Sean Connery as William Forrester

Rob Brown as Jamal Wallace

F. Murray Abraham as Robert Crawford

Anna Paquin as Claire Spence

Damany Mathis as Kenzo

Busta Rhymes as Terrell Wallace

April Grace as Ms. Joyce

Michael Pitt as John Coleridge

Michael Nouri as Dr. Spence

Richard Easton as Prof. Matthews

Glenn Fitzgerald as Massie

Lil' Zane as Damon

Stephanie Berry as Janice

Fly Williams III as Fly

Damion Lee as Clay

Tom Kearns as Coach Garrick

Matthew Noah Word as Hartwell

Charles Bernstein as Dr. Simon

Matt Malloy as Bradley

Matt Damon as Steven Sanderson

Jimmy Bobbit as Rapper

Capital Jay as Opposing Player

Jim Titus as Student

Cassandra Kubinski as Claire's Friend

Sophia Wu as Librarian

Gerry Rosenthal as Student Speaker

Tim Hall as Student Manager

Tom Mullica as Old Money Man

David Madison as Kid in the Hall

Joey Buttafuoco as Night Man

Jaime McCaig as Referee

William Modeste as Referee

Daniel Rodriguez as Hallway Boy

Samuel Tyson as Creston Player

Vince Giordano as Big Band Leader

Dean Pratt as Trumpet Player

Kerry MacKillop as Trumpet Player

Harvey Tibbs as Trombone Player

Jack Stuckey as Sax Player

Mark Lopeman as Sax Player

Marc Phaneuf as Sax Player

Larry Wade as Sax Player

Conal Fowkes as Piano Player

Matt Munisteri as Guitarist

John Meyers as Drummer

Ron Morgan as Mailor Priest

Alison Folland as Jeopardy Contestant

Alex Trebek as Alex Trebek

Gus Van Sant as Library Assistant (uncredited)