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)