A native of Toronto, she initially began her career in Halifax, where she released her 2002 debut, A Note to Follow So. From the start, Barber's range included a mix of jazz, Americana, and folk-inspired pop, not unlike her older brother, roots pop songwriter Matthew Barber. She continued to develop this mix over the course of her next two releases, 2004's Oh Heart EP and 2006's For All Time. A couple of years later, she relocated back to Toronto, where she and producer Les Cooper began developing a new approach that relied heavily on the lush, orchestrated style of old jazz standards and torch songs.

Released in 2008, Chances was a departure from Barber's earlier style and proved to be a turning point in her career. The album, which featured a handful of songs co-written by Ron Sexsmith, was nominated for two Juno Awards and introduced her music to a much wider, international audience. Her follow-up, 2011's Mischievous Moon, followed a similar path and spent 13 weeks atop Canada's jazz charts. For 2013's Chansons, Barber worked with producer Drew Jurecka on her first French-language set, featuring covers of songs by artists like Édith Piaf, Henri Salvador, and Serge Gainsbourg. That same year, her song "Chances" was featured in the first season of Netflix's original series Orange Is the New Black. Her sixth album, 2015's Fool's Gold, showed a continued evolution in her sound, with nods to Motown, soul, and classic country. Although they've shared the stage together multiple times, 2016's collaborative set The Family Album marked Jill and brother Matthew's first album as a duo. ~ Timothy Monger