks from the rock band Letters to Cleo. Here are 10 fascinating facts about this iconic late ’90s teen movie.
1. THE TITLE WAS INSPIRED BY SCREENWRITER KAREN MCCULLAH’S HIGH SCHOOL ROMANCE.
In a Q&A session, Karen McCullah shared the origin of the film’s title. “It stems from a diary entry I wrote in high school,” she revealed. “I had a boyfriend named Anthony who often frustrated me, so I made a list titled Things I Hate About Anthony. While working on the script, I revisited my old diaries for inspiration, and when I mentioned the list to Kirsten [Smith], she immediately said, ‘That’s our title.’”
Her ex-boyfriend, it seems, is a fan of the film. “Anthony takes great pride in that,” McCullah shared. “We’ve remained friends over the years. Occasionally, I’ll receive a late-night call: ‘My nephew won’t believe the title is about me. Tell him.’ I’ll respond, ‘Yes, I really disliked Anthony back in high school.’”
2. DIRECTOR GIL JUNGER INITIALLY DECLINED THE PROJECT, UNINTERESTED IN DIRECTING A “TYPICAL HIGH SCHOOL FILM.”
When Gil Junger’s agent handed him the script for a teen adaptation of The Taming of the Shrew, he initially refused. “I said ‘no way,’” Junger revealed in the film’s production notes. “I had no desire to make a run-of-the-mill high school movie. I wanted to create a heartfelt romantic tale. However, after my agent insisted, I read the script and was captivated. Its depth surprised me. It’s truly a romantic love story, with a cleverly woven plot and humor that stems naturally from the characters.”
3. HEATH LEDGER BROUGHT A TOUCH OF “EDGE” TO HIS ROLE AS PATRICK.
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Patrick Verona marked Heath Ledger’s debut in Hollywood. “There were some worries about Heath’s Australian accent, but I argued, ‘Why? It adds to his intrigue, mystery, and charm,’” Junger remarked. The character of Patrick draws inspiration from Petruchio in The Taming of the Shrew. “I borrowed elements from Richard Burton’s portrayal in the famous adaptation of The Taming of the Shrew, but my Patrick also carries a Jack Nicholson-like edge with his playful smirks and charisma,” Ledger explained.
4. DAVID KRUMHOLTZ BELIEVES THE FILM’S SUCCESS STEMS FROM THE CAST’S AUTHENTIC BOND.
David Krumholtz, who portrayed Michael, shared his thoughts in a Vulture article, crediting the film’s success to the cast’s instant camaraderie. “Joseph Gordon-Levitt introduced me to Phish, and I got him into Wu-Tang,” he wrote. “Gabrielle Union kept us laughing, Julia Stiles brought her unique SoHo-inspired intellect (at just 17), Larisa Oleynik’s laughter lit up the set, and we were all in awe of Andrew Keegan’s impressive physique (he was such a good sport!).”
Filming started without Ledger, and the cast was unsure how his arrival would affect the group dynamic. “Those concerns vanished a few days later when he joined us and instantly became part of the team. With Heath, the group’s bond only grew stronger. Before long, we realized we had something rare: a cast with perfect chemistry, free of any negativity. We all agreed it was the best summer of our lives.”
5. JULIA STILES SHED REAL TEARS WHILE PERFORMING HER POEM.
In the film's final scene, set in a classroom, Kat recites a poem detailing her grievances against Patrick, only to break down in tears as she confesses she doesn’t hate him, “Not even a little bit, not even at all.” Speaking to Cosmopolitan, she revealed those tears were unplanned. “I knew I needed to show some emotion, as during the table read, I merely recited the poem, which felt as mundane as reading a phone book,” Stiles shared. “However, during filming, I unexpectedly started crying. I’m unsure if it was due to personal circumstances or the overwhelming experience of starring in my first major film.”
6. ANDREW KEEGAN STRUGGLED WITH DRAWING GENITALS.
In a memorable scene, Krumholtz’s character approaches Keegan’s and persuades him to pay Patrick to date Kat. During their conversation, Joey impulsively grabs a marker and sketches a penis on his face. “I recall having to instruct Andrew Keegan on how to properly draw a d*ck on my face, which was an odd experience,” Krumholtz mentioned to The Huffington Post.
7. LETTERS TO CLEO WAS FRIGHTENED BY THE HELICOPTER SHOT.
The band makes a few appearances in the movie, including a rooftop performance where they sing their rendition of Cheap Trick’s “I Want You to Want Me.” Lead vocalist Kay Hanley told Popdose that the scene was nerve-wracking. They had to perform on a small section of the roof, comparable to the size of Hanley’s kitchen, amidst windy conditions.
“They informed us, ‘This helicopter shot costs $500,000 each time it takes off, so don’t mess it up!’” Hanley remembered. “As we began playing, we noticed the helicopter in the distance. It was hard to gauge how far it was initially, given our altitude. Suddenly, the helicopter dove straight toward us! Was it out of control? Was this part of the plan? All I could think was, ‘Don’t mess up, keep singing, it’s $500,000 per take.’ It was terrifying, but the final shot turned out incredible.”
8. THE MOVIE INSPIRED A SHORT-LIVED TV SERIES.
During the 2009-2010 season, ABC Family aired 21 episodes of a 10 Things I Hate About You TV adaptation. While Junger directed the pilot, Carter Covington developed the series. Covington chose to focus on the relationship between two sisters rather than strictly following the movie’s plot. “I adore the film, and I know many others do too,” Covington told The Futon Critic. “I was aware of the potential backlash, but I’ve always wanted to explore sibling dynamics, which are a goldmine for comedy.”
9. JUNGER CREATED A QUASI-SEQUEL, BUT IT REMAINS UNFINISHED.
Between 2012 and 2013, Junger wrote and directed 10 Things I Hate About Life, an unofficial follow-up to the original. “It’s about two ordinary people with seemingly perfect lives that have spiraled out of control,” he explained to Variety in 2012. “They meet at the same place, intending to end their lives, but their encounter is so awkward and humorous that they decide to delay their plans and part ways.”
Hayley Atwell was initially considered for the role, but Evan Rachel Wood ultimately secured the female lead. However, in 2014, the producers filed a lawsuit against Wood, seeking over $30 million after she withdrew from the unfinished project. Wood claimed production had halted in 2013, and the producers failed to compensate her as agreed.
10. JOSEPH GORDON-LEVITT BELIEVES THE MOVIE SURPASSES CITIZEN KANE.
During a 1999 appearance on The Daily Show to promote the film, Gordon-Levitt’s interview took an unexpected turn. When Jon Stewart inquired about the movie, Gordon-Levitt enthusiastically declared, “It’s the greatest film ever made. It will overshadow Citizen Kane.” He added, “Julia Stiles, who stars in it, is the finest actress of all time. Every actor in this film is among the top eight best in history.”
