She's All That (1999)
Starring Freddie Prinze Jr., Rachael Leigh Cook, Paul Walker, Jodi Lyn O'Keefe, Kevin Pollak, Anna Paquin, Kieran Culkin, Elden Henson, Matthew Lillard, Usher, Lil' Kim, Gabrielle Union, Dulé Hill, Tamara Mello, Clea DuVall, Tim Matheson, Debbi Morgan, Alexis Arquette, Dave Buzzotta, Chris Owen, Charlie Dell, Michael Milhoan, Carlos Jacott, Ashlee Levitch, Vanessa Lee Chester, Patricia Charbonneau, Katharine Towne, Wendy Fowler, Flex Alexander, Robert Baglia, Debbie Lee Carrington, Sara Rivas, Clay Rivers, Amon Bourne, Takbir Bashir, Anthony 'Click' Rivera, Jarrett Lennon, Brandon Mychal Smith, Milo Ventimiglia, Kente Scott, Kim Cottom, T.J. Espinoza, Brian Friedman, Tony Fugate, Caroline Girvin, Alicia Gilley, Scott Hislop, Jennifer Lee Keyes, Richard Kim, Stephanie Landwehr, Dani Lee, Joe Loera, Mayah McCoy, Ayesha Orange, Robert Schultz, Josh Seffinger, Sarah Christine Smith, Christopher Smith, Bree Turner, Christine Vincent, Jerry 'Flo Master' Randolph, Sarah Michelle Gellar
High school hotshot Zach Siler is the envy of his peers. But his popularity declines sharply when his cheerleader girlfriend, Taylor, leaves him for sleazy reality-television star Brock Hudson. Desperate to revive his fading reputation, Siler agrees to a seemingly impossible challenge. He has six weeks to gain the trust of nerdy outcast Laney Boggs -- and help her to become the school's next prom queen.