Wakefield was known for his collaborations with a number of well-known musical artists, including Red Allen, Jimmy Martin, Don Reno, Jerry Garcia, David Grisman, The Stanley Brothers, and the Greenbriar Boys.
[1] Born into a musical family in Emory Gap, Tennessee, Wakefield by age eight already knew how to play harmonica, guitar and bass.
The duo called themselves The Wakefield Brothers and in 1951, made their first radio appearance playing gospel and old-time music on WHIO in Dayton.
This innovative style offered him the opportunity to play with the New York Philharmonic, led by Leonard Bernstein in 1967 and an invitation to appear as a guest with the Boston Pops in 1968.
By mid-decade Wakefield began working with his newly formed band, The Good Ol' Boys with whom he would enjoy a productive collaboration until the mid-1980s.