Shain got his first acoustic guitar after being influenced by watching childhood friend Fran Cleary play a cheap Univox electric model.

For high school, Shain attended The Governor's Academy in Byfield, Massachusetts, where he met up with other aspiring musicians among its small student body.

Almost immediately, Shain joined a student rock band called Positive Feedback, where he played electric rhythm guitar and first performed live on stage.

[2] The Partisans achieved minor notoriety throughout the region, playing dances and private parties during Shain's remaining years in high school.

Eventually mixing in originals by Shain and Barr, The Partisans live set mainly consisted of classic rock staples from Chuck Berry, The Beatles, The Rolling Stones, The Clash, R.E.M., and U2.

Through Slewfoot, Shain met North Carolina blues artists such as Big Boy Henry, John Dee Holeman, Lightnin' Wells, and jazz pianist Brother Yusef Salim.

"[4] Shain also took opportunity of Duke's jazz program, studying one semester with saxophonist Paul Jeffrey, a veteran of Thelonious Monk's group.

In 1992, John Whitehead left the band and was replaced by bassist Aaron Oliva and Ben Saffer on guitar and banjo.

In 1997, Cole left to join Squirrel Nut Zippers and he was replaced by Darrell Dixon on bass and John Currie on guitar.