Every death in Gurren Lagann.
Also,
EVERYONE in the penultimate arc of Higurashi Kai, and for completely different reasons,
Rip van Winkle in the fourth Hellsing OVA. Why?
Not only was she a great character, but her death was ridiculous, and marks the worst point i've seen in Hellsing. For one, because of it, Alucard killing the Villain Of The Week at the end of each OVA is becoming predictable. They could have easily had Schrodinger step in and shake up the formula, but no. And then there's her sudden personality 180 when she realises Alucard is nearby. And the daftest thing is how it actually happened. Alucard turned into a jet (like a boss) and bombed the Nazis (like a boss), dove in, and penetrated Rip's chest with a large phallic object whilst she blushed and made moaning noises.
Yeah.
The only thing that could have redeemed the fourth OVA from being an utter Shark-jumping moment is The Major's speech that immediately followed, which is one of my favourite moments in the history of anime.
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