"10 Things I Hate About You" is loosely based on Shakespeare's "The Taming of the Shrew."

The rom-com used many of the play's character names and put a modern twist on its plot.

The play, like the movie, centers on two very different sisters, and the younger, Bianca, can't get married until her strong-willed sister Katherine is wed.

Similarly, in "10 Things I Hate About You," the main plot is that Bianca can't date until her sister Kat does.

In addition to following the play's plot, "10 Things I Hate About You" has little details that connect it back to the source material.

For example, the location shifts from the Italian city of Padua to Padua High School, and the story follows the Stratford sisters — a nod to Shakespeare's hometown, Stratford-upon-Avon.

Patrick Verona's last name is also a nod to one of the settings in Shakespeare's "Romeo and Juliet." 

Along with these more subtle details, one of the film's characters, Mandella, is obsessed with Shakespeare and brings him up often. She even gets a Shakespearean "promposal" complete with a themed gown.  

"10 Things I Hate About You" was a launching point for actors Julia Stiles, Heath Ledger, Joseph Gordon-Levitt, and Gabrielle Union.

Stiles, who played Kat, went on to star in the teen classics "Save the Last Dance" and  "The Prince and Me," and she's well-known for her role in the "Bourne" franchise.

Ledger starred as Patrick Verona, and he became a legendary actor starring in "Brokeback Mountain" and "The Dark Knight," which earned him a posthumous Academy Award for best supporting actor after his death in 2008.

Gordon-Levitt played Cameron, and since then, he's starred in "500 Days of Summer," "Inception," and "The Dark Knight Rises."

Union, who played Chastity, is well-known for her work in other classic romantic comedies, such as "Bring It On" and "Love and Basketball."

Alongside the film's rising stars, Allison Janney played the school principal, Ms. Perky.

"10 Things I Hate About You" was released about five months before "The West Wing" premiered on NBC and catapulted Janney into superstardom as C.J. Cregg. 

Since then, Janney has worked on many successful projects, including CBS' "Mom" and the film  "I, Tonya," which landed her an Oscar.

In a 2019 interview with The New York Times, the film's casting director, Marcia Ross, said that Josh Hartnett, Eliza Dushku, Katie Holmes, and Kate Hudson were all considered for roles in "10 Things I Hate About You."

Ross even said that she "loved" Hudson's audition, but the actor ultimately passed on the role because her mother, Goldie Hawn, didn't think it was a good fit.

In one of the film's DVD extras, director Junger described the challenges he faced while casting Patrick Verona.

"He needed to be masculine without trying to be masculine. He needed to be smart, he needed to be removed, he needed to be unbelievably charming," Junger said. "A complicated role."

After seeing Ledger's audition, however, Junger said he knew the actor was "special" and that he would be a "movie star."

In a 2019 interview with Entertainment Weekly, Stiles said she was "desperate" to play Kat in the film.

"It was so refreshing to see a teenage girl who was so feisty," she told the publication. "I thought that the writers had a healthy dose of cynicism with their humor that you don't always find with teen romantic comedies."

In a 2015 interview with Cosmopolitan UK, Stiles said, "I'm so grateful to have been in that movie. It was my first big break, and such a fun part. I have so many good memories from filming, but I don't really like to watch it back."

She continued, "If you could imagine a home video of your 17-year-old self, broadcast for all the world to see, you might feel slightly uncomfortable, too. I was such a baby."

In a similar vein, the actor told People in 2019, "I usually just look away. I'm glad that people enjoyed it, and I'm glad that they're still talking about it. I don't take that for granted, but I look away pretty quickly."

"10 Things I Hate About You" was written by screenwriters Kirsten Smith and Karen McCullah, who got the idea for their film after seeing the success of "Clueless" a few years prior.

In 2015, McCullah told The Script Lab, "We knew we wanted to write a teen movie, and when 'Clueless' came out. We thought Amy Heckerling was a genius for contemporizing a classic, so we decided to try that as well."

"Clueless" was inspired by Jane Austen's "Emma," and that successful framework ultimately led McCullah and Smith to adapt "The Taming of the Shrew."

After "10 Things I Hate About You," the writing duo went on to create classic rom-coms like "Legally Blonde," "Ella Enchanted," "She's the Man," and "The House Bunny."

In 2019, the film's production staff told The New York Times that Ledger thought he "bombed" his audition for Patrick Verona. But the production team was totally dazzled by his "star power."

After the audition, Junger recalled saying to the women on the production team, "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."

Union was 26 when "10 Things I Hate About You" was released. In comparison, Oleynik was 17, Gordon-Levitt and Stiles were 18, and Ledger was 19. 

In the 2019 interview with The New York Times, Union said, "I was over 10 years older than my younger cast members, some of whom were still in high school. 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."

While talking about his acting career in a video for Vanity Fair in 2020, Gordon-Levitt said he was "not sold" on being a teenage romantic comedy.

But, he said, his agent encouraged him to try something different with his career. Ultimately, he said he was glad he took on the role, not only because of the film's success but also because of his experience on set. 

"The experience is actually what I love the most about that whole thing," he said. "Even if people didn't like the movie, we had such a good time. All of us hung out, all the time."

When Gordon-Levitt auditioned for the film, he tried out for both Cameron and Michael, and he was more interested in the latter at first. 

The actor told Vanity Fair that he "auditioned for both of those parts, and the director offered me the role of Cameron and I was like 'eeh.'"

"I remember having a meeting with them where I was like 'This doesn't make sense and that does make sense, and this feels cheesy and that feels cheesy,'" he continued. "And they listened, I think, to some of my ideas, but mostly I think I was probably just wrong and kind of being too serious about the whole thing."

During a 2016 interview with Andy Cohen on Bravo's "Watch What Happens Live," Union spoke about her favorite memory of working with the late Ledger.

She said that when she first met the Aussie actor, he was just a "mysterious 19-year-old."

"... He told me, and anyone else who was over 21, to go meet him up at the top of the bar, at the top of the hotel at this bar," she said. "And we walk in and he's just got this wild hair — and again he's 19 and he's got like a dad drink — and he gets up and he was just such a man and such a gentleman."

She went on to say that "the whole cast was a dream" and that they would hang out and eat dinner together while they were filming.

While trying to win Kat over, Ledger's character Patrick performs Frankie Valli's "Can't Take My Eyes Off You" in the school's stadium — and yes, it was really Ledger singing.

McCullah told The New York Times in 2019 that the number was originally supposed to be set to The Partridge Family's "I Think I Love You" or Divinyls' "I Touch Myself," and it was actually Ledger who proposed the Valli song.

In a 2017 interview with Vice, Smith said that Ledger also had his own costume ideas for the scene. 

"He was so specific about what he wanted to wear; it had to be this certain type of dark shirt with a precise fit," she said. "Oddly, it's kind of a nondescript ensemble when you actually watch the movie, but seeing him architect the costume as part of his preparation [to act] was so impressive, especially because he was only 19."

Built in the late 1800s, the real-life structure for the film's Padua High School was originally supposed to be a luxury hotel financed by the North Pacific Railroad Co. and the Tacoma Land Co.

But after the financial crash of 1893 and a fire a few years later, they had to abandon work on the project.

After sitting empty for years, the building opened as Tacoma High School in 1906 and was later renamed to honor its famed stadium, which is heavily featured in the film. 

Stadium High School, as it's now called, still operates today, and it even held a screening of "10 Things I Hate About You" in celebration of the film's 20th anniversary in 2019.

At the end of "10 Things I Hate About You," Kat cries while reading a poem she wrote about Patrick for English class.

In the 2015 interview with Cosmopolitan UK, Stiles described the emotional scene, saying, "I never expected that I was going to start crying. I don't know why I did, whether it connected to something going on at the time, or if I was just overwhelmed by the whole experience of making my first big movie." 

Junger told The New York Times that her performance also made him cry.

"I did everything I could to cover my mouth and nose because I was crying so hard. It was such an amazing performance," he said. "That take [in the film] is the first take. I think I jumped up and just hugged her for the longest time."

In addition to its star-studded cast, "10 Things I Hate About You" is also fondly remembered for its iconic soundtrack.

It was filled with classic 1990s hits, and throughout the film, the band Letters to Cleo was featured live in several scenes, including at the concert Kat attends and at the school prom.

In the final scene of the movie, Letters to Cleo performs a cover of Cheap Trick's "I Want You to Want Me" on the roof of Padua High School.

But Disney originally told the director that he couldn't do it because the shot would be too expensive. They also didn't have permission to film on the roof, but Junger decided to shoot it anyway. 

The band's lead singer, Kay Hanley, told The New York Times in 2019, "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."

She continued, "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."

The film continued to be successful with audiences throughout the 2000s, so ABC Family took advantage of its popularity and turned "10 Things I Hate About You" into a TV series.

The sitcom ran for one season and starred Lindsey Shaw, Meaghan Martin, Ethan Peck, Nicholas Braun, and Dana Davis.

Larry Miller even reprised his role as Kat and Bianca's father, Dr. Stratford. 

"10 Things I Hate About You" was filmed in Washington, and Seattle's tourism industry has taken advantage of the movie's cult following.

To celebrate the film's 20th anniversary in 2019, Seattle magazine published a "10 Things I Hate About You" dating guide that detailed all the filming locations fans can visit for real-life dates.

Among these spots are Lake Union, where Kat and Patrick went paddle-boating, the Fremont Troll, where Bianca and Cameron went to talk after school, and the Paramount Theatre, where the prom was held. 

The list also included Gas Works Park, but unfortunately, it doesn't really have a paintball course.

This story was originally published in August 2020 and most recently updated on September 30, 2025.