Oh, Doffy, Doffy - where do I begin?
It should be obvious but MAJOR SPOILERS FOR ONE PIECE
I think currently Donquixote Doflamingo has to be one of the greatest villians of all fictional history, or at least he's definitely on the top ten list, especially when considering recent chapters.
In the world of One Piece the new age is defined by the pirates who roam the seas searching for treasure, status, freedom and fame. Of those pirates Doflamingo has made a name for himself by not only becoming a warlord for the Marines, but overtaking an entire country as it's king
His is a long history of manipulation, terror and violence.
Honestly, Doflamingo is one of the most nuanced, well-written complex villians I've come across since... I don't even know.
On the one hand, dude's fucking evil. No question, no doubt, he is sadistic, has a god-complex, is violent, cruel, vindictive, cold, and more than willing to deal out damage to man, woman or child.
Let's take a laundry list of the things we know he's done past and present; he murdered his father, started a pirate gang, accepted/allowed children into his mafia-style pirate family and actively encouraged them to be as ruthless and cruel as he is, lied, cheated, stole, murdered his way to the top of the underworld, murdered his own blood brother, screwed countless lives over, KIDNAPPED CHILDREN WITH THE EXPRESS PURPOSE TO EXPERIMENT ON AND KILL THEM, took over a country through trickery and violence and has oppressed/slaughtered countless of lives.
His personality is that of someone who actively enjoys and even gets off on psychologically fucking with people in the cruelest ways possible, as evidenced by shooting Law. Not only is that the exact same way he executed his brother and Law's savior but he used LEAD BULLETS in reference to Law's traumatic childhood with dealing with the Amber Lead Syndrome - an extra twist of the knife to make his brutal beating that much more brutal. Seriously, Doffy, there is such a thing as too much.
Holy shit, that's a lot for one person.
HOWEVER, instead of giving us a cardboard cutout villian Oda-sensei threw in some complex background elements that almost, almost make you sympathize with him.
Doflamingo came from an extremely privileged background as a Celestrial Dragon - a status in the world of One Piece that means they are considered gods and above human beings.
His father gave up the title and wanted to live as a normal human, giving up everything and demonstrating empathy and compassion (rare for a Celestrial Dragon)
however he made a huge mistake and soon his family was torn apart by the mobs of people who had suffered at the hands of the Celestrial Dragons.
Doffy was nearly crucified, lived in squalor and terror, was beaten and hunted during his childhood.
It doesn't excuse ANY of the things he's done but it makes him more complex then just 'I'm evil!'
Unlike any other villian we've come across in One Piece he has shown that on some level he actually cares for his close crew-mates and has said himself, 'you are my only family in this world.'
Granted, he will still willingly sacrifice them for his cause but he has shown to have remorse - something Crocodile NEVER showed.
In return, it has been shown that his closest 'family' members gladly will thrown their lives down for their master. In a way, it's amost reminiscent of a cult-like mentality, such is his charisma and intelligence.
Therefore, I give you Donquixote Doflamingo - crazy, charismastic, fascinating psychopath villian whom I can't wait to see fall by the hands of Luffy.