Roger Hayden is a jailed gangster (later retconned 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.
Hayden returns to prominence when he insidiously begins influencing prominent Gotham City citizens Bruce Wayne and Alan Scott, the former a wealthy businessman and now commissioner of Gotham's police force, the latter the President of television station WXYZ. Initially, Scott is the most affected as he, in his Green Lantern persona, begins exercising his frustrations upon humanity for the failures of his private life, such as the impending bankruptcy of his station. After creating a disturbance at Gotham International Airport, he is subdued by his Justice Society comrades, who assists both Scott and teammate Flash who has also been under Hayden's control. The Society has to next battle a civil war within their membership instigated by Wayne, still under Hayden's control and determined to rid Gotham of all superheroes.
Hayden later joins the Secret Society of Super Villains, having been recruited by the Ultra-Humanite to defeat Hayden's old foe Hourman. While he is successful thanks to a device Ultra devises that amplifies and projects Hayden's face and hence his control, ultimately both the Justice Society and the Justice League defeat Hayden and his teammates after their betrayal of fellow Secret Society members. The villains are deposited into an interdimensional rift known as limbo for lack of a better term.
From there, Ultra gains mental contact with his younger self from the 1940s, and the two Ultras are able to pull the Secret Society, including Hayden, back to that era where they confront and are defeated by the All-Star Squadron and the time lost Infinity Inc.
Hayden appears in the 1987 Outsiders special. He impersonates the villain Baron Bedlam in order to gain power in the fictional Eastern European country of Markovia. Since the Outsiders hero Geo-Force is a Markovian prince, his team becomes involved, assisted by another superhero team Infinity Inc.. Despite Geo-Force's knowledge of his childhood castle, Hayden quickly subdues him and the other heroes involved. The story is continued in a similar Infinity Inc. special.
Hayden shows up again in Grant Morrison's run on Animal Man, imprisoned in Arkham Asylum. He ends up releasing characters destroyed during the Crisis back into the world. Many of these characters come to realize they are just characters in a comic book. After an intervention by Animal Man, Hayden, seemingly happy, fades away into nothingness (due to the strain from releasing all the forgotten characters), removing him from reality); heading to comic book Limbo. James Highwater, one of the Asylum staff, is left to wear the Medusa Mask and keep the forgotten worlds contained. The other staff members come to accept Highwater as a patient, not realizing anything is wrong.
Psycho-Pirate does not appear again until 1995, when he becomes part of the crossover event, Underworld Unleashed. Like many other villains, Psycho-Pirate sells his soul to the demon Neron in exchange for more power. The process results in a costume change as well. Hayden now wears a black leather jacket. His mask morphs into an eyepatch. Now sane and making no mention of the events of Crisis on Infinite Earths and the existence of the multiverse, Psycho-Pirate goes on to fight the knife wielding mercenary incarnation of Doctor Fate, for now just called Fate, several times before being arrested and sent to jail.
After his appearance in Fate, Psycho-Pirate makes two brief appearances during the Joker's Last Laugh crossover event. He is first seen locked up in the maximum security prison called the "Slab". He is once again insane and rambling of the existence of the multiverse. He also has his original costume. All but one eye is covered. It is noted how his eyebrows and have have been shaved off so as to reduce his ability to express emotion. The Joker iniates a breakout and infection of the inmates; they now follow his orders and commit dangerous pranks. Hayden is seen shouting 'Fire!' in a crowded theatre.
Finally, in the final issue of the storyarc, Psycho-Pirate reveals that he and Power Girl are refugees from Earth-Two. Along with other individuals (such as Donna Troy, her evil alter ego Dark Angel, and several others), they were missed in the restructuring of the Multiverse into a Universe. Hence, Power Girl's original origin is her one true origin.
It is eventually revealed that the whole purpose of Psycho-Pirate's scheme is to weaken Power Girl mentally so that she could be captured as part of Alexander Luthor, Jr.'s plot involving characters originally from different universes. Psycho-Pirate flees and vows to make Power Girl his love slave once Luthor is finished with her.
When Nightwing, Superboy, and Wonder Girl attack Luthor's base, they free all the captive heroes, including Power Girl and Black Adam, who then confronted the Psycho-Pirate. Psycho-Pirate tries to instill feelings of fear in Black Adam, but he resists, saying "No more silly faces," and then proceeds to gouge out the Psycho-Pirate's eyes and pushes the Medusa Mask through his head, killing him. When Power Girl asks if that was necessary, Adam replies, "Absolutely".
With the Medusa Mask, Roger Hayden is able to project emotions into people. Often, it seems to intensify emotions a person already feels, no matter how small. Hayden later shows the power to manifest DC multiverse characters that had been destroyed during the Crisis on Infinite Earths. This power expands to any multiverse character, including the still living. Psycho-Pirate has also shown some sort of regeneration of body control as he is able to reform after being crushed by Power Girl, and also disguises himself as a Legion flight ring. It appears he has also returned from the destruction of his head at the hands of Black Adam.
During his 90s revamp, Psycho-Pirate was an 'emotional vampire,' able to drain emotions from people.