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I've recently begun replaying the original Ninja Gaiden on the Virtual Console. It's still a great game, and the difficulty is generally overstated: it's certainly challenging, but I rarely died more than once on any given stage.

Until, that is, I reached Stage 6-2. More specifically, the part of 6-2 where a sword-throwing enemy and a homing hawk each spawn on or above a narrow platform. I'm sure any and every Ninja Gaiden veteran knows exactly the part I'm referring to. Being a dumbass, I did not keep the appropriate power-up. So now it doesn't matter if you kill one of those foes, they'll instantly respawn in the same place. Screw that jump. Screw it hard.

 

One of my runner ups is this asshole, from Final Fantasy Tactics.

Now, Tactics is not a particularly difficult game. In fact, its mechanics let you completely break the game early in the first chapter. Even if you don't deliberately try to break it, the game automatically hands you Orlandu in the fourth chapter, after which point there remains no pretense of challenge.
Velius exists to punish you for not breaking the game.
The first time through the game, when you probably haven't mastered the mechanics well enough to break them yet (and why would you; it's not otherwise a hard game!), you'll stumble cluelessly into this fight, and it won't be pretty. Hope Ramza's a fighter class, or else the duel with Weigraf is going to end real quick. Hope you used the duel to power up Ramza, or else the fight's going to end fairly quick. Hope your teammates can survive two consecutive hits from Summons and ranged demon attacks, or else the fight's going to end super quick. For added funsies, you were probably stupid enough to save right before this battle, huh? Well tough, cause now you can't grind or restock items without winning this battle (and the luck-based battle after it, for that matter).
So there are two of my "screw this game" moments. What are some of yours?