GUARDIAN APE (SEKIRO: SHADOWS DIE TWICE)
Pure nightmare fuel. In terms of pure mechanical difficulty, there are certainly harder bosses than the Guardian Ape in Sekiro (though not many), but the combination of its design, its moves, and the fact that its a literal monkey makes it shockingly tough. It’s a literal poop flinging monkey with literal poisonous farts, not to mention that fact that it can leap at you from like a gazillion feet away. After you cut off its head and revel in your hard-fought victory, it even comes back to fight you without a head (but with a sword), to really drive your frustration up a wall.
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