Hmm, you know it's funny how threads like this can draw up some long repressed memories. I would be very surprised indeed if anyone agrees with me on the segment I'm about to detail, but here goes.
The segment I most associate with a feeling of dread from any game is Battle 6, Mission 5 of Star Wars: X-Wing Alliance. This is the mission that requires you to steal the Imperial shuttle Tydirium, the very same shuttle that appears in Return of the Jedi as the one Han, Luke and pals use to infiltrate Endor. For lack of a better way to describe it, this is essentially a stealth mission in a freakin' Flight Sim!
X-Wing Alliance was pretty much the first game I really sunk my teeth into. I was probably only about ten when I first played it. With my atrocious video game skills at the time, it probably took me the better part of a year or two (playing on and off) to get this far into the game. Certainly I remember a whole bunch of missions it took me a while to get past.
I think this mission probably took me the better half of a decade to finally complete. I failed it so many times I got scared of playing it. I restarted the game a couple of times, so I could go back to having fun. But, sooner or later, I would arrive back at this hellish challenge and that feeling of dread would overwhelm me again. To be honest, if I reinstalled the game and had another run through, I would probably still be nervous starting this up.
I mean, this was my Everest as a kid.
Let me break it down for you. For this mission, you need to pose as a civilian contractor to sneak onto a heavily defended Imperal space station and deploy a team of crack commandos so that they can steal the shuttle. To do that means going undercover, so you can't just fly in with the Rebel fighters you've been using for 80% of the game. That means no manouevrable X-Wing, no heavily armed B-Wing - not even my beloved but awful Z-95. For this mission, you're flying a freighter. A YT-1300, to be exact. Think a much more sluggish version of the Millennium Falcon, but without the dish, the bottom turret or anywhere the same level of shielding or manouevrablity (and if you know the Falcon, that really is saying something). This thing is not a dogfighter. It is a flying target. Worse, you own a much cooler freighter called the Otana [http://starwars.wikia.com/wiki/Otana], that as well as looking way cooler than the Falcon is an absolute machine when it comes to blowing up TIEs. You can't use that either. You're stuck with the shitty Sabra.
Before you can even get close to the space station, you have to pass through Customs at the edge of the system. Yes, boys and girls, not even hyperdrives can save you from the horrors of Customs and Immigration. There are TIE Fighters patrolling everywhere. All you can do is transmit your faked manifest to the station and wait an agonizingly long time for clearance. The distance between where you enter and leave the Customs area is, by XWA's standards, rather large. Even if you fly straight towards the place you will be able to make the jump to lightspeed from the off, you're stuck there for a good ten minutes just cruising in a straight line. The catch is that if a single one of those TIE Fighters gets within a kilometre of you, they will scan you, find what you're really carrying and it's mission failed.
So you can't shoot anything, you don't move very quickly and those TIE Fighters can turn on a dime. The entire trip past customs involves you nervously scrolling through your targets, and veering frantically away if a TIE Fighter gets too close.
AND THIS IS THE EASY BIT!
Once you jump nearer the station, the same rules apply. Wait until they let you land. Avoid the TIEs. Only now, there are even more of them, and some of them are the even faster TIE Interceptors. Put one foot wrong, and you fail the mission.
AND THAT STILL ISN'T THE HARD PART!
Once you've made it through there, you've docked with the station and found the right shuttle, you have to help the shuttle escape. The commandos spent what feels like an hour breaking into this shuttle, and the guy controlling the station gets pretty pissed about it. They figure out what you're up to, and send every frigging TIE in the area after you. It's okay, though, because for once in them game you get to call in backup without penalty. Four X-Wings show up. Yup, four. Four X-Wings, and your shitty underpowered transport against thirty odd TIEs.
And then the shuttle delays leaving. You have to keep switching frantically back to the shuttle, because as soon as it does decide to leave, the station spawns a load of TIE Bombers whose only goal is to obliterate that shuttle. So you have to ignore the dozens of TIEs pounding away at your shields and prioritise the Bombers. Because they will catch up, and the shuttle is hilariously defenceless.
Achieving all that without at least turning on the Invincibility cheat is hard to this day. As a twelve year old, or whatever, it was utterly impossible. Like I said, I put so many attempts in that and failed it so many times that I still feel horror at the prospect of doing it again.
The icing on my sad little cake is that one of the later Rogue Squadron games had a mission where it was the Alliance's own Peter Fuckin' Perfect, Wedge Antilles, who stole it. And that's the one that's canon!. All the struggles I put into Ace Azzameen's proudest moment were wiped invalid by Lucasart's infuriating canon policy and nerd boner for Wedge Antilles. Oh yeah, I forgot to mention. The X-Wings that turn up as your back up? Yeah, they're from Rogue Squadron...
*HEADDESK*