- Ridge Runner
- Rift
- Rigney Family Bluegrass
- Rikka Z
- Rikki Leigh Heard
- Riley
- Riley Baugus
- Riley Coyle
- Riley Crabtree
- Riley Puckett
- Riley Siebert
- Rio Grand
- Riochet
- Rip Ramsey
- Rip Ramsey & His Texas Wanderers
- Rita Coolidge
- Rita Faye Wilson
- Rita Francia
- Rita Hosking
- Rita Remington
- Rita Rose
- Ritchie/Watson
- River City Extension
- River Country
- River Road
- RiverBluff Clan
- Rivers
- Riverside
- riverview
- Riviera
- RJ McClintock
- R.J. Verette
- Roach Bros
- Road Music
- Roadcrew
- Roadkill Bill
- Roadrunner
- Roadside Theater
- Roanoke
- Rob Baird
- Rob Baird a
- Rob Bates
- Rob Bruce
- Rob Chiossi
- Rob Crosby
- Rob DeMorrow
- Rob Dewbre
- Rob Dubois
- Rob Hajacos
- Rob Hajocos
- Rob Heath
- Rob Kaufelt
- Rob Kirkham and Neon Rain
- Rob McCoury
- Rob McNurlin
- Rob McNurlin
- Rob Robinson
- Rob Russell
- Rob Ryan
- Rob Walsh Project