Rae Billing first came to notice as the lead vocalist for Crybaby, an alternative country group based in Toronto, Ontario, Canada. Her talents as a songwriter helped to propel the band into the limelight in her native country with the 1996 release of Paintings, the band's first album. Her vocals and songs also won the band some fans further south in the U.S. the following year, when the group played the South by Southwest Festival in Austin, TX. Crybaby fell apart in 1997, three years after its formation, but not before the band's debut garnered a lot of attention on the local Toronto scene. The city's Eye Magazine named the album one of the year's Top Three in country offerings, placing it in a class with Lyle Lovett.
Billing grew up in the town of Metchosin on Vancouver Island. During her youth, she helped her mother run the family farm. Before she hit 20, she packed up and headed for the open road. Billing landed in London, where she spent a couple of years employed by the fashion trade. When she went back to Canada, she became an art student. Her restlessness remained, however, and she started to skydive. She pursued the sport in Toronto, Calgary, and Edmonton, and later settled in Toronto. Following the death of a friend in the early '90s, Billing began to pen her own songs. She put together a demo after building up her confidence with a few open mic nights that were hosted by local nightspots. The demo's half-a-dozen tunes caught the ear of disc jockeys on CKLN, a college station in Toronto that gave Billing some heavy airplay. From there, she went on to establish Crybaby.
When Crybaby disbanded, Billing joined forces with Peter J. Moore, a producer based in Toronto. The two had worked together on Crybaby's debut a few years earlier. He pulled together a group of musicians to back Billing on an eponymous album, including Rob Philipp and Rick Whitelaw on guitar, Kevan McKenzie on drums, Peter Cardinali on bass, and Dave McMorrow on keyboards. Billing later pulled together a band comprised of drummer Michael Clifton, bassist Chris Bennett, and guitarist and backing vocalist Bob McNiven.