GTA: San Andreas
Learn to fly
50 tries. 50. That's when the disc went flying.
It was especially insane if you'd already figured out how to jump into first airport early and had taken several joyrides. Even if you had your pilot stat mastered, I believe you still had to go through the flight tests! There was also a side mission with the David Cross voiced character where you had to fly a remote control plane that was a regular "I want to slam my head in a door" experience.
There was something similar involving a flying creature in one of the Harry Potter games. I had to help a friend's fiancee get through that one. That reminds me of one that I actually couldn't beat, at least in the time I had with it. Same friend's fiancee was trying to get anyone who came over to the house to help her get past a "Save Giles" level in one of the Buffy the Vampire slayer games. We all tried it a few times before giving up.