He was born in John H Jackson in Woodville, Virginia, United States into a musical family, and learned to play guitar at a young age. He moved to Fairfax in his twenties, where he worked as a gravedigger, among other jobs.
His first recordings were released the early 1960s on the Arhoolie Records label. He visited Europe several times, played at folk festivals, and also recorded for Rounder and Alligator Records. He also appeared around Washington, D.C. with ‘the Travelling Blues Workshop’, which included Jackson, Archie Edwards, Flora Molton, Mother Scott, Phil Wiggins and John Cephas.
Jackson died in 2002 of liver cancer in Fairfax Station, Virginia, at the age of 77.
Jackson had six boys and one girl with his wife Cora Lee Carter Jackson. He was preceded in death by his wife Cora Lee (1990), and his sons John Jackson Jr (1978), Ned Jackson (1978), and MacArthur Jackson (1996). Two of his remaining sons died after him; Lee Floyd Jackson (2006) and Timothy Jackson (2008). His daughter Cora Elizabeth (Beth) Johnson and James Edward Jackson still live in the Fairfax, Virginia area.
In January, 2011, Jackson was nominated in the Blues Album and Live Performance Album categories for the 10th Annual Independent Music Awards.