I think I'll nominate TIE Fighter (Collector's CD-ROM), Battle 13 Mission 5 (The Emperor's Will: Return to Vorknkx) at the highest difficulty:
https://www.youtube.com/watch?v=8AK84RnocoY (well, in this video, someone apparently is able to finish it?)
The developers had chosen to do many many things simply to annoy you, it seems.
- You had to fly a weaker TIE Advanced against TIE Defenders. Your shields were so weak that if a TIE D missile ever hit you, you would take damage to hull. So if a missile gets on your tail, you have to waste time (that you don't have) to try to avoid them, flying in circles.
- The Defenders are so fast that there is no realistic chance to fight them head to head. They are stronger, faster, have more firepower. If you got on a tail of one, it would outrun you quite easily.
- You really needed to have a tractor beam installed in your TIE A in order to slow down TIE Ds so that you could actually destroy them. That's fine, except that then you can't install the jammer device which would be sorely needed against the enemy transports afterwards (otherwise they will constantly do major damage to you with their turrets when you try to fight them). It is like the developers are mocking you "ha ha, choose either way, you are screeeeewed!".
- The transports in this particular mission are odd "flat type", which makes most of your shots miss when you are on their tail. Normally the transports are thicker, easier to hit, just in this mission they happen to be like flounders.
- Being able to carry more missiles would help greatly in this mission, but naturally you have to fly a TIE A that carries less missiles, and don't have much of time to replenish either during the mission.
- It seems the game expects you to do pretty "lucky" things like being able to shoot some enemy torpedos with potshots from afar, while avoiding TIE Defenders. Also it seems the real key to success it to carefully analyze from failed mission runs that which enemy transport you should try to destroy at any point. There are so many of them and more coming in waves, and somehow you are supposed to memorize which of them to attack in which order. Just trying to destroy them one by one as fast as you can will not be enough.
- There were just so many things happening at the same time that you weren't sure where to concentrate, especially at the start of the mission. Try to kill TIE Defenders as fast as you can? Try to destroy some of those early enemy torpedos with lucky potshots from far away? Try to concentrate on enemy transports ASAP, hoping to somehow avoid enemy TIE Defenders (your wingmen were mostly useless, maybe they could destroy one TIE Defender together, and then die, leaving you alone)?
Add to that that since you needed both to rush everywhere, and also use either the tractor beam or the jammer a lot, you needed to constantly change the ship energy distribution on the fly. And when you try to target the correct transports out of dozen(s), good luck cycling through all of them. Or alternatively, trying to find from a different view which transports were attacking which platform, and which platform was closest to death.
After one or several hundred retries, I finally gave up and passed the mission with the easiest difficulty level, then changing the difficulty level back to Hard for the rest of the game. Phuck that mission!