Born March 6, 1923, in Indianapolis, Montgomery grew up in Columbus, Ohio, and became smitten with the guitar after he heard Christian's "Solo Flight." Soon he committed himself to learning his mentor's solos from records. However, since he was a welder by trade, Montgomery was slow to throw his hat into the jazz ring, preferring instead to play local clubs until he was recruited by the Lionel Hampton big band to hit the road in 1948. That gig proved to be short-lived, as the guitarist retreated home to support his family. Ten years later, Riverside artist Cannonball Adderley caught the singular guitarist playing a club date in Indianapolis and alerted producer Orrin Keepnews, who immediately signed Montgomery and recorded several discs.
Montgomery was a revelation to jazzheads in the '60s. Unschooled on his instrument, Montgomery had developed a unique way to play the guitar, picking notes with his thumb instead of a pick and running his single-note lines into octaves. After Riverside went bankrupt, Montgomery recorded for Verve, opting for more pop-oriented jazz fare to capitalize on the changing tides in the music world. In 1967, he moved over to A&M, in the midst of the pop music revolution, playing even more accessible fare on three commercially successful albums. Montgomery died on June 15, 1968, at the age of 45.
In 1968, Montgomery was elected by the Readers into the Down Beat Hall of Fame.