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.