My sixth graders recently read through The Devil and Daniel Webster, which they enjoyed. For my own part, it struck me that the devil in that story is really less of the devil of Christianity than he is a fairy. He takes the role of Rumpelstiltskin, offering gifts, but at an unacceptable price, accepting the challenge of games and becoming powerless once he is beaten (a trope more associated with the fair folk than the Father of Lies).
The same is true for a lot of devil stories. Take Devil Went Down to Georgia, for instance (which is a great song, but not a very good devil story). The devil in that one is much more of a dark fairy than he is the Prince of Darkness, for the simple fact that, having challenged Johnny to a contest, he owns himself defeated because Johnny’s playing is just that good.
This is why I say it’s not a good devil story: Johnny is ultimately rewarded for his hubris by having his pride confirmed. He really is just that good. That’s a shallow, self-flattering tale of the sort you’d expect to come out of the 70s music scene.
There are, broadly speaking, only two ways a devil story should end. The first is that the hero wins, but only by being clever and outwitting the devil with his own rules, or by adopting a strategy the devil couldn’t predict or counter. Devil and Daniel Webster is a good example of the latter: Daniel wins the trial, not by giving the thundering denunciation he’d been planning, but by appealing to the humanity of the jury of damned souls, arraigning them on his side against the devil.
A decent example of the former is Printer’s Devil from The Twilight Zone (which isn’t a brilliant episode, but casting Burgess Meredith as Old Scratch covereth a multitude of sins). In that one, a newspaper editor sells his soul to save his paper, which Scratch does by modifying the linotype machine so that whatever it prints comes to pass. The editor gets out of his contract by using the machine to print an article saying that the Devil disappeared from town and the contract was declared null and void.
The other ending, of course, is that the Devil wins and the protagonist pays for his hubris in challenging him. There’s a folktale that I read in elementary school, but for the life of me cannot remember the name of (and Google is being unhelpful) about the world’s toughest fighting man, who could lick any challenger. But every fight was too easy, so one day, desperate for a real fight, he declared he’d even fight the devil. The devil then showed up and agreed to the match, and they had a fine knock-down, drag-out brawl, just like the guy wanted. Only, he’d forgotten that he was only mortal, and the devil wasn’t, so in the end he tired out and the devil won.
Me, I think Devil Went Down to Georgia calls for the second ending: Johnny pays for his hubris in accepting the devil’s challenge and loses the contest before it even begins.
Devil stories are essentially Christian variations on classical myths like Arachne in which mortals challenge the gods and pay the price. The core idea is that you cannot beat elemental forces like nature, death, the devil, and so on, or at least not by tackling them head on, strength to strength. That is, the main point is that man is limited and had best remember the fact.