1) Ursula from Kingdom Hearts (HD or otherwise)
Holy crap was this battle the worst! With her ability to shoot lasers out of the sky down at you while they follow (the first of what would later be many of this category of an attack for characters later in the game) but she also has this vacuums ability that was simply her breathing it. The only way to beat the vacuums was to swim the hell away (and pray that the lasers wouldn’t start shooting) because if you don’t she will chomp down on you and take a crap ton of your health. Add on that this is the first real boss battle that involves three health bar stacks (previously the highest being two up to this point) and you better hope you leveled up properly before starting this battle. I could also add on several other Kingdom Hearts bosses that were particularly hard to tackle, but I’ll just add one more with…
2) Chernabog While also being one of the coolest boss battles of the game, Cherabog is also very difficult. This is because you have to fly to fight him. If you weren’t so great at flying in Neverland when you fought Hook or The Phantom (and the latter boss should defiantly be considered on this list) then you are going to have issues at first getting used to flying again. Remember those lasers that shot from Ursula before? Well they are back and they come in different patterns this time around. In fact, Chernabog fights with several other types of long range attacks that are meant to keep you away from him. And they hit veeeeerrry hard. To do damage, you have to fly right up to him and crack him over the head as much as you can before he blows the mountain he’s sitting. If you get hit, your down to half your life or more. And he’s got some of the highest health in the game…all that being said, he’s sadly also the most underwhelming boss. Here we are, the second to last boss battle (which, oh by the way, this is Disney’s version of THE DEVIL) and…he doesn’t say anything, doesn’t really do much of anything other then plug up the hole you need to get to Ansem and thats it. No dead being raised like in Fantasia and no other reason for him being their then just because it would look cool in the game (and it does). So all in all, the major factor here is that he’s difficult but unnecessary. Hell, the game guide describes him as this all powerful being that lives in the darkness (possibly a heartless even) but ends up being a pushover if your are leveled right.
I’m thinking I’ll come back and add more to the list later when I can think of them also, this is a really fun idea!