Dark Gaia in Illusion of Time. Only ever beaten it once
Raven King in Heavenly Sword mainly because his wings get in the way so you cant see what attacks he is doing and switch your stance accordingly. Nailed him in the end though.
Super Macho Man in Punchout. I could never get passed him, funnily enough on Super Punchout I handed his ass to him on a plate every time.
The Nephrack in Hunter the Reckoning: Wayward. Probably the hardest boss I've ever fought - massive health, if you shoot it, it hurts you instead, spawns loads of enemies, has attacks that damage both your health and spirit severely. Never beaten it.
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