Popular, pretty Bianca Stratford (Larisa Oleynik) is in dilemma. A family rule forbids her from dating until her unpopular, rebellious, boy-hating older sister Kat (Julia Stiles gets a suitor of her own. In an attempt to win Bianca, a potential boyfriend (Andrew Keegan) desperately attempts to set Kat up with Patrick Verona (Heath Ledger), another rebel whom may just be able to win Kat's heart. Meet the Stratford sisters: pretty and popular Bianca (Larisa Oleynik), who has never had a date; and Kat (Julia Stiles, her older sibling, an ill-tempered harridan whose acerbic wit is matched only by her steadfast determination to alienate any guy who might be remotely interested in her. Unfortunately, strict rules in the Stratford household forbid Bianca from having a boyfriend until her odious sister has one of her own-a situation that seems highly improbable considering Kat is a social disaster. Bianca's desperation for romance turns into a convoluted scheme to match Kat with her male equivalent--a guy whose reputation is so infamous, Kat might rise to the challenge and find him worthy of her concealed charms. Mating mayhem ensues when Patrick Verona (Heath Ledger)--a sullen young man with a mysterious past--is bribed by Bianca's wannabe boyfriend (Andrew Keegan) to woo and win Kat, in order to clear the way for Bianca to begin dating. Bianca Stratford (Larisa Oleynik) is dying to go out with Joey Donner (Andrew Keegan) the babe of their school. Kat Stratford (Julia Stiles would rather die than go out with a boy. Mr. Stratford has this rule where Bianca can date... when Kat does. Bianca begs her sister to have a night of "teenage normalcy" Little does Bianca know that not only Joey is trying to set her sister up but also Cameron (Joseph Gordon-Levitt) her cute, but also unpopular French tutor. Joey and Camereon's "set up guy" Patrick (Heathe Ledger) is trying to get Kat to go out with him. But does it work, will Kat go out with him? Will Bianca go out with Joey?

release year: 1999

star(s): Allison Janney