The fiddler started playing at the age of 12 with his brothers George and Jerry under the moniker the Rose Swingsters before finding a career in 1949 when he joined Bob Wills' Texas Playboys. Gimble toured with the group for a decade, uniquely playing the five-star fiddle and the electric mandolin, save for the two years he went off on his own from 1951 to '53. It was then he had his first hit: Marty Robbins' 1953 debut No. 1 song "I'll Go on Alone."

Gimble's own debut solo hit "One Fiddle, Two Fiddle" happened decades later, thanks in part to its feature in Clint Eastwood's 1982 film Honkytonk Man, where Gimble played Wills in a supporting role.