 | Monica Arnold | ... | Herself (segment "Angel of Mine") (as Monica) |
| Erykah Badu | ... | Herself (segment "On & On") |
| Eric B. | ... | Himself (segment "Eric B. Is President") (as Eric B. & Rakim) |
| Mary J. Blige | ... | Herself (segment "You're All I Need") |
| Ishmael Butler | ... | Himself (segment "Rebirth of Slick [Cool Like Dat]") (as Digable Planets) |
| Deborah Cox | ... | Herself (segment "Sentimental") |
| Dalvin DeGrate | ... | Himself (segment "Forever My Lady") (as Jodeci) |
| DeVante DeGrate | ... | Himself (segment "Forever My Lady") (as Jodeci) |
| Omar Epps | ... | (segment "Sentimental") |
| Jo Jo Hailey | ... | Himself (segment "Forever My Lady") (as Jodeci) |
| K-Ci Hailey | ... | Himself (segment "Forever My Lady") (as Jodeci) |
| Humpty Hump | ... | Himself (segment "The Humpty Dance") (as Digital Underground) |
| Montell Jordan | ... | Himself (segment "This Is How We Do It") |
| Juvenile | ... | Himself (segment "Back That Thing Up") |
| R. Kelly | ... | Himself (segment "Bump 'n' Grind") |
| Method Man | ... | Himself (segment "You're All I Need") |
| P.A. Pacemaster Mase | ... | Himself (segment "Me, Myself and I") (as De la Soul) |
| Darryl McDaniels | ... | Himself (segment "Walk This Way") (as Run-DMC) |
| Brian McKnight | ... | Himself (segment "Anytime") |
| Jason Mizell | ... | Himself (segment "Walk This Way") (as Run-DMC) |
| Money-B | ... | Himself (segment "The Humpty Dance") (as Digital Underground) |
| Prince Paul | ... | Himself (segment "Me, Myself and I") |
| Joe Perry | ... | Himself (segment "Walk This Way") (as Aerosmith) |
| Posdnous | ... | Himself (segment "Me, Myself and I") (as De la Soul) |
| Rakim | ... | Himself (segment "Eric B. Is President") (as Eric B. & Rakim) |
| Usher Raymond | ... | Himself (segment "My Way") (as Usher) |
| Shock-G | ... | Himself (segment "The Humpty Dance") (as Digital Underground) |
| Joseph Simmons | ... | Himself (segment "Walk This Way") (as Run-DMC) |
| Trugoy The Dove | ... | Himself (segment "Me, Myself and I") (as De la Soul) |
| Steven Tyler | ... | Himself (segment "Walk This Way") (as Aerosmith) |
| Mary Ann Vierra | ... | Herself (segment "Rebirth of Slick [Cool Like Dat]") (as Digable Planets) |
