As a young teen he sang in the choir, and then joined the Jubilee Hummingbirds.[6] At age 16, Jackson was drumming with bluesman R. L. Burnside. Burnside's daughter Linda had Jackson's son 1978, Cedric Burnside, and they would later marry.[7] Jackson appeared in recordings of Burnside's band, sometimes called The Sound Machine,[8] starting in 1979.[9] Beside the traditional influence, David Evans credited him with bringing in the modern funk, RnB and soul influences of the band.[10]
In the mid 1990s he moved to the Netherlands to continue his musical career[18][19] His son Cedric would take his place at Burnside's drums. In 1999 he released the only album under his own name, Calvin Jackson & Mississippi Bound's Goin' Down South.[12][20] Participating were Cass Ian (vocals, guitar), Caret De Neeve (double bass) and Ludo "lazy lew" Beckers (harmonica). The album was nominated for a Blues Music Award in the category of "Best New Artist Debut".[21]