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Bobby
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dum dum

When I first played the game the creepy, seemingly inanimate and permanent smile on Bobby's lips gave me the impression that he was indeed wearing a mask (a bit like the Toy Man villain from the Superman animated series) :
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Upon playing more of the game and eventually reaching the climactic ending in the clock tower I noticed that Bobby's facial features actually do change as he is clearly in pain and frowning when the clock bells go off, when he is attacked by the crows et cetera.

So I vote that he is indeed deformed, likely since birth or through thorough child abuse and bad hygiene around the house.
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Bobby's face, is it real or is it a mask? · Clock Tower (~The First Fear~)