I've been replaying Earthbound with
Ketkat since she's never played it before and we've been having a hoot. But after about 15 hours of playing we've come to the lovely point in the game where if you want to get Poo's only usable weapon in the entire game you've gotta grind one specific enemy that only exists on one specific screen, and disappears forever after you beat the boss of the dungeon.
We've been at it for about 2 1/2 hours and I'm pretty much ready to break. It isn't even the worst drop rate in a video game by a looooong margin, at a 1/125 chance, but there's just something about this one that gets under my skin. It might be the way all the funky graphics in Earthbound slowly wear into you , or how wild it is that the item is attainable for such a short period of the game. I dunno.
Anyway, what item in what game takes the cake as the most obnoxious drop?