The daughter of an amateur musician and a visual artist, Cole was born and raised in Rockport, Massachusetts. Following her high school graduation, she went to the Berklee College of Music to study jazz singing and improvisation. After she graduated from Berklee, Cole became a professional musician in order to make a living; she continued to write original material on the side.
Her first big break arrived when Peter Gabriel invited her to perform on his 1992-1993 world tour. Shortly afterward, she signed to Imago Records, where she released her debut album, Harbinger, in 1994. Imago went out of business within a year of the record's release, though, which prevented the set from getting exposure on radio and in the press. In 1995, she signed a contract with Warner Bros., which reissued Harbinger in the fall of that year. Cole returned with her second long-player, This Fire, in October 1996. The album and its accompanying single, "Where Have All the Cowboys Gone?," became word-of-mouth hits and eventually broke into the mainstream during the first half of 1997. That summer, she participated in the first Lilith Fair, a traveling festival that had been designed by Sarah McLachlan to showcase female artists. Cole was one of the performers to receive a significant boost in profile from the tour, and was the subject of many articles in the mainstream press.
In 1998, Cole won the Grammy for Best New Artist, despite the fact that she released her debut album in 1994 and, therefore, was technically ineligible. That same year, she scored another hit with the single "I Don't Want to Wait," popularized as the theme to the television hit Dawson's Creek. Her third album, Amen, followed in 1999 and broadened Cole's sound with electronica and hip-hop textures. It wasn't nearly as popular as This Fire, though, prompting her to drop out of the limelight and focus on raising her daughter.
Eight years passed before she returned with a fresh single, "14," and her fourth album, 2007's Courage. Although only modestly popular, the record represented something of a stylistic return for Cole, who had settled into an eclectic, jazz-influenced adult contemporary vein. She began recording and touring on a more regular basis, releasing her fifth album, Ithaca, on Decca in 2010.
Cole undertook a crowdfunding project to complete and self-release her next recording, Raven, which she issued in 2013 on her own label, 675 Records. Recorded live in the studio as an acoustic quartet, 7 arrived in 2016, the same year that brought the live LP This Bright Red Feeling. She relied again on crowdfunding for the covers album Ballads. Released in 2017, it debuted at number ten on Billboard's jazz albums chart. With a cover of Marvin Gaye's "Mercy Mercy Me (The Ecology)" among its track list, the human rights-fueled Revolution followed in 2019. Two years later, Cole released American Quilt, a covers album that found common threads between country, blues, pop, rock, and jazz. ~ Stephen Thomas Erlewine, Rovi