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Tear Jerker: Hellsing
The death of Pip Bernadotte. Your only consolation is the immediate Crowning Moment of Awesome that follows as Serastakes a level in badass, and the Unstoppable Rage commences. The OVA somehow managed to make this even more tragic, with the blind Seras desperately trying to find him, and pathetically grasping at the wall when he slips to the ground, dead.
And the kiss. Pip kisses Seras as he dies. And then teases her. I...just...-I... this trooper needs to find a secluded place to go cry her eyes out now.
Are we going to ignore the credits sequence for that episode, which is a slideshow of Pip's life alongside music that is clearly sung from his perspective, and which ends with a shot of Seras cradling Pip's mangled body?
Studying the pictures from Pip's childhood makes you even sadder as you realize that those kids with him are the other Wild Geese, they've been together since they were children— the classical definition of True Companions— and then one of their own is Killed Off for Real in front of their eyes and they're powerless to do a thing about it.
For that matter, there were four kids in that picture. Two of them are the last survivors of the Wild Geese, one of them is Pip, and the last one is the Merc whose unit was cut off from the rest of the Geese, and who was killed by Zorin after being shown an illusion of his dead daughter. Suddenly, Pip's refusal to close the barricade before the man returned makes a lot more sense.
This troper was already crying at Pip's speech to his men. It was impossibly badass, yes, but it was clear that they knew they were going to die.
Father Anderson's death is painful. Even Alucard is taking it hard, having to be chided for crying by the dying priest, and Iscariot members, some of whom he probably even raised, are visibly falling apart, especially Yumie. Then Walter, having officially gone evil, has to come in and ruin the moment, driving Yumie into full berserker rage and killing her without a care just seconds after he ground what was left of Anderson's ashes under his boot.
The single panel that Alucard tried to convice Anderson to not become a monster like him. You can see how much it hurt him to see such a "great warrior" reduced to what he sees as the worst punishment possible, and how much he regrets that single moment of rage against god that made him what he is.
The OVA managed to ramp it Up to Eleven with Alucard looking, for once in the whole series, very human. He lost all the Large Ham he and other characters had been exploding with, and seemed to genuinely be pleading with Anderson to not become like him. Damn.
Underrated Admiral Penwood performing a genuine Heroic Sacrifice to try to maintain a chain of command at his base and organize some sort of defense againt the vampires, and telling the other staff members to leave the soon-to-be-invaded base. Only for them all to volunteer to stay behind and die with him, organizing a last line of defense rather than leave him. It makes up for EVERY cowardly action made by Penwood.
The credits for OVA V make it even worse with them showing Sir Islands paying respect to Arthur Hellsing's grave while flashbacks of Hellsing, Islands and Penwood as young men, are interspersed throughout. All while the haunting Song of Demeter plays.
To add to Penwood's Tear JerkerCrowning Momentof Awesome, all of his men at the command center refusing to leave certainly qualify. Despite his insistence that they leave and not throw away their lives, they ALL volunteer to stay with him to assist him in what they can clearly see is a doomed effort, in part because he couldn't possibly do all the tasks required alone (despite him saying so, establishing a chain of command is complicated and requires at the very least a handful of people to effectively accomplish), and in part because they obviously take their duty just as seriously as he takes his (even if he is, as he honestly puts it, a man who "gets nervous."). It's not just the fact that they decide to stay and die with him—it's the fact that they obviously respected him enough to do so in the first place. The worse thing they say, and only out of honesty, is that if he doesn't stay at his chair in the command center, he might get in the way of various duties being performed, hinting that they still consider him their commanding officer (however reliant on them), and a man worth dying alongside, in spite of (and probably in part because of) his immediate admittance that most of his position is owed to money and heritage than anything else shortly before accepting that he could very well die performing his honor-bound duties, and then proceeding to commit to them. Not so much a Father to His Men moment as it is Sons To Their Commander, but tear-jerking no less on their part.
This troper had just finished watching Death Note when she read the manga chapter 'Castlevania.' Words cannot express how perfect/wrong her headspace was for that flashback. It made AlucardThe Woobie, for Christ's sake. Also, Integra having to give the order for Walter's execution was brutal.
Realizing that the real Vlad the Impaler probably wasn't that different from his Hellsing version is worse. As is asserting that in spite of everything he did for his people and for Christianity (seriously, the guy was a martyr) today he remains mostly remembered as a monster.
Rip Van Winkle's death was this troper's saddest part of Ultimate. The fact that she knew that Alucard would tear her to shreds and actively tried to run from him made her death so depressing. Her being Affably Evil made her interesting, but to see that she had enough common sense to realize that she stood no chance against Alucard made it hard to watch him pretty much rape her (or at least act like it) as he killed her.
How is this gem from the TV version not in here? In episode 10, when Ferguson dies.
And then there are the credits of OVA 8 that show Anderson with the very young Heinkel, Yumie, and Enrico Maxwell. Yumie and Heinkel seemed to be examining their weapons for the first time. Enrico was simply reading from the Bible, possibly under Anderson's instruction. They all looked fairly happy, like a group of friends. Tear Jerking because, earlier in that OVA Maxwell had been killed by his own teacher. Said teacher then became a monster while his students Yumie and Heinkel had to watch. Also, later in the manga, Yumie and Anderson would both die in front of Heinkel. Which would leave her all alone. Yikes.
After the reveal of Walter's betrayal, Integra gives the order to Alucard to kill him. In the final panel of the order, she looks absolutely crushed.
And then just before the fight, Seras thanks him for everything he's done for her, and just for a brief moment Walter actually looks like he might be regretting his decision.
Almost all the protagonists have had, both in the past and in the present, their downhill moments. The winners, however, are arguably Walter followed by Anderson
Walter's death is just one long train wreck of tearjerking sorrow. From the moment he snaps out of his single-minded determination to slay (or at least defeat) Alucard after the latter disappears, he seems to realize just how blind he was for accepting a superpowers from Millennium and casting aside his comrades, to the point where he just sits there and allows Heinkel to shoot him, even goading her into doing it.
His actual death is outdoes the moment above though. For some reason his simple sigh of "I just wanted to win against him" as he sits there, waiting to either burn to death or die from his Deadly Upgrade is a thousand times worse than his final goodbye to Integra.