I don't actually know of many super difficult bosses. I don't find most of the bosses in Bloodborne/Dark Souls all that hard, just a matter of not being an impatient twat. Take your time, pick your attacks, and don't get greedy. The enemies WILL open up for an attack.
That said, I agree with OP. Probably the hardest boss in that game was Defiled Watchdog, simply because you had half health, and a single mistake could result in your instant death. Plus, his attacks were super hard to dodge, he was hard to parry (if at all, I never was able to do it), and many of his attacks had additional flame damage.
The hardest boss I've fought recently, however, would have to be the Nameless King. Dark Souls III. In retrospect, really not THAT difficult, but when I was still learning how to fight him, I found he hit like a tank to the point where any one hit would take 2/3-3/4 of my health, had physical and magic damage, was hard as hell to see/fight, many of his attacks had weird delays that made them hard to dodge, he was flying around on a dragon so he didn't open up for attacks often, he sometimes did this fire-fall attack that, if it hit you, was an instant attack, and the arena was on a shifting cloud so I found it hard to judge how far away he was when I went to attack, resulting in MANY untimely wasted attacks.
And hat was just form 1. Once you kill his dragon you fight the Nameless King himself, which is even harder. He's faster, has a more varied attack pool, twice as much health, even trickier attack delays, and combos that mix up horizontal with vertical attacks, so dodging to the side or back isn't good enough unless you know exactly what variation of the combo he's doing. Hits even harder, doesn't give you time to heal, and has a massive health pool.
Probably the one boss that vexed me the most of the last six months. Even then it only took about 20 tries. Beat it the first day I attempted it. or was it day two? I think it was day two, I GOT to the nameless king at like 2AM, tried him once, said fuck it and tried again the next day.beat him after only a couple hours worth of attempts. .
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