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- R.A. the Rugged ManCity: Long IslandStarted in: 1990s
- Rae KhalilCity: TorranceCountry: United States
- RaekwonCity: BrooklynStarted in: 1990s
- Rah DiggaCity: NewarkStarted in: 1990s
- Rah SwishCountry: United StatesGenres: Brooklyn drill
- Raheem JarboStarted in: 2000sCountry: United States
- Rahsaan PattersonCity: New York CityStarted in: 1980s
- RahzelCity: QueensCountry: United States
- RakimCity: New York CityStarted in: 1980s
- Ramin FallahCity: TehranStarted in: 2010s
- RampageCity: BrooklynStarted in: 1990s
- RandomStarted in: 1970sCountry: United States
- Rapper Big PoohStarted in: 1980sCountry: United States
- Rappin' 4-TayCity: San FranciscoStarted in: 1980s
- Rappin' GrannyStarted in: 1980sCountry: United States
- Rappin’ 4‐TayStarted in: 1960sCountry: United States
- Ras KassCity: WattsStarted in: 1990s
- RascoCity: San MateoStarted in: 1980s
- RasheedaCity: AtlantaStarted in: 1990s
- RauryCity: Stone MountainStarted in: 2010s
- Raven-SymonéCity: AtlantaStarted in: 1980s
- Raw YounginCity: Lake CityCountry: United States
- Ray DaltonCity: SeattleStarted in: 2010s
- Ray JCity: McCombStarted in: 1990s
- Ray William JohnsonCity: Oklahoma CityStarted in: 2000s
- Raz-BCity: ClevelandStarted in: 1990s
- RBXCity: Long BeachStarted in: 1990s
- Real Boston RicheyCity: TallahasseeStarted in: 2020s
- Rebekah KimCity: HonoluluStarted in: 2000s
- Red CaféStarted in: 1970sCountry: United States
- RedfooCity: Los AngelesStarted in: 1990s
- RedmanStarted in: 1970sCountry: United States
- Reef the Lost CauzeCity: PhiladelphiaStarted in: 1990s
- ReksCity: LawrenceStarted in: 1990s
- Rella GzCity: New York CityCountry: United States
- RemedyCity: Staten IslandCountry: United States
- RFG GRiMCity: West MemphisStarted in: 2020s
- RFG Osama BCity: MemphisStarted in: 2020s
- RhymefestCity: ChicagoStarted in: 1990s
- Rican Da MenaceCity: BaltimoreCountry: United States
- Rich AmiriCity: BostonStarted in: 2010s
- Rich Homie QuanCity: AtlantaStarted in: 2010s
- Rich the KidCity: QueensStarted in: 2010s
- Richie RichCity: OaklandStarted in: 1980s
- Rick RubinCity: Lido BeachStarted in: 1980s
- Ricky ReedStarted in: 2000sCountry: United States
- Rico LoveCity: New OrleansStarted in: 2000s
- Rico NastyCity: LargoStarted in: 2010s
- Riff RaffCity: HoustonStarted in: 2000s
- Rio da Yung OGCity: FlintStarted in: 2010s
- RiotUSACity: ManhattanStarted in: 2020s
- RJD2City: EugeneStarted in: 1990s
- RMC MikeCity: FlintCountry: United States
- Rob SwiftStarted in: 1980sCountry: United States
- Rob49Started in: 2020sCountry: United States
- Robb BanksCity: BrooklynStarted in: 2000s
- Roc MarcianoCity: HempsteadStarted in: 1990s
- Roc RaidaCity: New York CityStarted in: 1980s
- Rockie FreshCity: ChicagoStarted in: 2000s
- RockwilderCity: QueensStarted in: 1990s
- Rod WaveCity: St. PetersburgStarted in: 2010s
- Roddy RicchCity: ComptonStarted in: 2010s
- Roderick Vonn Thornton Jr.Country: United StatesGenres: hip-hop
- Rodney HunterCity: WiesbadenCountry: United States
- Rodney JerkinsCity: PleasantvilleStarted in: 1990s
- Rome FortuneCity: PhiladelphiaStarted in: 2010s
- Rome StreetzStarted in: 1980sCountry: United States
- Romeo MillerCity: New OrleansStarted in: 2000s
- Ron BrowzCity: New York CityStarted in: 1990s
- Ronald "Slim" WilliamsCity: New OrleansStarted in: 1980s
- Ronald JenkeesStarted in: 2000sCountry: United States
- Ronnie HudsonCity: Washington, D.C.Started in: 1970s
- RoscoeCity: PhiladelphiaStarted in: 1990s
- Roscoe DashCity: AtlantaStarted in: 2000s
- Roshon FeganCity: Los AngelesStarted in: 2000s
- Rowdy RebelCity: BrooklynStarted in: 2010s
- Roxanne ShantéCity: QueensStarted in: 1980s
- Royce CaldwellCity: BrooklynCountry: United States
- Royce da 5′9″Started in: 1970sCountry: United States
- Ruben SlikkStarted in: 1990sCountry: United States
- Ruben StuddardCity: FrankfurtStarted in: 2000s
- Rubi RoseCity: LexingtonStarted in: 2010s
- Ruby MountainCity: OaklandCountry: United States
- Rucka Rucka AliCity: JerusalemStarted in: 2000s
- RussCity: SecaucusStarted in: 2000s
- Russell SimmonsCity: QueensCountry: United States
- Ryan LewisCity: SeattleStarted in: 2000s
- Ryan TreyCity: St. LouisStarted in: 2010s
- Rye RyeCity: BaltimoreStarted in: 2000s
- RZAStarted in: 1960sCountry: United States
- SabaCity: ChicagoStarted in: 2010s
- SabiCity: InglewoodStarted in: 2000s
- Sadat XCity: The BronxStarted in: 1980s
- SadistikCity: YakimaStarted in: 2000s
- Safaree SamuelsCity: FlatbushStarted in: 2000s
- SagatStarted in: 1990sCountry: United States
- Sage FrancisCity: MiamiStarted in: 1990s
- Sage the GeminiCity: FairfieldStarted in: 2000s
- SahBabiiCity: ChicagoStarted in: 2010s