Jackson's mother played gospel guitar, and he played early on in a gospel group, the Blue Eagle Four. He became a mechanic and served in the Army during World War II, after which he pursued a career as a blues musician He recorded a demo and sent it to Bill Quinn, the owner of Gold Star Records, in 1946. Quinn signed him to a recording contract and released "Freedom Train Blues" in 1948, which became a nationwide hit in the United States.
Jackson recorded for Imperial Records between 1950 and 1954, both as a solo artist and with a backing band. His 1950 song "Rockin' and Rollin" was recast by later musicians as "Rock Me Baby". Jackson was injured in a car crash in the mid-1950s and gave up his music career, returning to work as a mechanic. He recorded an LP released by Arhoolie Records in 1960 but did not resume his career as a musician during the blues revival in the 1960s. He died of cancer in 1976 in Dallas, at the age of 60.