My vote goes to Subaru from Re:Zero. I have never hated an anime character so viscerally.
Not only is he a useless waste of meat, an arrogant prick who refuses to ever learn or better himself in any way despite having the ultimate cheat to do so… He had Rem – the best best girl that ever was best girl – confess to him in possibly the most beautiful moment ever, and he’s like “that’s nice but I still love the boring cardboard elf chick who has been mostly ignoring me all this time.”
For me, Cowboy Bebop, hands down.
Shin Sekai Yori. I don’t think I can say literally anything about this without spoiling it; it’s one that is so much better if you go in blind.
Couple of people beat me to Violet Evergarden, which I maintain is my #1 pick for “you will NOT be okay” shows.
BUT
In a thread about “anime that will mess me up,” how has nobody beaten me to Grave of the Fireflies? HO-LY SHIT. If you don’t feel like your soul has been torn out and stomped on watching this movie, you straight up don’t have one.
Came here for Violet Evergarden. My wife could always tell when I was watching it because I straight up sobbed like a child every single episode. Bring tissues; you will not be okay.
You would not believe how many people I usually get lining up to defend both the show and him.
I honestly had to stop watching before it finished because I just could not stand him.