The game I had the hardest time clearing as a kid (and I eventually went back and beat) was Shadowgate for the NES. That game will not only kick ur ass, it will feed it to a mutated dog, throw it down a well, let you wander through deathing darkness, strike you with lightening, and about a billion other random things that results in ur heroes death.
It's a point and click mystery game and you'll pick up about 100 items and use only 25 or so. With a walkthrough, the game is about 30 minutes long. Without one, you'll be using every item on everything you can "touch" or "open" or "take". Either ur right or your dead.
Some of the challenges are jsut ridcuolous. Like use vial 3 to float. well how was I suppose to knwo that til that one room I needed it? There's no label or anything like that! and you game me 8 vials with no indication what room or situation I'd need ANY of them in.
Fun but frustrating game. Way too scary for an 8 year old. The grimm reaper you see everytime you died use to scare the piss out of me.