FFT for the PS.
I'm actually playing through it again for the first time in years and have made it laughably easy due to a RIDICULOUS amount of grinding at the beginning of the game...seriously, I had 2 ninjas with ignore height before I got to the 5th story battle, and I had 2 master calculators before I completed the first chapter (of four) of the game.
But we're not here to talk about being OVERprepared, we're here to talk about being underprepared. At the end of Chapter 3, you've gotta do a series of 3 back-to-back battles in a lovely little place called Riovanes Castle. The first battle is pretty standard: you're at the gates and have to kill a couple knights, some archers, I think there's a monk in there, and a black mage or two. Pretty tough, but not too much of a headache. Then comes Mr. Wiegraf to challenge your main character to a 1v1 battle.
Here's a bit of info about Wiegraf. He's powerful ranged attacks that can kill you in one shot and if they don't they can inflict Stop upon you, meaning he gets a few turns to kill you at his leisure. The only way to prevent this would be to break his sword, but he's got the Maintenance ability which means you can't break his sword. The only other option is to try and steal his sword...and good luck with that. If you fail you're dead.
So that leaves you with having to kill him before he kills you. Well your best shot is to go straight offense with two swords and try to do enough damage to him to knock him down. Well as it happens he's got a kick ass shield that makes it nigh-impossible to hit him from the front and pretty hard to hit him from the sides...add to it his accessory which increases his side defense and your only left with trying to attack him from behind...the problem is that since he's got strong ranged attacks, he doesn't feel too keen on the idea of letting you get around behind him.
In short: if you go against him and you're not overleveled for the fight, you're going to lose. Period. And if you've been working off of one save file and saved your game after the first battle at the gates of Riovanes, then that means you're essentially stuck...meaning you have to start the entire frickin' game all over.
Assuming you do manage to knock him down, the rest of your party shows up as he turns into a massive spell-casting demon with powerful summon spells that can wipe out your entire party very quickly. You'd think spreading out would be a good idea but due to the layout of the battlefield, you're pretty much forced to remain clumped together. Again, unless you're overleveled for the battle, you'd completely boned.
Assuming you do manage to beat him, you go to the 3rd and final battle on the rooftop. The good news is that there's only three opponents, the better news is that all you have to do is knock one of them down to being "wounded" and they all retreat. The bad news? They're all incredibly fast (so they usually get to go before you), you lose the match if they kill an NPC that you don't have control over (and they can do so in one shot on their first turn), and unless you have someone with Ignore Height/Teleport and a very strong attack, you're not going to even be able to make it to the enemies in time.
In short: Riovanes Castle fucking sucks. It's easily the hardest part in the entire frickin' game and will basically do this to you if you're not prepared:
In case the metaphor wasn't clear: Riovanes is the clown.
For that matter, Adam Sandler represents the average player's response to Riovanes.