R
- Rakim Rap/Hip-Hop
- Ralph Macchio Actor
- Randy Macho Man Savage Other
- Red Man Rap/Hip-Hop
- Redhead Kingpin Rap/Hip-Hop
- Reggie Miller Basketball
- Richard Hatch Other
- Rick Fox Rap/Hip-Hop
- Rob Base Rap/Hip-Hop
- Robin Givens Actress
- Roger E. Mosley Actress
- Rosario Dawson Actress
- Ross Bagley Actor
- Run DMC Rap/Hip-Hop