While studying history at Duke University, Shain's interest in Southern roots music deepened, eventually leading to a shared gig with Richard "Big Boy" Henry. In 1989, Shain founded the Flying Mice, a folk-rock group based in Chapel Hill, NC; later, he would also help form WAKE, a spin-off from the Flying Mice. Between 1989 and 1998, Shain toured with these bands, traveling to festivals and clubs along the East Coast, and sharing the stage with luminaries such as David Grisman, Leon Russell, and the Dave Matthews Band. Following the breakup of WAKE, Shain went solo and toured the blues circuit. In 2001, he released his sophomore effort, Fools and Fine Ladies. "Call it musical maturity," wrote David Potorti, "or an intangible intersection of solid tunes and solid musicianship: Fools and Fine Ladies marks a giant step for Jon Shain, from folky tunesmith to artist to be reckoned with." The Washington Post likewise praised the album, noting that "...Shain and his bandmates are clearly in their element here, making music that has plenty of rootsy appeal." In 2003, Shain released No Tag, No Tail Light, an album produced in Boston by Dave Mattacks and Tom Dube, followed in 2005 by Home Before Long with the Jon Shain Trio. "It's a notable truism that sometimes it doesn't matter what you say so much as how," wrote Chris Parker of Home Before Long. "In the case of Shain, it's part of an easygoing confidence that amplifies the charm of his songs." Shain also maintains a busy touring schedule, appearing with Keb' Mo', NRBQ, and John Hammond. When not touring, Shain offers private instruction and teaches workshops on blues guitar. ~ Ronnie D. Lankford, Jr.