If they actually go for a Devil-and-Sam-Winchester scenario, they better make it AWESOME.
I had occasion to look up that short story recently, hoping it would tap into local lore and give some good fic cues, and remembered abruptly that it was written in the 1930s, not the period when Dan'l Webster himself was alive. The prose is very modern, in a way I found disappointing. And that the upshot of the story is that Webster doesn't even win on procedural grounds; he persuades a jury of dead souls with the power of his emotional rhetoric. (How he persuades the Devil to put his deal in the hands of a jury requires a bit of handwavium.)
Goethe, on the other hand, does use a technicality -- the only fate that ever hinged on a subjunctive verb!! -- or anyway a technicality and the overwhelmingly generative power of female genitalia. (Don't ask. The whole story is like that.)
I don't remember what Kit Marlowe did for his Faustus, because I've never read all of it, but it's possible his is the only one that dates from later than Medieval times where Faustus actually gets damned like the deal says.