Source: wordpress.com
4. Psycho Pirate
Psycho Pirate had one of my favorite costumes in superhero comics. He looked like a court jester who tried to become the Phantom of the Opera.
The Pirate used the Medusa mask to manipulate people’s emotions to a drastic degree. Doing this also drove him completely banana-pants insane. When the cosmos was in danger during the Crisis, he decided, “Oh, well, I hated living in this universe, anyway.†He then teamed up with the Anti-Monitor, who wanted to annihilate all of reality.
He mostly helped his boss by torturing Barry Allen a lot. Barry broke loose, and forced Psycho Pirate to cause chaos among the Weaponeers of Qward, which allowed Barry to save everyone. After this, the Pirate kind of bounced around the DC Comics universe for a while. He popped up in Animal Man as an embodiment of fourth wall breaking, and was later used as a seat filler for the big villain-focused event that was Underworld Unleashed.
Finally, he appeared in Infinite Crisis, in which Black Adam pushed his eyeballs through the back of his head and killed him. Ew.

