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Thought about it, and the most frustrating game I've ever played was Ghosts n' Goblins.
The game is pretty easy on the 1st level, but then turns into a gauntlet of brutality. The kicker is even if you get to the final boss, you can't beat him without a cross.
So, if you don't have the cross, you have to play the final level over so you can get one.
Here's the really frustrating part; even if you defeat the final boss, you're informed that everything you just did didn't matter, because it was all a trap laid by Satan. So then, in order to get the 'real' ending, you have to play through the entire game again on a harder difficulty.
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