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1. 10 Things I Hate About You (1999)
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Heath Ledger started his career in a few romantic comedies! 10 Tings I Hate About You is no exception. In 10 Things I Hate About You, Heath Ledger’s character, Patrick, and Kat are set up to date by Kat’s younger sister. However, their romance starts off with mutual hate. While we do mourn his absence in the modern Hollywood scene, we can always revisit this time in his career as the love interest of Kat Stratford (Julia Stiles) in this well written film on young love.