[2][1] Self-taught on the guitar at an early age, from watching a local minister-cum-barber playing his own flat-bodied guitar,[3] Gilmore initially headed a band of youths who appeared in local clubs long before they were legally able to enter such establishments.

[1] In the 1960s, Gilmore relocated to South Florida, and he became a popular local attraction which led to him accompanying many touring blues, R&B and soul musicians.

[6][7] It took until the mid 1990s before Gilmore began recording more frequently, and he appeared at numerous blues, jazz and soul festivals which included dates in Fort Lauderdale, Hollywood, Mississippi Valley, Montreux, Riverwalk, and in Taiwan.

[1] Among Gilmore's sidemen in the mid-2000s were Regi Oliver (saxophone/keyboard), George Caldwell (bass) and Dave Wooten (drums).

[3][12] He continued to regularly play throughout his native Florida, including an appearance at the Pompano Beach Seafood Festival,[13] and beyond.