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, and then led his own Golden Melody Band from 1920 to 1923. In 1926, he performed with his St. Louis Charleston Peacock Band on the Streckfus Steamboat Lines' new steamer, Capitol. He continued to be a regular performer on riverboats into the early 1940s, heading his own groups and working as a sideman for Creath and Fate Marable. His only major stint off boats during this time was in 1926, when he played for four months with Andrew Preer at the Cotton Club in New York City.
Jackson played little in the 1940s but returned to work in the 1950s with Singleton Palmer and Don Ewell. He recorded four sides as a leader in 1926 and the album Live At The Barrel, 1952 with 10 tracts on the Delmark label, released in 2006. Among his sidemen were Pops Foster, Willie Humphrey, Don Stovall, Morris White, Albert Snaer, William Thornton Blue, and Clark Terry.
- "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; "Steamer Capitol." The Times-Picayune (1 April 1926): p.4.