Don't get us wrong, this cartoon is generally a happy one and does a great job of being positive. However, the show also does an excellent job of making us really feel for these candy-colored ponies. You really need the sad bits to make the happy bits richer after all.
open/close all folders
The Mane Cast
The Mane Six
When asked about Applejack's parents, Lauren Faust said that she did consider the idea of them being deceased. Of course, it was deemed too sad and other suggestions were made - ranging from them being salesponies to explorers. But since the subject has never been brought up in the show, it remains a mystery until the writers choose to define it. Until that day comes, fanon continues to run with the tragic stories in particular.
Applejack's hat is commonly believed to have been passed down from her late father, hence why she seems almost inseparable from it.
Her stubbornness in Applebuck Season, where Applejack tried to harvest all of the apples alone without any help, is seen by some fans as her trying to live up to some standard she set herself between her parents passing away, and her taking on most of the responsibilities of the family business.
In Apple Family Reunion, it was confirmed by Senior Storyboard Artist Sibsy that the two shooting stars that appeared a couple of times in the episode were a nod to Apple Jack's parents. As it was said in-episode that the whole family was coming to the re-union, but we didn't see her parents at all, they could well be deceased, although it still isn't certain.
Fluttershy oozes woobie to such a degree that even PinkiePie avoids playing harmless pranks on her. In fact, the other 4 ponies have tried to be Cool Big Sisters towards her, despite being around the same age (and at least older then Pinkie).
It is considered an unforgivable sin by bronies to make Fluttershy cry. [1]
It doesn't really help that while most of the Mane 6 are known for their strengths (Be it athletic ability, amazing talents or winning personality), she's mostly known for her weaknesses. They usually play up the "shy" part of her personality a lot. In the Discord two-parter, she admits herself that she's weak and is glad that her friends point out her flaws. If she was being sincere, she seems to have a very low opinion of herself. Even The Hub labels her as "The Misfit" in their commercials.
"Hurricane Fluttershy" seems absolutely dedicated to turning Fluttershy into a woobie, what with the flashbacks to her time at flight camp and her inability to fly nearly as fast as the other pegasi helping with the tornado. It also gives her one heck of a happy ending.
Ironically, though, if you think about it, Pinkie Pie actually qualifies as a Woobie just as much as Fluttershy, maybe even moreso, she just doesn't act it. Think about it: On the surface, Pinkie is a fun-loving Genki Girl who loves to throw parties. But as someepisodes show us, she actually comes off as something of a Stepford Smiler and she throws parties as a way of validation- and she thinks that if nobody likes her parties, then nobody likes her. This alone caused her to famously and completely lose it for a short while during "Party of One". Not to mention, grew up on a Rock farm. In her own words, "There was no talking. There was no smiling. There were only rocks." And then there's how viciously Discorddealt with her. And her breaking down in Berserker Tears in 'Baby Cakes' because of the twins antics and how desperately she wanted to prove she could handle the responsibility of looking after them. (Look at her hurt and offended reaction when Twilight tells her to her face she didn't think Pinkie could handle it.) Her desperation to get Cranky to accept her friendship also called into question why Pinkie Pie wants so many friends. And then in "Too Many Pinkie Pies", she's so desperate to make her friends happy and spend time with them, she clones herself and it all blows up in her face. And in "Wonderbolt Academy", she's convinced Rainbow Dash will have forgotten about her and the others, to the point where she has to go see Dash in Cloudsdale, although she seems resigned to the possibility that it's too late. Poor Pinkie Pie...
Although she sometimes seems more like a Jerkass Woobie, Rainbow Dash has woobieish elements when you consider her talent: Winning. Winning is everything to Rainbow Dash and she almost has a breakdown in "The Sonic Rainboom" when she's scared of failing in front of her friends and The Wonderbolts. The amount of fear/desperation she demonstrates during times where she does badly at something (Has a temporary Heroic BSOD in "The Mysterious Mare Do-Well", is scared of her friends mocking her over something she loves in "Read It And Weep", wants to beat the record in "Hurricane Fluttershy" to impress Spitfire and can't) makes you wonder just how low is Rainbow's self-worth that she thinks she absolutely must be the best or she's an unlovable loser?
In Wonderbolt Academy she desperately tries to please Spitfire, being crushed when Spitfire chose Lightning Dust over her as a leader. It turns out Lightning Dust doesn't give a crap about the other recruits and would do whatever it takes to become a Wonderbolt. This causes Rainbow Dash to give into peer pressure and help Lightning Dust make a tornado nearly killing Rainbow Dash's friends. When Spitfire finds out about this, she is enraged and gives Rainbow Dash the team leader insignia. Rainbow Dash definitely needs a lot of hugging especially having a sort of Ron the Death Eater status among certain fans.
There's also her disturbing tendency to be the victim in fanfics... at least two come to mind. If you know them, you'll really want to give her a hug.
Her crushed expression when Cloudsdale, her home town doesn't host the Equestrian games is heart wrenching.
Rarity is kinda a woobie as well when you think about it. She puts so much effort on her work in the boutique and gets little appreciation most of the time. Suited For Success, and Sweet Elite definitely proved it. While she may seem prissy and a bit prim, she has the element of generosity for a reason. Not only that but despite her overdramatic breakdowns and difficult to understand at times, it's fairly easy to relate to many people whom work hard.
"Lesson Zero" implies that Twilight Sparkle was regularly teased in school as a filly, invoking this interpretation for some fans.
Even outside fan interpretation, she has a high order case of Super OCD, and (at least once literally) drives herself crazy trying to make everything perfect and appease her self dictated high standards, terrified of losing the approval of her peers and friends, especially Princess Celestia.
Spike
Spike is this to a lot of fans. Especially when he and Twilight Sparkle are like family to other each other. The reason of his woobie status is that one of his worst fears is no longer being Twilight's assistant and he often tries to help out whenever he can. Episodes like Owls Well That Ends Well and The Crystal Empire Part 2 proves that Spike cares about Twilight Sparkle very much.
Even if he isn't considered a woobie at the moment, he definitely has woobie in his future as due to his elongated lifespan, he will in all likelyhood outlive Twilight and all of her friends (including one he has a crush on) by a long way, excluding the apparently immortal alicorns.
However, since Twilight is an alicorn now, one potential source of angst may now have been eliminated.
Here's a thing to consider: Spike is pretty much an outsider in a lot of respects. Not only is he the only male character in a group of females (not that unusual), but he's the only dragon in a society of mostly ponies. A society that barely knows just what is considered normal for a dragon. At best he's probably treated as a page boy or servant and at worst he's an exotic pet. It also doesn't help that it is in his nature as a dragon to become a greedy destructive monster. This is made worse when he actually meets other dragons and has a bad experience with them due to his upbringing, making him an outsider to his own kind as well. This gives the implication that while ponies appear to be inherently good by just being themselves, in order to "fit in" with what he knows, he has to fight against his natural instincts to get to the same level of "good". So it's very easy to feel bad for him when he's left out of things.
Also no one seems to appreciate Spike when he does something good.
The Cutiemark Crusaders
Apple Bloom also qualifies as a woobie. To elaborate, before she made friends with the Cutie Mark Crusaders, she was led to believe that she was the only one without a cutie mark, right after Twist got hers. It's also implied that Diamond Tiara and Silver Spoon just love bullying her rather than bullying ponies with "blank flanks." Plus, in the episode "The Cutie Pox," she desperately wanted to earn her cutie mark so badly, she steals the "Heart's Desire" plant from Zecora to get one, without thinking of the possible consequences. All goes well until she ends up having the cutie pox and she is unable to stop performing her talents. She then confesses to what she did to Zecora and ends up as a blank flank again. Poor, poor Apple Bloom....
Look at the above woobie section for Applejack. These also apply for Apple Bloom as well, only she may have been too young to really know her parents. Granted, she has Applejack, Big Macintosh and Granny Smith, but it doesn't change the fact that she's greatly implied to be an orphan.
In some ways, Scootaloo can be seen as this, even without fan-interpretations. Within the show, Scootaloo has never been seen legitimately flying, and can only manage to hover above the ground while dragging her hooves at best. This is probably why she has a crazy obsession with Rainbow Dash, who is arguably the best flier in Equestria, to the point that she'd be her personal servant if it meant spending time with her.
This video claims that during the 2012 Brony Con, Lauren Faust said that Scootaloo was originally planned to be a character with a disabilty, and that an idea for an episode centered around Scootaloo involved the pony learning to accept that she cannot fly. While it hasn't been confirmed nor denied by Lauren Faust, leaving it's validity in the air, it has served as further fuel to the fan-theories that place Scootaloo in Woobie territory.
Another thing that makes her a target for easy Woobie-dom is the fact that unlike Apple Bloom and Sweetie Belle, she isn't related to any of the Mane 6, nor does she have any known relatives or seem to live anywhere in particular. Rainbow Dash and Fluttershy don't have any known relatives either, but Scootaloo is only a child. Naturally, fans have come to the conclusion that she's an orphan, homeless or both. To add insult to injury, there was a time when the trend of "Scootabuse" (fanart or fanfiction of Scootaloo being abused in some way, most often by Rainbow Dash) was popular. This plus the inability to fly gave rise to "Scootalove" (Fanart or fanfiction of Scootaloo being loved by somepony, most often Rainbow Dash).
Finally, we have a canonJerkass Woobie antagonist in the form of Babs Seed. Just look at her face when her blank flank is brought up and how she pathetically covers it with her tail, and it's easy to see why she chose to hang with the bullies.
Discord of all characters becomes one in the episode Keep Calm And Flutter On. He's both genuinely suprised when Fluttershy admits that she says that they're friends and then is hurt when she gets angry and denies that same friendship later after she was tricked. Just his saddened reaction alone is enough to make you want to hug him (And this is the same character that did absolutely horrible things to the Mane Cast)).
Despite thenumerousatrocities he committed in his first appearance, the revelation that he's never had a single friend prior to Fluttershy, makes it pretty hard not feel sympathy for him, especially considering that he's likely gone more than a few centuries without one. It makes you wonder if his lack of companionship took a toll on his sanity and lead him to becoming the being we saw prior to Fluttershy reaching out to him.
After the events of "Boast Busters", Trixie's career and life were ruined due to her becoming a laughingstock throughout Equestria. She turns into a Woobie, Destroyer of Worlds due to becoming bitter as a result and obtaining an Artifact of Doom that corrupts her mind to try and carry out her revenge.
Princesses
Princess Mi Amore Cadenza aka Cadance from the two-parter episode "A Canterlot Wedding". Imagine being taken prisoner on your wedding day by someone who you see taking your own form.
Worse than simply that: she was kidnapped in imprisoned alone in some forgotten mines without food or water while a shape-shifter takes her form and intends to marry her beloved so she can drain all his love for her. Even after being rescued, she has to find her way to the surface in despair (albeit with Twilight's help), witness her husband-to-be brainwashed, her aunt defeated in combat, and her home city invaded. She really has to go through a lot before she has her happy day.
Princess Celestia herself is starting to be as seen as a woobie as well. Mainly since a few people got sick of the Ron the Death Eater treatments.
Furthermore, having to banishher own dear sister for a thousand years... one wonders if she's been laughing to keep from crying all these centuries.
There's also Princess Luna, who, alongside Derpy Hooves, is one of the most popular characters despite appearing for only a few seconds in one episode of the entire first season. Fans jumped on the fact that the reason she went crazy and turned into Nightmare Moon was because she just wanted friends due to the fact that everyone was asleep at nighttime and she felt unappreciated. Until season two rolled around, one of the most popular interpretations of her was a traumatized filly who needed lots and lots of hugs and forgiveness. When she finally returned in "Luna Eclipsed," she was desperately trying to make up for her previous actions and convince everypony that she really wasn't evil anymore, but she was still afarcry from the sad little Shrinking VioletFanon had thought she was.
Still needs hugs, though. Her delivery may have serve to hide it a bit from modern viewers during that episode, but when she simply tried to address the other ponies in what is (to her) a perfectly normal, friendly fashion, consider what the other ponies' reactions to her must have looked like from Luna's perspective.
Supporting & Other Characters
Cranky Doodle Donkey is this in retrospect. Having spent most of his life wandering in search of his love, whose fate he never knew, he eventually gives up in his old age to live out the rest of his days with his distant memories. The moment he arrives in town, he gets harassed by an unwanted Pinkie Pie, briefly blinded, loses his wig, gets publicly embarrassed for his baldness, and then loses the most precious book he has to the pony who inflicted all this on him. And then he gets relentlessly chased all over Equestria and driven to paranoia by the same pony after he thought he'd thrown her out, to the point where he boards up his house and yells at her to go away. If it hadn't been for the contrived happy ending, that episode would have been incredibly sour.
Tank the tortoise. He just wanted to be loved...
Admit it, you cheered loudly when Rainbow Dash picked him!
The Crystal Ponies in general. This is one those cases where an entire kingdom can be considered to be made out of Woobies. Their memories from before Sombra ruled are gone, leaving them with only memories of being his Slave Race under such awful conditions they're absolutely terrified of him. On top of that, they spend most of the episodes in a state of complete and utter depression due to what he did to them. Is it any wonder they didn't hesitate one second to blow him to kingdom-come? Oh, and they're now a thousand years behind the rest of Equestria.