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When I first picked up Demon's Souls, was hyped as hell for it, looked awesome, liked the idea of the brutality of it, JRPG. Thought it was a good idea to pick the balanced character with the club and a crappy wooden board for a shield thinking it would allow me to best figure out what style I wanted to play (having heard that the lvlin system allowed that flexibility) spent the best part of 3 hours dieing on the bridge and going towards the two knights guarding the first fog gate, holy crap wanted to cry.

Old King Allant when first facing him.

In Darksouls the mutherfucking archers, holy crow, must have spent 5 hours trying to get past them untill I did, then about 2 hours later when I hit Fat boy and Slim T. T. Ng 4 kings and NG++ going (this is most recent) through Anor Londo with about 90mill souls dieing, and dieing again before I could get to them :'(

On Crushing mode in Uncharted 3, when Drake is tripping and there's the two inline rectangle waterfountains and you'r fighting the fire demon guys, holy crap.