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Well most frustrating would have to be old school, nothing more fustrating than having a hawk respawn over and over in ninja gaiden and being knocked back into a pit. Also, as already mentioned, Mike Tyson. The newer games are difficult, sure, but don't induce as much frustration, at least not to me.
That is except for:
History's lamest and most unecessary challange in games - FFX Lulu's dodge 200 lightnings side quest. This little challange probably made me curse like no other. Nothing worse than dodge 170 strikes in a row and then BAM you have to start from scratch. At the end I didnt even feel good about beating it, the reward was completely unsatisfying.
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