According to the Bo Schitt Blog's cast of characters, Chuckles the Cheat (Charles Olsen) worked extensively in programming before the Combine invasion of Earth. As a method of coping for grief he experienced after the Combine takeover, Chuckles learned to alter reality with a simple cell phone. This enables him to use video game cheats in real life, such as Aimbot and Noclip. It is unknown what happens if his phone is destroyed while he is hacking the world around him or himself. Thus hacking has corrupted him.
Chuckles is first seen in an office with a bunch of other Half Life 2 characters (Alyx, Grigori, ect.) playing a LAN match of Counter-Strike. He dominates everyone in the game, secretly using cheats, which brings much irritation to the other players, especially Grigori who destroys everything in his work space. It is only until Dr. Hax realizes the situation and takes action by knocking him out with a computer monitor. Chuckles wakes up hours later in a car attached to a huge catapult which launches him into a deep pit where he is tormented by Über Kleiner.
He apparently escaped only to get stuck in an elevator to his office and spent long, agonizing hours there with no help. It was only until he used noclip to escape through the walls and to his office only to be attacked by Dr. Hax, again. After being knocked out by two computer monitors, he wakes up to find himself imprisoned in the pit once again and is further tormented by "the most annoying sound in the world". This, however, turns out to be a dream and he wakes up in Dr. Kleiner's lab supposedly being revived from his nightmare.
Two weeks after the incident, Chuckles locks himself in his house and deletes his hacking documents stating that he is "better safe than sorry". In the following week, he became mad as he could no longer win in a Counter-Strike match. After his final game, he is surprised by a hunter but manages to noclip before it could pounce him. Soon after, while "flying", Dr. Hax is seen chasing close behind him. After this, he went about pulling harmless pranks which turn into horrible accidents and cost lives.
- He uses the male_04 Citizen model, which uses the face texture of Eric Kirchmer.