- Sheri Lynn
- Sheri Porter
- Sheri Timsak
- Sheri Vandiver
- Sherie Austin
- Sherie Mulvaney
- Sheriff Johnny Denis
- Sherman Collins
- Sherman Hayes
- Sherman Lawson
- Sherri Jerrico
- Sherri Nourse
- Sherrié Austin
- Sherry Bryce
- Sherry Garland
- Sherry Kean
- Sherry Kennedy
- Sherry Lee
- Sherry Leece
- Sherry Lynn
- Sherwin Kaufman
- Sheryl Crow
- Sheryl Paige
- Shevy Smith
- Shields
- Shifty Morgan
- Shilo
- Shiloh Circle
- Shiloh Lindsey
- Shimek
- Shiny Johnson
- Shipcote's Foot Tappers
- Shiregreen
- 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