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I haven't played MM8 in a while, but I remember the fortress bosses there being super annoying the last time I played. That accursed bag worm thing particularly comes to mind.
MM1: CWU-01P (Dodging the thing is rather difficult, ESPECIALLY when/if there are no Super Arm blocks to stand on. Also, if you die AFTER using the Super Arm blocks, you're pretty much screwed, as the final few ones go so fast you can only get, like, ONE Mega Buster shot at it until it moves away.
CWU-01P is particularly nasty in Powered Up, where it also has a laser and drops Super Arm blocks from the ceiling. There's also much less room to navigate.And if you're playing as Fire Man...
I thought the twin devil in 9 was harder than the wilysaurus. If you don't know to stand right in the center it becomes insanely hard to dodge things coming from both sides at once.
Any boss with the word "devil" in it is hard