"10 Things I Hate About You," 1999 The Role: Julia Stiles as Kat Stratford Her Prom Song: "Cruel To Be Kind" by Letters to Cleo Why We Love It: Despite the most unceremonious entrance in prom ... more 

"10 Things I Hate About You," 1999 The Role: Julia Stiles as Kat Stratford Her Prom Song: "Cruel To Be Kind" by Letters to Cleo Why We Love It: Despite the most unceremonious entrance in prom history (Kat threw the outfit on, stomped out the front door and hunted down her date at the event), this navy slip dress and a string of pearls is all she needed to wow Patrick. Kristen's Stewart's Transformation Buena Vista/courtesy Everett Collection less