Born William Henry Jackson, he originally performed in minstrel and medicine shows. From the early 1920s into the 1930s, Jackson played frequent club dates in Chicago, and was noted for busking at Chicago's Maxwell Street Market. In August 1924, he recorded the commercially-successful "Airy Man Blues" and "Papa's Lawdy Lawdy Blues" for Paramount Records. One of his following tracks, "Salty Dog Blues", became his most famous song. Among his recordings are several in which he accompanied classic female blues singers singers such as Ida Cox, Hattie McDaniel, and Ma Rainey.
Jackson achieved a musical peak of sorts in September of 1929 when he got to record with his longtime idol, Blind (Arthur) Blake, often known as the king of ragtime guitar during this period. 'Papa Charlie and Blind Blake Talk About It' parts one and two are among the most unusual sides of the late '20s, containing elements of blues jam session, hokum recording, and ragtime. A few more recordings for the Paramount label followed in 1929 and 1930. In 1934, Jackson recorded for Okeh Records, and the following year he recorded with Big Bill Broonzy. Altogether, Jackson recorded 66 sides during his career.
Jackson was an influential figure in blues music, the first self-accompanied blues musician to make records. He was one of the first musicians of the "Hokum" genre, which uses comic, often sexually suggestive lyrics and lively, danceable rhythms. He wrote or was the first to record several songs that became blues standards, including "Spoonful" and "Salty Dog".
Jackson's "Shake That Thing" was covered by Mother McCree's Uptown Jug Champions in 1964. "Loan Me Your Heart" appeared on The Wildparty Sheiks eponymous album in 2002. The Carolina Chocolate Drops recorded "Your Baby Ain't Sweet Like Mine" on their Grammy Award winning 2010 album, Genuine Negro Jig, and often played the song in interviews after its release.
In 1973, Jackson's song "Shake That Thing" was briefly featured in the Sanford and Son episode, "The Blind Mellow Jelly Collection". Fred, played by Redd Foxx, could be seen dancing and singing to it at the beginning of the episode.
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