Montgomery often worked with his brothers Buddy and Monk and with organist Melvin Rhyne. His recordings up to 1965 were oriented towards hard bop, soul jazz, and post-bop, but around 1965 he began recording more pop-oriented instrumental albums that found mainstream success. His later guitar style influenced jazz fusion and smooth jazz.

Montgomery was born in Indianapolis, Indiana. According to NPR, the nickname “Wes” was a child’s abbreviation of his middle name, Leslie.WESLEY is more likely The family was large, and the parents split up early in the lives of the children. Montgomery and his brothers moved to Columbus, Ohio, with their father and attended Champion High School. His older brother Monk dropped out of school to sell coal and ice, gradually saving enough money to buy his brother Wes a four-string tenor guitar from a pawn shop in 1935. Although Montgomery spent many hours with the guitar, he discounted this time later in life, saying he had to start over when he got his first six-string several years later.

He and his brothers returned to Indianapolis. In 1943 Montgomery found work as a welder and got married. At a dance with his wife, he heard a Charlie Christian record for the first time. This motivated him to buy a six-string guitar the next day. For nearly a year, night and day, he tried to imitate Christian and teach himself the guitar. Although he hadn’t intended to become a musician, he felt obligated to learn after buying the guitar. He received no formal instruction and couldn’t read music.

By the age of twenty, he was performing in clubs in Indianapolis at night, copying Christian’s solos, while working during the day, first at a milk company. In 1948, when Lionel Hampton was on tour in Indianapolis, he was looking for a guitarist, and after hearing Montgomery play like Christian he hired him.