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Most frustrating/annoying boss?

I would count it. Only other songs that I felt were really difficult were those from Guitar Hero 1 since the HO/PO was still rather picky about if it worked or not.

It's not that it was picky, it was that it worked completely differently. There's a reason one of the loading messages in Guitar Hero II said something along the lines of "We promise that HOPOs work in this one. Honestly."

It's why things like Bark at the Moon and Trippolette are not as feared as they were before.
 
Nihilego-Lusamine's Cleffable

That thing is bulkier than competitive Chansey coupled with the ability that prevents poisoning. So I couldn't just have my Salazzle use Toxic on it for it to eventually go down.
 
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Bed of Chaos, Dark Souls. It's a non-optional endgame boss that takes everything the game has taught you about bosses up to that point - stamina management, reading and reacting to attacks, patience in learning the moveset - and burns it in a big, chaosy fire, replacing it with god-awful platforming of all things, in a game which usually takes perverse pleasure in making you a fat, ponderous bucket of meat with the jumping ability of a legless sloth. Dark Souls' reputation for being a game of two very distinct halves is well-deserved.
 
He's been mentioned before, but it bears repeating: Xaldin in Kingdom Hearts 2 is the devil incarnate. Mainly because of his wind shield mechanic, that protects him from all damage and causes any contact with him to damage you. This turns the strategy that the game has trained you into "whack the bad guy when he's wide open after an attack" into something actively harmful to your progress. The only way to drop his shield and make him vulnerable is to trigger a reaction command that makes your next attack break through. It's only one extra step, but it's enough to throw your entire balance out of whack. You spend half the time fighting Xaldin and half the time fighting your own muscle memory.

One boss that I haven't seen mentioned so far is Sho Minamimoto in The World Ends With You. Most of the fight is fine, but once he enters his Noise form and heads to the top screen, his attack patterns are so hectic that it's hard to land more than one or two hits in Joshua's combo. Add on the fact that Josh is the only one doing damage in the latter half of the fight, and you can put two and two together to see how annoying the fight can be.
 
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The Hanged Man from Hyper Light Drifter is perhaps one of the most difficult and frustrating boss I've fought in a game (I think the Moon Lord from Terraria is perhaps the most difficult; I could never defeat it alone).

Incredibly fast, strong, summons allies (though you can prevent this), and can knock down the player. He was the first boss I fought, and in my first fight he killed me within, like, five seconds of the start of the boss fight. I ultimately gave up after a few more tries (with him beating me within 5-30 seconds every time), and fought the other two main bosses before going back to him. Even with all the new upgrades to my character, it took me many, many tries to finally defeat him.
 
He's been mentioned before, but it bears repeating: Xaldin in Kingdom Hearts 2 is the devil incarnate. Mainly because of his wind shield mechanic, that protects him from all damage and causes any contact with him to damage you. This turns the strategy that the game has trained you into "whack the bad guy when he's wide open after an attack" into something actively harmful to your progress. The only way to drop his shield and make him vulnerable is to trigger a reaction command that makes your next attack break through. It's only one extra step, but it's enough to throw your entire balance out of whack. You spend half the time fighting Xaldin and half the time fighting your own muscle memory.
I do remember that fight. I feel you on that. There is also Xigbar from the same game. Dude was a massive pain to fight. One thing I HATE is teleport spam. It's just ridiculous.
 
The last level of Kirby star allies is a weird boss rush.. sort of? It goes
Hyness, Hyness again in a different form, Void, Void again in a different form, Void again in a different form, Void again in a different form, Void again in a different form, and finally Void again in a different form (I think...). Yup. You fight once boss twice in one level, and another boss 6 times in 1 level. Also, in the Hyness battles, (he? she?) uses one of your most powerful attacks which is really hard to dodge. Not annoying, just long and hard.

Also Ganon in Smash Ultimate. You have to go all the way around to hit the tail, and if your character doesn't have a good recovery, that can be really hard. When you finally get behind Ganon, there are certain attacks he uses to spin and turn the other direction, towards you. I'm pretty good at smash bros, so it isn't too hard for me, but if you don't know how to dodge and shield Ganon's attacks, it can be really hard.
 
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Kid Icarus Uprising is one of my favorite games, but it has its share of annoying enemies. The entirety of "Chapter 23: Lord of the Underworld" is a grueling circuit of difficult monsters, but the boss Hades's Heart is by far the most challenging and obnoxious enemy in the entire game in my opinion.
 
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