Freddie Prinze Jr. as Zach Siler

Rachael Leigh Cook as Laney Boggs

Paul Walker as Dean Sampson

Jodi Lyn O'Keefe as Taylor Vaughan

Kevin Pollak as Wayne Boggs

Anna Paquin as Mackenzie Siler

Kieran Culkin as Simon Boggs

Elden Henson as Jesse Jackson

Matthew Lillard as Brock Hudson

Usher as Campus D.J.

Lil' Kim as Alex

Gabrielle Union as Katie

Dulé Hill as Preston

Tamara Mello as Chandler

Clea DuVall as Misty

Tim Matheson as Harlan Siler

Debbi Morgan as Ms. Rousseau

Alexis Arquette as Mitch

Dave Buzzotta as Jeffrey Munge Rylander

Chris Owen as Derek Funkhouser Rutley

Charlie Dell as Man in Falafel Barn

Michael Milhoan as Principal Stickley

Carlos Jacott as Prom Photographer

Ashlee Levitch as Melissa

Vanessa Lee Chester as Girl #2

Patricia Charbonneau as Lois Siler

Katharine Towne as Savannah

Wendy Fowler as Harmony

Flex Alexander as Kadeem

Robert Baglia as Beatnik

Debbie Lee Carrington as Felicity

Sara Rivas as Vampire Girl

Clay Rivers as Gustave

Amon Bourne as 'She's All That' Rapper

Takbir Bashir as 'She's All That' Rapper

Anthony 'Click' Rivera as 'She's All That' Rapper

Jarrett Lennon as Naylon

Brandon Mychal Smith as JV Cleaning Boy

Milo Ventimiglia as Soccer Player

Kente Scott as Sophomore Boy

Kim Cottom as Dancer

T.J. Espinoza as Dancer

Brian Friedman as Dancer

Tony Fugate as Dancer

Caroline Girvin as Dancer

Alicia Gilley as Dancer

Scott Hislop as Dancer

Jennifer Lee Keyes as Dancer

Richard Kim as Dancer

Stephanie Landwehr as Dancer

Dani Lee as Dancer

Joe Loera as Dancer

Mayah McCoy as Dancer

Ayesha Orange as Dancer

Robert Schultz as Dancer

Josh Seffinger as Dancer

Sarah Christine Smith as Dancer

Christopher Smith as Dancer

Bree Turner as Dancer

Christine Vincent as Dancer

Jerry 'Flo Master' Randolph as Dancer

Sarah Michelle Gellar as Cafeteria Girl