I don't really care about difficulty because I don't play games much. Just Train Simulators (Yes, I'm that sad) and I usually put that on normal and let the AI do my work for me.
Only games that I recall that I set out to best on Hard are Silent Hill 1 2 3. Other then that Im a pretty simple gamer. Usually just play normal.
i always have my first play through on medium difficulty so that it's hard enough to make the game a challenge but easy enough to give me a chance to get to know the plot... after finishing it the first time I'll play it on the hardest difficulty. also what's the most difficult game anyone has played? i'd go for bioshock on elite mode which would be pretty much unplayable if it wasn't for unlimited saves
I almost never play on hard, I just keep it on normal/medium. Dark Souls is the only game that doesn't piss me off when i die lol, strange kind of enjoyment >.<