Jackson was born in Culpeper, Virginia, United States. After playing in Atlantic City, Jackson moved to New York City in 1923, where he played with Lionel Howard's Musical Aces in 1924, and recorded with Bob Fuller and Elmer Snowden. He led his own ensemble, the Krazy Kats, for recordings in 1930, and following this group's dissolution he played extensively as a solo pianist in nightclubs in New York. During this time he also accompanied singers such as Viola McCoy, Lena Wilson, Sara Martin, Martha Copeland, Helen Gross, and Clara Smith. He recorded with Sidney Bechet in 1940-41, and recorded as a soloist or leader in 1944-45, 1961, and 1969. As house pianist at Cafe Society from 1943 until 1951 he was a success; he also toured with Eddie Condon in 1946. He also played with Garvin Bushell (1950), J.C. Higginbotham (1960), and Joe Thomas (1962).