The most annoying boss in any video game you've played.

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although, its probably Soul of Cinder from Dark Soul III. Who thought of that. "Oh I can't think of a new boss." "Why don't we just make Gwyn again?" "Yyyyyyyeah!"
 
Watchdog of the Old Lords in Defiled Chalice, one of if not the most difficult boss in all of main-game Bloodborne.
 
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