I spent several hours rerolling skills on Helel in P4 trying to get the right combination of null/absorb/repel passives so he'd only take Almighty damage. The worst part about that was that I couldn't just hit X and circle over and over, I had to actually pay attention to the skills he got on each roll to make sure I didn't accidentally skip over the setup I wanted. I think I eventually gave up and made an invincible Metatron instead, which was way easier.
Besides that, shiny breeding in Pokemon, hunting beetles for cash in New Leaf, and the majority of FF13 were all pretty brutal.
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