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4. 10 Things I Hate About You (1999)
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This 1999 rom-com is not merely a tale of high school love; it's the retelling of Shakespeare's The Taming of the Shrew. Heath Ledger's version of "Can't Take My Eyes Off You" is going to win hearts, while Julia Stiles' quick-think puts the icing on the cake as the lead actress. It's infinitely re-watchable in the way that it combines comedy, teenage defiance, and romance. This is where Ledger and Joseph Gordon-Levitt broke out.
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Edited by Zainab Shaikh
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