By Theia, Lady of the Picture Palace
There are films that belong unmistakably to their time, and then there are films that somehow manage to belong to every generation that discovers them. 10 Things I Hate About You, Gil Junger’s delightful 1999 romantic comedy, has always struck me as belonging to both categories. It is wonderfully, unapologetically a product of the late 1990s, with its alternative-rock soundtrack, questionable teenage fashion, and distinctly pre-smartphone understanding of high school romance. Yet beneath those charming period details lies a story about independence, vulnerability, and the terrifying business of allowing oneself to fall in love.
Twenty-seven years after its theatrical debut, the film has found itself back in the spotlight, thanks to a touching tribute to the late Heath Ledger on Tuesday night’s Dancing with the Stars.
During the October 20 broadcast, Julia Stiles honored her former co-star with a contemporary dance performed alongside professional partner Ezra Sosa. Their music was Frankie Valli’s “Can’t Take My Eyes Off You,” a particularly fitting selection considering Ledger’s unforgettable performance of the song in the original film. The tribute became even more moving when Stiles was joined by fellow cast members Joseph Gordon-Levitt, Larisa Oleynik, Gabrielle Union, Susan May Pratt, and Andrew Keegan.
It was a reunion filled with affection and an unavoidable absence. Ledger, who died in 2008 at just 28 years old, should have been there with them.
And perhaps that is part of what makes this particular film so enduring. We aren’t simply revisiting a beloved teenage romance. We’re returning to a moment when a remarkable young ensemble stood on the threshold of careers that would carry them in extraordinary directions, unaware of how precious those memories would eventually become.
Shakespeare, High School, and a Rather Wonderful Romance
Released March 31, 1999, 10 Things I Hate About You borrowed its foundation from William Shakespeare’s The Taming of the Shrew, transporting the Bard’s romantic complications into the hallways of Padua High School.
Julia Stiles plays Kat Stratford, an intelligent, fiercely independent young woman whose refusal to conform to the social expectations of her classmates has earned her a rather intimidating reputation. Her younger sister Bianca, played by Larisa Oleynik, is considerably more interested in the usual teenage pleasures, particularly dating. Unfortunately, their overprotective father has established a rule: Bianca cannot date until Kat does.
Naturally, this leads to a thoroughly dishonest arrangement involving the charmingly earnest Cameron, played by Joseph Gordon-Levitt, the insufferably self-satisfied Joey Donner, portrayed by Andrew Keegan, and the mysterious school outsider Patrick Verona, played by Heath Ledger.
What follows could easily have been another disposable teenage comedy. Indeed, the premise contains enough contrivances to fuel several lesser films. But screenwriters Karen McCullah and Kirsten Smith understood something that elevates the material considerably: these characters needed to possess personalities beyond their designated romantic functions.
Kat, in particular, is a splendid creation. She’s sharp-tongued, stubborn, principled, and occasionally unfair, but the film never asks us to believe that her intelligence or independence constitutes a character flaw requiring correction. Her real struggle concerns the walls she’s constructed around herself, and the difficulty of recognizing when self-protection has become self-imprisonment.
Stiles plays her beautifully. There is an appealing honesty to the performance, particularly in those moments when Kat’s formidable confidence gives way to emotions she would rather nobody witness.
And then, of course, there is Patrick.
The Irreplaceable Charm of Heath Ledger
It is difficult to discuss 10 Things I Hate About You without acknowledging how effortlessly Heath Ledger commands the screen.
Patrick Verona could have been an insufferable collection of romantic clichés: the dangerous outsider with a mysterious reputation, a rebellious attitude, and a conveniently concealed heart of gold. Instead, Ledger gives him warmth, humor, and a wonderfully mischievous charisma.
His famous serenade on the school bleachers remains one of the great romantic-comedy moments of its era. What makes the scene so delightful isn’t simply the song or Ledger’s willingness to make a spectacle of himself. It’s the combination of sincerity and ridiculousness. Patrick understands perfectly well that he’s making a fool of himself, and for once, he doesn’t particularly mind.
That kind of romantic confidence is difficult to manufacture. Ledger makes it seem effortless.
Yet I would argue that the film’s most affecting moment belongs to Julia Stiles, when Kat reads her poem aloud in class. Her carefully maintained composure gradually crumbles as she confronts feelings she can no longer disguise. What begins as an exercise in anger becomes an unexpectedly devastating admission of love.
It is a beautiful scene, made all the more effective because the film has earned it. Beneath the elaborate dating schemes and comic misunderstandings, these characters have become people whose emotions genuinely matter to us.
Knowing how brief Ledger’s life would be lends his performance an added poignancy today, but I would hate for that sadness to overshadow the joy of watching him. His Patrick Verona is alive with possibility, and that is how I prefer to remember him.
Why the Film Still Works
Not everything about 10 Things I Hate About You has aged gracefully. Certain jokes and attitudes belong very much to the era in which the film was made, and its romantic schemes involve deceptions that would be considerably less charming without the performances holding everything together.
But good romantic comedies rarely survive because their characters behave perfectly. They survive because their characters feel human.
Director Gil Junger maintains a breezy pace while allowing his ensemble room to develop genuine chemistry. Larry Miller is gloriously funny as the Stratford sisters’ overprotective father, David Krumholtz brings a welcome dose of sarcasm as Cameron’s friend Michael, and Joseph Gordon-Levitt gives the film an earnest romantic counterweight to Ledger’s more flamboyant approach.
The soundtrack, the Pacific Northwest setting, the wonderfully theatrical school interiors, and the late-1990s atmosphere all contribute to its personality. This is a film that knows exactly what it wants to be, and achieves it without embarrassment.
But its greatest strength is the respect it ultimately shows for its young characters. Kat isn’t required to surrender her identity to find love. Patrick must demonstrate that his affection extends beyond the arrangement that initially brought them together. Even Bianca learns that popularity and attention aren’t necessarily the same things as genuine affection.
These aren’t revolutionary ideas, but they’re timeless ones.
And perhaps that is why the film continues finding new admirers. Every generation experiences the exhilarating confusion of first love, the anxiety of being misunderstood, and the difficult realization that allowing someone to know us also means giving them the power to hurt us.
Shakespeare understood those emotions centuries ago. 10 Things I Hate About You simply dressed them in 1990s clothing and gave them an excellent soundtrack.
A Reunion Worth Remembering
Watching the cast reunite to honor Heath Ledger is a reminder of how profoundly a comparatively modest film can affect the people who make it and the audiences who embrace it.
For some viewers, 10 Things I Hate About You is a treasured memory of their own teenage years. For others, it is a film discovered long afterward, perhaps through a parent’s recommendation or an evening spent exploring the romantic comedies of a bygone decade.
For its surviving cast, it represents something more personal: a shared experience with a gifted young colleague whose remarkable future was cut tragically short.
I find something deeply moving about Julia Stiles and her fellow performers returning to celebrate Ledger through the very film that introduced so many people to his extraordinary charm. There is sorrow in remembering someone who cannot join the celebration, certainly, but there is also tremendous warmth in recognizing that the work remains.
Twenty-seven years later, 10 Things I Hate About You is still making people laugh, still making them fall in love with its characters, and still reminding audiences of the remarkable young man who once danced across a school stadium singing his heart out.
Some films fade into nostalgia.
Others become part of the memories we carry with us.
This one, rather wonderfully, has managed to do both.
— Theia, Lady of the Picture Palace
More From the Halls: If you’re revisiting the films of years gone by, join us for our look back at The Mummy (1999), another beloved late-90s favorite, or explore our reviews of Death to Smoochy (2002) and Hitchcock’s timeless North by Northwest (1959).
