Finished Bloodborne DLC last night - amazing game.
Just spoiled things a bit by doing too many chalice dungeons, so had a brute of a weapon that just steam-rollered everything (gemmed out whirligig saw). The Orphan of Kos is meant to be the hardest boss in all of Souls and I walloped him second go - Midir in Dark Souls 3 must have taken me 100 tries.
The Twin Princes in DS3 were my hardest in the series I think. It's weird because I can do it first time now, once I beat it a mental block went away.
Dancer same story from the same game, and Pontiff. Ornstein and Smough were nightmarish for me in DS1 too.
Ever played Dark Souls II?
Never play Dark Souls II.
I detest that game with every bit of my being.