Sean Connery
William Forrester
F. Murray Abraham
Robert Crawford
Busta Rhymes
Terrell Wallace
Michael Pitt
John Coleridge
Richard Easton
Prof. Matthews
Matthew Noah Word
Hartwell
Charles Bernstein
Dr. Simon
Matt Damon
Steven Sanderson
Capital Jay
Opposing Player
Cassandra Kubinski
Claire's Friend
Gerry Rosenthal
Student Speaker
David Madison
Kid in the Hall
Daniel Rodriguez
Hallway Boy
Samuel Tyson
Creston Player
Vince Giordano
Big Band Leader
Kerry MacKillop
Trumpet Player
Harvey Tibbs
Trombone Player
Alison Folland
Jeopardy Contestant
Gus Van Sant
Library Assistant (uncredited)