Sean Connery
William Forrester
Acting
Rob Brown
Jamal Wallace
Acting
F. Murray Abraham
Robert Crawford
Acting
Anna Paquin
Claire Spence
Acting
Damany Mathis
Kenzo
Acting
Busta Rhymes
Terrell Wallace
Acting
April Grace
Ms. Joyce
Acting
Michael Pitt
John Coleridge
Acting
Michael Nouri
Dr. Spence
Acting
Richard Easton
Prof. Matthews
Acting
Glenn Fitzgerald
Massie
Acting
Lil' Zane
Damon
Acting
Stephanie Berry
Janice
Acting
Fly Williams III
Fly
Acting
Damion Lee
Clay
Acting
Tom Kearns
Coach Garrick
Acting
Matthew Noah Word
Hartwell
Acting
Charles Bernstein
Dr. Simon
Acting
Matt Malloy
Bradley
Acting
Matt Damon
Steven Sanderson
Acting
Jimmy Bobbit
Rapper
Acting
Capital Jay
Opposing Player
Acting
Jim Titus
Student
Acting
Cassandra Kubinski
Claire's Friend
Acting
Sophia Wu
Librarian
Acting
Gerry Rosenthal
Student Speaker
Acting
Tim Hall
Student Manager
Acting
Tom Mullica
Old Money Man
Acting
David Madison
Kid in the Hall
Acting
Joey Buttafuoco
Night Man
Acting
Jaime McCaig
Referee
Acting
William Modeste
Referee
Acting
Daniel Rodriguez
Hallway Boy
Acting
Samuel Tyson
Creston Player
Acting
Vince Giordano
Big Band Leader
Acting
Dean Pratt
Trumpet Player
Acting
Kerry MacKillop
Trumpet Player
Acting
Harvey Tibbs
Trombone Player
Acting
Jack Stuckey
Sax Player
Acting
Mark Lopeman
Sax Player
Acting
Marc Phaneuf
Sax Player
Acting
Larry Wade
Sax Player
Acting
Conal Fowkes
Piano Player
Sound
Matt Munisteri
Guitarist
Acting
John Meyers
Drummer
Acting
Ron Morgan
Mailor Priest
Acting
Alison Folland
Jeopardy Contestant
Acting
Alex Trebek
Alex Trebek
Acting
Gus Van Sant
Library Assistant (uncredited)
Directing