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Man, I remember Grunty from Banjo-Kazooie...MAN!!! I hated her! Also whoever said Jack-In-The-Box from Donkey Kong 64 needs a friggin' medal. All of the Weapons in Final Fantasy 7 was hard for me, too. However, there's a game series that always had abunch of hard bosses: MegaMan! Robot Masters like QuickMan, PharoahMan, and CrashMan always gave me problems! Some were easy like ToadMan, but for the most part I'm guaranteed to lose at least one life to each Robot Master. I'm not even gonna get into the Dr. Wily bosses and such.
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