10 Things I Hate About You (1999)

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.