William Forrester
Sean Connery
Jamal Wallace
Rob Brown
Massie
Glenn Fitzgerald
Damon
Lil' Zane
Janice
Stephanie Berry
Fly
Fly Williams III
Clay
Damion Lee
Coach Garrick
Tom Kearns
Hartwell
Matthew Noah Word
Dr. Simon
Charles Bernstein
Bradley
Matt Malloy
Steven Sanderson
Matt Damon
Robert Crawford
F. Murray Abraham
Rapper
Jimmy Bobbit
Opposing Player
Capital Jay
Student
Jim Titus
Claire's Friend
Cassandra Kubinski
Librarian
Sophia Wu
Student Speaker
Gerry Rosenthal
Student Manager
Tim Hall
Old Money Man
Tom Mullica
Kid in the Hall
David Madison
Night Man
Joey Buttafuoco
Claire Spence
Anna Paquin
Referee
Jaime McCaig
William Modeste
Hallway Boy
Daniel Rodriguez
Creston Player
Samuel Tyson
Big Band Leader
Vince Giordano
Trumpet Player
Dean Pratt
Kerry MacKillop
Trombone Player
Harvey Tibbs
Sax Player
Jack Stuckey
Mark Lopeman
Kenzo
Damany Mathis
Marc Phaneuf
Larry Wade
Piano Player
Conal Fowkes
Guitarist
Matt Munisteri
Drummer
John Meyers
Mailor Priest
Ron Morgan
Jeopardy Contestant
Alison Folland
Alex Trebek
Library Assistant (uncredited)
Gus Van Sant
Terrell Wallace
Busta Rhymes
Ms. Joyce
April Grace
John Coleridge
Michael Pitt
Dr. Spence
Michael Nouri
Prof. Matthews
Richard Easton
Producer
Laurence Mark
Executive Producer
Jonathan King
Stunt Coordinator
G. A. Aguilar
Director
Set Decoration
Carolyn A. Loucks
Costume Design
Ann Roth
Writer
Mike Rich
Casting
Bernard Telsey
Francine Maisler
Director of Photography
Harris Savides
Rhonda Tollefson
Editor
Valdís Óskarsdóttir
Supervising Sound Editor
Kelley Baker
David Vaccari
Dany Wolf
Production Design
Jane Musky
Art Direction
Robert Guerra
Darrell K. Keister
Susan Bode Tyson
Lynn Tonnessen
Sound Effects Editor
Patrick Winters
Richard Moore
Michael "Gonzo" Gandsey
Visual Effects Supervisor
Bob Munroe