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You don't need to choose multiples, one will suffice but I'm going to list three. 

1. Bed of Chaos - Dark Souls Little needs to be said. Worst designed boss in a good game ever. You throw yourself at the screen praying you'll do what needs to be done without being sent to the void by spasmodic tree branches. And you'll do it because the game was good up until this point. Sadly the game goes down hill, it's already gone down hill and you just didn't notice. 

2. Folding screen monkies - Sekiro You can't even call it a battle, you chase monkies and kill them as all they can do is lightly cloak themselves but leave a trail of smoke to indicate exactly what route they took through the arena and they are quick little buggers. Frustrating, pointless and zero fun. 

3. Lady Osakabe - Nioh 2 A boss that requires a summons, some say it's very doable solo but I can't see it unless you use ranged attacks adn they're limited in the game so you'd need to really overlevel. You have two tentacles on either side of the arena that shoot ranged attacks, to fight one you have to turn your back to the other and there is no audio cues to help you out. No cue at all. This combined with the games dark realm phase mechanic where you get stripped of stanima regeneration make one of the most awkward, frustrating fight to take on solo. You better hope someone is online to help you through this or you're gonna feel intense pain. Quite possibly the most RNG luck based fight there is. 

Last edited by LegitHyperbole - on 08 September 2024