2016 Anime Villains Tournament - Round 3, Match 4
Jake Martinez - Tiger & Bunny
Ototo Toguro - Yu Yu Hakusho
My vote goes to the younger Toguro.
My vote goes to Jake Martinez.
Jake is basically The Joker if he had force field powers, mind-reading abilities, and was voiced by Steve Blum. He even has his own little Harley Quinn sidekick and everything. Voting for Jake.
Still haven't seen Tiger & Bunny yet, I'll hand my vote to the Toguro brother.