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The most annoying boss in any video game you've played.
Nightmare from Monolith. It uses attacks that are irritating enough to dodge on their own, but then you add the big floating blocks drifting all over the place (which damage you on contact) and the name becomes apt. And that's only the first of three phases...
I've to dive deep in my annoying boss history for this.
But for one that stands out currently, it's Monster X and The Core in Cave Story+ Hardmode.
In Cave Story+ Hardmode, you don't get any health capsules, and the bosses mentioned above all spam projectiles that kills you in one hit. The bosses are also invincible most of the time. And if you die, you have to walk to the section again before meeting the boss. Also filled with enemies and traps that kills you in one hit.
Pthumerian Descendant From Bloodborne. Luckily Only Meet These Cheap s In The 2 Ihyll Chalice Dungeons, But Still. Extreme Range Attacks? Check. Nearly Undogdable Attacks? Check. Being Able To Completely Destroy Your Health Bar If You Get Within Striking Distance? Check. Why The Hell Does Blades Of Mercy Only Suck For Me?
Not quite the boss himself, but the entire level. The mission in Crimson Skies in which you have to find and shoot down Ulysses Boothe is easily the worst-designed and most annoying level in the entire game. Why? Well, let me explain:
It's one of the very few missions in the game that don't let you choose your aircraft. This is made even worse because you're given a stock Hoplite. For those who haven't played the game (Or even heard of it, considering that pretty much the only place you're likely to see it mentioned is in forum threads about weird airplanes), this means that you're stuck flying an autogyro that has the draw of being the most maneuvrable aircraft in the game, but has no other draws: It's slow, weakly armored, and weakly armed (To be fair, in order to get here, you have already had to deal with them as enemies in previous games, and they can be very frustrating to fight). You cannot even bring a custom one, so you're stuck with the very light armor, 2 .30 machine guns (Which deal little damage and rely on their fire rate to be effective) and only 2 hardpoints for rockets.
You're alone. In most missions, you have a wingman, and even in the ones in which you don't, you often have allies of some sort.
The mission is luck-based. It consists of passing through "Danger Zones" in order to find Boothe's hideout (At least doing this is what the Hoplite does best, due to it's slow speed and high maneuvrability). There's 5 possible hiding places, and the actual hideout is randomly chosen. Every time you fly through a Danger Zone, you get ambushed by two Black Hat fighters, talking about which...
Said fighters are Brigands. That particular aircraft model is already a bit of a Goddamned Bat, as it's a bit of a jack of all stats that tends to be on the "slow but powerful" side, which means that it can evade relatively easily (Althrough it's the least maneuvrable single-engines aircraft in the game) while still taking a decent amount of punishment because they have decent armor and have powerful weapons. That alone isn't the frustrating part, as getting to their tails isn't difficult because you're more agile and it's easy to take advantage of their higher speed in order to make them overshoot you. The problem with that particular plane is that it has a rear turret, which, on a default configuration (Which is what AI planes seem to normally be), also has 2 .30 MGs, so your maneuvrability is practically cancelled by this, unless you somehow can dodge enough hits (I finally figured out than an AP Rocket hit can strip off their armor, and the remaining health can be quickly cut down, but you can only carry 8 in total, and you have to fight some more Brigands along with the boss, so you have to hope you find him in 2 attempts or less).
What is even worse is that it's not like they had to give the Black Hats different planes just for this mission, as they also have Hoplites (In fact, Boothe flies one when you find him), which could have made sense and would have given them more use (The only other time in which they appear is in a later mission, and you have so many buddies in that one that you're likely to not even notice that they're in it).