It's interesting how certain images or concepts can evoke strong feelings or memories, even if they don't seem inherently frightening to others! "Where's Waldo?" has a unique vibe because Waldo is often hidden in busy, chaotic scenes, which can create a sense of anxiety or tension as you search for him. The idea that he’s right there, almost watching you from the shadows before you find him, can definitely feel unsettling.
Many people have different reactions to characters or art styles that are meant to be whimsical or fun; personal experiences and interpretations play a big role in shaping those feelings. It's completely valid to feel that way—it can even make the search for Waldo feel like a more intense challenge! Do you have other examples of things that you find creepy?