It turns out my son has an advanced case of gamer add. Seriously. We've played a total of about six sessions of Labyrinth Lord with three different characters in two different worlds. I'm doing everything on the fly and I haven't gm'd in years and years. He is having loads of fun but we haven't developed either of the worlds very much. Well, one of the settings is Arthurian. He read several King Arthur stories and wanted to play Gawain. He rolled up a first level fighter and away we went. Gawain was still a squire and he was ordered to escort his lord's niece back to her home, two days ride away. Well they just happened to camp near an old barrow which, unbeknownst to the characters, had become inhabited by a small roving band of morlocks. They abduct the girl from the camp and adventure ensued.
This brings me to the second portion of the post title. Chaos. The third character he created is a chaotic aligned elf. That is what he wanted. I don't know where he got the idea because I don't think he knows about Drow. I grabbed a free one-page dungeon off the web and away we went. The one-page is Goblin Gully by Dyson Logos. We've done two half-hour sessions and once again, he's loving it. Ok. He's hacking and slashing goblins. He stated that any wounded goblins he would kill. That's what chaotic creatures do, he explained. He understands alignment and such. Great. But later he secretly informed me that once they completed the adventure he was going to back stab his younger brother's character and take all of his treasure! What have I created! =) (Apparently a dedicated role-player. I told him that the gods and the game master would not be pleased. Hopefully I've squelched the idea.)
After reading about the adventure in the elephant's tower type game, I'd suggest looking at roleplayingtips.com. In articles like this one - http://roleplayingtips.com/readissue.php?number=52#1 - he seems to lean toward suggestion rather than coercion. Players should feel like they have free reign, as their character, in the game world, within its limitations. If they are told point blank it's not a good idea to do something, they lose this sense. I'm thinking that is one possible reason your player is really into evil characters. He might be wanting to try and find ways to exercise freedom just for the sake of it. If a player wants to do something very stupid, you can put 'signposts' into the game itself to communicate the foolishness of that action. This should be clear so they fully understand it, and then if they set themselves on fire they only have themselves to blame but they still feel that they made their own choice. And Roleplayingtips has an article about 'winging it' for when players do things you completely didn't expect.
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