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The Dark Aeons and Penance weren't tough, the preparation for them just took ages. The only one which was vaguely challenging was having to fight the three Dark Magus sisters together, especially as I was stuck with only 2 characters for nearly all of the battle. Penance himself was just a test of concentration....

I never even tried Sephiroth in Kingdom Hearts, I knew he was too hard

The hardest boss of this generation I can think of is General RAAM from Gears of War 1