Sippie Wallace followed her brothers to Chicago in 1923 and worked her way into the city’s bustling jazz scene. Her reputation led to a recording contract with Okeh Records in 1923. Her first recorded songs, “Shorty George” and “Up the Country Blues”, the former written with her brother George, sold well enough to make her a blues star in the early 1920s. Other successful recordings followed, including “Special Delivery Blues” (with Louis Armstrong), “Bedroom Blues” (written by George and Hersal Thomas), and “I’m a Mighty Tight Woman”. Hersal Thomas died of food poisoning in 1926, at age 16. Wallace moved to Detroit in 1929. Matt Wallace and George Thomas both died in 1936. For some 40 years Wallace was a singer and organist at the Leland Baptist Church in Detroit. Mercury Records reissued “Bedroom Blues” in 1945. Aside from an occasional performance or recording date, she did little in the blues until she launched a comeback in 1966, after her longtime friend Victoria Spivey coaxed her out of retirement, and toured on the folk and blues festival circuit. Sippie Wallace recorded an album, Women Be Wise, on October 31, 1966, in Copenhagen, Denmark, with Roosevelt Sykes and Little Brother Montgomery playing the piano. She recorded another album in 1966, Sings the Blues, on which she accompanied herself on piano on the title song, with Sykes or Montgomery playing piano on other tracks. Both albums include her signature song, “Women Be Wise”. These recordings helped inspire the musician Bonnie Raitt to take up singing and playing the blues in the late 1960s. Raitt recorded renditions of “Women Be Wise” and “Mighty Tight Woman” on her self-titled debut album in 1971. Wallace toured and recorded with Raitt in the 1970s and 1980s and continued to perform on her own.

Sippie Wallace contributed to Louis Armstrong’s album Louis Armstrong and the Blues Singers (1966), singing “A Jealous Woman Like Me”, “Special Delivery Blues”, “Jack o’Diamond Blues”, “The Mail Train Blues” and “I Feel Good”. She and Spivey recorded an album of blues standards, Sippie Wallace and Victoria Spivey, released in 1970 by Spivey’s label, Spivey Records. In 1981, Wallace recorded the album Sippie for Atlantic Records, which earned her a 1983 Grammy nomination and won the 1982 W. C. Handy Award for Best Blues Album of the Year. Sippie Wallace’s backup group was pianist Jim Dapogny’s Chicago Jazz Band, consisting of Paul Klinger on cornet, Bob Smith on trombone and Russ Whitman and Peter Ferran on reeds. She appeared at the Newport Folk Festival in 1966 and 1967, toured Europe with the American Folk Blues Festival in 1966, performed at the Chicago Blues Festival in 1967 and the Ann Arbor Blues Festival in 1972, and appeared at Lincoln Center in New York in 1977. She appeared in the 1982 documentary Jammin’ with the Blues Greats. She shared the stage with B.B. King at the Montreaux Jazz Festival on July 22, 1982, in a performance that was filmed and later broadcast. With the German boogie-woogie pianist Axel Zwingenberger she recorded a studio album, Axel Zwingenberger and the Friends of Boogie Woogie, Vol. 1: Sippie Wallace, in 1983 (released in 1984), which included many of her own groundbreaking compositions and other classic blues songs. In 1984 she traveled to Germany to tour with Zwingenberger, where they also recorded her only complete live album, An Evening with Sippie Wallace, for Vagabond Records.