10 Things I Hate About You

Released on March 31, 1999, 10 Things I Hate About You is a high school romantic comedy loosely adapted from William Shakespeare’s The Taming of the Shrew. Directed by Gil Junger and written by Karen McCullah and Kirsten Smith, the film stars Heath Ledger and Julia Stiles and is set at Padua High School in Seattle, Washington.

It remains one of the best-regarded films of the late-1990s teen movie renaissance and holds up remarkably well to contemporary viewing — smarter than its genre usually demands and emotionally resonant in a way that transcends nostalgia.

The Plot

New student Cameron James (Joseph Gordon-Levitt) falls immediately for Bianca Stratford (Larisa Oleynik), the beautiful, popular younger sister. But Bianca’s overprotective father has a rule: Bianca cannot date until her older sister Kat does, and Kat (Julia Stiles) — feminist, book-smart, pointedly antisocial — has no interest in dating anyone.

Cameron hatches a scheme: find someone to take out Kat so Bianca becomes dateable. The job goes to Patrick Verona (Heath Ledger), the school’s mysterious, rumored-to-be-dangerous resident bad boy, who agrees to pursue Kat in exchange for money funded by Joey Donner (Andrew Keegan), Bianca’s shallow, self-absorbed admirer who has his own reasons for wanting Bianca available.

What develops — predictably but satisfyingly — is that Patrick actually falls for Kat, and she, over her determined resistance, falls for him. The film builds to a climax involving a school poetry reading and the sonnet Kat writes about Patrick — which gives the film its title and is one of the better emotional payoffs of the genre.

The Shakespeare Connection

The Taming of the Shrew is one of Shakespeare’s more troubling plays to modern audiences — a comedy premised on the “taming” of a strong-willed woman into wifely compliance. 10 Things I Hate About You updates the source material cleverly: it preserves the basic plot structure while flipping the moral orientation. Kat is not a shrew to be tamed but a feminist with her own reasons for her attitude, and the film ultimately validates her autonomy rather than the romantic lead’s authority over her.

The film also preserves the play-within-a-play quality of Shakespeare’s work — characters are consistently performing for each other — while grounding everything in a high school environment recognizable to contemporary audiences.

The Cast

Heath Ledger’s performance as Patrick Verona is the film’s magnetic center. The scene in which Patrick performs “Can’t Take My Eyes Off You” in the high school stadium — hiring the marching band as accompaniment — is one of the genuinely memorable romantic gestures in contemporary cinema. Ledger’s charisma, deployed with intelligence and restraint, made him an instant star.

Julia Stiles matched him scene for scene. Kat requires an actress who can be genuinely thorny without being unlikeable, and Stiles threads that needle with care. The film’s emotional payoff depends entirely on the audience wanting these two people together despite Kat’s resistance, and both actors earn that investment.

Joseph Gordon-Levitt and Larisa Oleynik handle the secondary romantic plot — which is inherently less interesting — with likability and game commitment. The supporting cast, including Larry Miller as the magnificently absurd father and Allison Janney as the guidance counselor, is uniformly strong.

The Soundtrack

The 10 Things I Hate About You soundtrack is a late-1990s time capsule in the best sense: Letters to Cleo, Semisonic, Save Ferris, and Garth Brooks’s recording of “She’s In Love With the Boy” all appear, and the period choices feel right rather than arbitrary. The Letters to Cleo contribution — including their version of the film’s title song — gives the movie a musical identity specifically calibrated to its era and tone.

Why It Still Holds Up

Most films from the 1990s teen movie cycle have not aged especially well — many are embarrassing about gender, race, and teenage authenticity in ways that are uncomfortable to revisit. 10 Things I Hate About You is an exception. Kat’s feminism is not mocked; it is shown as both admirable and, in some of its expression, a defense mechanism worth examining. The film’s comedic sensibility is quick without being mean. The romance is earned rather than just asserted.

The film’s lasting quality is ultimately the same thing that makes the best romantic comedies durable: it is genuinely about two people who are worth caring about, written with enough intelligence to make their connection feel real rather than inevitable, and performed with enough specificity and feeling that the audience actually wants them to find each other. That combination is rarer than it should be, which is why 10 Things I Hate About You is remembered as more than a nostalgia object — it is one of the better films of its kind, period.