He made his first appearance in Diner Dash Hometown Hero. He is an extremely high tipper, but is impatient. He hates noise to the point that it will reduce his happiness by one half of a heart. If customers are seated near him, they will get starstruck and become happier.
He also made appearances other games such as Avenue Flo Special Delivery, Soap Opera Dash, DinerTown Detective Agency and the Cooking Dash series (specifically DinerTown Studios and Thrills and Spills).
In the Cooking Dash games, most customers will want to take a picture with him. Taking a successful photo will improve both Simon and the customer's moods.
Not much is known about Simon's history, but he started out as a regular person and really followed up with his dreams into becoming a big star.
Simon wears fancy clothes and has his hair styled in an afro. He's always shown wearing sunglasses, giving him his trademark celebrity look. Underneath these glasses are simple black pupils, but in later installments such as the Cooking Dash series he gains blue eyes. In Cooking Dash 3, Simon's hair is styled in a poofy mullet and he wears a blue t-shirt with white, blue, and orange splats. He's also got a gold chain around his neck, jeans with a brown belt, and checkered shoes.
Though Simon can sometimes come across as a bit high maintenance, he is a positive presence and is well liked. He enjoys charming fans with his dazzling smile. However he's prone to major meltdowns, so it is important to keep the celebrity happy. He can also be a bit of a player, as shown in Soap Opera Dash where he often brings dates.