Roy grew up in the 1800s to a largely military family, his father fighting in the Civil War for the Confederacy, Roy later going on to be drafted into the Army for World War I, spending a lot of time in Germany, however as a prisoner of war, rather than a hero, where he was horrifically tortured. His snarky personality doing him no good. He never talks about this time in his life, despite wearing the damage ever so clearly. To make up for his failure, he took on the role of an Historian, keeping his father's legacy alive, in an attempt to forget about his embarrassments, his family's military line ending with him.

After his father passed away, Roy inherited the Greyson family farm, which he takes care of with Shirley down in Alabama, the heart of Dixie. Here he became a Civil War reenactor, forming a close group of trouble making- atrocious friends that he attends several reenacting events with. The group very well known, almost getting arrested quite a few times, but Roy easily helping them escape.

Although one night after a gathering with his pals, a wondering prostitute tried getting in with Roy and his friends, flirting with Greyson, his buddies cheering the woman on. Until he was caught in a corner he couldn't get out of, pulling a knife out on the woman, stabbing her to death.  His friends of course helped him hide the body, by Roy dismembering it himself, scattering the missing body parts in various locations across the Alabama River, never to be spoken of again, Roy's victim forgotten forever. This event only made Roy's group closer, him making them swear to protect his wife, them soon becoming "under cover" body guards for the Greyson family and their infant daughter, Oleanna, called "Ole." Who he subconsciously named after the woman he murdered. 

As Roy grew near to his dying age, his closest friend could no longer bare the guilt of what he witnessed, going on to write a book about the murder of that woman, becoming a famous author, however doing time for aiding and covering up a killing. The book became so popular, that it launched a warrant into Roy's arrest. After reading the book's entirety himself, Roy ended up going back to the same river, ending his own life with a bullet to the head before police could arrest him, knowing what his sentence would be, unwilling to accept his fate and greatest fear of Yellow Mama.

The murder weapon used to kill the prostitute was displayed in a crime museum, after Roy's daughter found it again, when the book was released, remembering he told her where it was when she was a young child. The knife and other artifacts hidden under the floorboards in Oleanna's room of all places, kept in a safe only she knew about. Which also contained a map of where body parts were dropped, including the woman's ID. However, every limb was long gone since the incident, except a severed skull found by a boy playing in the river.

An aggressive, greedy, and irascible man. He isn't the wisest in the world and often goes with his gut rather than his brain. A very quick thinker, clashing with quick reactions. He can be selfish, despite claiming he doesn't mean to be. Although he's extremely loyal and loving to his wife, Shirley Greyson, the one he always puts first. Everything he does is for her, even if it may seem like the opposite or something completely insane. In recent years, he's protective of his daughter as any father would be, however, entrusted her with his deepest, most darkest secrets, unintentionally harming his own child, along with her security in her family, plus her sanity.