She's All That (1999)

Synopsis
If Hollywood can shoehorn William Shakespeare into the teen-movie treatment with Romeo and Juliet, and Jane Austen with Clueless (from her novel, Emma), why not George Bernard Shaw? While his Pygmalion has been staged and filmed endless times, most famously as the musical My Fair Lady, here Shaw goes to high school. This time around, a Los Angeles' school's most popular guy Zack (Freddie Prinze, Jr.) loses his girlfriend Taylor (Jodi Lyn O'Keefe) to television star Brock Hudson (Scream's Matthew Lillard). Zack then vows to his friends that he can take any girl in school and turn her into the prom queen. With five weeks until the prom, his friends pick weird, art nerd Laney Boggs (Rachael Leigh Cook). Zack predictably gets more than he bargained for as he falls in love with his "creation." Eldon Hudson and Kieran Culkin, stars of The Mighty, play Laney's best friend and little brother, respectively. Robert Iscove, director of television's Rodgers and Hammerstein's Cinderella, makes his big-screen debut. ~ Chris Gore, All Movie Guide