[1] Montgomery was known for his unusual technique of plucking the strings with the side of his thumb and for his extensive use of octaves, which gave him a distinctive sound.

His older brother Monk dropped out of school to sell coal and ice, gradually saving enough money to buy Wes a four-string tenor guitar from a pawn shop in 1935.

By the age of twenty, he was performing in clubs in Indianapolis at night, copying Christian's solos, while working during the day at a milk company.

He joined his brothers Buddy and Monk and saxophonist Alonzo "Pookie" Johnson in the Johnson/Montgomery Quintet, somewhat in the style of George Shearing.

[4] Buddy and Monk Montgomery formed The Mastersounds and signed a contract with Dick Bock at Pacific Jazz.

The Mastersounds remained in California when Montgomery returned to Indianapolis to work in his trio with organist Melvin Rhyne.

The Mastersounds had broken up, and Buddy and Monk had signed with Fantasy and recorded (with Wes) The Montgomery Brothers, followed by Groove Yard.

Montgomery recorded another album as a leader, So Much Guitar, then while visiting his brothers had a chance to perform with John Coltrane's group in San Francisco.

Keepnews sent him back to California to record a live album with Johnny Griffin, Wynton Kelly, Paul Chambers, and Jimmy Cobb.

It quickly sold more than 100,000 copies and repositioned Montgomery within the recording industry as a crossover artist capable of significant LP sales.

After moving to A&M, Montgomery had his biggest radio hit, a version of "Windy", a pop song originally recorded by The Association.

[5]According to jazz guitar educator Wolf Marshall, Montgomery often approached solos in a three-tiered manner: he would begin the progression with single note lines, derived from scales or modes; after a fitting number of sequences, he would play octaves for a few more sequences, finally culminating with block chords.

[specify] Jazz guitarist Bobby Broom said that on A Dynamic New Sound in 1959, Montgomery "introduced a brand new approach to playing the guitar...

[14] Eric Johnson paid tribute to Montgomery on his 1990 album Ah Via Musicom in a song titled "East Wes".

[15] Guitarist David Becker paid tribute to Montgomery on the 1991 album In Motion with the song "Westward Ho".

[17] While the production and arrangements are typical for the time, he performed the entire album in Montgomery's style on a Gibson L-5 model.