Sid Meier's Pirates! I had gotten the difficulty all the way up, so when I had to duel this dude for the castle I was attacking, I could NOT beat him. Basically you're supposed to see what move the opponent is about to do (There's three possibilities), then do the one to counter it. But on the hardest difficulty there's a 0.000001 second window to see, and I got sooooooooooooo irritated. I finally beat him an hour later out of sheer luck. >.<
The first Zelda game that was on the N64 (Ocarina), the final bad guy... I arrived there poorly equipped and didn't have a previous save to go to, could not leave to get re-armed or more health, I tried countless times but could not do it!!
Trying to get the target time on a few of the Goldeneye missions in order to unlock the cheats. Some were possible... just (I virtually programmed several missions in to my brain in a Pavlov Dogs kind of way! I can still run through them in my mind today, every bad guy and bullet accounted for) but others like Statue Park, I was missing about 30 seconds somewhere.
There's this mission in which you have to infiltrate a factory or a warehouse of somekind, steal a bunch of documents, knock the manager out and kidnap him. The jist is that within a few turns of knocking the guy out the factory will be blown up and all the documents will be destroyed. I had a fun few hours finding this out... what adds to the fun is that the guy is basically in a walking tank, a bloody body armor with rocket launchers. So having that around for more than necessary is not a good idea. Also, you can't leave the combat area if an enemy sees you. So basically if an enemy decides to chase you when you try to get away, you lose the mission. Great fun.
Whether it was a Boss you couldn't kill, a riddle you couldn't figure out. Etc.
Let us know what got your temper rising.
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*pErplex-edNESS is my Little Panda.
.:: "Save The Cheerleader, Save The World" ::.