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20 Secrets to Love From 10 Things I Hate About You

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“10 Things I Hate About You” With Heath Ledger: E! News Rewind

Remember the 1990s, when Shakespeare was all the rage?

Not that he’s ever gone out of style, but a slew of his most famous works made their way to the big screen during that decade, and on March 31, 1999—a banner year for teen rom-coms and scathing drama if there ever was one—the Bard was given an update for the ages in the form of 10 Things I Hate About You.

Based on The Taming of the Shrew, the scene shifts from Padua in northern Italy to Padua High School in Seattle to tell the tale of the Stratford sisters—the younger one, Bianca (Larisa Oleynik), who enjoys fitting in and being popular while the other, Katarina, or Kat (Julia Stiles), is totally over it and ready to go far away to college. Their protective single dad  Walter (Larry Miller), who as a gynecologist has seen far too much teen pregnancy, says that Bianca can’t date until Kat does. 

Bianca has two potential suitors: Cameron (Joseph Gordon-Levitt), a chivalrous sweetheart, and Joey (Andrew Keegan), a rich d-bag jock. Cameron and his nerdy but ballsy friend Michael (David Krumholtz) conspire with Joey to pay the mysterious and conveniently hunky Patrick Verona (Heath Ledger) to woo Kat, thinking that’ll clear the way to date Bianca (who doesn’t quite yet realize that Cameron is better than Joey).

Kat, of course, spurns Patrick’s advances until he shows her what he’s really made of, starting with his unabashedly corny, endlessly romantic rendition of “Can’t Take My Eyes Off You” in the football stadium.

All the while, prom is imminent.

Touchstone Pictures; Melissa Herwitt/E! Illustration

The setting is idyllic and glossy and one boy is paying another to take a girl, whom they all say awful things about because she marches to the beat of her own drum, out on a date. But Kat, who pines for a guitar and bemoans the lack of feminist writers on the curriculum, is the queen of the woke comeback (“I guess in this society, being male and an a–hole makes you worthy of our time”) and it all holds up.

As the story has for 400 years, since translated from the original misogyny.  

But 10 Things I Hate About You wouldn’t be nearly as watchable—and rewatchable—if the cast wasn’t impeccable. Aside from all of the above (and a re-shout-out to Ledger as the misunderstood bad boy who falls head over heels for the intelligent, untrusting and delightfully tempestuous girl he’s hired to romance, Susan May Pratt and Gabrielle Union are Kat and Bianca’s respective best friends, Allison Janney is the guidance counselor writing an erotic novel on the side and Daryl Mitchell is spot-on as the English teacher who rolls his eyes at the woes of the suburban white-privileged.

It’s much ado about everything, featuring more than a few star-making performances and toting its fair share of behind-the-scenes secrets.

Buena Vista Pictures/Entertainment Pictures/

Reader, They Dated

As Kat and Patrick were falling for each other onscreen, according to some of their co-stars on the DVD commentary, Julia Stiles and Heather Ledger became an item off-screen—the only thing that can make a choice movie romance even better, as with the star-crossed couples in The Notebook or Twilight.

Moreover, Heath was Julia’s first onscreen kiss.

“He was so nice. He was such a force; he was—even at that age—a very, very powerful, lovely human being,” Stiles remembered her late costar to Us Weekly in 2014, calling the experience of working with him “amazing.”

Opening up a little more to Australia’s ABC in 2016, Stiles said, “Heath and I did not keep in touch after filming ended, but when I heard about his death, I was incredibly sad, I was very shocked. He was such a force, such a vibrant person, right at the really exciting time of his life.”

Kevin Winter/Getty Images

First Time’s the Charm

The screenplay was the work of first-time movie scribes Kirsten Smith and Karen McCullah Lutz, who went on to write Legally Blonde, Ella Enchanted, She’s the Man, The Ugly Truth and The House Bunny.

“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 [Jane Austen‘s Emma], so we decided to try that as well,” McCullah told The Script Lab in 2015. “We chose Taming of the Shrew and figured out which story lines we wanted to keep and update and how we’d go about it and then outlined all the characters and the story while we sat on a beach in Mexico.”

They were long-distance writing partners and would send pages back and forth via express mailing service Airborne.

It’s easy to see where the empowered Kat got her modern-day spirit—and the entire movie got its fresh, witty and whip-smart vibe.

McCullah described their work to BuzzFeed News as “badass and full of mirth.”

“I think our legacy is just these fearless, funny female characters who are sort of radical by their confidence,” Smith said. “They’re changing the world even though they don’t really know that they’re doing it.”

“We did get a note that said, ‘Why is she so angry?'” Smith recalled. Added McCullah, “they didn’t understand that sometimes as a teenage girl you’re just angry at all the bulls–t you have to put up with.”

Moviestore Collection/Shutterstock

What’s in a Name

McCullah and Smith, hearing that Disney’s Touchstone Pictures wanted to make a teen romance, stat, raced to finish their rewrite to hopefully beat out the other script the studio had purchased—called School Slut.

Somehow, that one didn’t end up getting made. By Disney.

The title of the winning 10 Things I Hate About You, meanwhile, was inspired by an actual list McCullah made about a high school boyfriend.

“The title is based on a diary entry I made in high school,” she said in a sit-down with UCTV. “I had a boyfriend named Anthony that I was frequently unhappy with. I made a list called Things I Hate About Anthony. When Kirsten 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.'”

Moreover, “Anthony is very proud of that fact,” McCullah added. “We’re still friends today. And every now and then I’ll get a random phone call in the middle of night: ‘My nephew doesn’t believe that this title is about me. Tell him.’ On the phone, I’m like, ‘Yes, I hated Anthony in high school.'”

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What If Goldie Hawn Said Yes?!

“We saw hundreds and hundreds of actors,” recalled producer Andrew Lazar, “but halfway through the process we did stumble upon an amazing girl, who we felt was perfect for the lead role, and that was Julia Stiles. And then we really turned out attention to finding the perfect guy to play opposite her.”

It’s impossible to picture this movie with anybody else in the lead roles, but ponder this for a minute: Larisa Oleynik, perhaps the biggest star of the bunch going in thanks to her Nickelodeon-fostered fame from The Secret World of Alex Mac, wanted to play Kat. And that begot the rumor, since debunked, that Julie Stiles was interested in the role of Bianca.


And at one point it might not have been Stiles—or Ledger—at all in the pivotal roles of Kat and Patrick. Josh Hartnett and Ashton Kutcher were in the running for Patrick, and Hartnett screen-tested with Eliza Dushku, hot off her turn as Faith in Buffy the Vampire Slayer

“They were all terrific,” producer Andrew Lazar recalled about all three potential male leads, noting that they saw “hundreds and hundreds of actors” before whittling it down to Stiles and 

“But Julia and Heath just had the best chemistry together,” casting director Marcia Ross recalled to The New York Times in 2019 for an oral history about the film. “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 didn’t like the script for her, so she passed.”

Well, don’t all of those names sound familiar. High school still beckoned for Hartnett, who was the BMOC in The Virgin Suicides, and Dushku, whom we cheer to this day in Bring It On. And luckily Goldie Hawn saw the promise in Almost Famous, for which Hudson earned an Oscar nomination.

Buena Vista Pictures/Entertainment Pictures/

Sister Act

“I auditioned for both Kat and Bianca pretty much up until the very end, and I really wanted Kat,” Oleynik told the New York Times. “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.”

And no wonder Oleynik thought she was right for Kat. In real life, she’s the one who went on to attend the elder Stratford sister’s dream school, Sarah Lawrence College, in New York.

“College was the best decision I’ve made,” she told Girls’ Life in 2006. “I knew that I wanted to go to school and I wanted to go for four years and in New York. My favorite [classes] were the writing workshops. I took poetry classes, and courses in playwright and screenwriting. They were very comforting and productive. Everyone was respectful of each other. No one claimed to know everything.”

As for Stiles, she told Entertainment Weekly, “I was desperate for the part. It was so refreshing to see a teenage girl who was so feisty. I thought that the writers had a healthy dose of cynicism with their humor that you don’t always find with teen romantic comedies.

“I was an auditioning actor and mostly I would go out for commercials and they would tell me that I wasn’t bubbly enough. They always thought I was angry so to read a part like Kat I was like, ‘Ah, this is perfect for me!'”

Richard Cartwright/Touchstone/Kobal/Shutterstock

He’s All That

Turns out Joseph Gordon-Levitt and David Krumholtz wanted each other’s parts too!

“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,” Krumholtz told the New York Times. “I know that Joe wanted to play Michael.”

Said Gordon-Levitt: “I auditioned both for Krumholtz’s part and my part, because I thought [that role] was funny. Then [Gil] wanted me to play Cameron.”


International Man of Mystery

“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,” director Gil Junger recalled in an interview included in the 10th-anniversary DVD extras about the specific requirements for the part of Patrick Verona. “A complicated role, a very complicated role, and we had read a ridiculous amount of guys.”

Enter Australian actor Heath Ledger, who had yet to be in an American film, and everyone who watched his audition thought “movie star.” “He was just magnetic,” Karen McCullah said.

Ledger said that he most aspired to play Hamlet, but a close second was Petruchio in The Taming of the Shrew, “and this is the closest thing I’ve had to playing Petruchio so far,” he said, flashing that full-faced grin of his.

In another set interview, the 18-year-old explained, “I’m using bits and pieces of Richard Burton’s portrayal of that character in perhaps the best known The Taming of the Shrew film, but my Patrick has also got a Jack Nicholson edge to him with his cheekiness and his smiles.”

It’s still unclear how Ledger could look remotely like the sort of guy who would eat a live duck, as one of the rumors about Patrick claimed, but the actor himself was as much of a mystery when he finally arrived on set a week into filming, fresh from the Australian swords-and-sandals TV series Roar.

“We had only heard stories from the producers about the disarming charisma of a handsome Aussie from Perth with an infectious smile,” David Krumholtz wrote in a piece for Vulture in 2015. “We had all established such strong friendships … We worried about how someone named Heath could possibly manage to find his place in our inner circle.” Quickly they realized that “the group, with Heath, only got stronger.”

Buena Vista Pictures/Entertainment Pictures/

Queen of the Teens

At 27, Gabrielle Union was almost a decade older than the actors who played her peers in the film—but, as anyone who saw Bring It On in 2000, age was (and still is, really) but a number for the relentlessly youthful-looking actress.

“I was over 10 years older than my younger cast members, some of whom were still in high school,” Union told the Times. “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.”

Wikimedia Commons

That’s a Real High School

Padua High is actually Stadium High School in Tacoma, Wash., a public school overlooking Commencement Bay that was originally going to be a fancy hotel, hence it having the bones of a French chateau.

Construction began in 1891. The Panic of 1893 sent investors scurrying and the unfinished building was used as a storage facility until a fire gutted the structure in 1898. The Tacoma School District purchased the shell in 1904, local noted architect Frederick Heath finished the job and the school was open for learning in 1906.

The 15,000-seat Stadium Bowl where Patrick did his song and dance is shared by Stadium and Woodrow Wilson High School.

Chris Haston/NBC/NBCU Photo Bank


Joseph Gordon-Levitt and Larisa Oleynik also played an off-and-on teen couple in 3rd Rock From the Sun, which bridged the child-to-teen stardom gap for JGL, and he never looked back. 

“If I’m really honest, I didn’t want to do a high school romantic comedy,” Gordon-Levitt admitted to the Times. “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.”

Touchstone Pictures

Dave’s Anatomy

David Krumholtz had to give Andrew Keegan some, er, pointers when it became obvious Keegan was out of his artistic element drawing a penis on Krumholtz’s face, when Mike goes to Joey to float the big idea.

“I remember having to teach Andrew Keegan how to draw a proper dick on my face,” Krumholtz recalled to Huffington Post in 2014. “Which was a little strange to have to do? He was nervous; I was like, ‘I draw tons of dicks. Start with the head, do the shaft, get to the balls. Make sure to put hair on the balls.’ It’s a nice dick. It’s a chub. It’s halfway there.”

Touchstone Pictures

Catching up with the New York Times in 2019, Keegan concurred, “Quite frankly, I did not know how to draw a dick on someone’s face, and I believe David was the one that helped creatively with that.”

The actor turned founder of Full Circle, a spiritual and wellness center in Venice, Calif., concluded, “I have heard about that scene for my whole adult life, so I think I did a pretty good job.”

“You know, people still say, ‘I have a dick on my face, don’t I?'” Krumholtz added. “And I have to be like hey, you got me. It’s haunted me for the rest of my life. It’s wonderful.”


All’s Well That Ends Well

“I remember on 10 Things, seeing Kat’s room for the first time and being like, No, why does the room look like that? I was upset about the music, because I had envisioned way more of a hardline, riot grrrl soundtrack,” Smith told Broadly. “I was certain those things were going to sink the whole vibe, but obviously I was wrong, and it turned out great. Part of it is just growing up as an artist and a writer. You can cling to the idea of what something should be, but the beauty of collaboration is that a new take on it could turn it into the best version it could become.”

Another big tweak: Kat and Bianca’s mom was originally present, but she was made into an absent parent who up and left to give some more relatable context to Kat’s perpetual state of defensiveness.

Touchstone Pictures

Her First Dance

Stiles’ drunken dancing atop a table to Notorious B.I.G.’s “Hypnotize” during the house party apparently won her the role of a ballet dancer with Juilliard aspirations in Save the Last Dance

Junger told the Times that he was thinking of bringing his pal Paula Abdul on to choreograph the scene, but Stiles volunteered to just figure it out.

“I would never have the guts to do that now,” Stiles said. “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.”

Touchstone Pictures

Seattle’s Finest

The movie was shot entirely on location in the Seattle-Tacoma area, from the opening credits—an aerial view of Kerry Park and Queen Anne Hill—to the Stratford family’s 5-bedroom Victorian home on North 28th Street, which sold for $1.54 million in the spring of 2018, to Lake Union, where Kat and Patrick go pedal-boating.

Touchstone Pictures

And We Couldn’t Take Our Eyes Off Him

The script originally called for Patrick wooing Kat with the Partridge Family’s “I Think I Love You.” Then it was the Divinyls’ “I Touch Myself.” But Ledger insisted upon Frankie Valli and the Four Seasons’ “Can’t Take My Eyes Off You” for the big musical number in which Patrick serenades Kat with the help of the school marching band—and he took creative control of the instantly classic 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,” Smith told Broadly. in 2017. “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 was so impressive, especially because he was only 19.”

(No word on whether Jerry McConnell serenading Neve Campbell with “I Think I Love You” in Scream 2 in 1997 and Austin Powers having already conquered the fembots to “I Touch Myself,” also in 1997—and the fact that Kat never would have gone for that—had anything to do with the change-ups.)

Touchstone Pictures

Going With the Flow

Stiles famously nailed her emotional reading of her poem in one take, the unplanned tears coming naturally.

“They were not intentional,” the actress told Cosmopolitan UK in 2015. “On some level I knew that I was supposed to be somewhat emotional, because when we did the table read I remember I just said the poem, and I could have been reciting the phone book.”

In the moment, “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.”

There is a bit of a discrepancy when it comes to the moment that ties the film and the title together, but, to be fair, “14 Things I Hate About You” doesn’t have the same ring to it.

Meanwhile, without further explanation, Stiles told the Times that her reaction was probably a combination of joy and sadness that the shoot was about over, but she also acknowledged being “just in a very raw place.”

“I remember Heath,” she said, “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.”


Pam Berry/The Boston Globe via Getty Images

Dear Cleo

Letters to Cleo—the band that played the club, the prom (Kay Hanley and Michael Eisenstein performed “Cruel to Be Kind” with Save Ferris) and closed the film covering “I Want You to Want Me” on the roof of Padua High—was basically the official house band of 10 Things I Hate About You, adding a hefty helping of mainstream fame to their already impressive indie rock credentials. They split up in 2000, but later reunited for a reunion tour and the EP Back to Nebraska in 2016. 

And yes, that was really them—singer Hanley, guitarists Eisenstein and Greg McKenna, bassist Scott Riebling and drummer Jason Sutter—up on that roof.

“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,” Hanley, who went on to provide Rachael Leigh Cook’s singing voice in Josie and the Pussycats, told the New York Times. “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 dive-bombs 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.”

ABC FAMILY/Randy Holmes

Lost in Translation

Most TV show adaptations of hit movies don’t work, and the short-lived 2009-’10 sitcom 10 Things I Hate About You on ABC Family (now Freeform) was no exception—but not because it wasn’t good. It’s just that the movie was so good.

“The movie has such cult status that it seems almost sacrilege to tamper with it for television, but as a series 10 Things is not terrible; it is even at times fun. It’s just not very inventive,” wrote the New York Times‘ Alessandra Stanley in her review at the time.

Lindsey Shaw and Ethan Peck (grandson of Gregory) valiantly played Kat and Patrick, while Meaghan Martin and Nicholas Baum did swell turns as Bianca and Cameron. But comparisons were inevitable and an audience more nostalgic for the original than anything else wasn’t all that interested.

Still, it had its devoted fans and lasted for 20 episodes, and before the back 10 aired in the spring of 2010, Shaw told Pop Sugar, “Obviously coming from a remake, you have a whole slew of things stacked against you. Nobody wants to see a remake because it’s everybody’s favorite movie. But we came at this and wanted to create something different and entertaining, and I think we’ve done that.”

Added Peck, who had the tougher role of not just stepping into a beloved character but also one played by an actor who had passed away, “I think the pressure really always only came from within, speaking for ABC Family and for the television show, because we knew that we weren’t trying to replace anything or anybody. We all came to it seriously and with big open hearts and open minds and I think that’s why we are where we are today.”

After they were canceled, series creator Carter Covington told, “I was telling someone it feels kind of like a breakup. Like you got dumped by this person and you’re like, ‘Wait a second. But we had such a great thing going on. Why would you dump me?'”

10 Things Films

More Things to Hate

There was brief talk of an 11 Things I Hate About You sequel, but a tonally synonymous follow-up called 10 Things I Hate About Life did get underway in 2012. It starred Evan Rachel Wood and Thomas McDonnell as two kindred spirits who meet when they’re both in the middle of trying to commit suicide—and it never came out.

But director Gil Junger, reteaming with producer Andrew Lazar, hit the ground running. “We were open, we wanted to get a fresh, young cast,” Lanz told Vumanity, “but it just so happens, as we started meeting girls, Evan Rachel Wood—much like Julia Stiles did—just so out-shined all of the other actors in terms of talent, in terms of depth and emotion, that we settled on her.”

After six screen tests to pair Wood with the right guy, “we ended up with somebody phenomenal.” Lazar called the chemistry between McDonnell and Wood “electric.” They also had Skylar Grey in the Letters to Cleo role as the cool-live-music presence.

Production, however, was halted in February 2013 when the CEO of Intandem, the U.K.-based company financing the film, stepped down.

Also by then, Wood was pregnant with her son, who was born that July; the new Intandem CEO claimed the production was delayed because of her pregnancy but would resume in September. Instead, in June 2014, 10 Things Films sued Wood for breach of contract and $30 million, claiming she was paid $300,000 and then “seemingly changed her mind about desiring to complete the film during principal photography, ultimately refusing without any legal justification to fulfill her contractual obligations and instead opting to walk out on the project.”

A rep for Wood called that “preposterous,” stating that Wood was ready to resume work in November 2013, when producers promised they’d be ready, but they “still could not get their act together.”

Anthony Harvey/Getty Images

Heath Ledger Was the Real Deal

Not surprisingly, every single person involved in 10 Things I Hate About You (plus a billion other people) wishes Ledger was here to reflect on the film’s 20th anniversary. Hell, he tragically wasn’t even there for the 10th anniversary, having died in 2008 of an accidental prescription drug overdose.

“I loved Heath,” Krumholtz told the Times. “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.”

Remembered Gabrielle Union, “Heath had the ability to look at you, and 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.”

Heath pretty much left comedy behind after this film, going on to do some incredible dramatic work—he would have made a compelling Hamlet one day—and won a posthumous Oscar for his haunting turn as the Joker in The Dark Knight.

But the list of reasons to love 10 Things I Hate About You, in all its light teen romance glory, will always start with him.

(Originally published March 31, 2019, at 3 a.m. PT)

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