William Forrester

Sean Connery

Acting

Jamal Wallace

Rob Brown

Acting

Robert Crawford

F. Murray Abraham

Acting

Claire Spence

Anna Paquin

Acting

Kenzo

Damany Mathis

Acting

Terrell Wallace

Busta Rhymes

Acting

Ms. Joyce

April Grace

Acting

John Coleridge

Michael Pitt

Acting

Dr. Spence

Michael Nouri

Acting

Prof. Matthews

Richard Easton

Acting

Massie

Glenn Fitzgerald

Acting

Damon

Lil' Zane

Acting

Janice

Stephanie Berry

Acting

Fly

Fly Williams III

Acting

Clay

Damion Lee

Acting

Coach Garrick

Tom Kearns

Acting

Hartwell

Matthew Noah Word

Acting

Dr. Simon

Charles Bernstein

Acting

Bradley

Matt Malloy

Acting

Steven Sanderson

Matt Damon

Acting

Rapper

Jimmy Bobbit

Acting

Opposing Player

Capital Jay

Acting

Student

Jim Titus

Acting

Claire's Friend

Cassandra Kubinski

Acting

Librarian

Sophia Wu

Acting

Student Speaker

Gerry Rosenthal

Acting

Student Manager

Tim Hall

Acting

Old Money Man

Tom Mullica

Acting

Kid in the Hall

David Madison

Acting

Night Man

Joey Buttafuoco

Acting

Referee

Jaime McCaig

Acting

Referee

William Modeste

Acting

Hallway Boy

Daniel Rodriguez

Acting

Creston Player

Samuel Tyson

Acting

Big Band Leader

Vince Giordano

Acting

Trumpet Player

Dean Pratt

Acting

Trumpet Player

Kerry MacKillop

Acting

Trombone Player

Harvey Tibbs

Acting

Sax Player

Jack Stuckey

Acting

Sax Player

Mark Lopeman

Acting

Sax Player

Marc Phaneuf

Acting

Sax Player

Larry Wade

Acting

Piano Player

Conal Fowkes

Sound

Guitarist

Matt Munisteri

Acting

Drummer

John Meyers

Acting

Mailor Priest

Ron Morgan

Acting

Jeopardy Contestant

Alison Folland

Acting

Alex Trebek

Alex Trebek

Acting

Library Assistant (uncredited)

Gus Van Sant

Directing