In the aftermath of Chimera, I was thinking about playing villains in theatreform, and in what ways these characters and their players are important to the artform. I ended up writing a blog post about it: The Art and Duty of Being a Bastard
I thought it might be an interesting starting point for a discussion, and I would love to hear people’s thoughts on the topic 
I recognise two of those anonymised games
I like to think of it this way: story requires conflict. In some genres, conflict requires bastards. Being a bastard means you are going to define other people’s game and give them something to struggle against. So play hard, to give them the opportunity to do the same. If in your dastardlyness you win, that’s great. And if you get gunned down by your own secret police because you’re too ruthless even for them, that’s great too (and it gives you an epic war story to tell afterwards).
Post-game goes both ways. If someone has been a good bastard to you, let them know. It will make them fell that doing all that horrible stuff was worthwhile, and that you don’t think they’re really like that (which is one of the big reasons people shy away from proper bastardry).
Ding ding ding! We have a suspicious-looking post here!
But this is a good opportunity to respond to the thread anyway. I really struggle with playing villains, to be honest. I don’t like being a bastard, even in fiction, and I think a lot of that comes from the fact that I like people to think good of me. It’s not that I think people will watch me be a dick in LARPs and think ‘Ah, he must be a monster’, but more that I hesitate to do anything that I feel will screw over another player’s enjoyment.
When I was playing in ‘Fleet Street’ a few years ago, I had a character who wanted to kill someone, and that person happened to be a first-time LARPer. I didn’t know what to do - in the end, I went through with it, and I apologised profusely OOC, but that was it. The rest of my evening was plagued with the fear that I had ruined her night, and potentially the hobby: now she was forced to spend the rest of the evening as a ghost, visible only to two other people. I felt like I had to punish my character for that action, rather than playing him through as evil as he was clearly written to be. I think that sort of thing comes when I can’t read the character’s motivation for doing something. Very few characters are outlandishly evil, and I don’t remember what my character’s motivation was for that action. Something about cults, I think. It’s part of my playing style that I’m constantly trying to improve.
I think the trick to being a villain in a LARP is to find ways of being horrible that actually create RP opportunities for other players, rather than simply killing them. This means lots of lying, cheating, threatening, mocking, gloating, and generally making all the classic movie villain mistakes. Unfortunately this means you’re far less likely to be IC successful, but the other players will love to hate you.