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SPOILERS
When I think of Nightmare Moon, I can’t help but think that she pales in comparison to Darkrai, specifically his incarnation in the Mystery Dungeon games.
Seriously, Darkrai was scary in that game. He’d go through ridiculous lengths to achieve his goal of eternal darkness and never-ending nightmares, and he always had a backup plan in case you managed to thwart him. It took nothing short of the direct intervention of Palkia, the God of Spacial Dimensions to finally stop him.