On screen
Cast
49 credited performers
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
Artwork unavailable
Fly Williams III
Fly
Artwork unavailable
Damion Lee
Clay
Artwork unavailable
Tom Kearns
Coach Garrick
Artwork unavailable
Matthew Noah Word
Hartwell
Artwork unavailable
Charles Bernstein
Dr. Simon
Matt Malloy
Bradley
Matt Damon
Steven Sanderson
Artwork unavailable
Jimmy Bobbit
Rapper
Artwork unavailable
Capital Jay
Opposing Player
Jim Titus
Student
Artwork unavailable
Cassandra Kubinski
Claire's Friend
Artwork unavailable
Sophia Wu
Librarian
Artwork unavailable
Gerry Rosenthal
Student Speaker
Artwork unavailable
Tim Hall
Student Manager
Artwork unavailable
Tom Mullica
Old Money Man
Artwork unavailable
David Madison
Kid in the Hall
Artwork unavailable
Joey Buttafuoco
Night Man
Artwork unavailable
Jaime McCaig
Referee
Artwork unavailable
William Modeste
Referee
Artwork unavailable
Daniel Rodriguez
Hallway Boy
Artwork unavailable
Samuel Tyson
Creston Player
Vince Giordano
Big Band Leader
Artwork unavailable
Dean Pratt
Trumpet Player
Artwork unavailable
Kerry MacKillop
Trumpet Player
Artwork unavailable
Harvey Tibbs
Trombone Player
Artwork unavailable
Jack Stuckey
Sax Player
Artwork unavailable
Mark Lopeman
Sax Player
Artwork unavailable
Marc Phaneuf
Sax Player
Artwork unavailable
Larry Wade
Sax Player
Artwork unavailable
Conal Fowkes
Piano Player
Artwork unavailable
Matt Munisteri
Guitarist
Artwork unavailable
John Meyers
Drummer
Artwork unavailable
Ron Morgan
Mailor Priest
Alison Folland
Jeopardy Contestant
Alex Trebek
Alex Trebek
Gus Van Sant
Library Assistant (uncredited)