Oh god, you reminded me of the misery of Super Paper Mario's pits for me. On the first, first run, I get to the final boss at room 100, and die. But fine, I screwed up. Do it all over again, beat the boss, hooray. This opens up the Flopside Pit of 100 Trials. =P

I wait till much later in the game to try it. Stock up on good items, and even have a fancy cake that launches meteors at the enemy cooked up. I dive in, narrowly survive 98 rooms and get to room 99. I figure my cake item won’t be much use against the boss in the next room, so I go ahead and use it to clear out this one. I use the cake, the attack starts, and the game locks up. Yep, it locked up. The Wii’s air horn of death sounds, and there’s nothing I can do.

Well after my doctor put most of my blood back in, I decide to try yet again. This makes me forth time trekking through 100 damn rooms in this game. I sell off that fucking cake before even entering, get through the rooms somewhat easier than before because I already fucking did them, and get to the 100th room. There’s no boss, it’s empty, instead a voice says something akin to “That was impressive, do it again and we can meet.” A pipe appears, and it takes me back outside.

What the fuck?! Do it again, that’s my damn reward? I’ve already done in twice! So after more yelling, I decide to do the Flopside pit, yet again. It’s exactly the same as the first (and in my case second) time you run through it. And it’s all the easier because surviving one run with it nets you major XP, money, and actual experience on how to finish it. It’s just tedious and pointless to have run it again. I get to the last room, AGAIN, and fight the lame boss fight which is easy considering how high my HP and attack are at this point, get my lame reward which makes me even more obscenely strong than I already am, and leave.

I was so delighted later in the game when you get to Sammer-Guy's "Showdown of 100 Warriors" or whatever the hell he called it. =P

 I was going to say RE4 had a good escort mission but it really isn't that good in the sense of an escort mission.  Her escort mission is easy because you can clear a small area, tell you to stay put or hide, go on with the level, and then come back and get her.  For the most part doing that doesn't screw you over (there are a few spots you can't leave her) and breaks the point of escort missions.

Of course I actually like that since I hate escort missions.  :-p 

 It helps she actually knows to STAY THE HELL BEHIND you when you're shooting stuff, and when that fails, she'll actually duck when she's in the line of fire. The fact she's helpless and REALIZES that is also useful, she never runs towards a horde of enemies in hopes of both dying and blocking your shots. =P

Getting all the coins in the Rolling Gizmo Galaxy in SMG was frustrating as hell... especially when you just had to finish the level, and you miss that last jump over the moving cube.

She had very good AI.

If you pointed your gun at her, she ducked and ran behind you.

If you suddenly moved backwards, she also circled around behind you.

These two seemingly small facts made guarding/escorting her a breeze.

-Trying to unlock Petey in Mario Strikers Charged. Once you get on the last Strikers cup, the AI seems to love to go into 'Extreme Kick Your Ass' mode.

-In FFX, trying to get used to the Sphere Grid or agreeing to help a friend on their file to realize that they have minimal use of the Sphere Grid and they're on a boss fight.

I agree. Everyone can be easy and then you run into that one enemy where the difficulty ratchets way up.  I've gone from winning games 15-0 to losing 2-3. Single elimination makes it even worse.

@ RolStoppable Unpacking my N64 this week to look how many homming missiles Juno has ;) Edit Only 20 HM for Juno.

Yeah, Ashley easily is the best escort AI I've ever had the pleasure of dealing with.  Every other escort mission can go to hell.

^Just wait 15 minutes.