Stewart was born in Sunderland, England, in 1952 and he attended Barnes Infants and Junior School and Bede Grammar School for Boys. Whilst still in his teens, he secured a record deal as part of folk-rock band Longdancer. Despite being signed to Elton John's record label, The Rocket Record Company, they did not achieve commercial success. He also collaborated with Brian Harrison to produce an EP on the Sunderland Multicord label (label number MULT-SH-1, producer Ken McKenzie), recording two songs ("Girl" and "Green She Said") from a school musical production written by teacher Dick Bradshaw, one traditional number ("A Blacksmith Courted Me") and a song written by Dave and Brian ("Deep December"). After leaving Wearside Stewart spent several years living in squats in London. In late 1976, he was introduced to Annie Lennox by Paul Jacobs. Soon, Stewart and Lennox became romantically involved. By 1977, the pair had teamed up with Sunderland musician Peet Coombes, releasing a single on Logo Records as The Catch. The band then developed into The Tourists who enjoyed modest success, including a hit in 1979 with a cover of the Dusty Springfield hit "I Only Want to Be with You".