Split Head wrote:
In Origins the painting was likely there as an Easter Egg for fans, but it could also have implications of PH's history with the town itself as well. That's the way I look at it.
Same. People have theorized that James went to the Historical Society when visiting Silent Hill with his wife, and saw the painting "Misty day, remains of the Judgment", which may or may not have looked exactly as it does in when seeing it again in the game. Still, if the painting was there and the "judge" resembled what James later sees as his own personal demon, Pyramid Head, then you can make a case as to why Pyramid Head can show up in other games.
In fact, one of the things I used to tell myself to personally feel better about P-Head being included in Silent Hill: Homecoming was that maybe people are more likely to see him in Silent Hill if their baggage/past crimes involve murder in some way, especially if they feel guilty about it and wish for punishment. (Of course we all know the real reason that P-Head is in SH:H is not that deep lol)