That One Level/Boss

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Ornstein and Smough.
Sans.

OKAY I've freaking got some:

Mario Maker, the "official" level set (not the 10-mario challenge ones), ANY of the Bowser levels. Any of them.

I'll just put it this way: the next time someone I know starts going on about how Nintendo ONLY ever makes "casual" stuff, I'm going to sit them down in front of that, and force them to play those until they either A: beat one of them, or B: start crying blood. Either way, they wont say that too much anymore.

Lego Star Wars: The Complete Saga level Death Vader. Fast-paced jumping and if you miss you have to start over. I really hate those kinds of levels

I struggled with Totem Lurantis in Lush Jungle, Pokemon Sun and Moon. Despite using Flying and Fire Pokemon that were some levels higher than Totem Lurantis, this strong Pokemon with its Synthesis nearly beat me.

^Oh my goodness, that darned Synthesis! Totem Mimikyu took two tries, and the second time it was only thanks to my Pikachu and a hefty amount of luck that I was able to lower its Attack completely, and even then I still had to finish off the Haunter and Gengar before I defeated the Mimikyu.

Boss: Arietta, a giant Liger, and a giant bird-thing
Game: Tales of The Abyss
Reason: You have to fight all three of them at once. Arietta is a powerful spellcaster, with the result that if she is able to cast defensive and offensive buffing spells, most attacks will just end up being scratch damage.

That final bloody boss in the Brutal Doom Hell On Earth Starter Pack (20b)! I managed to 'beat' it, but only by saving my game 18 times in the process. I've seen a couple of YouTube clips in which players drift casually around the arena without attracting much attention from the numerous (or on these occasions not so numerous) monsters spawned by this boss, and who apparently never get caught by the huge rolling walls of fire he breathes out, but I'm more than a little sceptical about some of this. More representative perhaps was the Youtuber who awarded himself 10,000 health points via the in-game console, and still lost most of them before the end of the contest....

I recall also beating D'Sparil at the end of Heretic, playing on the highest difficulty level, and that it took about 20 minutes of continuous play.

Just to prove that I'm not a hopeless case as a gamer, I did complete the final level of Brutal Doom 64 on my first attempt, and somehow did it without losing a single health or armour point.

Kintaro, Mortal Kombat II. I would throw myself at him for hours on end and he would just beat the s**t out of me for hours on end. I did occasionally beat him though. I had nowhere near as much trouble with Shao Khan.

Any of the Raid Bosses in Borderlands games.

That bloody stupid dragon from Dark Souls 2. It's the one boss that I haven't beaten in a Souls game (sans Souls 3 DLC which I haven't yet played), and probably never will, because it is absolute nonsense. He has like, a bajillion HP and attacks which affect a wide area and can straight up kill you immediately. There are some cheese strategies to make it more tolerable, but honestly, I have no patience for it either way.

Jedah from Darkstalkers. That is all.