Although the Kentucky native grew up with a passion for music, when she arrived in New York City in the late 1980s, it was to attend New York University's prestigious film school. But she couldn't resist the pull of the city's live music scene for long, and soon she was performing her own songs in downtown rock clubs and emerging as a popular presence in a vibrant scene of rootsy new acts that included such then-unknowns as Jeff Buckley, Chris Whitley, Blues Traveler and the Spin Doctors. In 1992, Osborne launched her own indie label, Womanly Hips, and released the live Soul Show: Live at Delta 88 and the studio EP Blue Million Miles.
Osborne's regional success led to a major-label deal and the release of her 1995 multi-platinum breakthrough album Relish, which included her #1 single "One of Us." Her albums include 2000's Righteous Love, 2002's How Sweet It Is, 2005's Christmas Means Love, 2006's Pretty Little Stranger, 2007's Breakfast in Bed, 2008's Little Wild One and 2012's Bring it on Home.