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There is this main boss in Silent Hill 2, the Pyramid Head.
Legend has it that he was part of one of the prisons last taste of freedom, either to be hung or to be tortured to death by the Pyramid Head.

He appears throughout James' search, wielding at first the Great Knife(seen pictured left), and later a large javelin of sorts (seen pictured below).
There are also two small bosses you have to battle: Angelas "Father", the door man, and the hanging caged men in the hospital.
Both are not very easy to beat, and are good opponents.
The caged boss comes in a group of three to four, depending on the difficulty.
The door man is on it's own, but comes back in a weaker form in the Hotel.
This is Eddie, he's one I didn't originally concider to be a boss, but the battle between him and James is a major one.

Although James starts off as Eddies friend, James soon realises Eddie is a lot more disturbed than he likes to make out.
On several occasions he mentions murders, and a story of a dog he shot is brought up a few times.
This is the final boss, not much of a boss really. Easily beaten and weak attacks.
You can fight her as either Mary or Maria, depending on your ending. It's kind of like James realising what he has just gone through, and that is what determines who he battles.
Both women are exatly the same in this form.
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