Sheaffer performed in duo with multi-instrumentalist Tom Duval during his college years at clubs in Greenwich Village in New York City. After receiving a B.A. in English literature from Columbia University in New York City in 1986, Sheaffer began performing with the Jack Hardy Band in the U.S. and in Europe from 1986-1989. Hardy was a folksinger and founder of Fast Folk magazine. Sheaffer recorded with the Jack Hardy Band on The Hunter (Entente) and Through (Great Divide). Tom Duval and Brady Rhymer were the trio's bassists. Sheaffer joined From Good Homes in 1989 and spent a decade with the group, which was originally formed from members of Sheaffer's high school band called Old Crow Band. From Good Homes disbanded in August, 1999.
Shortly after starting his solo career in September 1999, Sheaffer joined the bluegrass-rock group Railroad Earth, which started informally in the fall of 2000 during bluegrass jam sessions at the Long Valley, NJ, home of multi-instrumentalist Andy Goessling. The group featured former members of From Good Homes and of the New Jersey swing band Blue Sparks from Hell, including Sheaffer (vocals, acoustic guitar), Goessling (acoustic guitar, mandolin, banjo, pennywhistle, saxophone), Tim Carbone (violin, acoustic guitar), and session player John Skehan (mandolin, guitar, piano), as well as drummer/percussionist Carey Harmon and upright and electric bassist Dave Von Dollen. Railroad Earth recorded its debut CD, The Black Bear Sessions, in 2001. ~ Robert Hicks, Rovi