PS3: Demon's Souls definitely takes the cake for hardest boss fights, but I never really had A LOT of trouble with any of them...I think I died the most on Flamelurker trying to take him on by myself, without any ranged attacks...not the best idea, but take it from me, it's possible.
All-Time is much harder to remember, but I'll do my best:
Emerald and Ruby Weapon, without KOTR or Mime.
The Fear from MGS3. It took me forever to defeat him using only tranquilizers on the hardest difficulty. That frustrated me to no end, but was extremely satisfying.
Multiple bosses from Turok 2. When I was playing that as a 12 year old it was hard as hell.
....and that's all I can think of for now. Never really had a problem with bosses.
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