He graduated from Cornell University in 1991 with a Bachelor of Arts degree, in English.
He has collaborated with several musical artists including Norah Jones, Melody Gardot, Madeleine Peyroux, Nikki Yanofsky, and Lizz Wright. Harris gave guitar lessons and performed in "various musical groups" before he formed the duo Once Blue with singer/songwriter Rebecca Martin. Once Blue released its self-titled debut on Electric and Music Industries Records in 1995 and nine additional songs were included in the album"s re-release in 2003.
Harris became a songwriter for Sony Publishing for a time and then created three self-released recordings with his new band, the Ferdinandos consisting of Harris, Tony Scherr, Tim Luntzel, and Kenny Wollesen.
The band released two more albums on Verve Records and Harris later recorded three solo albums Mineral, Feel, and Watching the Sky on his own label, Secret Sun Recordings. In 2003 he was awarded a Grammy Award for Song of the Year for "Don"t Know Why," performed by Norah Jones.
In 2007, Harris contributed new and existing songs to the soundtrack of the film The Hottest State. Harris also acted in the film and sang some of his songs, with Willie Nelson, Emmylou Harris, Feist, Cat Power, M. Ward and others singing the rest of Harris" compositions.
Harris has toured throughout North America, South America, Australia, Europe and Japan and has been an opening act for Norah Jones, American Music Club, Bright Eyes, Joshua Radin and Ani DiFranco.
Harris was a judge for the 10th annual Independent Music Awards to support independent artists. In August 2010 Harris released his album Through the Night and recorded a new version of his song "The Secret Sun" for a Corona (beer) commercial. Harris" 11th album, Sub Rosa, was released in July 2012 and features guest vocals from Conor Oberst, Melody Gardot, and Norah Jones.
Harris" 12th album, the stripped down Borne Away, was released on June 25, 2013.
His music has been described as a "blend folk, rock, jazz, and world rhythms.".