This article is about a subject that is from official sources but is not considered canon.
Roy was a hunter who, in 1993, noted a string of strange disasters in Laurel Hill, New Jersey over the course of a few days and after checking the lore, suspected an oni, a monster from Japanese folklore. The strange mass deaths ended before Roy could investigate but to be on the safe side, Roy bought an American holly shrub from a local plant nursery and planted it in his backyard as holly protected against an oni's powers.
Roy was active until 1996 when he lost his wife Sally and half of one of his arms destroying a ghoul nest in Philadelphia. According to Bobby Singer, Roy's mother-in-law blamed him for her death and he got out of hunting life. For years following Sally's death, Bobby feared that Roy would commit suicide but realized that he was staying alive for the sake of his son Lucas who he kept out of the hunting lifestyle. In 2007, Lucas, now a junior patrol officer, was killed in action when, during a routine traffic stop, an old man confused by the lights hit Lucas and dragged him for two hundred yards under his car before he found the brake pedal. Three months after Lucas' death, Roy had a conversation with Bobby about how he never missed hunting because there was too much killing and dying. Afterwards, Bobby realized that Roy was out of the life and meant it.
In 2011, when noticing a rash of strange deaths in Laurel Hill, Bobby contacted Roy for a place to stay. Though Roy refused to have anything to do with the hunt, including even knowing about it, he agreed to allow the Winchesters and Bobby to stay in his cabin and use it as their headquarters for the hunt. Soon after their arrival, Roy left for his mother-in-law's funeral. Before leaving, he asked Dean to feed his stray cat Shadow for him while he's gone and puts in a good word for Bobby with the local police chief to help the hunt, stating that its only a phone call.
Roy eventually returns to his cabin as the Winchesters and Bobby are trying to figure out the monster's weakness and why it has come to Laurel Hill in the first place. After learning that they are hunting an oni and need holly, Roy tells them about his holly bush in the back and his suspicions about an oni being in Laurel Hill 18 years earlier. Though Roy doesn't know how to kill an oni, he tells them about the obake, friendly shapeshifting Japanese monsters that take on animal form and are the enemy of the oni. Roy's information causes the Winchesters to decide to try to use K9 units to combat the oni. As Roy helps Bobby get the holly, Sam figures out that 18 years before, the oni had impregnated three women and was back for his sons. The group then gets a call from Sergeant McClary who informs them that the oni is attacking the Cheshire Theater. Knowing that hundreds of people could die, Roy decides to come out of retirement and aid the Winchesters and Bobby in stopping the oni, telling them that he should've killed it 18 years before.
At the theater, Roy teams up with Dean as the group and several police officers split up to take down the four oni who kill or seriously injure hundreds of people. Dean and Roy come up against Dalton Rourke who murders his grandfather during the rampage and threatens his grandmother, enraged at how awful they treated him. Roy, using his own experiences as a father, attempts to talk Dalton down, but Dalton is beyond reason and kills his grandmother. Dalton then stabs Roy in the chest with a knife, mortally wounding him. As Dalton tries to kill Dean, Dean shoots him in his third eye, killing Dalton and revealing the oni's weakness. Near death, Roy tells Dean to tell Bobby that he's too old to keep hunting and to never unretire as it never ends well. Roy then dies in Dean's arms.
Following Roy's death, his cat Shadow, who is revealed to be an obake, is adopted by Sumiko Jones who renames him Lucky. When the oni are dead, Bobby decides to stay at Roy's cabin for a few days more until Roy's remaining out-of-state family can make funeral arrangements for him to be laid to rest beside his wife and son. Bobby later tells the Winchesters that hunters never really retire and Roy was on more of an extended sabbatical meaning that if the oni hadn't drawn him back, something else would've eventually.
Roy once embraced the hunting life and had a good knowledge of lore. He took precautions against any monster he thought might be in the area, including an oni even after it was gone, something he called "Boy Scout mode."
Following the death of his wife Sally in a ghoul hunt and loss of half of his left arm, Roy was left a broken man who only stayed alive for the sake of his son Lucas. Roy was immensely proud of his son and his achievements and loved him deeply. Roy was devastated by his death in a freak accident while Lucas was doing a routine traffic stop.
Following the death of his wife and the loss of his arm, Roy got out of the hunting life, though Bobby Singer always believed he would return someday. After Lucas' death, Roy called Bobby and in a long conversation, talked about how he didn't miss hunting which had too much killing and too much dying. As Bobby was a reminder of that life, Roy cut all ties with him and Bobby recognized that that phone call was the final end for Roy and hunting. When the Winchesters and Bobby contacted him for a base of operations, Roy only agreed reluctantly but refused to know anything about their hunt, let alone participate in it. Despite this, Roy still showed some willingness to help by putting in a good word for Bobby with the local police chief. After learning that the Winchesters and Bobby were hunting an oni, though Roy still refused to help them directly, Roy told them what he knew about oni and previous activity 18 years before. Despite his aversion to hunting, after learning that hundreds of people were in danger, Roy unhesitatingly threw himself back in to help rather than continue to stay out of the matter. After being mortally wounded by Dalton Rourke, Roy told Dean to pass the message to Bobby that he should get out of the life and never unretire as it never ends well. Bobby later states a belief that despite his aversion to hunting, something would've drawn Roy back in if the oni hadn't because he wouldn't have been able to ignore people in danger.
- Despite being aware of obake and how they take on animal forms and sometimes protect humans, Roy was apparently unaware that his feral cat Shadow was an obake.
- Roy tells the Winchesters and Bobby that obake sometimes serve as protectors to humans. Given the obake that spent so much time around his cabin, it is likely that it was protecting Roy without him ever being aware of it.
- Roy's cabin featured outdated technology including a dial-up modem and basic cable rather than WiFi and more advanced cable options.
- Roy owned a police scanner he hadn't used in years. It aided the Winchesters in tracking the oni when the oni's presence disrupted their cell phone communications.