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Tear Jerker: Super Robot Wars
Super Robot Wars. A series where Hot Blooded pilots of justice trample on evil with extreme prejudice in the most epic ways possible. Also contains things that would make you cry your tears out, be it normal or Manly Tears.
YMMV, some people feels it's worse than the game version.
OG Gaiden gives us the cruel Player Punch of trying to invert the Spared By Adaptation: Lamia, after all her efforts to assert her steel will... was unceremoniously shot down by an ODE-possessed Juergen, claiming her useless and making every of her development null... all because Kyosuke dropped his guard. The supposedly 'epic' song of Meikyuu no Prisoner by JAM Project becomes hard to enjoy when some of your team members was attacking Juergen with Berserker Tears (especially Seolla and Latooni) to avenge Lamia. Once all's done, Juergen was shot down, totally obliterated by Duminuss and the team is forced to retreat by the Swordian fortress, leaving Kyosuke to mournfully and solemnly declare that Lamia became a victim of war, killed in action.
It gets worse later on: Turns out Lamia is not dead, she's recovered by Duminuss and reprogrammed in such a way that even if Kyosuke would try to fulfill his old promise (in case Lamia loses control of herself, he'll personally kill her), he'll fail. Kyosuke is just this close to cross the Despair Event Horizon... though thank goodness Axel came Back from the Dead to set things straight.
The origin of the MX Story was just a passing by story that made it easy to just pass it up, but in OG Gaiden, it sets it up for a more tragic spin. Foglia Esto has a much more developed personality and a good going with Hugo and Albero. Then after all Albero was sidelining him against his wishes, Foglia sacrificed himself from Jetzt attack. The shock was too much for Albero and followed by Hugo getting heavily wounded, it was such a bad and tragic day for Albero, making his eventual Face Heel Turn much more tragic.
The children of Duminuss had it quite rough despite their antagonizing nature. Tis and Laliar, after all their obedience to Duminuss, were forcefully absorbed by Duminuss as she ended up as an Evil Matriarch here. When Duminuss retreated to her remaining child, Despinis, she ignored her in favor of re-summoning Dark Brain... who proceeded to splat her dead, along with Tis and Laliar inside her. All in front of Despinis, the resident Shy Blue-Haired Girl of the villains. At that time, even for villainy, it totally sucked being Despinis that time, thank goodness Raul and Fiona are willing to spare, forgive and protect her...
The Masou Kishin section also had one in form of Ricardo's death. Sure, he's supposed to be Doomed by Canon for being created as the first herald of Zamzeed, after in EX they already had Mio becoming its herald. But it doesn't make his final moments easier to watch, what with Tytti, who used to ignore his advances, were genuinely crying over his death and her efforts to save him declared too late. It's no wonder that afterwards, Tytti ended up becoming Allergic to Love.
2nd Original Generations... Doesn't pull the punches.
Midway of the series... Hugo died. Yes, everyone thought he's dead. And the cause? Aqua found out that Albero's co-conspirator is her revered mentor Eldy Mitte, and was being the Bigger Bad of the two, to the point that she didn't help Hugo out of shock. Of course, way later, we find out that Hugo came back to life, somehow. But at that time, it was a pretty shocking event (at least Hugo didn't even die in the original MX), and Aqua's crying was much more visibly understandable, as she blamed herself over Hugo's death, and Eldy was constantly taunting her for that.
Destiny was already Darker and Edgier, so it ends up taking things harder for their heroes... especially Rim.
First, she and Joshua managed to convince Ventus and Glacies to join the team, but in process, there was a flash of light and when Rim woke up... she found out that her Split Personality Chris has vanished. This would've been taken normally like a Split Personality sickness cured... except consider this: Rim (Liana) has accepted that Chris is her own person, and the two of them are okay with Sharing a Body, considering each other family. To have her lose a close person like that... on top of for the first time telling the whole Steel Dragon Battle Group about the existence of Chris... Making matters worse, when you use Dea Blanche Neige's final attack afterwards, Chris' spirit won't be around anymore to support Liana unlike before, just to remind you that she's gone forever.
And after defeating Perfectio, the team realized that the only way to defeat him is to seal him and someone needs to do the job, sacrificing himself/herself for it... Just before Rim can say a thing, Ventus immediately volunteers, and despite Rim's protests, he's adamant of his choice for everyone's happiness. Worse yet, Chris' spirit appeared once again and told Liana to keep going as she and Ventus vanish forever in front of Rim. Wow, and you thought being experimented amorally back then by Felio in Destiny was bad enough for Rim.
Oh and you know what's worse? Beforehand, Liana found out that she's an incomplete Melior Esse/Ruina General, and Chris was the original Cliana... therefore, Liana felt extremely horrible for killing the real Rim, and she was reduced to begging to sacrifice herself to take Chris' place... which got refused. And the next thing she resorted aside of crying, was only begging at Chris not to go. Which she couldn't do a thing about it too. Sheesh, it sucks to be Rim, in particular Liana.