I think probably Clotho in God of War 2.
Gaping Dragon from Dark Souls
That was cool not disgusting.
On-topic: Probably Succubus from DmC
The Dead Hand guy in Ocarina of Time, think he gets my vote just for the context of that game, he's like something out of Silent Hill thrown into an otherwise kid friendly game
In a most disturbing sense...
Silent Hill 2 - Mary
In more obscene sense...
House of the Dead Overkill - Sindy & Coco
Dante's Inferno - Cleopatra
If you have never seen the Cleopatra boss you should check it out on youtube to get the full effect, it's quite disturbing.
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