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Tear Jerker: Devil May Cry
DMC 1 has Dante didn't take well on Trish working for Mundus. Even if he saves her because she looks like his dead mother, he doesn't want to see her ever again, going so faras to cross the line by put her at gunpoint, shouting that even if she looks like his mother, Trish is just a soulless demon, then drops his gun, and walks away in anger and sadness.
Trish: "Uh... Dante! Dante why did you save my life?"
[There is a pause and Dante looks away.]
Dante: "Because you look like my mother... Now get out of my sight! The next time we meet it won’t be like this."
[He starts to walk off again and Trish moves to stop him.]
Trish: "Dante!"
[Dante spins around brandishing one of his handguns, held pointing at Trish.]
Dante: "Don’t come any closer you Devil! You may look like my mother but you're nowhere close to her. You have no soul! You have the face but you'll never have her fire!"
[He drops his handgun and walks away]
Trish even makes that look in the face after the last statement.
To think this is the scene where he's all serious instead of snarking her about it.
Before that, there is a revelation of Nelo Angelo: It's Vergil!
And then she takes an attack from Mundus that was aimed at Dante, and apparently dies because of it. His tears after the first two battles with Mundus made me weep a little.
How about when Trish tries to apologize to Dante for selling him out to Mundus, she has Tears of Remorse?
Dante realizing who Nelo Angelo really was... after he's destroyed him.
It seems to be the same for Vergil, which makes it even worse. Depending on whether you consider the manga canon, it gets very, very worse... and never really gets better.
The ending of Devil May Cry 3. First there's the part where Vergil tells Dante to return to the human world and takes a very deliberate, implicitly suicidal fall off the edge of the cliffs where they fought. Knowing his REAL fate actually makes it worse in a way. But what really gets me is when Dante cries for his brother — and, being Dante, says that it's "only the rain." *sniffle*