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Finishing a 'S Rank, No Heal' run of Malicious was quite hard, especially the final boss.
Colossus #3 Hard Time Attack from Shadow of the Colossus was a slight headache for a few hours too...but the game itself was fun to play.
I'm going to attempt Muramasa Rebirth/Metal Gear Rising/Catherine some time soon, to see what all the fuss is about (difficulty wise that is, I can already tell they're great games that will appeal to me).
GT: Exiled Irenicus PSN: EnviableKira "People look stupid when they cry" - Frank.
I think that Dynasty Warriors 3: Xtreme Legends on very hard mode to get the 5th level weapons. Pretty much every character will get destroyed in this mode. Thankfully, you could do it two player split-screen. The character you wanted to get the weapon for you would move to a safe location. There was only one or maybe even two characters who you could use to fulfil the conditions to get the weapon. All other difficulties on that game were easy though.
Not taking difficulty levels into the question I don't know.
The fine line between honour and vengeance will be crossed by one.