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Tear Jerker: Kingdom Hearts: Birth by Sleep
Before you even start the game, you know the main trio, Eraqus, and the princesses they're saving are Doomed by Canon.
At least the Birth By Sleep characters have hope of a happy ending at some point in a future installment.
The scene where Ventus asks to be erased in the Keyblade Graveyard. Thanks to Ven's Puppy-Dog Eyes.
It isn't just what he's asking that's the tear-jerker. No, it's the way Terra puts his hand on the kid's shoulder, saying they're his friends and will make sure nothing bad will happen to him, and Aqua bends down to look at Ven and cup his face gently in her palm. And then Ven says he may still have to go through with everything, slowly moving Terra and Aqua's hands off him, knowing that his friends can't help him this time, no matter how much they may want to.
Ven: I'm asking you as a friend... Please... Put an end to me.
The cutscene shown when you begin the Final Episode. Particularly the part where Aqua comes back to the utterly DESTROYED Land of Departure, and the camera pans over all the doom and gloom, and finally comes to rest on Eraqus' Keyblade. And when that heartrendering remix of "Fate of the Unknown" is playing...
Hell, try visiting the Land of Departure as Terra or Aqua to collect treasure chests. All the other worlds, even the Keyblade Graveyard, has music playing, characters to interact with, or at least enemies to fight. The Land of Departure is completely barren, no music, no enemies, no life left. There is really nothing left of their home. They're on their own now.
The sheer depth of the remorse and sorrow Terra feels after he is suckered into contributing to the death of Master Eraqus and the destruction of their homeland. At the end of his story, the Lingering Will is left alone on an empty battlefield, having lost Xehanort, Ventus, Terra, and Aqua in the aftermath of the horrific battle. As he kneels in the dust, prepared to wait for as long as it takes, one thought is left in his mind.
"Aqua. Ven. One day, I will set this right."
Watch the interaction between Lea and Isa, and then go and watch their interactions in the yearsto come. Cry at what happened to their friendship.
Lea's wish to be "immortal", knowing how he went out.
Keeping that in mind, Days and the prologue of II just got even sadder. All Lea/Axel wants is to be remembered, and one of his two best friends forgets all about him and he himself forgets the other one even existed.
The Secret Reports in Days makes it even worse, driving it home how that dorky kid and his snarky best friend are effectively dead, and how much their relationship has deteriorated over the last ten years.
Axel: Talking to Roxas and Xion always brings back memories of my human life, back when I was a kid. It's a weird sensation. I ought to be able to share all this with Saïx, but I just don't feel like it anymore. It's strange, but I'm content with just missing what's gone. I'm not the one who changed. You did.
Saïx: ...What were you really after, Lea? We joined the Organization at the same time, and formulated our plan. At this point, it's just an idle fantasy. Everything changed. You, and me.
It's even more tragic as of KH3D: Saïx is one of the Xehanort clones!
The end of every damn story. If you managed not to cry at Terra's story... wait until "Hikari Instrumental" kicks in...
The entire latter half of Birth By Sleep. It's so tragic, Sora is driven to tears in-game, and he doesn't even know why. The tearjerker is simply so powerful it draws the most empathetic into it like a black hole.
During the credits, Mickey Mouse is so devastated over the fate of the three protagonists, he hands over both his starshard and his keyblade to Yen Sid. As he turns to leave, Yen Sid gives him back the keyblade. Between Yen Sid not approving of Mickey's training before, the events of the game, and what's to come, it was quite a gut punch.
Ventus's Theme. At about 0:39, where the melody restarts, it sounds about the same as the beginning for a second, but then, the string portion goes up an extra octave to repeat the melody from "The Other Promise." As if the music itself is crying.
Aqua's Theme is pure depression. It makes you wonder how much longer she can last without going suicidal or something.
Aqua. Her fate. My God. When she sacrifices herself to save Terra, and those three words she says with a smile: "I'm with you!" And then, when she's wandering around in the Realm of Darkness and she sees Terra, and Ventus, and Eraqus, and everyone she met in every world...
"Ven, I'm sorry. I won't make it back as soon as I thought. But I promise I'll be there one day to wake you up."
What Aqua says to Sora on Destiny Islands:
Aqua: So then, if something happens, and Riku's about to get lost... or say... he starts wandering down a dark path alone — you make sure to stay with him, and keep him safe. That's your job, Sora, and I'm counting on you to do it, okay?
The sad thing is that Sora couldn't keep his promise: Riku wanders down a dark path alone and Sora is unable to stay with him to keep him safe. It all ends happily though, but the fact still stands that Aqua's intentions were ruined: Riku ended up like Terra.
Actually he didn't, Sora WAS there to interfere unlike they were. And unlike Terra who shuns the darkness in him, Riku is the darkness that leads to the light (Road to Dawn)
The secret ending of Birth by Sleep.
The battle with Eraqus. Hearing Fire Lord Ozai express anguish over having to kill the student he saw as a son was more tear jerking than expected.
"The Masked Boy" features Ven's first talk with Vanitas... followed by a flashback of the former's interactions with Terra. During one of said interactions, Terra's telling Ven off, prompting poor Ven to cry. We don't get to hear why Terra was upset at Ventus, but boy howdy, does Ven have quite the Puppy-Dog Eyes.
"That would be the last night we ever spent beneath the same stars." Now, let's be honest. How often do you replay that section?
Though this definitely pales in comparison to moments later on in the game, the conclusion of Experiment 626/Stitch's story is really depressing. He finally understands through his encounters with Terra, Aqua, and Ven what friendship really is, but Gantu's inability to understand that 626 could change leads 626 to escape from the ship on a cruiser with a faulty navigation system that separates him from Ven.
Before that, it's hard not to cry a little at Gantu breaking 626's makeshift Wayfinder that he fashioned after seeing Terra's. It's the fact that 626 stares at it for awhile afterwards even while Gantu is threatening him that gets you.
Stitch's friendship with Terra allowed him to start to grow a heart of his own, and Aqua and Ventus helped even further.
The fact that the trio have not only lost their home and master, they've lost over a decade of their lives. Ven's gonna wake up suddenly twenty something with all of his friends aged, moved on, and just plain different thanks to maturing, Aqua is now gonna be in her late twenties or early thirties after spending all that time in isolation in what is basically helll with monster fighting on a daily basis which is gonna make recuperation and reintegration all the more difficult, and Terra might not even be completely himself ever again: he might be so tied to Xehanort that it'll be impossible to completely remove the shadow from his heart no matter how clean he ends up of Xehanort's influence.
It's more of bittersweet in the first two's cases as of Kingdom Hearts 3D [Dream Drop Distance]. Ven never appeared to age one bit as he still looks 15 even as a 27-year-old (the castle probably had a spell casted to prevent him from ageing while comatose). And time goes much faster in the realm of darkness. Aqua still looks around 18 even after spending what to us was 11 years (KHII). I just hope that when Master Xehanort was restored to his true body, Terra will be restored to his 19-year-old self (provided that he was even revived).
Okay sure, let it be known that in this verse, Cinderella's stepfamilies are absolute monsters. But then, recall thesequels, where Anastasia would meet a baker that will slowly make her renounce her evil stepsister way and becoming a lot more decent. Everything that happened in this game takes place before that chance meeting, meaning that Anastasia was in her absolute worst and was driven to do all those things before the idea of Heel-Face Turn ever crosses her head rather than rejecting it, and then died as an evil bitch. We can certainly cheer for the deaths of Tremaine and Drizella, but maybe we could spare a tear or two for Anastasia, who cruelly received something of a Heel Face Door Slam (or rather, the door was slammed when she was far from it), and also that baker who redeems her. His life would never be the same, or if he finds a new love, it won't have the same amount of joy because he's not redeeming anything.
And if Anastasia was aware of another verse after her death (in which the sequel happened), maybe she would be crying and regretting that if she didn't bite in to her jealousy to Cinderella, her life would be A LOT better because of that sequel. Yeah.
Terra and Aqua's argument after they defeat the giant Unversed at Radiant Garden. In a somewhat of a Third Act Misunderstanding, Terra finds out that Aqua was sent by their master to spy on him, and he just walks away giving her the cold shoulder when she tries to explain why. You can just hear the anger and sadness in his voice when he finds out. The music during that scene doesn't help much either.
Terra: Just stay put! I'm on my own now, alright?!
Aqua(looking and sounding like she's about to break down crying): Terra please listen to me! it's not that the master doesn't trust you, he's just worried!