Sharp was discovered by Miles Copeland, who managed the Police and ran I.R.S. Records in the '70s and '80s, and signed Sharp to his Ark 21 label. In 1997 Sharp released her debut album, Hardly Glamour, but Ark 21 was not destined to last long in the marketplace and she didn't cut another album until 2002, when she released the self-titled Maia Sharp for Concord Records. That same year, Sharp served as a backing vocalist and session musician on Art Garfunkel's album Everything Waits to be Noticed, as well as helping the famed singer set two of his poems to music. Three of Sharp's songs would appear on Bonnie Raitt's 2005 release Souls Alike, and Sharp was invited to play sax on the sessions. Also in 2005, Sharp released her third solo album, Fine Upstanding Citizen, through Koch, co-producing the album with Brad Jones as well as playing many of the instruments. In 2006 Sharp was back with album number four, Eve and the Red Delicious, recorded with Darren Embry, and in 2009 she released Echo, which was produced by Don Was; the album also featured a guest appearance from Bonnie Raitt.
By this time, Sharp had become more deeply involved in studio work, producing Edwin McCain's 2011 album Mercy Bound and producing two new tracks for the 2012 release The Singer: The Very Best of Art Garfunkel. Sharp would also produce sessions for Donny Anderson, Jenifer Freebairn, and Crystal Bowersox. In 2012, Sharp joined her parents, Randy Sharp and Sharon Bays, as well as songwriter Jack Wesley Routh, for a Western-themed collaboration, Dreams of the San Joaquin; she also completed and released an album of her own, Change the Ending, released on Blix Street. In 2015, Sharp signed a new recording deal with Entertainment One Music and released The Dash Between the Dates, which included performances from Eurythmics founder Dave Stewart. ~ Mark Deming, Rovi