She's All That (1999)

Zach Siler is the most popular jock at his California High School; he's an honor student, class president and plays soccer. When his bossy, snobbish girlfriend Taylor Vaughan comes back from spring beak she dumps him for Brock Hudson, reality star of The Real World. Zach is pissed off and is convinced that he can easily replace her, and transform any girl in the school into prom queen. So his friends Dean and Preston make him a bet that he can't, and they get to choose the girl. And of course they pick the artsy misunderstood, self-conscious girl Laney Boggs. Although Zach isn't too successful with Laney at first, he befriends her little brother Simon. However when Laney is invited to Preston's party, Zack's sister Mackenzie "Mack" gives her a makeover, Zack starts falling for her. Typical teen chick flick with a dozen cliches and stereotypes, but with a few really funny moments. Starring Freddie Prinze, Jr., Rachael Leigh Cook, Anna Paquin, Paul Walker, Jodi Lyn O'Keefe, Kevin Pollak, Kieran Culkin, Usher Raymond, Matthew Lillard, Gabrielle Union, Clea DuVall, Tim Matheson 6/10