- Shirley
- Shirley Ash
- Shirley Bates
- Shirley Brown
- Shirley Caddell
- Shirley Cline
- Shirley Collie
- Shirley Evans
- Shirley Frederickson
- Shirley Frederickson
- Shirley Jones
- Shirley Martin
- Shirley Myers
- Shiva Burlesque
- Shogun
- Shoji Tabuchi
- Shoot Low Sheriff
- Shooter Jennings
- Shooter Jennings & The . 357s
- Shooters
- ShoreGrass
- Short Creek Trio
- Shortbuckle Roark & Family
- Shorty Ashburn
- Shorty Bates
- Shorty Boyd
- Shorty Lindsey
- Shorty Sargent
- Shorty Smith
- Shorty Warren & his Western Rangers
- Shot Jackson
- Shot Jackson & His String Band
- Shotgun
- Shotgun Party
- Shoun Brothers
- Shug Fisher
- Shurman
- Shy England
- ShyAnne Mailen
- Si & The Ozark Ramblers Jenkins
- Siara Sol
- Sid Campbell
- Sid Cox
- Sid Griffin
- Sid Harkreader
- Sid Hausman & Washtub Jerry
- Sid King
- Sid King & The Five Strings
- Sid Melancon
- Sid Selvidge
- Sid Spencer
- Side Wheel Sallie Duffie
- Sidesaddle
- Sideshow
- Sidna Myers
- Sidney Campbell
- Sidney Harth
- Sidney Maker