For myself, there have been several games that have been frustratingly hard.
I beat Halo Reach on Legendary (solo), which was no mean feat. Lots of time spent watching my corpse flail to the ground whilst elites (or quite often, grunts with stickies in hand) run about laughing. Still, not the hardest game.
Bayonetta on the harder difficulties became extremely difficult at times, and I gave up eventually. The game play was only fun up to a certain point.
Then, there's Apple Jack, and Xbox Indie game. Fun, quaintly British, and a right pain in the arse. I'm still working on completing this game...
And finally. The one true bane of my gaming history.
Gitaroo Man on the PS2.
I must have spent countless hours, perhaps in the hundreds, attempting to beat the Sanbone Trio on Master's Mode, and failing. I even got close once, being about 15 seconds from the end of the final. That's about the only time I've ever thrown a controller in a fit of rage.
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