Shiroe, the ''Villain in Glasses'' (LOG HORIZON)

So Arkada of Glass Reflection called Shiroe basically a "kind-hearted" version of Lelouch or Light Yagami, and I wasn't really seeing it that much, until Episode 9, and now I most definitely do.

ALL HAIL SHIROE!!!

But in all seriousness (as if, this being the internet), he's such a nice and supportive guy, and yet he's so devious and ruthless and underhanded he'd have no problem fitting in with more well known ruthless-mastermind-anime-anti-heroes. And unlike most of them, he actually hasn't intentionally or unintentionally caused the deaths/downfalls of anyone close to him (granted, nobody is even capable of dying yet at this point, but whatever).

From the relatively new anime Log Horizon, which you should probably be watching. And no, it's not a rip-off of SAO in the least, they're completely different in so many ways.