The Boss (real name unknown) was the supervisor of an office when a race of interdimensional beings began to tempt his employees into a portal to the Imaginary World of Trumbledon. He fought back, trying to keep his workers at work.
History[]
Boss was walking among the cubicles of the office checking on everyone while one of his employees was tempted by Chauncey. Boss didn't see this at the time, though if he had he would have fired the employee. That employee passed Chauncey to Marshall, who himself was tempted and went through the portal. (PCG Roundabout 1: "First Game")
Boss soon became aware of this happening to more employees, at the hands of more imaginary beings like Chauncey. He interfered, preventing an employee from leaving through a portal in a garbage can and took that can into his office. (PCG Roundabout 1: "Second Game")
Unfortunately, he accidentally fell into the portal once in his office. He arrived in a strange room in Trumbledon, populated by a Lid Guy as well as a number of spiders. He solved a puzzle there involving a light bulb, and got the light levels in the room just right. Lid Guy then said "Hey, ya did good" and used magical beams from his eyes to open a magical door back to the office. (PCG Roundabout 1: "Third Game")
When Chauncey and Moto again infiltrated the office, Boss captured them both, apparently killing Chauncey by nailing him to the wall and putting Moto in a cage. Moto tricked Boss into letting him out by offering to clean the floor; Boss did, and Moto soon released Chauncey who then created Plant. They knocked out Boss and escaped. (PCG Roundabout 1: "Fifth Game")
Vendetta[]
Boss became obsessed and pursued them back to Trumbledon after another wave of incursions. He did so by jumping in one of the portals after one of the beings. Over the next years, he put together a team of mercenaries, L and Skuz, with whom he traveled across Trumbledon, killing more of the interdimensional beings and keeping their heads.
Boss & team preparing to storm Marshall's celebration.
Finally they came upon a celebration of the anniversary of Marshall's arrival in Trumbledon, as he's since been crowned King. Chauncey and Moto were present, as well as Rogley. Boss approached them, leading Marshall to feel awkward, and tried to get Marshall back to work, but Marshall refused.
Saving Game to before he approached them, Boss tricked Chauncey into opening a portal back to the Office, by capturing Marshall, hiding him behind the boulder, and leaving a message with Rogley that they'd already escaped to the office. They jumped in after him. (PCG Roundabout 1: "Sixth Game")
Behind the screens[]
Despite being a minor character in his first appearance, First Game, he became a surprisingly major player throughout the rest of PCG Roundabout 1. He was the player character in three of the six games, and appears in some capacity in all but Third Game.
Although he was initially created by Xaq for First Game, he was subsequently fleshed out by Kurt Elfman and Keith Doomsday, as they created the games featuring him.