Montgomery was inspired to pick up the guitar after hearing Charlie Christian. As a young man, he worked as a machinist during the day and played clubs in Indianapolis at night. He developed his muted playing technique so he didn’t wake his young family when practising late at night. Montgomery recorded with his brothers Buddy and Monk as the Mastersounds, as well as several solo albums for Riverside. His smooth, soulful jazz stylings found a perfect partnership with Verve Records, where his versions of contemporary hits were gladly received by a wide audience. Montgomery died of a heart attack aged 45.