- Silver, Wood and Steel
- Silverhands
- Silvertone Gospel Harmonizers
- Silverwood
- Simani
- Simon Balkey
- Simon Chardiet
- Simon Crum
- Simon Joyner
- Simon Pollard Band
- Simone Moraes
- Simple Gifts of the Blue Ridge
- Sindacato
- Sindicato
- Singer Silvertone Singers
- Singing Cowboys
- Singing Gospelaires
- Singing Mountaineers
- Singletree
- Sir J. Vincent Roberts
- Sissy Spacek
- Sister Girl
- Sisters Wade
- Six Deadly Venoms
- Six Gun Sly
- Six Market Blvd.
- Six Shooter
- Six String Eric and His Lazy Ranch Hands
- Six String Story
- Sixth Great Lake
- Sixwire
- Skeet Anglin
- Skeet Ring and the Hillbilly Swingers
- Skeeter Biscuit
- Skeeter Davis
- Skeets Bennett
- Skeets Martin
- Skeets McDonald
- Skip Beckwith
- Skip Bessonette
- Skip Cleavinger
- Skip Ewing
- Skip Gorman & The Waddie Pals
- Skip Jackson
- Skip Orlando
- Skooter Jones
- Skooter Jones
- Skott Skibba
- Sky Wyatt
- Skye Moore
- Skyla Spencer
- Skyland
- Skyline
- Skyline Serenaders
- Skymonters
- Skytoppers
- Slabtown
- Slack Family Bluegrass Band
- Slam Dunks
- Slant 6 Cowboys
- Slavek Hanzlik
- Sleep Station
- Sleepercar
- Sleepy Hollow
- Sleepy Johnson
- Sleepy LaBeef
- Sleepy Man Banjo Boys