He was given the opportunity to play with Charles Mingus, Milt Buckner, and Fats Navarro, but not the opportunity he hoped for, and he returned to Indianapolis a better player, though tired and discouraged. When arriving at a club, the first thing he did was call home to his wife and family.
Fear kept him from flying with the rest of the band, so he drove from city to city, town to town, while fellow musicians marveled at his stamina. Montgomery spent two years with the Hampton band. 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. 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. He received no formal instruction and couldn't read music. Although he hadn't intended to become a musician, he felt obligated to learn after buying the guitar. For nearly a year, night and day, he tried to imitate Christian and teach himself the guitar.
This motivated him to buy a six-string guitar the next day. At a dance with his wife, he heard a Charlie Christian record for the first time. In 1943 Montgomery found work as a welder and got married. He and his brothers returned to Indianapolis. Montgomery in a mid-1960s publicity photo shot by Bruno of Hollywood studios for Verve Records