Born in the Humberside town of Scunthorpe in northern England, Simpson began playing guitar at the age of 12, and just two years later was playing local pubs. Well-known on the regional circuit by the early '70s, he recorded his debut album, Golden Vanity, in 1976, for Bill Leader's Trailer Records. Instead of aligning itself with the new contemporary folk songs or their traditional precursors, Golden Vanity borrowed elements of both, with Dylan covers alongside ancient ballads. He toured with Steeleye Span and the Albion Band during the late '70s, and began a long relationship with June Tabor, working on her solo albums and earning a co-billing for 1981's A Cut Above. His next three albums, released from 1981 to 1986, were quite good, and though they generated little fanfare, Shanachie Records signed him just after his move to the U.S. in 1987. That same year, he released a duet album with his wife Jessica entitled True Dare or Promise. His first Shanachie release, 1989's Leaves of Life, signalled another period of artistic excellence, exemplified by its follow-ups When I Was on Horseback, A Closer Walk with Thee, and Red Roses, again recorded with Jessica. During the mid-'90s, the Simpsons played with a group called the Band of Angels and recorded for such labels as Rhiannon, Red House, and Water Lily Acoustic. A new collection of British traditional folk songs called Bramble Briar arrived in 2001, followed by Righteousness and Humidity, a bluesy set inspired by the deep south, and featuring Steeleye Span's Rick Kemp. 2005 saw a return to English folk with Kind Letters, followed by the award-winning Prodigal Son (2007), the genre-hopping True Stories (2009), and the star-studded Purpose & Grace (2011).