Sullivan began her music career singing in her uncle's band, The Red Hot Peppers, in her native Pennsylvania, in which she occasionally played the flugelhorn and the valve trombone, in addition to singing.In the mid-1930s she was discovered by Gladys Mosier (then working in Ina Ray Hutton's big band). Mosier introduced her to Claude Thornhill, which led to her first recordings made in June 1937. Shortly thereafter, Sullivan became a featured vocalist at the Onyx Club in New York.During this period, she began forming a professional and close personal relationship with bassist John Kirby, who became her second husband in 1938.
A photo of Maxine Sullivan in Village Vanguard, NYC around March 1947
Sullivan in 1947
Early sessions with Kirby in 1937 yielded a hit recording of a swing version of the Scottish folk song "Loch Lomond" featuring Sullivan on vocals.This early success "branded" Sullivan's style, leading her to sing similar swing arrangements of traditional folk tunes mostly arranged by pianist Claude Thornhill, such as "If I Had a Ribbon Bow" and "I Dream of Jeanie".Her early popularity also led to a brief appearance in the movie Going Places with Louis Armstrong.
In 1940, Sullivan and Kirby were featured on the radio program Flow Gently Sweet Rhythm, making them the first black jazz stars to have their own weekly radio series.During the 1940s Sullivan then performed with a wide range of bands, including her husband's sextet and groups headed by Teddy Wilson, Benny Carter, and Jimmie Lunceford. Sullivan performed at many of New York's hottest jazz spots such as the Ruban Bleu, the Village Vanguard, the Blue Angel, and the Penthouse.In 1949, Sullivan appeared on the short-lived CBS Television series Uptown Jubilee.