Cummings began with Melbourne's the Pelaco Brothers during the mid-'70s. He then fronted the Sports for six years before they disbanded in 1981. Cummings' debut single, "We All Make Mistakes," was released in January 1983 and a debut dance-oriented album, Senso, in August 1984. A non-album single, "What Am I Going to Do?," was released in August 1985, before the more laid-back This Wonderful Life in September 1986. In 1987, he collaborated with ex-Sports guitarist Andrew Pendlebury for the single "She Set Fire to the House."

Another low-key outing, Lovetown, was released in January 1988, and Cummings formed Stephen Cummings Lovetown to tour. His third album, A New Kind of Blue, won the 1989 Australian Record Industry Award (ARIA) for Best Adult Contemporary Album. Good Humour, released in 1990, marked a return to his earlier dance style. His 1992 outing, Unguided Tour, produced a more rock-driven sound. Steve Kilbey of the Church produced Cummings' next two albums, Falling Swinger (1994) and Escapist (1996). In between albums, Cummings recorded a duet with Toni Childs called "Fell From a Great Height." In 1996, Cummings' first novel, Wonder Boy, was published followed by a compilation album in 1997, Puppet Pauper Pirate Poet Pawn & King. Cummings is also the voice and co-writer behind the TV advertisement I Feel Better Now, a popular Australian advertisement for health insurers Medibank Private. ~ Brendan Swift