The couple also ran a roadside cafe situated between Helena, Arkansas, and Memphis, Tennessee, which regularly played host to blues musicians from neighbouring States.
He thereafter branched out on his own as a traveling musician, playing in Memphis, then across Florida, in St. Louis, Missouri, before finally, in around 1950, coming to a halt in Chicago, Illinois.
The French music historian, Gérard Herzhaft, later commented that "The guitar style of Lee Jackson, sharp, jazzy, with sparse but brilliant and bluesy notes was quite original for the immediate post-war Chicago blues scene, reflecting his years playing with swinging jug bands".
[2][5] The following year, Jackson switched to playing the bass guitar on Billy Boy Arnold's, More Blues on the South Side.
[7] In 1969, Jackson supplied bass guitar work on half of the tracks on Johnny Shines with Big Walter Horton,[2] as well as on Hound Dog Taylor's "Watch Out" single.
[4] In 1970, Jackson was part of entourage on the American Folk Blues Festival's European tour and two sides of his from that event were issued on the subsequent album release.
[5] His guitar provided part of the backing on the early 1970s Big Boss Men live collection of Willie Dixon and Jimmy Reed,[1] and Jackson was in the rhythm section that played on J.
[9] The following year, Jackson recorded an instrumental track, "Apallo 17" (sic), which commemorated the final mission of the Apollo program.
By the end of the decade, Jackson played more frequently in Chicago North Side blues clubs, connecting with a younger clientele.
[2][5] In view of Jackson's three decade tenure as a session musician, recorded music containing his input has appeared on numerous compilation albums.