Jill won the Female Artist Recording of the Year award for her debut album Oh Heart at the 2005 Music Nova Scotia Awards. In 2007 Barber earned her fourth win as Best Local Solo Artist (Female) in The Coast’s annual "Best of Music Reader’s Poll", and her first win as Best Canadian Solo Artist (Female).
From February to March 2007 she toured eastern Canada with Dan Hill as part of Stuart McLean's CBC Radio show The Vinyl Cafe. She returned to the Vinyl Cafe Tour in 2009 performing across Canada with Matt Anderson.
In 2008 Jill Barber released Chances, an album with full orchestral arrangements which was partially co-written with her producer, Les Cooper, while also collaborating on several songs with Canadian music legend Ron Sexsmith. This album led to a new level in touring reaching audiences across the globe while earning two Juno Award nominations including New Artist of the Year.
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