Synopsis
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.
Cast

Freddie Prinze Jr.
Zach Siler

Rachael Leigh Cook
Laney Boggs

Paul Walker
Dean Sampson

Jodi Lyn O'Keefe
Taylor Vaughan

Kevin Pollak
Wayne Boggs

Anna Paquin
Mackenzie Siler

Kieran Culkin
Simon Boggs

Elden Henson
Jesse Jackson

Matthew Lillard
Brock Hudson

Usher
Campus D.J.

Lil' Kim
Alex

Gabrielle Union
Katie

Dulé Hill
Preston

Tamara Mello
Chandler

Clea DuVall
Misty

Tim Matheson
Harlan Siler

Debbi Morgan
Ms. Rousseau

Alexis Arquette
Mitch

Dave Buzzotta
Jeffrey Munge Rylander

Chris Owen
Derek Funkhouser Rutley
Charlie Dell
Man in Falafel Barn

Michael Milhoan
Principal Stickley

Carlos Jacott
Prom Photographer

Ashlee Levitch
Melissa
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