Dark Souls 1 and it was Chaos Witch Quelaag. I don’t know how many times she killed me, but it has to have been over 20. I got destroyed over and over again.

In dark souls 2 the pursuer killed me so many times I almost quit. I don’t know what it was about that fight but I could not beat the fella.

Also in dark souls 1 I got killed by Havel the rock so many times and once I killed him and found his armour it held a special place in my heart. I’d try to wear as much of it as I could without fat rolling. Which usually left me wearing no ar in some slots.

Haven’t yet beaten Malenia. Not even close. Just a lot of bullshit mechanics i can’t deal with.

Also on Crystal Sage: I found it funny how he was an absolute pushover for my first character (melee build) and a pretty hard challenge for my second (magic)

The first Headless I encountered in Sekiro. I was seeing enough progress and understanding what was being asked of me just enough to be stubborn as hell and kept trying to fight it head on, without having any knowledge yet of any helpful items that make the fight less rage-enducing.

Outside of Fromsoft, my NG+ encounter with the green swamp monster thing in Lies of P seemed SO much harder than the first time. So I’m not sure if this boss is considered easy or hard, but I didn’t consider it to be very hard going in for a second time and got quite stuck for a while…

The second phase of the final boss in Elden Ring.

Not because of the actual fight.

But I struggled the whole game with the extremely narrow FOV and motion sickness from that, and during the final boss, the FOV was actually too small to fit the entire boss during its animations or look at it when it rises (I think they later extended the camera max motion upwards in a patch?), and that excaberated the issue massively. And beating that boss while feeling semi-sick constantly was just not a nice experience. :(