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