Considered one of the great jazz guitarists, Wes Montgomery admitted to influences that included Charlie Christian, and then later the saxophonist John Coltrane, with whom he played briefly in an unrecorded group.

Wes's development and use of octaves became both influential and a trademark, but it took Wes a long time to become an overnight success. He achieved commercial success with his Verve recordings during his last few years, only to die of a heart attack prematurely.

Like his idol, Charlie Christian, Wes came from a musical family and taught himself guitar by learning the solos of Charlie Christian and Django Reinhardt, from whom he developed the idea of playing octaves. He tried to use a pick in the conventional style but eventually opted to use his thumb because he preferred the thick, warm sound it produced. He toured with Lionel Hampton's big band from 1948 through 1950 and can be heard on a few broadcasts from the period. Then he returned to Indianapolis, where he played in relative obscurity during much of the 1950s, working a day job and playing at clubs most nights.

He recorded with his brothers, pianist and vibraphonist Buddy and bass player Monk, during 1957 through 1959, and in 1959 he made his first album, The Wes Montgomery Trio, with organist Mel Rhyne.

In 1960, the release of his album, The Incredible Jazz Guitar of Wes Montgomery, made him famous in the jazz world. Later that year he spent some time playing with the John Coltrane Sextet.

Montgomery's Riverside dates (1959–1963) are among his most inventive jazz recordings, in small-group sessions with such sidemen as George Shearing, Tommy Flanagan, James Clay, Victor Feldman, Hank Jones, Johnny Griffin, and Mel Rhyne.

From 1964 through 1966, Montgomery moved to Verve and recorded a series of orchestral dates with arranger Don Sebesky and producer Creed Taylor. These records popularized him with the general listening audience, widening his appeal from a pure jazz base. In 1967 he continued this trend, signing with Creed Taylor at A&M, where he recorded three best selling albums that featured him playing pop melodies backed by strings and woodwinds.

Wes Montgomery died of a heart attack at the height of his success. However, his influence is still felt through many young guitarists, notably Pat Metheny.