OK sorry for the 2 month late reply, I saw this question right before I went to visit my friend over at another city and decided to spend the weekend there just thinking about the question... eventually I just forgot to answer it. But I have been thinking... It's just so hard to pick one! So I'll tell you about a few.

I really, really like Dostoevsky's dudes. No doubt people know this if they've talked to me for a while. I think I may have posted about them once or twice on certain places.

From Crime and Punishment is Svidrigailov, who has a huge list of crimes associated with him... He's a very fascinating and enigmatic character despite of how much of a degenerate he is. Well, more like he's fascinating BECAUSE of how much of a degenerate he is. In my eyes, he's supposed to reflect the "extraordinary man" that Raskolnikov describes and wants to be--somebody who is permitted to kill people, even in the dozens, no, hundreds. Svidrigalov is one such man, having almost no conscience and an incredible charisma around him. Whenever Raskolnikov is confronted by Svidrigalov, he's always disgusted by him, in spite of how Svidrigalov is more or less his model of an "extraordinary man". The chapter where he has a long fever dream before he ultimately commits suicide is amazing, as well as the chapter where he confronts Dunya, backs her into a corner, puts his arm around her waist, and asks her if she'd ever be able to love him... When she says "no, never", he's utterly crushed. And to think just moments before, he was completely unshaken by Dunya pointing a revolver at him. I think about those chapters occasionally. Dostoevsky definitely gets it.

Then there's the Underground Man, from Notes from Underground. A pathetic character, but one I could empathize with (for better or worse). When I first started reading that, I thought to myself "yes, this guy gets it! he understands!" in response to him going on a 30-page rant about how humans are irrational creatures that shouldn't be treated as mere numbers. Then, in the second half, you see this guy stumbling around, making a fool of himself in public while simultaneously feeling like he's better than other people because he's educated, etc... I could understand his feelings. In the very end of the book, when he's given one chance at genuinely connecting with another human being, he rejects it (out of fear?) and decides to remain an Underground Man, completely isolating himself from other people... That really got to me.

For something completely different: Lou Zhen Jie from Thunderbolt Fantasy, or just Di Kong when he's in his monk form. There's something about the way that Urobuchi writes about love that picks at my heart. Lou himself is a character archetype that I love, just somebody so utterly removed from normal human values and is suffering because of it (Kirei is another good example). When he meets his "princess", a bloodthirsty sword who charms whoever looks at her, he goes full murderhobo mode and reveals his full power! The man breaks a sword with his KNEE! He goes around happily slaughtering people in the dozens, all in the name of pleasing his beloved princess... and to think, he'd spent most of his life without any meaning. Most yandere characters suck but I can get behind something like this.