Jackson began playing professionally at an early age, with the Odd Fellows Boys' Band (1912), Tommy Evans (1916–17), and George Reynolds's Keystone Band. He played with Charlie Creath on riverboats, then led his Golden Melody Band from 1920 to 1923. In 1926, he performed with his St. Louis Charleston Peacock Band on the Streckfus Steamboat Lines' steamer Capitol.[2]
He continued to be a regular performer on riverboats into the early 1940s, heading his groups and working as a sideman for Creath and Fate Marable. He was briefly away from boats in 1926 when he played for four months with Andrew Preer at the Cotton Club in New York City. From 1937 to 1941, Jackson led the Dewey Jackson's Musical Ambassadors on riverboats but also led bands on land.[3]
^"The Behrman Civic League invites you to attend Grand Moonlight River Ride and Dance DeLuxe." Ticket. February 25, 1926. Martin Shepard Office Records, Southeastern Architectural Archive, Special Collections Division, Tulane University Libraries; "Steamer Capitol", The Times-Picayune (April 2, 1926): pg. 4.
^Owsley, Dennis (2006). City of Gabriels: The History of Jazz in St. Louis, 1895-1973. Terry, Clark., Sheldon Art Galleries. St. Louis, Mo.: Reedy Press. pp. 67–68. ISBN1933370041. OCLC71122278.
"Steamer Capitol." The Times-Picayune (1 April 1926): p. 4.
"The Behrman Civic League invites you to attend Grand Moonlight River Ride and Dance DeLuxe." Ticket. 25 February 1926. Martin Shepard Office Records, Southeastern Architectural Archive, Special Collections Division, Tulane University Libraries