Dewey Jackson's limited recorded output stands in sharp contrast to his prominence as one of the leading figures in St. Louis jazz throughout the 1920s, a status that kept him regarded as a legend for many decades afterward. Early engagements took him through the Odd Fellows Boys' Band in 1912, Tommy Evans between 1916 and 1917, and George Reynolds' Keystone Band. Following riverboat work with Charles Creath, he directed his own Golden Melody Band from 1920 to 1923. Between 1924 and 1941 the trumpeter remained a constant presence on the riverboats, leading units that included the St. Louis Peacock Charleston Orchestra or performing as a sideman with Fate Marable and Charlie Creath. The single break in that routine came during a four-month interval in 1926, when Jackson appeared with Andrew Preer's Orchestra at New York's Cotton Club. Part-time playing marked the 1940s while he held a daytime job, yet he performed with greater regularity in the 1950s, including dates with Singleton Palmer and Don Ewell's Trio in 1951. Activity continued into the 1960s. As a leader Dewey Jackson cut only four titles in 1926, among them the classic "She's Cryin' For Me"; further recordings occurred in 1927 with Charlie Creath and on a Singleton Palmer session in 1950. Sidemen who passed through his groups over the years included Pops Foster, Willie Humphrey, Don Stovall, and Clark Terry in 1937.
