Stagolee

My initial reaction on first hearing is that it reminds me of some of the songs of Jim Croce.  I realize that this is from a much earlier period and thus the influence would run the other direction, but that is the first association that came to mind.  Croce has long been a personal favorite with his story songs that seem to follow directly from this tradition being exemplified here - the songs telling stories of "bad men" who eventually get their comeuppance either ending in prison, severe injury or death.  (eg: Bad, bad Leroy Brown http://www.youtube.com/watch?v=QvwDohEEQ1E and You don't mess around with Jim  http://www.youtube.com/watch?v=-4qUXcXuMSE)
In reading through the narrative in the listening guide and its description of the genesis of this "bad man" character in the post Civil War south as a cathartic figure, it does make sense why this would resonate with so many former slaves who were severely oppressed even while they were technically "free".  It would seem that some of this also is reflected in some of today's urban African-American music - particularly in some strains of rap and hip-hop.
It is noticeable in listening to Stagolee that the harmonic backing is becoming more sophisticated than many of the previous examples.  Also the guitar playing is moving closer to what we are familiar with in some current fingerplucking styles used even now in ballads and country music.