The Psycho-Pirate is the name of two DC Comics supervillain, dating back to the Golden Age of Comics.
Charles Halstead is a minor character who first appears in All-Star Comics #23, created by Gardner Fox and Joe Gallagher. He was originally a linotyper for the Daily Courier who became jealous of his boss's success, later he becomes a criminal mastermind under the name Psycho-Pirate. He plans crimes based on emotions, hoping to ruin his boss. The Justice Society of America captures and puts him in jail. He continues to research the mysticism of emotions until his death sometime in the 1960s.
Roger Hayden, first appeared as the second Psycho-Pirate in Showcase #56, created by Gardner Fox and Murphy Anderson.
Roger Hayden is a jailed gangster (later retcon into a young twenty-year-old who was sentenced to a year in prison for attacking his emotionally abusive psychiatrist father) who is a cellmate to Halstead. Halstead's dying wish to have a legacy prompts him to tell Hayden of a secret which he has divined in his jail years, the existence of the Medusa Masks. These golden masks bestow upon the wearer the power to project emotions onto others. Hayden finds these masks, merges them into a single faceplate and uses its powers to become a supervillain. It becomes increasingly apparent that he is addicted to absorbing others' emotions, though it causes him pain, possibly brought by the combination of all masks into one. He is eventually imprisoned after a battle with Doctor Fate and Hourman.
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Official Site: DC Comics
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