Pony POV Series/Tear Jerker

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Derpy Hooves' fate in Discord's universe. Dinky has been turned into a foal-shaped muffin, and Discord has promised to turn her back when Derpy has walked enough laps around his palace. Every day Derpy marches around the castle, starting in the morning as a foal and continuing until she's pratically undead, carrying Dinky on her back. All the while she defends her daughter-turned-muffin from hungry birds, screaming, "Not my baby," assuring Dinky she'll have enough laps soon. She's done over a trillion now...
- The audio adaptation takes Epilogue's sadness Up to Eleven.
- And now someone did a sequel to it. Everything gets even worse as the girls finally recover from what Discord did, only to learn that centuries have passed, everyone they loved is dead, often at their hooves, and they remember this only to die soon after. And oh yes, Twilight Sparkle becomes Nightmare Purgatory. Okay, they finally stop Discord and everypony is reborn into their main timeline counterparts thanks to Twilight managing to Set Right What Once Went Wrong, Twilight managing to snap out of it before she can fully succumb to the darkness, but you WILL be shedding tears.
The background ponies dealing with the mental trauma of Discord's "fun", as seen in Applejack's Healed chapter. They may be back to normal, but they aren't "better".
Applejack's heartbreak over her realization that the children she had in the "Orangejack" universe don't exist because of her choice.
- And then it gets even worse when, after Princess Gaia creates her false paradise, Applejack meets with her children from the vision. She takes the time to give them hugs and say goodbye before allowing that entire fantasy to fall apart.
- And unlike the others, she doesn't have the comfort of not knowing it's an illusion. She knows it's fake, but really wishes it wasn't. And then there's this line:

Applejack: Mama loves you. Dontcha ever forget that, ya hear?... And Ah wish this could be real.

- - Compare this to For the Man Who Has Everything. A similar situation, and just as heartwrenching.
Pretty much everything about Diamond Tiara and her mother Golden Tiara aka Screwball. Especially Discord's Mind Rape of Diamond Tiara.
- And then in "Mind Games Part 7" when we find out just why poor Screwball was sent away. To protect Diamond Tiara from her. You will shed more tears for poor Diamond Tiara then you ever thought possible.
This troper has to ask, what about when Trixie explains how she was afraid of dying into obscurity?
The Reveal about Scootaloo's Parental Abandonment...
- Speaking of Scootaloo, when Rainbow Dash accidentally snaps at her and makes her cry. The poor girl asks if Rainbow Dash is going to throw her in the Pegasus Machine (a Shout-Out to Rainbow Factory where said machine is used to melt down Pegasi fillies into rainbow goop, here it's just a story old Pegasi tell the fillies to get them to behave). Thankfully, it's followed by a Crowning Moment of Heartwarming.
Applejack reading about Mimic's horrific death is sad enough, but then she realizes there are tear stains on the paper from where Luna cried while writing the account...
Fluttercruel being prepared to fade away into nothingness, fully prepared to die and leave Fluttershy alone... Then realizing her well-intentioned last lesson has turned Fluttershy to evil and made her into a Knight Templar. She ends the chapter sinking into darkness as she tries as hard as she can to undo it to no avail.
- The author has expressed fear that he's alienated a good portion of his readers with this and felt the need to reassure the readers it was just a Cliff Hanger, not a Downer Ending. That is how tragic it is.
- And now, someone made a comic of it.
In this troper's opinion, when Applejack snaps herself out of Princess Gaia's fantasy and sees all of her friends under the effect of Gaia's mind control -- then realizing how hard it must have been for Twilight to go through the same thing when they were under Discord's influence.

Applejack: Twi', is this what it felt like for you?

- It's even sadder in picture form.
Princess Gaia's POV in the beginning of "Teacher Teacher". She just sounds so unwell, practically as if she knows there something wrong with her. And what's more, it's quite genuine-it's her insanity that turns her intentions into something so horrific.
One of the things Applejack sees when she looks into the Truth is an Alternate Ending to Story of the Blanks. Alternate!Applejack practically tears Everfree Forest apart trying to find Applebloom, and when she finally does, the poor girl is a traumatized zombie pony. Alternate!Applejack's reaction is perfectly understandable...
- When entering Princess Gaia's lair, the group comes across the residents of Sunny Town, who have been made to forget their past actions and happily working for Gaia... Until Applejack looks them in the eye. Their reaction to remembering how much they'd cared for Ruby and then killed her will make you feel sorry for them despite of what they did. Especially Mitta, who was already wracked with guilt in the game itself and even moreso here.
- It gets even worse if you pay attention to the blink-and-you'll-miss-it comment in the chapter centered on Luna, where we discover that it was Nightmare Moon who originally cursed and destroyed Sunny Town and its inhabitants. And the town itself? Was created by Celestia to try to give ponies a perfectly happy life. Now think about what Princess Gaia is doing...
- Even worse? Discord planned to Yank the Dog's Chain with them during Luna's sidestory by breaking the curse for a day or two, allowing them to think their curse was over, only to have it return so he can see the looks on their faces.
- And now that Princess Gaia/Nightmare Whisper has been 'dealt with', the ponies of Sunny Town returned to their normal condition... with each and every one of them screaming and begging to be saved by Princess Gaia as they go. "No! Not this again! Please, Princess, we'll do ANYTHING if you save us!"
The audio adaptation of Applejack's Discording. The original was sad enough, but just how broken the voice actor manages to make her sound makes it much sadder.
- Same goes for the adaptation of Pinkie Pie's Discording. It gets especially heart-rending when she reaches the the lines, "I hate laughter! I HATE IT!", and we realize just how utterly shattered Pinkie is by Discord's actions.
  - It made this troper feel like crying because of how close to home it hits. Especially the "NO ONE TAKES ME SERIOUSLY UNLESS THEY HAVE TO!" line.
- The adaptation of Fluttershy's Discording is equally as heartwrenching. The voice actor and the music just put such a feeling into the point when Discord does his Mind Rape that, even though Fluttershy's voice doesn't change that much, it changes with just enough subtleness to make it absolutely chilling and heartwrenching.
- Rarity's discordification is both this and Nightmare Fuel, as you can practically hear her going totally insane throughout.
StarSong's Heroic Sacrifice followed by Pinkie Pie desprately pleading Anarchy to restore her and erase her instead.
- StarSong's willingness to sacrifice herself for her friend counts doubly, as she knows that Pinkie probably won't even remember her after she's gone (it turns out Pinkie was allowed to remember her friends, but StarSong didn't know that would happen).
- Scratch that, the entire side story. Generation 3.5 gets a lot of hate from fans, but as the author points out, it did have its good points.
Nightmare Whisper. She's a horrifying monster, to be sure, but from the context of the event, it's also shown that she's ashamed of what she really looks like. It's almost as if there's enough Fluttershy left to be horrified at what she's become...
The Mane Cast having to fight their best friend turned Nightmare is just downright heartwrenching. As if that weren't enough, there's this line from Twilight when she thinks of what it was like for Celestia to be in the same position 1000 years prior:

Twilight Sparkle: 'Princess ... Is this what is was like for you?'

- Also, Rainbow Dash and Rarity feeling like that they have no choice but to use lethal force against Nightmare Whisper, both of them believing that Fluttershy would rather be dead than seeing what she has become.
Fluttershy, no longer Nightmare Whisper, still holding on to the pain and suffering of all of Equestria, refusing to let go so that others won't have to feel it. In what is also a moment of heartwarming, Pinkie Pie voluntarily taking up the burden as well, so that Fluttershy does not have to bear it alone. Just imagining what these two are going through is hard enough...
- Also Twilight (along with Rarity, Applejack, Rainbow Dash, and Trixie) helplessly watching their two friends literally torture themselves and trying to find some argument, any argument that will convince them to let go before the suffering destroys them.
Twilight almost breaking down in tears in reaction to Celestia's plan to use a tabloid article to paint herself as the Big Bad of the Princess Gaia incident so that Fluttershy can simply move on. She just can't bear the idea of her mentor and mother figure taking such a burden on herself. It doesn't help that two scenes before, Twilight outright says Celestia is like a mother to her.
Pinkie Pie finding a toy version of Generation 3.5 Ponyville, and recognizing it, talking about how she misses her old friends. Poor filly.
Subtle, but Trixie's reaction to Twilight calling her a "half-dirt unicorn" (for good reason, but still). Not so much what her reaction is but the fact she has that reaction. She takes it very hard, which rather heavily implies she's been a victim of Fantastic Racism for her race. Combined with the other things that she's gone through, it makes her quite the tragic character.
Spitfire revealing how Discord tortured her and the other Wonderbolts. She herself had visions of the other Wonderbolts, her parents, and her old flight teacher laughing at her and telling her she'd make a better flying clown than a performing Pony. On top of this, she also reveals that Fleetfoot got Discorded and brokedown crying when telling her, feeling like Discord violated her.
Orangejack revealing how Discord Mind Raped her. He made her drag her children around like ragdolls, treating them like toys and not even realizing she's hurting them. Orangejack even doubted if she was a good parent because of it.
- In the same chapter, the Cutie Mark Crusaders in the universe where the Mane Cast have basically created Brave New Equestria. Sweetie Belle literally begging Rarity to let their parents out of the reeducation camps, Apple Bloom reading off the lists of all the 'problems' for them to fix while trying not to think about them, Scootaloo being utterly abused by Rainbow Dash; the last of which is made all the worse after all the chapters of Dash being the epitome of Cool Big Sis.
  - You forgot to mention how Dash makes Scootaloo wear a jester outfit. Yes, this version of Dash is proud to let all Equestria know that she considers poor Scoots to be a total joke!
Just before being turned back into an adult, Golden Tiara realizes what will happen to her. She tells Celestia that she doesn't want to go and desperately pleads that she doesn't want to stop understanding, that she wants to see her "little princess" Diamond Tiara and her "prince" husband. Celestia is badly tempted to let her stay a foal, but ultimately decides against it.

Celestia: Everything won't be confusing forever. I promise you'll get better. I promise you'll find your way through the fog and find your family waiting for you. You'll become a stronger self. And hopefully, being reminded of the good times he had with you will help your prince guide you out of your fog....You're not dying, you're just becoming something new. I promise, what makes you 'you' will never disappear. You're not vanishing, you're growing.

It's not exactly "official" but this gives us a heartbreaking portrayal of how Princess Celestia was corrupted.

Celestia: He's right… Even… Even Twilight is afraid of me… The pony I love like a daughter is afraid of me… Terrified of me… They're all… They're all terrified of me…

"Butterflies Celestia" has the reveal that Celestia is really the G3 Pony Star Catcher, or at least remembers being her. Not only does this mean she's probably been through what Pinkie was, it also explains that her mother broke the immortality spell on herself by given birth to her, Celestia having to watch her own mother grow old and die right in front of her with no idea why except it was her fault for being born. Ouch...
Onyx Tiara's entry in the "Butterflies" series, detailing how his wife was gradually broken down by high society snobs.
- Even worse are the effects of his Discording: any pony he touched turned into a physical replica of her, allowing him to surround himself with a harem of mindless Replacement Goldfish... and when his real wife appeared, he rejected her.
- The way his Fantastic Racism colors his commentary is heartbreaking in its own way. To see a stallion consumed by so much hatred -- let alone one who canonically is a Good Parent and anything but a close-minded Jerkass -- that he rejects whatever help presents itself, including from Applejack, who should have been a family friend...!
- Diamond Tiara's POV in the same entry is even worse, and Screwball's drives the knife home.
  - And in the most recent entry, we see just how much Onyx Tiara misses his wife and daughter, and it is heart-rending. We also learn that he respects mules and donkeys, and supports civil rights groups working for better rights for sheep and cows.
The whole "Generation Transition" parts 2 and 3. Especially the song from the third part...
- MINTY! *breaks into tears*
- And after that, Pinkie coming across a severely wounded, dying Rarity. She tells her everything will be alright and they'll be back having a party with their friends, even though she knows its a lie.
We also see how Discord was born into the current version of Equestria. He's a bit of jerk growing up, but he loved his mother, lacked his normal cruelty, and was able to be happy and kind... until he met his real parents or memories of them. He tells them,

"Stay away from me! Go to Pony Hell!"
And they gleefully tell him:
"Child... You ARE the Gates of Hell!"

- Good!Discord is promptly consumed by Evil!Discord and reverts back to his true, evil nature, those who were his friends before he returned to his true nature left at a complete loss at what to do about their Evil Former Friend. His earthly mother? He exploits her Mama Bear nature to turn her into his loyal Dragon. 1000 years later, she finally realizes it has to end, sheds a Single Tear and, in her mind, helps Celestia and Luna Shoot the Dog.
  - Let's be honest; EVERYTHING about Origins belongs here.
"New Game Plus" manages to pull this off. Did you know that New Fluttershy's "The Reason You Suck" Speech in "Putting Your Hoof Down" could've been worse? Welllllll...
"Mind Games 7" has a series of flashbacks to when Diamond Tiara's mother went insane. Remembering it is enough to more or less finish breaking Diamond's mind.
And then in "Mind Games 8" Screwball finally recovers her sanity... and remembers everything she did or tried to do to Diamond Tiara. And she is reduced to sobbing hysterically as she begs for somepony, anypony, to tell her that it isn't true. And oh yes, just in case that didn't tear your heart out enough in that chapter, Discord shows Diamond Tiara what would have happened if she hadn't rummaged around in her mother's jewelery case. Basically, her mom got the help she needed; her father never became a racist conspiracy nut; she and Silver Spoon never became bullies and ended up friends with the Cutie Mark Crusaders; and DT was just plain happy. But no, she made the choice she made, so everyone's life became a total hell and it's ALL. HER. FAULT. Or at least that's how Discord set it up to look like from her POV. And the best part? This little revelation turned Diamond Tiara into a Nightmare!