- Rackhouse Pilfer
- Radim Zenkl & Ondra Kozák
- Radio Flyer
- Rahat Fateh Ali Khan
- Railroad Earth
- Ralph Blizard & The New Southern Ramblers
- Ralph Stanley
- Ralph Stanley & Friends
- Ralph Stanley & The Clinch Mountain Boys
- Ralph Stanley II
- Rambler's Choice
- Ramblin' Dog
- Ramona Jones
- Randall Hylton
- Randy Kaplan
- Randy Kohrs
- Rani Arbo
- Rani Arbo & daisy mayhem
- Ray Cardwell
- Ray Dearstone
- Ray Edwards
- Ray LP
- Ray Waters
- Raymond Fairchild
- Raymond Fairchild & The Frosty Mountain Boys
- Raymond Fairchild And The Frosty Mountain Boys
- Raymond W. McLain
- Rebecca Frazier
- Rebecca King
- Rebirth
- Red Allen
- Red Allen & The Kentuckians
- Red Concord
- Red Cravens
- Red Rector
- Red Smiley
- Red Smiley & The Bluegrass Cut-Ups
- Red, White & Blue(Grass)
- Redline
- Redwing
- Remington Ryde
- Remon Rey349
- Reno
- Reno & Smiley
- Reno Brothers
- Rev Peter Unger
- Revival Ridge Ministries
- Rhiannon Giddens
- Rhoda
- Rhonda Vincent
- Rhonda Vincent & The Sally Mountain Show
- Rhonda Vincent and the Rage
- Rice, Rice, Hillman & Pedersen
- Rice, Rice, Hillman and Pedersen
- Rich O'Brien
- Richard B. Greene
- Richard Bennett
- Richard Greene
- Richard Rodney Bennett
- Rick Faris
- Rick Lang
- Rick Monroe
- Rickey Wasson
- Rickie Simpkins
- Ricky Razu
- Ricky Skaggs
- Ricky Skaggs & The Whites
- RIGLI
- Riley Baugus
- Riley Puckett
- Rique Galiani
- Risto Milner
- River Bend
- Riverbend
- Rob Ickes
- Rob Ickes & Trey Hensley
- Rob McCoury
- Robbie Fulks
- Robert Burwell
- Robert Earl Keen
- Robert Hale
- Robert Lloyd Peeples
- Robert Meeks Jr
- Robert Porembski
- Robert Shafer
- Robert Stanley
- Robert's Rat
- Robin & Linda Williams
- Robin Bullock
- Robinella
- Robinella & The CC Stringband
- Robinella and the CCstringband
- Rocco und Marc
- Rock County
- Rockin Johnny Aitken
- Rockridge Brothers
- Rocky Alvey
- Rodney Dillard
- Rodney Miller
- Rodriggo Júnior
- Roger Cooper
- Roger Sprung
- Roger Sprung, Hal Wylie and the Progressive Bluegrassers
- Roland White
- Roland White & Friends
- Roland White Band
- Rollin' In The Hay
- Ron Block
- Ron Stewart
- Ronnie & Rob McCoury
- Ronnie Bowman
- Ronnie McCoury
- Ronnie Reno And The Reno Tradition
- Rootstand
- Rory Gardiner
- Rose Cousins
- Rose Maddox
- Rose Maddox with The Vern Williams Band
- Ross Nickerson
- Roy Acuff
- Roy McMillan
- Rual Yarbrough
- Rubberneck
- Rudy Cipolla
- Ruis
- Run Boy Run
- Rushbeat
- Russ Barenberg
- Russ Davis
- Russell Moore
- Russell Moore & IIIrd Tyme Out
- Rusty Horn
- Ryan Holladay
- Rye Davis
- Rüdiger Helbig