As an iterinant performer who played mainly on street corners and juke joints, Blackwell did not have a prolific career, but did record with musicologist Alan Lomax in 1942 and was rediscovered during the blues revival of the 1960s.

[2] He was introduced to the basics of the guitar by his father and neighbors, but, until the late 1930s, Blackwell performed on the piano in juke joints in Memphis, Tennessee.

[4] Undeterred and still hoping to pursue his music career, Blackwell reacquainted himself with the guitar, and allegedly received lessons from renown blues musician Robert Johnson.

[2] In 1942, while on Beale Street in Memphis with fellow musician William Brown, Blackwell met Alan Lomax, a musicologist collecting field recordings of authentic country blues.

From Lomax's own account in his book The Land Where the Blues Began, he took Blackwell and Brown to an Arkansas plantation in July 1942 to escape persecution from police for associating with the black musicians.