When the coolest guy in school, Zack Siler, gets dumped, he wagers with a classmate that he can quickly turn any girl, even the geeky Laney Boggs into the prom queen. He wasn't, however, betting on falling in love. Stars Matthew Lillard, Paul Walker, Anna Paquin, Kevin Pollak, Kieran Culkin.
Director: Robert Iscove
Producer: Larry Doyle
Producer: Paula Weinstein
Producer: Peter Abrams
Producer: Richard N. Gladstein
Producer: Robert L. Levy
Actor: Freddie Prinze
Actor: Jr.
Actor: Freddie Prinze Jr.
Actor: Rachael Leigh Cook
Actor: Matthew Lillard
Actor: Paul Walker
Actor: Jodi Lyn O'Keefe
Actor: Kimberly "Lil' Kim" Jones
Actor: Dulé Hill
Actor: Lil' Kim
Actor: Kevin Pollak
Actor: Anna Paquin
Actor: Kieran Culkin
Actor: Elden Henson
Actor: Usher Raymond
Actor: Gabrielle Union
Actor: Debbie Morgan
Actor: Ashlee Levitch
Actor: Vanessa Lee Chester
Actor: Katharine Towne
Actor: Amon Bourne
Actor: Jarrett Lennon
Actor: Milo Ventimiglia
Actor: Brian Friedman
Actor: Mayah McCoy
Actor: Sarah Christine Smith
Actor: Christopher Smith
Actor: Bree Turner
Actor: Dani Lee