Cast 49

1. 

   Sean Connery

   William Forrester

2. 

   Rob Brown

   Jamal Wallace

3. 

   F. Murray Abraham

   Robert Crawford

4. 

   Anna Paquin

   Claire Spence

5. 

   Busta Rhymes

   Terrell Wallace

6. 

   April Grace

   Ms. Joyce

7. 

   Michael Pitt

   John Coleridge

8. 

   Michael Nouri

   Dr. Spence

9. 

   Richard Easton

   Prof. Matthews

10. 

    Glenn Fitzgerald

    Massie

11. 

    Lil' Zane

    Damon

12. 

    Stephanie Berry

    Janice

13. 

    Fly Williams III

    Fly

14. 

    Damany Mathis

    Kenzo

15. Damion Lee

    Clay

16. Tom Kearns

    Coach Garrick

17. Matthew Noah Word

    Hartwell

18. Charles Bernstein

    Dr. Simon

19. 

    Matt Malloy

    Bradley

20. 

    Matt Damon

    Steven Sanderson

21. Jimmy Bobbit

    Rapper

22. Capital Jay

    Opposing Player

23. 

    Jim Titus

    Student

24. Cassandra Kubinski

    Claire's Friend

25. Sophia Wu

    Librarian

26. Gerry Rosenthal

    Student Speaker

27. Tim Hall

    Student Manager

28. Tom Mullica

    Old Money Man

29. David Madison

    Kid in the Hall

30. Joey Buttafuoco

    Night Man

31. Jaime McCaig

    Referee

32. William Modeste

    Referee

33. Daniel Rodriguez

    Hallway Boy

34. Samuel Tyson

    Creston Player

35. 

    Vince Giordano

    Big Band Leader

36. Dean Pratt

    Trumpet Player

37. Kerry MacKillop

    Trumpet Player

38. Harvey Tibbs

    Trombone Player

39. Jack Stuckey

    Sax Player

40. Mark Lopeman

    Sax Player

41. Marc Phaneuf

    Sax Player

42. Larry Wade

    Sax Player

43. Conal Fowkes

    Piano Player

44. Matt Munisteri

    Guitarist

45. John Meyers

    Drummer

46. Ron Morgan

    Mailor Priest

47. 

    Alison Folland

    Jeopardy Contestant

48. 

    Alex Trebek

    Alex Trebek

49. 

    Gus Van Sant

    Library Assistant (uncredited)

Crew 25