Presently watching reactions to Game of Thrones episode Battle of the Bastards. I think you know what's coming.
I was also a big fan of PC puzzle adventure game Riven. The canonical villain death for that isn't even a death in theory: the dude gets himself trapped in a dark void. A book that looks like a world but just transports you to a black screen in the game itself. Nothingness. And he's there forever. That's pretty dark, literally and thematically, and I love it.
So, what's your favourite? Be as dark as you like, no judgment here. I'm pretty -blam!-ed up myself.
-
Godcat and Akron from the EBF series, just because those fights are absolute BULLSHIT levels of difficulty. Godcat is a 7 stage boss fight, in three of these stages she can instakill you. One stage gives her a superpowered hyper beam which cannot be blocked, and instantly removes all your buffs. The other stages include switching elements, hitting you with four polar opposite elements at once, and huge amounts of accuracy and defense debuffs. Akron is annoying for similar reasons. He switches elements, summons minions, debuffs you, can unleash massive poison attacks, and also can use an attack that prevents you from reviving downed party members.