Second battle with Vergil in DMC 3, Agni & Rudra in DMC 3 and somehow not as hard to beat but incredibly hard to beat well is the Shadow, Griffon & Nightmare battle from DMC5. Beating it on the DMD difficulty gave me that game """PTSD""" where Stage 18 became "that level" to me haha.
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Gow Ragnarok. That last Valkyrie.
That stupid course in Star Wars Racer where you have to stay on a very narrow ledge. When you fall off you're relegated to a super long detour and basically have to start over because you have no chance of winning if you fail even once.
First time fighting Lothric/Lorian in Dark Souls 3. I was playing a mage which was not it for the fight. Also the runback was about a minute which really ramped up my hatred for the fight. On ng+ after a respec to greatsword wielder, that fight is painfully easy. Greatsword effortlessly hits Lothric's hitbox while he's on Lorian's back which trivializes it, but I didn't know that on first playthrough.
There's a lift right at the side of the main entrance into the bossfight arena that cut down the runback time. You can just rest at the dragonslayer armour and then take the lift up right to the entrance, skipping the annoying stairs of enemies.
The snake boss in Nioh 2. My friend kept coming back that day to say, "You haven't killed it yet?!"
Well, I've never beat Sans from Undertale, but if we're only counting those we did beat... Maybe it's Undyne the Undying from the same game. I'm deducing that from the time it took me, but to be honest there's a boss from another game that came to my mind first. See, neither of these bosses feel "unfairly" hard because you have to go out of your way to pick the hardest route to face them. There was one boss whose hardness seems unfair and bad, that was the third boss from the first Spectrobe game. This was really out of nowhere. The first boss took me a few tries because I wasn't used to he game mecanics yet, the second was easy, but the third? I had to look up strategies online, make dozens of trips between my ship and the bosse's location, fighting every mob on the way each time to level my spectrobes up in addition to digging up minerocs to feed them; got them from adult to evolved and finally then I could beat it. After this fight, my spectrobes honestly felt overleveled and every enemy from then on felt super easy.
Worst part is, the plot didn't even justify this boss to be so hard. It didn't make it feel important. It wasn't directly threatening a populated planet, it wasn't anounced before it appeared, it was just there, in the middle of the jungle. And your mission was to find a diamond. Not an important and powerful item that's key to saving the galaxy mind you, a dumb simple diamond, of which the only purpose is to be expensive. So why would you, Rallen, of the Nanairo cosmic patrol; charged with protecting the whole solar system, go look for it? Because some rich bastard has crucial information about the krawls and you need this information to go on, but he won't tell you unless you give him this diamond. BITCH, if there was any logic to the plot, I'd be pointing my canon beam at his head and screaming at him to tell me all he knows or else! How dare a human withhold info necessary to save humanity?
Oh, and if this diamond has no particular power, why is a powerful krawl guarding it? It's not! It's just standing on top of it by shear luck, because fuck you.
Hmm. Not sure. Some bosses that immediately came to mind were O&S in Dark Souls 1 and Hume in Eternal Daughter though. I think I had more trouble with the latter, but it's been so long that I'm not sure.
Dry'l in Wonderlands. Not particularly hard but it just took forever.
Growing up I struggled for so long on LittleBigPlanet’s Negativitron boss fight, most recently though I spent days struggling with Uncharted 4’s final boss fight (though somehow I had an easier time on Crushing difficulty on my second play through) and Halo 2’s Prophet Boss Fight.
The Lindwurm in Battle Brothers.