Once again, I learned this from the Cisco Houston songbook, and still sing it almost exactly as printed there, and like a lot of songs in that book it still comes into my head with the accompanying illustration, of a man who is presumably a prison guard, standing with his rifle.
Of course, like everyone else, I soon heard one of Lead Belly’s versions, which was undoubtedly Cisco’s source as well, since he includes many of Lead Belly’s points of reference: Sugarland penitentiary, where Lead Belly was imprisoned from 1918 to 1925, and the sheriff of Houston, Texas, whose name Cisco’s book gave as Benson Brocker (which is what I sing), but Lead Belly’s biographers give as Bason and Brock, explaining that A.W. Brock was the chief of police, but not giving any info on Bason.
The song was apparently known throughout the South, and was recorded several times in the 1920s, first by a white Oklahoman named Dave “Pistol Pete” Cutrell in 1926, then a year later by Crying Sam Collins, a black guitarist and singer from Louisiana and Mississippi, who has some wonderful variations on the standard melody. Bruce Jackson and other scholars have listed this as a popular prison song, circulated in oral tradition, but I’m struck by how similar the early recordings are, and have to wonder whether it also circulated in some more formal way, as a song sheet or performed by a popular black (or white?) vaudeville entertainer — though I have no basis whatsoever for that guess, aside from the fact that some relatively generic-sounding verses seem to have been firmly attached to this song all across the South.
In any case, pretty much everyone who now sings it uses variants of Lead Belly’s verses, with their Texas references and the mention of “Jumpin’ Judy,” which Steve Calt glosses as a slang term for a woman who would have sex with lots of men — a reasonable guess, since the word “Judy” was already noted in 1810 as slang for prostitute or, to be precise, for a “blowen,” a wonderfully archaic Briticism.
Some sources add that there was a legend in Sugarland (or in other prisons) that if the light of the midnight train shone on a prisoner through his window, he would soon be released. I am not aware of any solid evidence for this, and as far as I know it may have been invented by an imaginative folklorist… but if anyone out there knows more, please fill me in.