What sets Stanley apart is he's the most scared of IT in general. He's also the only one who really, really does not want to do what they're doing. That's laced throughout the film, like when he's constantly not trying to go to Neibolt. He's the voice of reason who no one listens to. He's always trying to tell everyone, Hey, maybe we shouldn't do this because, you know, we could die? And everyone's like, No, we gotta do this! They kind of push him through, and bad things happen.
What does the woman in the painting represent for Stanley?
Oleff: I'm not 100% sure on where Andy got the concept for the painting, but he kinda masked it for me, which kind of made it more mysterious. During filming I didn't see the woman on the painting at all. It was just a blank canvas. So having no idea of what she was gonna look like kind of freaked me out. He hasn't really told me a lot of what it means, but I think it was from one of his own childhood fears. I think he had a fear of this painting, and he's kind of translating that into Stanley, because it's definitely something he would be afraid of. Just her, in general, is terrifying to him. And IT as a concept. Stanley wants everything in line, and IT just throws everything off track. That's why he's the most scared of IT: He doesn't know how to react to IT, he doesn't know how to handle IT.