Kathleen Edwards was born in Ottawa, Canada, in 1979, the daughter of foreign service parents who played piano and guitar in their spare time. At five, Kathleen Edwards began to study classical violin. Kathleen Edwards continued to learn violin through her early teens. At that point, the Kathleen Edwards family moved overseas. Removed from the influence of mainstream North American pop music, Kathleen Edwards delved into her older brother's collection of Bob Dylan, Neil Young, and early Tom Petty records. After high school, Kathleen Edwards landed back in Ottawa, singing and playing her guitar in local clubs and networking with other musicians in the scene.

In 1999, Kathleen Edwards recorded her debut EP, Building 55, and toured throughout Canada to support it, busking and opening for acts like Hayden and Jane Siberry. A bad breakup led to more songwriting, much of which took place after Kathleen Edwards moved out of Ottawa and into rural Quebec. Those songs became the basis of Failer, her debut full-length, which she recorded in Ottawa in late 2001. The album was a heartfelt mixture of folk and country, and drew upon influences like Whiskeytown and Gillian Welch. A major critical buzz began then, and gigs at the 2002 South by Southwest and opening for Richard Buckner led to a deal with Zoe/Rounder, which released Failer on January 14, 2003. The album garnered rave reviews, and Kathleen Edwards and her band toured extensively in support, headlining clubs and theaters and playing arenas opening for Bob Dylan and the Rolling Stones. In 2004, Kathleen Edwards headed back into the studio to record her second album, with her guitarist and bandleader Colin Cripps serving as producer. The final product was called Back To Me, and arrived in stores in the spring of 2005.