I'll toss out any of the Fire Emblem battles with bosses using Killer weapons. There's nothing more annoying than to spend an hour or more fighting through waves of soldiers and working your way across a map, only to be struck down by the boss in a single lucky hit. This is usually the worst later on when your mages still aren't powerful enough to do much damage to the bosses from a distance, so you're forced to take that 25% chance of losing everything. Several times.
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Originally Posted by LeHah
The infamous "double boss battle" with Wiegraf. The first half of the battle is a one-on-one with the sonuvabitch and its tough. No support characters, no way to heal unless you waste an action for a round... but then Wiegraf transforms into a Zodiac demon and summons two lesser demons (which are fairly hard no matter what level you're at) and then you party shows up. Theres no break in battle, you just do two boss battles back to back. And by this point, your main character is probably really, really beaten down and easily killed meaning you just wasted a good hour plus on the first half of the fight, only to be frustrated for another hour as your team is being killed off slowly.
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The first part of the Wiegraf battle was never that bad as long as you had a skill set for the occasion. I always went Lancer. The big problem was that Velius is an incredible asshole and casts Cyclops, which is pretty much instant death for anyone caught in its large range on the restrictive map. Try silencing him to get rid of that and he starts petrifying everyone one at a time with a 100% chance. Plus his three demon buddies weren't exactly pushovers with their powerful attacks.
Then there's the battle right after Velius with Celia and Lede on the roof. That one isn't so much a difficult fight as it is somewhat dependent on luck. They move fast and can insta-kill the people you have to protect any time they like.
I've beaten FFT twice on PSX, gotten past these fights on PSP, and I'm still scared of the Riovanes Castle series of battles.
Jam it back in, in the dark.