Born on a plantation at Red Banks, Cannon moved to Clarksdale, Mississippi, then the home of W. C. Handy, at the age of 12. Cannon's musical skills came without training; he taught himself to play using a banjo that he made from a frying pan and raccoon skin. He ran away from home at the age of fifteen and began his career entertaining at sawmills and levee and railroad camps in the Mississippi Delta around the turn of the century.
While in Clarksdale, Cannon was influenced by local musicians Jim Turner and Alex Lee. Turner's fiddle playing in W. C. Handy’s band so impressed Cannon that he decided to learn the fiddle himself. Lee, a guitarist, taught Cannon his first folk blues, "Po' Boy, Long Ways from Home", and showed him how to use a knife blade as a slide, a technique that Cannon adapted to his banjo playing.
Cannon left Clarksdale around 1907. He soon settled near Memphis and played in a jug band led by Jim Guffin. He began playing in Memphis with Jim Jackson. He met harmonica player Noah Lewis, who introduced him to a young guitar player named Ashley Thompson. Both Lewis and Thompson would eventually become members of Cannon's Jug Stompers. The three of them formed a band to play parties and dances. In 1914 Cannon began touring in medicine shows. He supported his family through a variety of jobs, including sharecropping, ditch digging, and yard work, but supplemented his income with music.
Cannon began recording, as "Banjo Joe", for Paramount Records in 1927. At that session he was backed up by Blind Blake. After the success of the Memphis Jug Band's first records, he quickly assembled a jug band featuring Noah Lewis and Ashley Thompson (later replaced by Elijah Avery). Cannon's Jug Stompers first recorded at the Memphis Auditorium for the Victor label in January 1928. Hosea Woods joined the Jug Stompers in the late 1920s, playing guitar, banjo and kazoo, and also providing some vocals. Modern listeners can hear Cannon's Jug Stompers recording of "Big Railroad Blues" on the compilation album The Music Never Stopped: Roots of the Grateful Dead.
Although their last recordings were made in 1930, Cannon's Jug Stompers were one of Beale Street's most popular jug bands through the 1930s. A few songs Cannon recorded with Cannon's Jug Stompers are "Minglewood Blues", "Pig Ankle Strut", "Wolf River Blues", "Viola Lee Blues", "White House Station" and "Walk Right In" (later made into a pop hit by The Rooftop Singers in the 1960s, and later a hit rock/pop version by Dr. Hook in the 1970s). By the end of the 1930s, Cannon had effectively retired, although he occasionally performed as a solo musician.
He returned in 1956 to make a few recordings for Folkways Records. In the "blues revival" of the 1960s, he made some college and coffee house appearances with Furry Lewis and Bukka White, but he had to pawn his banjo to pay his heating bill the winter before the Rooftop Singers had a hit with "Walk Right In". In the wake of becoming a hit composer, he recorded an album for Stax Records in 1963, with fellow Memphis musician Will Shade, the former leader of the Memphis Jug Band.
Cannon can be seen in the King Vidor produced film, Hallelujah! (1929), during the late night wedding scene.
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