- Gary Simmons
- Gary Simmons
- Gary Sinise
- Gary Sivils
- Gary Skardina
- Gary Skelton
- Gary Sloan
- Gary Sloan
- Gary Smaby
- Gary Small
- Gary Small & The Coyote Brothers
- Gary Smalls
- Gary Smart
- Gary Smejkal
- Gary Smith
- Gary Smith
- Gary Smith
- Gary Smith
- Gary Smith Blues Band
- Gary Smulyan
- Gary Smulyan Quartet
- Gary Smulyan Quintet
- Gary Snider
- Gary Snipes
- Gary Snyder
- Gary Sparks
- Gary Speed
- Gary Spencer
- Gary Spencer
- Gary "Sphinx" Samuels
- Gary Sredzienski
- Gary Sredzienski & The Serfs
- Gary St. Clair
- Gary Stadler
- Gary Stadler and Wendy Rule
- Gary Steadman & Enchanted Mountain Boys
- Gary Steigerwalt
- Gary Stephen Sloyer
- Gary Stevens
- Gary Stewart
- Gary Stier
- Gary Stiliano
- Gary Stites
- Gary Stockdale
- Gary Stoddard
- Gary Stroutsos
- Gary Stryder
- Gary Stuart
- Gary Stuart King & Amigos
- Gary Stucka
- Gary Swan
- Gary Swindell Jr.
- Gary Szymik
- Gary T
- Gary T
- Gary T. 502
- Gary T. Bell