At the age of 24, Kim Stockwood began performing at a pub's folk nights in her hometown of St. Johns, Newfoundland, Canada. The year was 1990, and by the end of it, she was filling the weekend slots at the venue. At the time, Stockwood was working a day job, employing the skills she'd received in English and business at college. As a joke, Stockwood moved to Toronto in 1992 in order to see if she could receive a record deal. She arrived at the office of EMI Music Publishing president Mike McCarthy, talked to him for an hour, and jumped up on his piano stool and belted out her rendition of Patsy Cline's "Crazy." She walked out of the office with a publishing deal, and five months later, she received a recording contract with EMI. Three years later, EMI released the limited-edition promotional EP Greetings from Bonavista to the media, prior to the official release date of Stockwood's full-length debut album.