Inspired by legendary blues and gospel guitarist, Rev. Gary Davis, Simon has been involved in the British blues scene since the ‘60s. With his playing partner of twelve years, Steve Rye (harmonica), he first came to prominence on an album recorded and released in 1968, Blues Like Showers of Rain. The successful triumvirate of Simon, Steve and pianist Bob Hall performed throughout the ‘70s as the ‘All Star Medicine Show’. When Steve’s health declined, he was replaced by Kevin Stenson.

Simon also played occasionally with the late JoAnn Kelly and accompanied Sonny Terry when half of that legendary duo, Brownie McGhee, became ill. Since the ‘80s, Simon has performed solo and with actress and singer Masha Vlassova initially as part of the ‘Mobile Moaners’. Masha is a New Zealander of Russian extraction, and sings in the style of Bessie Smith, Ma Rainey and Sophie Tucker.