Here's the post on Stack A Dollar I promised several weeks ago. Since I have three versions of this song, all recorded within five years of each other, I decided to go all out and put 'em all up.
Before I start, I need to note that, despite a similarity in title, this song is almost entirely lyrically unrelated to the story of "Stag" Lee Shelton and Billy Delions. (You'll note a "rumbling underground," which occurs in a lot of versions of "Stag" when Stag is in hell, turning Billy upside down, but that's about it.) With that said, Stagger Lee and Stack O'Dollars are both pimps and baaad men. (At least, Stack O'Dollars offers money for sex -- it's close enough for the sake of this argument, anyway. I own a 70's novel entitled Stack A Dollar, which I haven't yet read, but it's about a young pimp who presumably took his name from this legend. Also, see this.)
(For more lyrically unrelated versions, click here and here and here and here.)
In the late 1920's Sleepy John Estes (wiki AMG discography) teamed up with James "Yank" Rachell (wiki AMG) to play dances and parties, and they eventually went into a studio to record in 1929. In 1930, they laid down "Stack O'Dollars."
Rachell recorded his own solo version in 1934. One year later, Big Joe Williams (wiki AMG) (best known as the original artist of "(Baby) Please Don't Go") recorded his take on it.
All three men worked together decades later, as Yank Rachell's Tennessee Jug-Busters, though sadly they didn't include this song on their only album. (However, please note that Mike Bloomfield, who did his own version of Stag, also worked on this record.)