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