While he started playing professionally as early as high school, over his 40+ year career, Sholle worked with such musicians as Vassar Clements, David Grisman, Peter Rowan, Tony Rice, Larry Campbell, Keith Carradine, Allen Ginsberg, Bela Fleck, and Bette Midler.

[2] In 1969, Sholle played a number of string instruments for beat poet Allen Ginsberg's 1970 LP Songs of Innocence and Experience, a musical adaptation of William Blake's poetry collection of the same name.

Sholle also released two solo albums with Rounder Records, Catfish for Supper and Out of the Frying Pan.

Sholle appeared in the 1979 film The Rose as a member of Midler's band, as well appearing on-screen and playing on the soundtrack for the Peter Bogdanovitch-directed Audrey Hepburn movie They All Laughed,[5] and playing dobro on the soundtrack for Disney's The Rookie, starring Dennis Quaid.

[2] Sholle won both the 1967 and 1968 "World Champion Guitar" at the Union Grove Fiddler's convention in North Carolina.