Bob Dylan - "Señor (Tales of Yankee Power)"
Dylan is obviously not obscure and I'm not sure that Señor qualifies either, but it's not one of Bob's better known songs. It was on "Street Legal" which is also not one of his more celebrated albums. Dylan creates a dark and foreboding atmosphere in the song that's almost downright frightening. One gets the sense that the singer is not going to like what the Señor has in store for him.