My Little Pony: Friendship Is Magic already has plenty of characters that qualify as the Woobie. This series is no different...
- Flash Sentry was originally dropped off at an orphanage by his biological parents, but the orphanage eventually caught on fire and forced Flash to flee and live on the streets, which is a memory that haunts him later on in life. With no one else to look after him, he was forced to get by in life by stealing food from restaurants and living in a treehouse, until he was taken in by Twilight Sparkle's family. Even so, he still faces threats that emotionally destroy him, from witnessing Discord corrupting all of his friends, being scarred for life by King Sombra, having Cold Steel harshly reprimand him for having no reason for being a Royal Knight, and experiencing a nightmare where all of his friends are killed and blame him for their deaths.
- Grand Hoof definitely qualifies as an Iron Woobie. His wife, Live Wire, was killed in an accident and it ultimately strained his relationship with his son, Doom Raizer. Then, his daughter-in-law, Daisy Chain, was killed in a mugging, which drove Doom Raizer into creating the Thunder Tomb, but the weapon was deemed too dangerous by Celestia and thus Grand Hoof was forced to arrest his son. However, Grand is soon alienated by his grandson, Lightning Blitz, who grew jealous that Grand Hoof chose Flash Sentry as his apprentice over him, which drove him to use the Alicorn Amulet, corrupting him to nearly destroy Canterlot and be exiled from Equestria after his plan failed. Despite all of this, Grand Hoof has still maintained his Cool Old Guy attitude and, thankfully, Grand Hoof's situation has been improving recently, as he's now found an appropriate apprentice in Flash Sentry and he eventually reconciled with Lightning Blitz.
- Iron Core was orphaned as a child when Longhorn murdered his parents for refusing to abet him by making weapons. When Longhorn escapes imprisonment and he tracks him down, he gets beaten near to death by Longhorn, who then proceeds to beat Fluttershy in front of him, the one pony that helped him break out of his stoic behavior.
- Skybreaker was initially a cocky Royal Knight who didn't take his duties seriously, until he was outmatched by a unicorn with powerful sword abilities. The unicorn cut off one of his wings and nearly killed him, until his mentor sacrificed himself to save Skybreaker, leaving him traumatized and covered in his mentor's blood. This resulted in Skybreaker taking his duties more seriously, practically to a fault when he doubts rookie Royal Knights like Flash.
- First Aid lived with his father in a small village when he was foal, but then his father contracted an unknown disease, which First Aid couldn't do anything about. His father suffered for several weeks before he died, which would eventually drive First into traveling around Equestria for three years to find a cure to every disease.
- Heather Bloom was once an innocent foal who was unaware that her parents contracted a deadly disease from a flower called the Vitiosus Viola and died. When First diagnoses them as deceased, Heather is practically wailing and screaming for her parents to "wake up," all to no avail. Even worse, she had no other family to look after her and would've probably remained alone if she hadn't traveled alongside First Aid.
- Ruby Scarlet shares the same tragic backstory of Radiant Hope, watching her friend, King Sombra, become corrupted and seemingly murder her Parental Substitute, Princess Amore. Despite condemning Sombra for his crimes, it's clear that she still anguishes over their former friendship and even makes an Anguished Declaration of Love to him, which still isn't enough to make him repent.
- Tidal Wave used to travel with his family on the seas, until their vessel was raided by pirates. To save him, Tidal Wave's father placed him in a barrel at sea, in which the rest of the family was killed when the pirates sunk their ship, leaving Tidal alone at sea for days until he was picked up by another ship. Despite seemingly recovering from this tragedy, this old wound emerges again when he faces Foggy Dreadbeard and his crew, in which he acts uncharacteristically brutal with them, showing that he's still yet to overcome his tragedy.
- Cold Steel witnessed his village get destroyed and exterminated by a group of bandits, whom killed his parents as well and nearly killed him until he used his magic to defend himself. After that, he was forced to wander the Equestria North for years on end, until he was finally picked up by Noble Banner, whom became his mentor. However, he lost Noble too when he was mysteriously killed by Storm Blade, which drove him to become the cynical and stoic pony he is today.
- Trixie Lulamoon was sent by her father to the Manehattan Institute for Magical Learning, in which she couldn't meet the high standards of the school and forced to drop out. This immensely dissapointed Trixie, whom was forced to travel around Equestria and put on a boastful veneer to seek appraisal from any pony.
- Soarin always looked up to Wind Rider for being the one that inspired him to become a professional flier in the Wonderbolts, but he suffers a major Broken Pedestal moment in "Rarity Investigates!". First, Wind Rider acts extremely hostile to Rainbow Dash for seemingly sending Spitefire away so she could fly for the Wonderbolts, in which he takes every opportunity to denounce her relationship with Soarin, implying that she only became accepted by the team by sleeping with Soarin, which already ruins his perception on him. When Rarity and Rainbow Dash reveal that Wind Rider was the true culprit, Soarin loses all respect for his former idol and wonders if all of the advice he was given by Wind Rider was based on a lie.
- Lightning Blitz felt overshadowed by Flash Sentry when he was chosen by Grand Hoof to be his apprentice. When he nearly destroyed Canterlot under the influence of the Alicorn Amulet, he was exiled from the city and forced to travel around Equestria. When he redeems himself, he is still met with hostility by many ponies, especially those from Canterlot, and he is only finally accepted when he and his friends save the city from Bomber, Shift, Gemini, and Kinetic.
- Discord, oddly enough, qualifies as well. Ever since his existence, nopony wanted to befriend or even interact with him, which drove him to crave attention, even if it meant drawing the ire and fear from others. This is further compounded when Flash gives him a "The Reason You Suck" Speech in "Detective Discord," after he unwittingly let the suspect get away, in which Discord can only listen to said speech, sadly admit that he'll never change, and storm off.
- Toxic Fang developed fangs and poison early in his childhood, alienating him from everyone, even his family. Eventually, the other thestrals drugged and mauled him, which nearly killed him.
- Hiveena was treated like a daughter by Chrysalis when she was born. However, Chrysalis feared that she would eclipse her in power and overthrow her, so she ordered her execution, forcing Hiveena to flee the hive and wander around Equestria, with no one else that would look after or love her, which would drive her into becoming Doom Raizer's servant.
- Doom Raizer lost his mother, Live Wire, when he was just eight years old and then lost his wife, Daisy Chain, in a mugging, which drives him to create the Thunder Tomb to protect Equestria. However, the weapon was deemed too dangerous by Celestia and thus she and Grand Hoof shut down the project and apprehended Doom, which finally drove him on the path to villainy.
- Evil Flash qualifies as a Jerkass Woobie. Even before his corruption, he was more selfish than the Prime version of Flash Sentry, but he was still a homeless orphan that barely survived on stealing food scraps from others in Canterlot. Eventually, the Canterlot restaurants began employing runes that made it impossible for Evil Flash to steal any more food, forcing him to leave Canterlot and steal food from other towns, in which he was never able to find a permanent home. Eventually, he was caught riding the Friendship Express without a ticket, so he was kicked out in the northern parts of Equestria and left to freeze to death, until he was corrupted by King Sombra. He was later caught in the time travel plot by Starlight Glimmer, in which he's been stuck in the same time loop of ten years every time the past is changed for over a hundred years. While Evil Flash is certainly heinous, he's been through a lot.
- Shadow Corrupter himself qualifies as a Woobie. Initially, he was an innocent foal who lived in a small village, until his parents tried to sacrifice him to revive the Corrupted Shadow, in which all of the cult members cut him with sacrificial knives. The process completely backfired and drove Shadow Corrupter into becoming the villain he is today.
- Tempera never received any love from another pony, not even her emotionally distant parents. Eventually, her parents forced her to marry Haunt Monde, a narcisstic misogynist who disregards her love for art and wanted her to Stay in the Kitchen. Upon recognizing that her parents don't truly love her, she ran away from home and was recruited by Shadow Corrupter, where she tries desperately to win his affection, but often fails and at most receives indifference from her master.
- Spike certainly qualifies as one in "Spike's Heartbreak". It starts with him hoping to spend his day off with his crush Rarity and all goes downhill for him from there. He finds what he thinks is Lightning Blitz trying to rape Rarity and attacks him to "protect" her, only for Rarity to stop him and reveal to Spike that the two of them are dating. This absolutely destroys Spike, and he runs off in tears, with Springer even claiming he could feel the sorrow coming off of him, and he is unresponsive to anyone trying to comfort him and cheer him up with his favorite things. He eventually gets the idea to try to change himself to something that Rarity will love, such as begging Twilight to use a spell to change him into a pony and running into the Everfree Forest by himself in the hopes of being recognized as a hero. Of course none of these attempts are successful. After a talk with Lightning, Spike is forced to admit he was deluding himself and his crush was never really going to work out. Though he starts to move on by the end of the chapter, a small part of him still hurts from the experience.
- Fire Heart has been through multiple traumatic events since his introduction, but what ultimately makes him one is what happens in the Season 8 finale "School Raze". Fire Heart has had a pretty obvious crush on Cozy Glow ever since he first met her and has slowly bonded with her over the course of the story. But then in the finale, Cozy betrays him and his friends with her plot to rid all the magic from Equestria, with her even trapping him and Soul in the same sphere of magic she has Starlight in. Heart tries to beg Cozy to stop, even wondering if someone is making her do this, but Cozy just says nobody is forcing her. Cozy offers Heart the chance to join her, stating once she is ruler she can officially knight him and they can keep having fun together, and if they decide to try being an official couple and like it, they can get married and Heart can be a King one day. Heart seems tempted by this offer, but ultimately rejects to stay loyal to his sister and friends, and Cozy has no problem leaving him to his fate in response. Although Cozy is defeated in the end and the day is saved again, it is noted by a few characters that Heart is not okay after all this. He is left heartbroken and devastated over his crush's betrayal and declares he is never letting himself get that close to anyone ever again.
