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.