Hurry up and spin me!
— Roulette Boy, when it's someone's turn to spin in Hell's Roulette

Roulette Boy is a boy with a roulette wheel on his head. He likes to wander down the hallways crying "Spin Me, Spin Me!"

Appearance in Gregory Horror ShowEdit

Roulette Boy appears in the first season and Last Train. In the first season, the First Guest and Gregory play a board game with him that probably served as the inspiration for Hell's Roulette; many spaces held dangerous hazards such as an explosion and a heavy weight. In Last Train, he turns the whole rail-line into a board game with Gregory spinning (and the Prompters assisting); obstacles in this game included a huge flood of water and a gigantic rolling boulder.

Appearance in Gregory Horror Show: Soul CollectorEdit

You get the soul Roulette Boy is holding by winning a game of Hell's Roulette. In order to first play the game, you must obtain the Dice from one of the hallways in Basement Level 3 and approach him when it is your active Key Item. After that, you can play again by talking to him whenever he's in a roulette room.

He also owns the three roulette rooms on the three basement floors. The only times he comes up from the basements is to play with My Son and Mummy Dog in the Courtyard or eat. When Roulette Boy gets stressed, he likes to unwind in the sanctuary of his roulette rooms and have a quick game of Hell's Roulette. Winning one game of Hell's Roulette will guarantee a place in the player's pocket for Roulette Boy's soul.

Appearance in Gregory Horror Show: Another World Edit

Roulette Boy appears in Chapter 9, "Roulette Boy".