David Beckham, Selma Blair, Whoopi Goldberg and More!
Cook's character in this 1999 teen rom-com is pretty, but her good looks are overshadowed by her dorky glasses and mismatched outfits. She doesn't seem to care what other people think, though -- until popular jock Zack Siler (Freddie Prinze Jr.) shows an interest. After betting his friends that he can transform her into prom queen material, Zack persuades his sister (Anna Paquin) to give her a chic new makeover. In the end, she loses the crown to mean girl Taylor -- but she wins Zack's heart.