I'd probably play a caster of some sort, because this concept will need power to be able to get away with his trolling. Good or Neutral aligned (definitely not Evil). I play 3.P.
If anything is unclear, let me know, I'll try to explain more in-dept (although I don't know what more can I say).
And in case anyone is wondering: NO. I won't be a dickhead in-game. It's all in good humor. So please, don't come in here with lessons "How to not be a jerk", thank you very much.