Colonel Roy Mustang (of Full Metal Alchemist), while possessing of an odd name, is a very interesting character. I love it when good characters are really morally questionable. (I'm assuming he's a good guy, at this point he still appears to be.)
He put a kid into a deadly situation, but in the end he twists it around quite nicely:
Yes! Evil steps...
Okay, not a smirk, but a frown, but added because it's the one that most reminds me of amegoddess's style:
Funny, but the art used on him reminds me a lot of amegoddess's style.