Simon Kirby is a photographer for The Calvintown Gazette.
When he was around five, Simon's father left him. Some years later, his mother was arrested after stealing a cheap heater during winter, being sent to jail. Because of this, he and his friends began alternating sleeping between the woods and the house of Vi.
While hanging out and studying in Vi's house, Simon and his friends were interrupted by the arrival of Kelly and James Olsen, fleeing. Simon headed to a store, attempting to steal some tinned ravioli. The owner threatened to call the cops, but Kelly intervened, buying it for Simon. James promptly invited Simon to dinner at their house. While preparing dinner, Simon thanked them, and explained how the local prison had changed the dynamic around town. James went to investigate the situation, getting in contact with a lawyer to help Simon with his mother. Discovering that James wasn't going to stick around, Simon thanked the two of them and left. However, James later returned, buying The Calvintown Gazette. He took Simon on board as an amateur photographer.