Trailer
Images
 | 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) |
| Directing | |
| Gus Van Sant | Director |
Editing | |
| Valdís Óskarsdóttir | Editor |
Production | |
| Sean Connery | Producer |
Camera | |
| Harris Savides | Director of Photography |
Production | |
| Rhonda Tollefson | Producer |
| Laurence Mark | Producer |
Sound | |
| Kelley Baker | Supervising Sound Editor |
Production | |
| Francine Maisler | Casting |
| Dany Wolf | Executive Producer |
| David Vaccari | Casting |
| Bernard Telsey | Casting |
| Jonathan King | Executive Producer |
Writing | |
| Mike Rich | Writer |
Art | |
| Susan Bode Tyson | Set Decoration |
Sound | |
| Patrick Winters | Sound Effects Editor |
Visual Effects | |
| Bob Munroe | Visual Effects Supervisor |
Art | |
| Darrell K. Keister | Art Direction |
| Lynn Tonnessen | Set Decoration |
| Jane Musky | Production Design |
Costume & Make-Up | |
| Ann Roth | Costume Design |
Sound | |
| Richard Moore | Sound Effects Editor |
Art | |
| Robert Guerra | Art Direction |
| Carolyn A. Loucks | Set Decoration |
Sound | |
| Michael 'Gonzo' Gandsey | Sound Effects Editor |
Crew | |
| G.A. Aguilar | Stunt Coordinator |
Directing | |
| David Webb | First Assistant Director |
Sound | |
| Bill Brown | Original Music Composer |
| Bill Frisell | Original Music Composer |
