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in all seriousness, it was ornstein and smough when i first started out, since then every other boss has been quite easy
Oh, uh *ahem* I mean, Soldier of Godrick
I don't know if it strictly counts as a "boss", but I stumbled upon its cave early on and stubbornly just kept at it with krap gear wondering what in the heck it was guarding only to get destroyed each time...too many deaths to count.
I still struggle occasionally but I wouldn't classify a lot of bosses as my hardest. No Halflight, Spear of the Church became my hardest in DS3 because, if it became a Player Controlled Entity, and I admit; I suck at PVP.
No opinion on DS2 xD
If we were to count game mechanics, the hardest boss that I have fought in a From Software game is the steady life drain in Otogi 2. I never did get Raikou out of the underworld when he is isolated from the team in one portion of the game.
I could flawless victory Midir right now and I havent fought him since DS3 servers went down initially (before being fixed) - he might be my favorite boss fight of all time, but I do love the Radagon fight as well - Elden Beast is meh - but I love fighting Radagon.
Second up would probs be Demon of Hatred
For reference I got Isshin in an hour on my first try
I was slightly burning out and ended up running through a lot of DS3 using my Slumbering Dragoncrest Ring and Hidden Body sorcery.
I remember having difficulty with the Nameless King.
Rather than take the time to learn the dance, I ended up just defeating him with Sunlight Spear in phase 1 and Dorhys' Gnawing in phase 2.
I keep meaning to go back to play DS3, but I get so bored in the beginning of the game. ;)
So I'm just going to say 'Nameless King' as I never felt like I properly defeated him.
Also I didn't fight any of the DLC bosses in DS3.