Proficient on fiddle, many styles of acoustic and electric guitar, pedal steel guitar and dobro, Bromberg gained a reputation through his session work for artists such as Jerry Jeff Walker and Bob Dylan. He contributed to the latter's 1970 albums "Self Portrait" and "New Morning", and was one of Dylan's preferred musicians. That same year, he backed folk singer Rosalie Sorrels at the Isle of Wight Festival and then performed an impromptu solo set. The success of this appearance led to him being offered a recording contract with Columbia Records.