Cast 57

1. 

   Sanaa Lathan

   Sidney 'Sid' Shaw

2. 

   Taye Diggs

   Andre Romulus 'Dre' Ellis

3. 

   Yasiin Bey

   Chris Anton 'Cav' Vichon

4. 

   Nicole Ari Parker

   Reese Marie Wiggam Ellis

5. 

   Boris Kodjoe

   Kelby Dawson

6. 

   Queen Latifah

   Francine

7. 

   Wendell Pierce

   Simon

8. 

   Erik Weiner

   Ren

9. Reggi Wyns

   Ten

10. Melissa Martínez

    Meghan

11. Aaliyyah Hill

    Young Sidney

12. 

    Marc John Jefferies

    Young Dre

13. 

    Angie Martinez

    Self (Radio DJ)

14. 

    Rosalyn Coleman

    Trish Hofmann

15. Keith Tisdell

    Richard Lawson

16. 

    Venida Evans

    Older Woman

17. Breece Wilson

    Woman

18. 

    Brette Taylor

    Woman 2

19. 

    Donna DuPlantier

    Woman 3

20. Robin T. Kirksey

    Bartender 1

21. 

    Sterling K. Brown

    Co-Worker

22. Kofi Boakye

    Host

23. Dena Atlantic

    Hot 97 Assistant

24. Gerry Pinzon

    Instructor

25. Sam McPherson

    Iridium Waiter

26. 

    Big Daddy Kane

    Self

27. 

    Tariq Trotter

    Self - Black Thought [The Roots]

28. 

    Questlove

    Self

29. 

    Kool G Rap

    Self

30. 

    Helmar Augustus Cooper

    Reverend

31. Wyking Jones

    Bartender

32. 

    Toks Olagundoye

    Sidney's LA Assistant

33. 

    Opal Alladin

    Crafts Vendor

34. 

    Dana Dane

    Self

35. 

    Doug E. Fresh

    Self

36. 

    Slick Rick

    Self

37. 

    Jermaine Dupri

    Self

38. Pete Rock

    Self

39. David Jolicoeur

    Self - Trugoy the Dove [De La Soul]

40. Kelvin Mercer

    Self - Posdnuos [De La Soul]

41. Vincent Mason

    Self - Maseo [De La Soul]

42. 

    Kimora Lee Simmons

    Self

43. 

    Russell Simmons

    Self

44. 

    Beanie Sigel

    Self

45. 

    Talib Kweli

    Self

46. 

    Common

    Self

47. 

    Method Man

    Self

48. Hadley Martin Fisher

    Backstage Bartender

49. Justin 'DJ' Spaulding

    Kid in the Park

50. 

    Liza Lapira

    Hot 97 Receptionist

51. 

    Ralph E. Tresvant

    Royale (uncredited)

52. 

    Kevin Watson

    Record Label Executive (uncredited)

53. 

    Vinny DeGennaro

    Bouncer (uncredited)

54. 

    Lamman Rucker

    Man on Couch at Radio Station (uncredited)

55. Erica Ise

    Bridesmaid (uncredited)

56. 

    Spencer Kayden

    Bridesmaid (uncredited)

57. 

    Chyna

    Woman at Party (uncredited)

Crew 78