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Sean ConneryWilliam Forrester
Rob BrownJamal Wallace
F. Murray AbrahamRobert Crawford
Anna PaquinClaire Spence
Damany MathisKenzo
Busta RhymesTerrell Wallace
April GraceMs. Joyce
Michael PittJohn Coleridge
Michael NouriDr. Spence
Richard EastonProf. Matthews
Glenn FitzgeraldMassie
Lil' ZaneDamon
Stephanie BerryJanice
Fly Williams IIIFly- Damion LeeClay
- Tom KearnsCoach Garrick
- Matthew Noah WordHartwell
- Charles BernsteinDr. Simon
Matt MalloyBradley
Matt DamonSteven Sanderson- Jimmy BobbitRapper
- Capital JayOpposing Player
Jim TitusStudent- Cassandra KubinskiClaire's Friend
- Sophia WuLibrarian
- Gerry RosenthalStudent Speaker
- Tim HallStudent Manager
- Tom MullicaOld Money Man
- David MadisonKid in the Hall
- Joey ButtafuocoNight Man
- Jaime McCaigReferee
- William ModesteReferee
- Daniel RodriguezHallway Boy
- Samuel TysonCreston Player
Vince GiordanoBig Band Leader- Dean PrattTrumpet Player
- Kerry MacKillopTrumpet Player
- Harvey TibbsTrombone Player
- Jack StuckeySax Player
- Mark LopemanSax Player
- Marc PhaneufSax Player
- Larry WadeSax Player
- Conal FowkesPiano Player
- Matt MunisteriGuitarist
- John MeyersDrummer
- Ron MorganMailor Priest
Alison FollandJeopardy Contestant
Alex TrebekAlex Trebek
Gus Van SantLibrary Assistant (sem créditos)