Born in the early 1890s about 21 miles from Memphis in the town of Hernando, Jim Jackson taught himself to play a guitar at an early age.  An early career in minstrel shows and show hawking "patent medicines" taught Jackson a vast repertoire of songs and theatrics.

Sometime in the early 1920s Jackson made his way to Memphis.  There he played Beale Street as well as local street corners.  He played guitar in various ensembles including Cannon's Jug Stompers.  His solo performances were marked by jokes and banter much in the style of vaudevillians.  Indeed Jackson's style may be considered more akin to W. C. Handy than Frank Stokes in that his repertoire included all types of popular music of the day.

In 1927 Jackson recorded his first song for Vocalion in Chicago.  The song was "Jim Jackson's Kansas City Blues Parts 1 and 2" (later shortened to simply "Kansas City Blues).  The song immediately became one of the most popular blues records ever.  Some believe it was close to a million seller although no record has survived.  From there Jackson cut 50 more tracks within the next 3 years.  At that point the Great Depression hit.  The blues scene died and Jackson moved back to his birthplace in Hernando, Mississippi.

He did continue to do what work was available reverting back to the touring shows.  Jim Jackson died in 1937 and is buried in his hometown of Hernando.