Heath Ledger and Julia Stiles Reinvented Shakespeare Before Anyone But You

The recently released Anyone But You not only helped revive romantic comedies in the theatrical landscape, but it also looked to the work of William Shakespeare for inspiration in a way that used to make it clear that the 16th-century English playwright had his finger on the pulse of the human condition that would prove to be timeless. Much Ado About Nothing serves as the blueprint for the Sydney Sweeney and Glen Powell-led rom-com, but it’s not the first film of this nature to use one of Shakespeare’s plays to spin a modern tale of mismatched romance. 25 years ago, fresh-faced stars Heath Ledger and Julia Stiles led 10 Things I Hate About You, a modern retelling of Shakespeare’s The Taming of the Shrew that not only emerged as one of the best loose adaptations of his work, but also quickly cemented itself as a film that defined a generation, one that still admires it today.

Much like Anyone But You, whose screenplay by Ilana Wolpert and director Will Gluck used the overall story structure of its Shakespeare source material to shape its story, Karen McCullah Lutz and Kirsten Smith’s script for 10 Things I Hate You has a similar DNA for its take on The Taming of the Shrew. But Shakespeare remains more of a mainstay in their modern retelling compared to Wolpert and Gluck’s fresh spin on Much Ado About Nothing. Anyone But You uses more subtle connections such as slightly changed character names, props and settings, and a few lines from the play as a wink and a nudge to the source material, while the 1999 film follows its inspiration more closely.

10 Things I Hate About You Takes William Shakespeare Out of Italy and Into a 1990s American High School

The setting is changed to a late 1990s American high school and the “shrew” in the updated tale is Katarina “Kat” Stratford (Stiles), inspired by the shrewish and headstrong Katherina, who becomes the challenge of Petruchio, a man doing all he can to woe her into a relationship. In 10 Things I Hate About You, Petruchio is switched out for Patrick Verona (Ledger), a “bad boy” from Australia tasked to “tame” Kat by two suitors who want the affection of her younger sister Bianca (Larisa Olyenik), who isn’t allowed to date until Kat does. On one side is love-sick but nice guy Cameron (Joseph Gordon-Levitt), a new student at Padua High School in Seattle (a nice little reference to where The Taming of the Shrew is set), and on the other side is the self-absorbed Joey Donner (Andrew Keegan), a high school senior that only wishes to sleep with Bianca.

As Bianca begins the story by being more superficial and popular, she wants to date Joey and sees an angle to doing so when Cameron asks her out. Informing him of her dad’s rules regarding her older sister, Bianca suggests finding someone willing to date Kat, so she can go about dating Joey, although this is a slight caveat she keeps from Cameron. Eventually, a plan is worked out that uses Joey and his considerable funds to pay Patrick to pursue Kat and break down her walls. As is the case in most teen films from this era, the mismatched pair grows closer, the superficial girl realizes the nice guy is better for her, the deception is revealed at the big dance, and all is forgiven by the time the credits roll in this considerably clever comedy of errors.

10 Things I Hate About You may use much of The Taming of the Shrew to frame its story, but some of the play’s themes are thankfully updated to do away with its obvious misogynistic undertones. In the source material, Bianca is viewed as the more “ideal” woman due to her beauty and more agreeable nature compared to her older sister. When Petruchio is attempting to court Kat, he goes about taming her by, in one example, keeping her from eating and drinking so that she will be more desirable and a better bride. Even in 1999, that certainly wouldn’t fly.

10 Things I Hate About You subverts much of its inspiration’s notions of submission to be a proper lady by making the modern-day Kat a feminist who is confident enough in her convictions to know that she doesn’t need to change herself to gain the attention of a man. Also, even though Patrick enters into this deception under misguided pretenses, another improvement from the source material is that he grows to respect Kat and her views regarding her frustration and distrust of basic high school society and its hierarchies. They come to a place of mutual admiration for each other, each meeting in the middle in terms of softening their edges a bit so that they both may see the best in each other.

Shakespeare plays a huge role not only in the plot of 10 Things I Hate About You but also in the clever ways he’s utilized throughout the film. Anyone But You does have nods to Much Ado About Nothing, with some lines even being lifted directly from the play, but 10 Things I Hate About You plays like the greatest hits package to the man himself.

Cameron, based on Lucentio from the source material, utters his line “I burn, I pine, I perish”, upon first laying his eyes on Bianca, and, during another moment, his nerdy but loyal friend Michael (David Krumholtz) states after they are almost run down by Kat in her car, “Just a minor encounter with the shrew”, the film’s first direct reference to Kat being the shrew who will later need to be tamed. Kat’s best friend Mandella (Susan May Pratt) is a total aficionado of Shakespeare’s work, while Mr. Morgan (Daryl Mitchell), a teacher of Kat, Patrick, and Joey’s English class, tasks them with creating their own poem based on the Bard’s Sonnet 141. This leads to the film’s most iconic moment, Kat reciting her take on the Sonnet inspired by her time with Patrick:

The film is also one of the funnier teen comedies of its era, emerging during a time when these films were becoming so hot again at the box office that just about every studio was making one. 10 Things I Hate About arrived in 1999 and within months of the releases of Varsity Blues, She’s All That, Jawbreaker, and Cruel Intentions, all films that either saw success at the time of their release or went on to become cult favorites down the line. All of those movies have their appeal, but 10 Things I Hate About You stood out from the pack in many ways because it wore its cleverness on its sleeve.

Through its Shakespeare sensibilities and wicked smart screenplay, it’s more in line with another teen classic, 1995’s Clueless, a film inspired by the work of the past in the form of Jane Austen’s Emma in terms of its intelligence equally standing out among all the elements that also make it a product of its era. For every witty quip, some tropes give the film its teen movie DNA, but it’s so in step with the freshness of the script that it’s clear, much like the work of Shakespeare, it could be loved by future generations who discovered it.

10 Things I Hate About You Was the big break for Stars Heath Ledger and Julia Stiles

The movie also had the advantage of a fresh cast, some of them noticeable from prior film and TV work, while others were achieving their big break here. The late Heath Ledger made his American film debut in 10 Things I Hate About You, and the movie made him an instant star who would go on to achieve even more greatness in various other roles before his life was tragically cut short at the age of 28. The project was also a breakthrough moment for Julia Stiles who, oddly enough, went on to star in two other Shakespearean adaptations soon after this film’s release, in Michael Almereyda’s Hamlet (playing Ophelia opposite Ethan Hawke) and Tim Blake Nelson’s O, a modern retelling of Othello set in a boarding school when she took on the Desdemona role. Together, Ledger and Stiles showcased great chemistry in 10 Things I Hate About You, and it’s also frequently listed as one of the film’s strongest components. Alongside the rest of the ensemble cast, the movie arguably has one of the best groups assembled for a high school movie.

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When the film was released on March 31, 1999, 10 Things I Hate About You became a hit with critics and moviegoers, registering a 71% fresh rating on Rotten Tomatoes and going on to gross $60.4 million on a $13 million budget. Its critical response was significant in relation to the other “Class of 1999” teen movie releases because it came out on top as the best-reviewed of the bunch, securing better scores than Varsity Blues (45 percent), She’s All That (41 percent), Jawbreaker (14 percent), Cruel Intentions (54 percent), and American Pie (61 percent), which arrived later that summer. Critics identified with the intelligence of its screenplay and the performances of its stars, while the target demographic connected with it on several levels, mostly because it didn’t speak down to them in a way that elevated it above teen fare before and after its release.

10 Things I Hate About You also made way for other modern-day Shakespeare adaptations that targeted various demos. The aforementioned O was released in 2001, after several delays due to the Columbine High School tragedy, while Get Over It starring Kirsten Dunst debuted the same year with its loose connections to A Midsummer Night’s Dream (the cast is also performing the play in the film). 2003’s Deliver Us from Eva, starring Gabriele Union also tackled The Taming of the Shrew, but for an adult audience, while 2006’s She’s the Man, starring Amanda Bynes and an early Channing Tatum, achieved its own level of cult status with its take on Shakespeare’s Twelfth Night.

Twenty-five years after its release, 10 Things I Hate About You still stands as a timeless classic from the era that managed to use the framework of Shakespeare’s original play to adapt it for a modern audience while also allowing it to stand on its own two feet. It stands as another shining example that the Bard’s work knew no bounds when being told across various generations, providing the perfect marriage of his immense talent and a fresh story that also continues to transcend time. Stream 10 Things I Hate About You on Hulu and Disney+