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

Matt Malloy

Bradley

Matt Damon

Steven Sanderson

Jim Titus

Student

Vince Giordano

Big Band Leader

Alison Folland

Jeopardy Contestant

Alex Trebek

Alex Trebek

Gus Van Sant

Library Assistant (uncredited)