The original concept for Pajama Sam was a character known as "Pumpkin Head Boy" who, fittingly, had a pumpkin for a head. This was scrapped as it was believed that Pumpkin Head Boy games would only be able to move units during Halloween, despite the game not being envisioned as a seasonal title. This is referenced in Pajama Sam: No Need to Hide When It's Dark Outside, with Sam reading a book titled Pumpkinhead Boy: A Brief Tragedy about a boy with a pumpkin on his head removing his pumpkin due to concerns of seasonality. Notably, the story in the game alludes to a "lawsuit by that big guy in Atlanta". It is unknown if that is a non-sequitur or another part of the real-world Pumpkin Head Boy story that has not yet surfaced. Later, in Pajama Sam 3: You Are What You Eat From Your Head to Your Feet, Sam would wear a pumpkin on his head as a disguise at one point in the game.