Right, there are a lot of long posts in this thread, so I stopped reading after page 2. I agree a lot with things that have been said - that it's hard to get into the head of a murderous psychopath, to know your villain is doomed not to conquer much of anything, and that it isn't easy for a villain to chill out with other villains for some regular social interraction. But I think the perhaps largest issue is that we roleplay against other people and their characters, so we can't just go around killing or maiming or completely destroying lives all the time. If one plays a prideful murderer, can we just slit a throat in the night if a cape acts condescending? For a villain to be a villain, he needs to harm people, and that means either faceless NPC's or PC's that someone likely wants to stick around a while longer. And if it's just, "Okay, so I killed a dozen faceless, unnamed NPC's off-screen", it lacks most any actual weight that such a deed would have. I think that's the issue that's the most difficult to circumvent. Well, I might be wrong for all I know.
