49. 10 Things I Hate About You (1999)
There are many reasons 10 Things I Hate About You stands the test of time better than most of its contemporaries in the glut of late '90s teen flicks, but we'll name two of them. For starters, child-star-made-good Joseph Gordon-Levitt turned in an
understated, endearing performance as a lovelorn (and totally undercover hot) geek. The film also served as a breakout role for a then little-known Aussie named Heath Ledger, who sung, danced, and smirked his way into the heart of ice queen intellectual punk Kat Stratford (Julia Stiles). That's without mentioning a stellar soundtrack, its brilliantly caricaturish deconstruction of high school cliquery, and a house party worthy of the name Bogey Lowenstein. Lanford Beard