Dragonslayer from gameboy. I don't know how to start that game
Back in the day on the original xbox there was a game called kill.switch. That game was pretty hard but unlike many shooting games it had a boss battle like an RPG would have.
The final boss was insane I legit quit and came back to it years later and finally beat the boss. Also the storyline was like so patchwork and incomplete. Part by design as you played through you regained memories but even when completed it was like whuuuuu....
Danganronpa, is a really great game. But within it is a mini game called bullet time battle. Something so terrible that it nearly made me drop the game itself. Literally the most frustrating thing I ever played.
probz gonna sound pathetic, but as iv played very few video games id have to say borderlands three
the fight with the yeti thing and fighting the psychos was annoying. first person hurts my eyes
as far as boss battles on games i really enjoy, i died 20+ times on the belial fight in diablo 3
having to use point and click movements with that aoe was HORRIFIC
i finished diablo on like, 5 deaths in comparison
as far as wow, the worst boss fight iv ever done that wasnt a legacy raid (as i was a mop baby) is probz one of the current expansion raids
g'huun is an annoying fight because of the orbs, and Uunat is extremely overtunes (but that is kinda fun, playing against a really hard boss) only annoying part is when people leave the raid after a certain number of wipes, and then you have to call it early without a kill ._.
legacy wise spine of deathwing is the obvious winner for most annoying boss mechanics and immersion because that fight takes fuckin forever (and unfortunately i do that raid nearly every week for those sweet sweet tusk shoulders)
probably lol, when bad players start the blame game and there's no hope of winning.
Its a toss up between league's bad balancing and overwatch's bad player base.
Sometimes you think you are doing well and then the game likes to remind you that you have no power there.
Even the original Ninja Gaiden was more fair than Battletoads.
Battletoads seems like it was designed to be purely frustrating...
And I'm going to stop before I get into a huge rant...
Chakan: The Forever Man.
Oh, all those sega genesis controllers that I have thrown across the room in the day.
Also Mario Party.