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Tear Jerker: Star Wars: The Old Republic
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The Exile's death. After an entire life full of pain, manipulations and deceit, she gets stabbed in the back by Scourge to prevent her from saving Revan. Read Revan for more details.
The ultimate fate of Revan in the game is in itself both heartbreaking and rage inducing. now batshit insane he has to be put down like a rabid animal by Sith players to stop him enacting near total genocide of Sith civilians, and as he dies, seemingly, he echos Malak's last words on how he is beyond redemption. Player Punch and Character Derailment do not even begin to cover how much this sucks for fans of the old games.
The moment in the "Return" trailer when Satele Shan senses her Master's death.
Initially, the quest to discover the fate of the Exiles on Taris is almost hopeful, and even after you find out their struggles, you still hold out hope that you're going to find their descendants. But as you read the increasingly bleak apocalyptic logs, this gradually turns to general depression, and the last log is downright heartbreaking.
Even more depressing, when the final speaker speaks in faltering, half-broken Basic, saying that they've lost most of their history and knowledge, but they know that Taris was once a city...then pauses and has to reassure herself that she knows what a city is. She then laments that this will likely be the last generation;;
Lurr: We have stopped having children. The old records say it is from "tak-sic radie-achon." We once called this the Promised Land. It was a lie. It is our grave.
The Foundry: Especially for the lightside players, but seeing how far Revan has fallen, to his monstrous plan to kill most of the Sith Empire... an awful lot of lines are desperate attempts to persuade him that he's been corrupted, all to no avail. And then his final words.
One quest on Dromund Kaaas involve an Imperial officer nicknamed "Duchess." She's a mother to her men and probaly the only Imperial officer on the whole karking planet who sees her troops as something other than cannon fodder. She's worried sick about them, being trapped in that sicko Lord Gratham's estate. Then, you find them...that twisted thing has been transforming the poor men into robots. One of them pretty much has forgotten everything except his loyalty to Duchess. The Light Side options are to Mercy Kill the poor guys and deliver the sad truth to Duchess, who is heartbroken to hear the news, but glad her men aren't suffering anymore. With what's left of her dignity, she goes off to write personal condolences to their families.
The ending of the Oricon questline, Republic side. Dread Master Calphayus comes stumbling out of the Dread Fortress, clutching his side in pain, and without wearing his mask. At first, he just stammers in a broken, defeated tone about how the other Dread Masters gave him strength and purpose, and questions how the player character even manages to function without 'chains to uplift' them, driving home how he - and most likely the other Dread Masters as well, to varying degrees - were as much a victim of their own Mind Rape powers as anyone else was, as Calphayus is quite clearly traumatized from prolonged exposure to it and then being forcibly ripped from the only thing keeping his mind even partially intact. And then, it get worse: He mentions that he used to be married, and wonders why he wasn't afraid of his (most likely deceased) wife, indicating that he now mentally associates familial love with fear, due to how long he has been a part of the Dread Masters' Hive Mind. Needless to say, it's really, really hard not to take the Light Side option.
Th Dark-sided ending for the 'Boarding Party' Imperial Flashpoint. After capturing the Republic cruiser with your team, you ordered the execution of all the surviving crew members as per standard Imperial procedures. As the crew was lined up against the wall by the firing squad, two of the crew mates accept that it's the end and silently look into each other's eyes and hold hands. It is is as touching as it is sad, and either makes you feel like a monster, or curse the social dices for letting a dark-sided character win the roll.
Jedi Knight Storyline
On Alderaan, seeing Orgus Din get killed by Darth Angral in a holorecording, after just finally having cornered his last apprentice. What makes it worse is that it was initially thought that he was killed in a Sith attack, but fortunately managed to turn up and reunite with the Jedi Knight for one last time.
Uphrades. Occasionally the knight acknowledges how much this affected them. The mail you get after the fact doesn't really lessen the gut-punch. Millions of people living on a pleasant agricultural world, and Darth Angral decides to turn the entire planet into a fireball with his Devastator weapon. Then you're told that only a hundred or so survived.
Lord Scourge, in a way. He reveals to you that his immortality came at the price of his ability to see color, his senses of taste and smell and touch, and the ability to feel emotion. He can't even really feel sad for his loss, though he does distantly remember what his favorite foods were and the color of his first love's eyes, and wants the ability to feel them back.
Jedi Consular Storyline
Senator Grell is captured from your ship at the end of Belsavis. You pull out all the stops; Tharan and Holiday do an epic job of hacking the kidnapper's systems, your crew moves to intercept. You and Nadia storm aboard as lightsaber-packing Big Damn Heroes...and it's just barely too late to save the Senator. Worse, the guy who tortured Grell to death is a Sith so badly screwed up he can't recall his own name, much less who hired him. The Sith's lying broken and babbling on the floor, having expended his use. Nadia is giving it everything she has with her uncontrolled Force abilities in a futile attempt to revive her dad, and there's nothing you can salvage from it.
The Reveal about the First Son can be played this way, especially if you have Tharan in the party at the time. Remember, Tharan openly distrusts Force-based mysticism. But he did consider Master Syo as his friend. So when he sees his friend taken hostage by something he cannot fight with science, logic, or reason, it turns into one of these, especially if the Consular picks the options that share in his dismay.
The Trooper's class quest on Tatooine culminates in a Sadistic Choice: let the Imperials escape with state-of-the-art new bomb designs that they plan to test on civilians on some other frontier world, or let your former teammate - the man who gave you the warning about what the Imperials were doing and gave you the chance to stop them in the first place - die when the base self-destructs. There's not enough time to stop the explosion and still catch the Imperials, and he begs you to leave him behind and go after them; if you do, the game shows him in his cell as the base blows, sadly resigned to his fate. The email you get from General Garza afterwards just twists the knife:
Late game you are forced into another such choice regarding the fate of Sgt. Jaxo. Jaxo is a cute Republic Special Forces agent who worked with the trooper earlier on in his storyline, and if you were a male, was a minor romance option (and well liked by the player base). Eventually, you have to decide between condemning her to die by Explosive Decompression (with her begging and pleading for you to let her live), or sacrificing 300 Republic citizens being held prisoner by Imperials. The sheer number of otherwise Light Side trooper players who made the Dark Side choice to save Jaxo rather than the 300 prisoners is telling.
Worse still is if she's saved. Once she finds out that literally 300 people died to save her, she's hit with a massive bout of Survivor Guilt and refuses to even see the Trooper again.
Incidentally, all of your companions will condemn saving her over 300 people, except for Tanno Vik who doesn't care what decision you make but wants you to make a decision before the Imperials blow the place up)...and M1-4X who points out that she's a Special Forces so highly trained that economically, the 300 people combined are worth less than her to the Republic.
And just to twist the knife, if Jaxo died, you will receive a message from one of her friends/colleagues (?), who is tasked with sorting through her personal belongings. As Jaxo turns out to have no living relatives, that person just sends some of her stuff to you with a message that reads rather businesslike and unemotional... except the final line: "I miss her so much."
YMMV but Feylara could be this. She is a former lover of your archenemy and is going to such crazy lengths to impress him. However, she suffers a Villainous Breakdown and is crying in front of you. You have the option to kill her, but you also can spare her and tell her to find a better man.
On Hoth, when you track down the White Maw lieutenant and their "secret weapon," you burst into the room and there's the badass Twi'lek Dark Action Girl holding an Ugly Cute alien boy who calls her "Mama" and is scared out of his mind. The poor little fellow is a brain-damaged Force Sentitive who can shield an entire base from view - but only if he's scared. The White Maw regularly tortures the kid to keep him in a constant state of fear. The Twi'lek lieutenant has been trying to protect him best she can, thinking the Republic and the Imperials will be worse for the tyke than the crime gang.
During your first companion conversation with Corso, he will comment how awesome it is to be out in space, to be free and independent. One of the response that you can choose is a surprisingly cynical and honestinterpretation of his/her own career, without any of the usual humor or charm present in the rest of the story. Spoken in a tone that was almost as if the captain is trying to talk Corso out of this line of work and walk away while he still can.
Smuggler: We are criminals for hire, at the mercy of every Hutt in the galaxy. Don't romanticize it".
Sith Warrior Storyline
If you play as a female Sith warrior and marries Quinn, one of his love letters to you is about one having children together one day (or in his own words, an 'infant contingency report'). In which he writes in formal military language about the risk of you being weakened during the pregnancy, how to protect the infant against your enemies once he or she is born, etc. Although it is heartwarming in a way, it also highlighted the fact that despite all your power and authority, as a powerful Sith, you will never be able to enjoy a happy family life the same way that a normal person can and have to be constantly at guard against everyone that want to harm your loved ones.
Sith Inquisitor Storyline
Starting the game as a Light Sided Inquisitor, the second exchange you have is with Kory, a kind ex-slave girl, who encourages you to put up with Overseer Harkun's abuse. You might think that you have just found yourself an ally on this Dark Side-drenched planet, but fast-forward a mission or so, and Kory is deemed too soft for the Sith teachings by your higher-ups and executed in front of other acolytes as an example of how the kind and the supportive are crushed by the Sith training machine. And considering it is perfectly possible to play the Inquisitor as pure LS from the start, Kory's short life becomes even more tragic in her misfortune of being born in the Empire with Force sensitivity but not the cunning to pass her kindness for shrewd manipulation, like the LS Inquisitor does all the time.
Maybe this troper's just soft-hearted, but the dark-side ending to the quest "The Path of Power". When the Inquisitor arrives on Balmorra, s/he is greeted by Major Bessiker, a friendly, somewhat odd soldier who has been assigned to assist you. Throughout the entire questline he's helpful and reasonable, and takes pretty much all the Inquisitor's Inquisitor-ness in stride. Then he asks you to rescue his son, another Sith, who has been captured by rebels. Well, when you get there, the son talks about a holocron he found that leads the way to a powerful artifact. Since you are a Sith, you naturally get the option to kill him, take the holocron, get the artifact, then return to base. There you are confronted by a panicking Major Bessiker, who reveals that they had an agent at the base who caught the whole thing on camera. He's visibly distraught over the death of his son, asking you why you killed him, saying he trusted you to rescue him, and calling you a monster, ultimately having a breakdown and trying to kill you. The entire scene is depressing, and the music that plays during it is just the icing on the cake.
Just as depressing is what happens if you resolve it light-sided. See, when talking with his son, he reveals his disdain for "that old fool" he calls his father and insults you both if you spare him. You can either tell Bessiker about it, who responds in an absolutely heartbreakingly confused manner, or keep it a secret, in which case he goes on borderline worshipping his son without having any clue how useless said son views him.
If playing Light-Side, the culmination of the Alderaan arc has Nomar Organa waiting for you with an ambush, revealing that he never had any intention of leaving the Jedi to reunite with Lady Rist, the woman who had pined for him for over 20 years. Considering that the Inquisitor had conducted themselves with honour throughout the quest, his callous betrayal and Holier Than Thou speech on Jedi virtues, makes it's very satisfying when you're forced to kill him.
At one point during a conversation to develop your relationship with her, Ashara will ask what you wish you could have been, if you weren't a Sith. One option, said very quietly with no trace of their usual snark:
Braden's death. It drives Mako to tears, and almost immediately lets the hatred for Tarro set in.
On Nar Shaddaa, the player character is sent to kill a legendary assassin. After gathering info and weakening his forces, he goes for the player character's main contact, killing him and a childhood friend of Mako. This gets even worse if the player kept teasing Mako about a possible romance between the two.
The main storyline on Taris. You've been sent to kill an exiled Mandalorian. Along the way, you talk with his son, future squadmate Torian Cadera. When you catch up to the man, Jicoln doesn't beg for his life. He just wants to talk with Torian.
Imperial Agent Storyline
The endgame of Chapter 3 is bleakly depressing, in a way. After chasing the Star Cabal for a chapter and a half, you finally get your confrontation with Hunter. What you're faced with is someone who never really had a chance; someone so utterly screwed up by life that the Agent is the closest thing she has to a friend. And once it's all over, it's likely no one will ever remember her, save for the Agent and their crew. The scene is heartbreaking, as is one of the Agent's potential goodbyes (the VAs manage to make the unlikeliest of lines sound comforting):
You were the best enemy I could have wished for.
Similar to the Inquisitor's "Not a slave" quote above, the IA may get a similar moment in the chapter two finale. When Watcher X asks you what you want to do now that you essentially mind-control yourself, one possible reply is: "No more codewords. No more control." The Agent may not be a Sith but they learned the price of freedom the hard way, and the utterly serious way they deliver that line, without a trace of their usual suaveness, shows how deeply being tugged along on a string has affected them.