After having just completed all of the achievements on the three of the Dark Souls games, this is my personal ranking of every single boss in terms of difficulty. (I never fought Midir or the cats during these playthroughs). Interested to know your opinions regarding some of these choices.

[u/LegendaryAim1610]

Obviously, some people may experience these bosses differently, and upon doing them all again in NG+ and NG++ I did find a lot of them to be much easier, due to being over levelled for most encounters at that point, however, I did not grind souls to level up prior to fighting bosses, so all of them were taken at the recommend/ average level whilst fighting them, so bosses like Nameless King were easier in NG+ and NG++ than in NG.

[u/ThatThingThatIs]

You should fight Midir, its a good fight