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1) Have you run such a game? What were the results?
I have. It went well enough, and it still gets mentioned by my home group occasionally.
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2) What was the biggest hurdle when it came to the game?
I'd say balancing expectations. The key was to acknowledge that it really wasn't a
huge departure. Character motivations were different, but not by as different as you might think. For a traditional dungeon-fantasy game like D&D, almost all characters can be motivated by the right amount of money. Just don't expect them to march off to heroically save the orphanage for nothing more than the warm fuzzy feeling they get from doing good.
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3) What surprised you about the game?
Because they were playing more manipulative, scheming characters, the party was actually
more interested in doing very public acts of good. For instance, they volunteered - without pay - to protect a frontier town from a horde of invading orcs, turning them into local heroes. Now, did the mayor of that town die tragically in the attack, far from the front line? Sure. But those orcs can be
devious, right? And who were the "heroes" to argue when the town wanted their saviors to take the reins of leadership? It would have been an insult
not to accept.
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4) What advice would you give on putting together a similar game?
Don't let your preconceived notions of "what evil characters do" to take over. Encourage your players to build conniving, scheming little devils, rather than simple murderous psychopaths (Not to say they can't be both!). Also, remind them that working well in a team means there'll be more people between them and those who want to do them harm. Discourage direct PvP, but allow them to screw each other over in little ways if they feel the need.
I also played in a fantastic evil-oriented game a while back, though it was unintentional. It was a Pathfinder game, using the Kingdom Building rules, which is to say, we were in charge of a colony. It just so happened that most of us were from Cheliax, a nation in the thrall of devils, so our colony ended up being a devil-worshiping theocracy. The leader of our colony was the local high priest (a PC), and I played the treasurer. The game was short-lived because of real-life circumstances, but it ended just before my character had the high priest assassinated (by a different PC, an assassin who I had secretly employed quite a while back) and arranged a marriage with a different character in power, who was also a PC.
It was a huge, intricate game of conspiracies and obviously at least a little competitive, but it was a blast for all involved. Playing the simpering courtier secretly plotting the downfall of his betters was a unique and really fun experience.