Legacy of Kain - Soul Reaver for the Dreamcast. This was easily the hardest and most frustrating game I have ever played, but not in the "i have no idea how to solve this puzzle" way, but rather the "i have no idea where there even was a puzzle or how to get there" sort of way. For instance, you'd be told to go east over the mountains to get to the next part. Only problem: there's no map or direction indicator and you're standing in a place surrounded by mountains on all sides. So you check literally every inch of the area you can get to without finding anything. Or another problem, which is you pass right by what was a puzzle but have no idea and don't reach the area that it is supposed to affect until 6 more hours of gameplay through. I only figured this out after trying to fall back on a strategy guide, but by then I couldn't figure out how to go back and get everything done. I would've had to use a walkthrough from the start, and I sure as hell wasn't going to start the game over after getting so many hours in. Never did finish that damn thing. It's really a shame too considering how awesome parts of the game were in general (the graphics, the storyline, the cutscenes, etc).
And another Dreamcast game:
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Originally Posted by Redjake
In a close second: The Egg Viper boss in Sonic Adventure for Dreamcast. That boss was DAMN hard also.
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That level was so simple in terms of what you had to do, but was too damn frustrating trying to pull it off. It was basically one long jumping sequence for a boss, where something would always happen to push you slightly off center and plunge to the death. Lather, rinse, repeat. Roughly 60-70 times if i remember correctly. I wish I was exaggerating.