10 Things I Hate About You (1999)

Yes. 87% of real audiences liked it based on 8,791 votes. Critics gave it 71%.

On the first day at his new school, Cameron instantly falls for Bianca, the gorgeous girl of his dreams. The only problem is that Bianca is forbidden to date until her ill-tempered, completely un-dateable older sister Kat goes out, too. In an attempt to solve his problem, Cameron singles out the only guy who could possibly be a match for Kat: a mysterious bad boy with a nasty reputation of his own. Wikipedia ↗

10 Things I Hate About You is a 1999 American romantic comedy directed by Gil Junger, a modern adaptation of Shakespeare's The Taming of the Shrew set in a Tacoma, Washington high school. Julia Stiles stars as Kat Stratford, a fiercely independent, feminist teenager whose overprotective father won't let her younger sister Bianca, played by Larisa Oleynik, date until Kat does. New student Cameron, played by Joseph Gordon-Levitt, hatches a scheme to pay the mysterious bad boy Patrick Verona, played by Heath Ledger, to take Kat out so Cameron can date Bianca.

What begins as a financial arrangement develops into a genuine romance as Patrick discovers the person behind Kat's defensive hostility. Heath Ledger's performance launched his career as a romantic leading man — his Australian charm, genuine warmth, and the now-legendary stadium bleacher scene where he serenades Kat with Frankie Valli's "Can't Take My Eyes Off You" while evading security guards became one of the most iconic romantic gestures in teen film history. Julia Stiles brought intelligence and emotional authenticity to Kat, making her abrasiveness sympathetic rather than alienating.

The film earned $53 million worldwide on a $23 million budget and has endured as one of the definitive teen comedies of the late 1990s, frequently cited alongside Clueless as the era's finest Shakespeare adaptation for teenagers.