Black Lantern Psycho-Pirate
One is Sōsuke Aizen, a renegade Soul Reaper who has a Zanpakutō called Kyōka Suigetsu that can seriously $%#@ with your mind until it has turned you into a raving lunatic who is literally incapable of surviving without Aizen unless the victims are able to undergo severe psychiatric rehabilitation ASAP.
The other was Roger Hayden, the second Psycho-Pirate and the wielder of the terrifying Medusa Mask. The Medusa Mask allowed Hayden to literally project any emotion he wished onto his victims thus allowing him to control them very much in the same way Aizen could...or perhaps even worse.
Unlike Aizen, who expired from the mortal realm countless ages ago, Hayden's death was a little more recent and very brutal. Black Adam poked him in the eyeballs and pushed his brain out the back of his head in one of the most gruesome death scenes in history.
But as they say...the dead don't always stay dead and unfortunately for Hayden he has been resurrected as one of Nekron's Black Lantern Corpsmen...without the insides of his head. He has been given custody of his vile Medusa Mask back and is now ready to make everyone feel the pain of being alive once more...with a huge hole going through your whole head.
In a fight between these two manipulative little bastards...who would win? Aizen or Hayden? A Renegade Soul Reaper with a God Complex or one seriously pissed off Black Lantern with a huge hole in his face that would make every male Hollow, Arrancar and Espada completely jealous of him?