Many "villains" can fall into a bit of a gray area, especially when it comes to anime. I tend to like characters who do bad things because they have an interesting perspective or justification for their acts, or those who simply genuinely don't understand that what they do is wrong. This often brings up the question of whether said villain is actually a villain in the first place. With that in mind, these are the "villains" that stand out to me and hold a special, dark place in my heart!
Izaya Orihara (Durarara!!)
The frontrunner: Izaya, the information broker of Ikebukuro who just loves humans! Izaya likes to stir up trouble, just to see how people will react. He caught my attention right away with his suicide ruse; I was just so fascinated with him! He's a manipulative bastard, and I love him!
As usual, I can't just stop at one!
Ulquiorra Schiffer (Bleach) **SPOILERS**
I always kinda liked Ulquiorra. He keeps a cool head, compared to his fellow Espadas, but you don't wanna mess with him. His interactions with Orihime are really what intrigue me (I kinda sorta maybe possibly ship it a little). He didn't understand humanity, Orihime and her friends, and why they were so driven, and he seemed genuinely curious. He grew and learned as the arc went on, and I think even evolved into an anti-hero for like a hot second before he faded away.
Light Yagami (Death Note)
I love that Death Note's main character is the villain! This genius with a god complex genuinely believed that he was building a better world and that he stood for justice. It was really cool to see his evolution throughout the anime.
Shogo Makishima (Psycho Pass)
Makishima is a bit like Izaya and Light. In this futuristic crime drama, I always saw him as the Moriarty to Kogami's Sherlock. He sees that the Sybil system is flawed and wants to bring it all crashing down. A literary enthusiast, he's a bit old-fashioned and has a sense of wisdom about him. His psycho-pass doesn't register on the Sybil system, so he can basically do whatever he wants, and the PSB can't do anything about it.
Kyubey (Madoka Magica) ** SPOILERS**
Kyubey's kind is very advanced and doesn't experience or understand emotion, so when he takes advantage of humans by forming contracts, creating magical girls, and profiting when they suffer and become witches, it never even occurs to him that he's committing any kind of wrongdoing. As easy as it might be to hate this adorable little monster, I can actually kind of understand him. I still don't like him, but as a villain, he's made an impact on me that puts him high in the rankings.
As always, hope you enjoyed! If you wanna learn more about me/ be my friend/ be tagged in these, please don't hesitate to ask! I'm nice, I swear (mostly ;p)! Or I guess you can follow my 100 Days of Anime collection, or both if you feel so inclined!
Until next time!