The Pool Shark (song)

The song tells the story of a young traveling man and hard-luck gambler who stops at a roadside bar. After watching one of the regulars, a middle-aged man, play pool for a while, the two strike up a conversation and agree to play a game. Eventually, the two play a long best-of series of the games, with the regular revealing himself to be a pro at the game who, under the guise of a friendly challenge, frequently hustles unwary opponents out of money.

The pro eventually winning all the main protagonist's money -- $187 plus his ring -- and leaves in a Cadillac with a beautiful young woman ("a blonde built like the rest of that car"). In the end, the protagonist asks the waitress out; the conversations with her had been interspersed occasionally with the main story.