After disbanding the Los Angeles new wave/power pop group the Plimsouls, Case launched a career as an important American singer/songwriter specialising in the flat-pick guitar style and semi-autobiographical stories of drifters delivered in a narrative style.

Born in the 1950s and growing up in upstate New York, Case was inspired, like any number of young men of his generation, by Elvis Presley and the Beatles. He was also a fan of the folk and blues of Mississippi John Hurt, Leadbelly and Woody Guthrie and as a teenager took to the troubadour's life, playing coffeehouses and busking.

He was discovered on the streets of San Francisco in 1976 by songwriter Jack Lee, with whom he collaborated in the Nerves, a short-lived but influential power pop act. The meeting led to a move to LA and the formation of the Plimsouls in 1980.

After some brief success, Case signed to Geffen in 1986. Recordings majored on hard folk acoustic material, including collaborations with choice musicians such as David Hidalgo, Ry Cooder and Benmont Tench. In a Rolling Stone interview that year, Bruce Springsteen cited Case as the songwriter he was listening to most at the time.

The liaison with Geffen ended in 1992 and Case tried some self-released material in 1993 which won him a contract with Vanguard in 1995. In 1996, the Plimsouls re-formed for some reunion shows and a recording session, while Case continued to tour and record as a solo act and produced some collaborative releases, including a tribute to Mississippi John Hurt featuring contributions from Lucinda Williams and Steve Earle.