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16 of 23 Josie Gellar, Never Been Kissed Josie (Drew Barrymore) looked totally "rufus"in her Shakespeare-inspired dress for the dance in 1999's Never Been Kissed , where the theme was "Meant for Each Other: Famous Couples Throughout History." The night may have ended on a sour note, but one thing's for sure: "She's not Josie Grossie anymore!" 17 of 23 Kat Stratford, 10 Things I Hate About You We can't watch 10 Things I Hate About You without getting emotional thinking about the late Heath Ledger, but this prom scene is one of the best in teen cinema history, thanks in part to Kat's simple navy slip dress, pearl necklace and piled-on-top curls

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