Terrife, you should really read I, Lucifer http://www.amazon.com/exec/obidos/tg/detail/-/0802140149/103-6983917-7409403?v=glance
Actually everybody should 
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Well, the granddaddy of such stories is Stephen Vincent Benet’s “The Devil & Daniel Webster.” In that one, farmer Jabez Stone sells his soul to the Devil for earthly riches, but gets famed orator/Senator Daniel Webster to represent him in a trial.
Webster’s skills as an orator are so great, a jury made of of the worst sinners in Hell is swayed to acquit Jabez Stone.
“Satan and Sam Shay”, Robert Arthur. Basically, the final twist is that selling insurance counts as a business, not as gambling…
Ummmm…did you click the link on my first post?
Speaking of Keanu, in the movie Devil’s Advocate, Keanu finds out that he is actually the devil’s son, and the devil has some bizarre plan for him to fuck his half-sister, thereby producing the anti-christ. But the devil tells Keanu that he never made him evil, it was all due to his free will; the devil just provided the opportunities. So just as Keanu is about to prove incest is best, he blows his brains out, thus thwarting the devil’s master plan.
And of course there’s the time that Bender outsmarted the Robot Devil.
It was on “The New Twilight Zone” and was adapted from a story by Joe Haldeman, “I of Newton.”
This is a very common trope, so much so much so that Michael Armstrong wrote “Absolutely the Last – This is It, No More – the Final Pact with the Devil Story.” That may have been the one where an author was required to get a particular story published or lose his soul. No editor wanted it, until, just in the nick of time, an editor bought it. For The Last Dangerous Visions
Others:
Damn Yankees book by George Abbott and Douglass Wallop, Music and lyrics by Richard Adler and Jerry Ross – classic Broadway musical & film. Joe Boyd sells his soul so that the Washington Senators can get into the world series. Songs include “Whatever Lola Wants,” “You’ve Got to Have Heart.”
“The Same to You Doubled” by Robert Sheckley – the devil gives the protagonist a wish, no strings attached: he can have three wishes, but his worst enemy gets each of them doubled.
“Dealer’s Choice,” another New Twilight Zone episode (by that I mean the 1980s version, not the UPN one). Dan Hedaya plays the devil who sits in on a poker game. He always has the highest hand, and eventually challenges M. Emitt Walsh for his soul.
Walsh is dealer, and chooses to play lowball – lowest hand wins.
*For those not in on the joke, Harlan Ellison announced in 1974 that the book would be published “in six months.” We’re still waiting.
I seem to remember reading a short story (can’t remember the title) about a guy who made a deal with a demon…he made a bet that the demon couldn’t perform three challenges he’d set up for him. I remember the first, which was to appear at a certain place, come outside, and greet him (the place he gave was a location inside the Pentagon, which, being a pentagram, would restrain the demon from leaving; the demon skirted this by shifting things temporally until after the Pentagon was renovated into the Hexagon). Can’t remember the second challenge, but the third was “destroy hell.” The demon admitted defeat, and the guy won the bet and his soul.
The twist, of course, is that the guy died shortly afterward and went to hell anyway. The reason given, as I recall, was that making a deal with a demon is something so evil that, whether the devil wins your soul by contract or not, you’re hell-bound anyway.
I always liked the portrayal of Lucifer in **Neil Gaimen’s ** Sandman story arc *Season of the Mists. *
In it Lucifer is a pulled together pragmatic charasmatic guy. He rants at one point about all the myths of “the devil made me do it” He calls bullshit and says people do whatever the hell they want and use him as a scapegoat. Buying souls like a fishwife at a market, Bah!
I wont give away the story but the Devil does win on his own terms at the end.
Tenacious D’s “Tribute to the Greatest Song In the World” is an excelent example of a story where the devil/soul-taking-demon is bested. In this case though, the (shiny) demon demanded that Jack and Kyle play “The Greatest Song In the World” or else they’ll loose their souls. So Jack and Kyle play the greatest song in the world, and the demon is defeated. The twist in this story, is that the greatest song in the world doesn’t actually sound “anything like this song” because they can’t remember how it went, hence, the song we listen to is merely a tribute.
Also, it’s just a great song anyways.
Just a side-thought on the devil’s incompetence. I always believed that a devil that wanted to make deals for people’s souls would -want- as many of these stories out as he could get. Make people think they have a fighting chance against losing their souls, and make them more willing to make deals due to that.
Back in the 80’s there were a series of books called “Heroes in Hell,” done in teh same manner as the Thieves World series. Principle characters included Caesar, Agamemnon, Cleopatra, Marc Antony, Napolean, etc. The idea was that none of these souls could leave Hell, so they plotted to take it over, and usually wound up failing because they kept backstabbing each other.
Hell is portrayed as a place where nothing works right. There is no infrastructure, order, or even any proscribed means of torment. There’s so many former societies and obsolete philosophies that not even the Devil can make sense of it all.
The introduction story centered around Yuri Andropov, the USSR’s late ruler, as he’s escorted into Hell for the first time. The Devil’s office is made to look like everything he despised about capitalism—plush chairs, lavish paintings, vulgar displays of commercialism, etc—and the Devil appeared as John F. Kennedy.
Satan gets in a few kicks for irony’s sake, but he’s hardly the main character in the stories.
The granddaddy of these all is Stephen Vincent Benet’s “The Devil and Daniel Webster”, which was turned into a movie. Since then, there have been a lot of such “Deal with the Devil” stories. There was even an early 1960s anthology entitled “Deals with the DEvil” There were a lot of fantasy and science fiction stories in the 1950s on this theme (as in Isaac Asimov’s “The Brazen Brass Box”, which combined The Deal with the Devil with the Locked Room Mystery.) I don’t know if anyone;s tried to make a comprehensive list, although this would be a good place to do it.
For my money Fredric Brown wrote some of the best DwtD stories. I can’t recall the title of my favorite, but it’s a good insight into human nature – because it’s not a fantasy story. Typical of Brown, that iconoclast.
On TV, there’s A Year at the Top, where Paul Shaffer sold his soul to become a rock star. Alas, we never found out how it worked out, since the show was cancelled before the year was up. Maybe it’s the reason Shaffer’s working on Letterman.
There was also God, the Devil, and Bob, a fairly good animated show.
Mmmmm… forbidden donut…
For a surfing contest between God and the Devil, seeThe Devil Went Down to Newport by Mono Puff.
Uh, not quite. I think that Goethe’s “Faust” predates most if not all of these examples, including Benet. And Goethe’s work was based on earlier stories that dated back into the Medieval period. Marlowe wrote a play called “Doctor Faustus” based on the same archetypal story; that would have been a few years prior 1600 (Marlowe was nearly a contemporary of Shakespeare). Probably the primal antecedant for all of these stories is the Book of Job, though Job does not in fact make a deal with Satan, but is merely the victim of a bet between Satan and the Lord. And even there, you probably have some stories in other myth systems which predate the Bible but have the same motif.
So this stuff goes way back. The details change, but the broad outlines tend to remain the same.
I just wanted to say that the story makes a sharp left turn into incomprehensibility by the end, IMO. I love P&T and all, but every time I read that story, I end up wondering WTF?
Just remember that we’ve only heard God’s side of the story so far. 
This always makes me think of an old cartoon I saw in a Playboy once. There’s a well dressed group sitting around a table having cocktails and seeming to be enjoying themselves. At the head of the table is a rather distinguished looking Devil addressing those at the table, and at the bottom it says “…Well you didn’t think it was going to be all THAT bad now did you?”
I’ve never read the story, but I’ve read jokes that used this as the premise. By any chance, does one of the wishes go something along the lines of “Scare me half to death”?
Hrotsvit of Gandershiem, who lived in the 10th century, wrote Basilius, which has a young man selling his soul to the devil to get a girl to like him. Later, however, he repents and is forgiven by God, so he gets the girl and gets to keep his soul anyway.
Not as old as Job, but older than most other examples mentioned here, is the story of Jesus’s temptation by Satan in the wilderness (found in Matthew 4 and in Luke 4). Satan does offer what might be described as a “deal with the devil” (enough so that this is one possible source for the idea in later fiction), though Jesus doesn’t take him up on it.