History Woobie / WebOriginal

* in ''WebOriginal/VesterAndFriends'' Yellow Yoshi Jr really wants be like his dad but since he is too stupid to do anything right his father frequently abuses and humiliates him.

** Junior himself can be this sometimes, specifically in the ''Bowser Junior Goes To Military School!'' mini-series [[TheChewToy where he gets tortured far beyond normal]] by Sergeant Brooklyn T. Guy. He is forced to squirt hot sauce in his eyes, watch ''Disney/BigHero6'', have Thomas burn in a fireplace in front of him, and eat dirt before breaking both physically and mentally. Thanks to Joseph and Cody though, he restores his original side at the end.

** Two, an emancipated [[KabbalicGolem golem]] who, despite her ostensible free will, enters the story with an incredibly flat affect - a sign of severe emotional damage. The cause of this eventually becomes clear; most golems are freed with a full if inexperienced personality but Two was given only one fundamental drive - she wants to do what she is told, whether she likes it or not. This makes her the victim of a horrifying array of abuses, the full extent of which is only implied. Since falling in with some of the kindlier inhabitants of Harlowe Hall, she has gotten better. Still desperately needs hugs, though. About a week of in-story time in, we got to see [[http://www.talesofmu.com/story/other/bonus-story-diary-of-a-golem-girl Two's diary]]. She needs so many hugs.

** Two, an emancipated {{golem}} who, despite her ostensible free will, enters the story with an incredibly flat affect - a sign of severe emotional damage. The cause of this eventually becomes clear; most golems are freed with a full if inexperienced personality but Two was given only one fundamental drive - she wants to do what she is told, whether she likes it or not. This makes her the victim of a horrifying array of abuses, the full extent of which is only implied. Since falling in with some of the kindlier inhabitants of Harlowe Hall, she has gotten better. Still desperately needs hugs, though. About a week of in-story time in, we got to see [[http://www.talesofmu.com/story/other/bonus-story-diary-of-a-golem-girl Two's diary]]. She needs so many hugs.

** Taylor's Woobie status is at least mitigated by her [[{{Determinator}} fortitude]] and numerous [[CrowningMomentOfAwesome crowning moments of awesome]]; Canary and Amy Dallon are purer examples of this trope.

* ''WebVideo/TenLittleRoosters'' has Chris, who seems to be trapped in his own little ''Literature/LordOfTheRings'' fantasy. It gets worse when you find out that he most likely blames himself for his parents' divorce, ''nobody'' in the company likes him and, worst of all, [[spoiler:ends up pulling a HeroicSacrifice saving Burnie from a hail of arrows after Burnie gives him a TheReasonYouSuckSpeech.]]

* Raven Queen of ''Franchise/EverAfterHigh'' webisodes, she's treated as a villain simply because her mother was an evil queen, even though she's really far from anything like her mother.

* ''WebVideo/TenLittleRoosters'' has Chris, who seems to be trapped in his own little ''Franchise/LordOfTheRings'' fantasy. It gets worse when you find out that he most likely blames himself for his parents' divorce, ''nobody'' in the company likes him and, worst of all, [[spoiler:ends up pulling a HeroicSacrifice saving Burnie from a hail of arrows after Burnie gives him a TheReasonYouSuckSpeech.]]

* FeliciaDay's character, Codex, in ''WebVideo/TheGuild''.

** As for NPCs, the helpful, {{Adorkable}} mapmaker Tyriok [[spoiler: loses an arm]] after Vox Machina finds him [[spoiler: turned to stone]] and they botch their attempt to fix him.

** And, of course, there's resident IronWoobie Percy, whose entire family was killed [[spoiler: but for his sister]], and who suffers through torture, betrayal, a bad case of DemonicPossession, the [[MyGodWhatHaveIDone guilt of having invented the universe's first firearms]] and even ''[[spoiler: his own death]]'' without giving up. Incidentally, he's played by Taliesin Jaffe, a former child actor whose role in ''Film/MrMom'' might have been the TropeNamer for the Woobie. He gets [[OldShame slightly irritated whenever it's brought up at the table]].

** Jay only wanted to look through the tapes from his old college friend's scrapped student film to try and find out why the project was abandoned in the middle of production. The result? Well, being stalked by a [[SlendermanMythos tall, faceless abomination]] turns out to be the ''least'' of his problems when he starts losing huge chunks of his memory and people are disappearing around him. By the time he finally meets up again with Tim, he's been living in a hell of paranoia and fear by himself for nearly ''four years''.

* Probably the point of the Grey Faerie in ''Franchise/{{Neopets}}''.

* In the ''Franchise/{{Neopets}}'' "Tale of Woe" plot, Bruno is a handsome, if gangly, young [[Characters/NeopetsSpecies Gelert]]. When [[SnakeOilSalesman Mr. Krawley]] offers him a potion that will make him stronger, he accepts it because he is desperate to impress his love interest. Unfortunately, he was tricked as the potion came with the side effect of turning him into [[TheGrotesque a grotesque monster]]. In the end, when an antidote is found, it does not work on him. It is assumed that this is because he's been under the effects of the potion for too long. He accepts his fate, saying that he is used to the way he looks now.

* In the ''Franchise/{{Neopets}}'' "Tale of Woe" plot, Bruno is a handsome, if gangly, young [[Characters/NeopetsSpecies Gelert]]. In an effort to impress his love interest, he took a potion from [[SnakeOilSalesman Mr. Krawley]] that made him stronger. Unfortunately, it also came with the side effect of turning him into [[TheGrotesque a grotesque monster]]. In the end, when an antidote is found, it does not work on him. It is assumed that this is because he's been under the effects of the potion for too long. He accepts his fate, saying that he is used to the way he looks now.

* In the ''Franchise/{{Neopets}}'' "Tale of Woe" plot, Bruno is a handsome, if gangly, young [[Characters/NeopetsSpecies Gelert]]. In an effort to impress his love interest, he took a potion from [[SnakeOilSalesman Mr. Krawley]] that made him stronger. Unfortunately, it also came with the side effect of turning him into a grotesque monster. In the end, when an antidote is found, it does not work on him. It is assumed that this is because he's been under the effects of the potion for too long. He accepts his fate, saying that he is used to the way he looks now.

* '' TheWoobie/UltraFastPony''

* Church from ''Machinima/RedVsBlue'' has gone from ChewToy in Blood Gulch Chronicles to either this or an IronWoobie in later seasons, due to the [[CerebusSyndrome tonal shift of the series]]. As Alpha, he's tortured with endless scenarios in which everyone he cares about dies and he can't do anything to help, so he splits off all the different facets of his personality into other AIs in order to cope. Then, with no memory of this, he's quietly stuffed in a useless backwater canyon where no one ever goes, gets "killed" by his own teammate, loses the woman he loves, and gets killed (for real this time) while stopping the BigBad. Then, as Epsilon, he meets the woman he loves (rebooted), gets betrayed by her just so she can face-off with the BigBad, loses her ''again'', gets trapped inside his own memories in a desperate attempt to find her, meets her '''again''', finally realizes he has to let her go in order to be at peace, then gets ripped out of his memories and back into the real world just as he comes to terms with all of his problems. And on top of all that, he finds he's been replaced in his friends' lives by the series' ''other'' IronWoobie, Agent Washington. Flashbacks show Wash as a (somewhat uptight but) [[WideEyedIdealist generally nice, slightly naive guy]]. Unfortunately, he's been so beat up, shoved around, betrayed and generally stomped on (usually by his own former partners) that in the present he's a [[ComicallySerious humorless]], [[DeadpanSnarker sarcastic]] AntiHero who readily commits his own betrayals if he thinks it'll secure him some peace for once. If Command has a keyboard shortcut for Caboose's team kills, they've also got one for Washington being shot in the back.
* The title character of ''SailorNothing''. Let's face it, when one's happiest moment in her life is realizing she no longer is tempted to ''slit open her wrists with her dad's razor'' when she wakes up, she needs a hug. ''[[ThereAreNoTherapists Badly]]''.
* A lot of abused/outcast characters tend to get this treatment among the users of ''SurvivalOfTheFittest''. For example, in v3 Matthew Wittany tends to receive considerable sympathy from a number of SOTF handlers, primarily because he's just such a complete {{Buttmonkey}} and treated harshly by so many of his classmates when he's mostly just looking for friends on the island. Nanami Nishida from v1, despite being insufferably annoying and nearly killing fan-favourite Madelaine Shirohara, got looked upon this way (if [[spoiler:posthumously]]) in retrospect and after people realized just how hard she had it living in Madelaine's shadow. Especially when [[spoiler:killing her]] caused a HeroicBSOD for Madelaine.

* Jake from the VideoGame/{{Minecraft}} Machinima {{Newbies}} has generated a lot of much deserved sympathy among fans for the way he is treated in the show. He shows up as a very friendly player who is using the Mine Little Pony mod to look like a cyan Pegasus. The newbie is afraid of him and Joe tells him to "Just ignore him and he'll go away." After Jake continually tries to get their attention, Joe demands that he go away and that nobody likes him. Jake plays this off like its okay, and is later seen alone in his house playing "The Way it is" on his music box.

* Andrew Tinker of ''TheMadScientistWars'' had his dad die, his cousin and first friend leave with no explanation (and harsh enough words that he repressed memory of ever knowing him), at ''14''. Not to mention said cousin, Desius, being an even ''bigger'' woobie who had a... [[TykeBomb horrific]] childhood, that ended when he got adopted by Andrew's uncles before having to leave, and forcing himself to deliberately hurt Andrew so as to keep him from getting hurt following him. Let ALONE what happens later in life.
** Chic Geek counts as well, especially with recent developments. Note that she's Cousin to Andrew and Desius - seeing a theme?
* ''WebAnimation/HomestarRunner'':
** Strong Sad. Though some of his status as a NoRespectGuy is fairly amusing, it's hard not to feel sorry for him given the regular abuse, much of it physical and some of it ''life-threatening'', [[BigBrotherBully his brothers]] put him through, the fact that he has no real friends at all (with Marzipan seeming to hang out with him mainly because ''she'' feels sorry for him and Homsar being too insane to notice), and his [[TheEeyore chronic depression]]--though this is dampened slightly by the fact that he sometimes feels the need to depress everyone else too, [[CharacterizationMarchesOn mostly early on]]. [[spoiler: One very obscure EasterEgg makes it even worse, by showing that he and Strong Bad once got along.]]
** Also Coach Z, no doubt thanks to his {{Flanderization}} from a well-meaning, but somewhat quirky coach into a colourblind, forgetful, perverted moron who thinks he's a mother. In ''Decemberween Short Shorts'', it's been shown that he spends Decemberween locking himself in his locker and drinking nothing but Listerine. Just wait until you see Baby Coach Z. The 2009 Halloween 'toon has Strong Sad alternating between wishing horrible dooms on his "friends" after not being invited to any of their parties, and [[spoiler:staging a surprise party for himself with cardboard cutouts of them]]. However, even he can't come up with a doom for Coach Z besides being Coach Z. "No sense in beating a dead horse."
** Reynold from the ''Cheat Commandos'' might fit the bill also.
** Parodied with the Strong Bad-created character Lil' Brudder. Explicitly designed to be as Woobie as possible� a hard-working, optimistic, unipod dog "with the heart of a champion� so Strong Bad can abuse others with tales of suffering. However, [[HoistByHisOwnPetard even Strong Bad feels sorry for the guy]]. His catchphrase is "I can make it on my own!"
** A case could be made for What's-Her-Face in ''WebAnimation/TeenGirlSquad''. Since the series is based on off-the-wall (even by ''Homestar Runner'' levels) humor centered on the characters dying in silly ways on a regular basis, this is saying something.
** New Paper. It's a ReplacementScrappy in-universe; its first five appearances all feature Strong Bad mocking it basically for not being The Paper. It also seems to be [[{{Dojikko}} rather prone to errors]] during this early period; in those five emails it comes down prematurely, runs a calibration test when it was supposed to print the FourthWallMailSlot email link thingy, and upon a request from Strong Bad to disappoint him it falls out of the printer. Then in the next email it prints The Paper's striped pattern and perforated edges onto itself to please Strong Bad (who seems to think it's trying to ''impersonate'' The Paper, but it "does make [him] feel a little better"). Altogether very {{Moe}}. Mind you, a handful of emails later the New Paper aids and abets Homestar's hostile takeover of the email-show niche, which makes it a little harder to sympathise with it. You could see that as the New Paper trying to get back at its verbally-abusive master, [[DownerEnding but that just makes things worse.]]

* Frances J. Worthington III from the ''Sims 2'' story [[http://strange-tomato.livejournal.com/26887.html Strangetown, Here We Come]] is the epitome of woobie. Especially when [[spoiler:he is rejected by his crush Tank Grunt, who he had secretly been pining over for months, and has a huge emotional breakdown.]]
** It's even worse because of his eyebrows (Okay, so he's Maxis made- but the author puts them to good use!) which make him look perpetually sad.
** Nervous Subject too. Personality-wise, his name pretty much says it all; that, and until [[spoiler:Olive sets their house on fire, killing them]], the people he lives with make a point of subjecting him to pretty much the worst living conditions they can possibly dream up.

* Gino Gambino is the king of this trope on ''Website/GaiaOnline'', subjected to neglect and [[WeirdnessMagnet shenanigans]] by his father for years, yet unwilling to so much as protest this treatment.

* On Website/DeviantArt - [[http://le0patra.deviantart.com/art/Eyeless-and-Starving-141195101 That]] [[http://le0patra.deviantart.com/art/Come-Over-Here-and-Help-Me-138442435 poor,]] [[http://le0patra.deviantart.com/art/Tail-cut-off-132221755 poor]] [[http://le0patra.deviantart.com/art/A-Slave-lion-Being-WHIPPED-132221539 lion]] from Leopatra.

* A few people who watched ''WebAnimation/SaladFingers'' think he is just too creepy, and others find him creepy but also endearing. The last episode has a scene where he's crying and some fans said they forgot he's scary because they felt bad for him.

* ''{{Literature/Worm}}'': Taylor is an [[TheFettered idealist]] in a world which practically breaks the SlidingScaleOfIdealismVersusCynicism and damn does [[NotEvilJustMisunderstood she]] suffer for it. Any time that things might be starting to look up, [[FromBadToWorse they don't]].
* Draco comes across as a bit of a Woobie in ''[[AVeryPotterMusical A Very Potter Sequel]]''. Just try to watch the scene where he's writing a letter to Lucius without wanting to give him a hug. Doesn't help that Lauren Lopez has some of the biggest puppy dog eyes I've ever seen....
** Starkid gives us Duder in ''LittleWhiteLie''. A fairly decent, honest guy is dragged into lie after lie by his pushy, {{Jerkass}} sister, then he gets awkwardly shot down by... Lauren Lopez's character, Tanya.
* 80% of the protagonists of various [[SlenderManMythos Slendyblogs]] tend to come across as Woobie-ish. Most notable are probably Noah from WebVideo/TribeTwelve, [[DamselInDistress 'Damsel']] from WebVideo/EverymanHYBRID and [[spoiler:the young Vincent from the Bag in the same ARG]].

* Waluigi from ''ThereWillBeBrawl''. Being a ManChild who Wario keeps locked in a pen would be bad enough, but Wario [[spoiler:using him to deliver a bomb to kill Red, and Waluigi ''never realising what he is doing is wrong'']] is what really clinches it.
* {{Fred}}: Funny or not, sometimes one has to feel bad for that poor kid.
* [[http://failbook.failblog.org/2011/02/15/funny-facebook-fails-sometimes/ This]] poor guy. Daaawww.
* The titular character, Lenny Penguin, in ''LittleLennyPenguinAndTheGreatRedFlood''. He was, until later in the beginning, damned to spend the rest of eternity alone in endless blankness even though he would eventually get out anyway and was ''destined'' to do so in the first place. And ''then'', out of pure curiosity, he enters a Time Crack and is sent to an otherwise terrifying DarkWorld full of equally terrifying {{Eldritch Abomination}}s. Talk about unfair...
* Allison Amber suffers heavily from this trope in ''Webcomic/{{Sonichu}}: [[AnimatedAdaptation The Animated Series]]'', a series of web cartoons that both rip off and rip on the infamous Webcomic/{{Sonichu}} webcomic. Poor Allison is depicted as a BeleagueredAssistant who somehow tries to deal with the fallout of the insane decisions [[TheCaligula Christian Chandler]] makes as Mayor of [=CWCville=], like his order that the [=CWCville=] waterworks circulate orange Fanta soda pop instead of actual water, which is the main reason some part of [=CWCville=] is always on fire. Even that's not as bad when Chris essentially forces Allison to clean him up whenever he soils himself, which is quite often. Allison appears to cope with having to clean Chris up by muttering over and over how much she hates her life, while her face has a glazed, vacant expression.
* [[WebOriginal/ProtectorsOfThePlotContinuum Ithalond]]. He's the Ithalond from ''Celebrian'', and even after being recruited to the PPC he is a HenpeckedHusband. And then there was the [[Literature/{{Discworld}}Dibbler meat pie]] incident...

* Probably the point of the Grey Faerie in ''{{Neopets}}''.
* Legacy -Battlers 2+ introduced Sparks, an upsetting backstory ensues through arcade mode and then [[spoiler: you are challenged to EXE in STAGE EIGHT, who in this case is a [[http://tvtropes.org/pmwiki/pmwiki.php/Main/HopelessBossFight Hopeless Boss Fight]] in which Sparks is literally killed by EXE upon losing. ]]
** [[spoiler: He comes [[http://tvtropes.org/pmwiki/pmwiki.php/Main/BackFromTheDead Back From the Dead]] in the 3D sequel as a [[http://tvtropes.org/pmwiki/pmwiki.php/Main/WoobieDestroyerOfWorlds Woobie, Destroyer of Worlds]] though. ]]

* Poor Donnie [=DuPre=] from WebVideo/DemoReel, with his always hopeful smile and tragic doe eyes. 42 but acts far younger, still misses his [[spoiler: dead mom]], is in an abusive and failing marriage, has such good intentions but keeps on getting crushed, is kidnapped twice and treated as a "pathetic fag" by comment sections when he's abandoned in the woods and is trying to survive in winter, has his present made lovingly by his friends destroyed by SWAG, and [[spoiler: dies scared and alone]].

--> '''Madoka''': [Through tears] I think they get it, Kyoko-
--> '''Kyoko''': If you interrupt again, I will ''feed you glass and throw you under a bus- '''have I made myself clear'''''? [...] CRAM IT WOOBIE!

* ''WebAnimation/{{RWBY}}'':
** Blake Belladonna was [[spoiler: born a Faunus, and endured FantasticRacism]] as a child, and was compelled to [[spoiler: leave the White Fang]] because of their [[spoiler: actions against humans]], and because their leader, [[spoiler:Adam Taurus, was a DomesticAbuser to her]]. She listened to Weiss rag on about [[spoiler: how awful the White Fang, if not Faunuses in general, are]], and ran away out of fear for a couple of days. She ends up working herself to the bone trying to decipher Torchwick's [[spoiler:plans with the White Fang]], causing her to become rundown and even more sullen. On top of that, she feels that the entirety of Beacon Academy, including her teammates and the professors, don't care about what's going on outside of Beacon, causing her to isolate herself from others even more than usual. She is forced to [[spoiler:fight Adam]], is beat up before [[spoiler:he promises to destroy everything she loves, gets stabbed, and watches her partner get her arm chopped off]]. Out of either shame, a desire to [[spoiler:track Adam down and stop the White Fang]], and/or desperation to keep him from harming anyone she cares about, Blake [[spoiler:goes into yet another self-imposed isolation from her friends, against an abusive ex-lover who dedicated his life to making hers a living hell]]. Unlike the rest of the members of Teams RWBY and JNPR, she [[spoiler:has no family or friends, or a home to return to after the trauma of Beacon's invasion)]].
** [[LittleBitBeastly Velvet's]] introductory scene in "Jaunedice" has her being harassed by [[TheBully Team CRDL]], with their leader Cardin painfully tugging on her ears and calling her a freak. She presumably leaves the cafeteria humiliated and in tears. Later on, she has to put up with Cardin suggesting that the Faunus' victories against humanity were because "it's easier to train an animal than a human". [[SarcasmMode That's really nice]].
** Taiyang Xiao Long, Ruby and Yang's father, could definitely be considered this after Yang tells her story to Blake in "Burning the Candle". After Summer Rose, Ruby's mother, never came back from a mission, Yang says that he just shut down after that. However, Summer wasn't the first love he lost, but the second. Yang's mother was the first and she just up and left after Yang was born. On top of all that, he came VERY close to losing both of his young daughters to a pack of Beowolves if Qrow hadn't shown up to save them in time. After hearing this, you just want to give the guy a hug. After the destruction of Beacon Academy, he nearly loses his youngest daughter, while his eldest is [[spoiler:disfigured, bedridden, and depressed]]. And then he finds his youngest has [[spoiler:left home, about to embark on a mission that will again put her in harm's way]].
** There's also Jaune Arc. His father, grandfather and great-grandfather were all great heroes. Jaune? He's the only male in a family of sisters. He's pathetic and cowardly and he doesn't want that anymore. [[spoiler:So he lied and cheated to get into Beacon Academy.]] And his troubles got worse - he tries to act cool and awesome yet comes off as too try-hard, his teammates tend to give him a hard time (even if it's good-natured teasing), Cardin took aim at bullying him for a time, he completely and utterly fails at trying to woo Weiss and at the same time fails to notice Pyrrha is horribly crushing on him. And this is on top of the fact that he has no idea what his Aura or Semblance is and that, in a world where just about every weapon doubles as a gun, he only carries a sword and shield. He's a wanna-be BadassNormal who [[IJustWantToBeSpecial just wants to be special]] and the world isn't giving it to him. [[spoiler:Then at the end of Volume 3, his mentor and lover Pyrrha gets murdered by the BigBad.]], after forcing him to flee, again reaffirming his incompetence at being able to fight alongside his friends as a hero.
** Pyrrha Nikos is singled out by the headmasters she came to trust, and has to decide if she'd [[spoiler:absorb the Fall Maiden's Aura]] with about a day to think about it. Doing so would [[spoiler:expose her to dangerous people that want the the power for themselves, she may lose her identity from essentially taking on another's ''soul'', and having rare, godly powers and needing constant protection from danger]] would place her on a pedestal and further isolate her, the very thing she resented about her life as a world-renowned fighter. The stress unravels her to the point where she [[spoiler:throws Jaune into a wall after he unwittingly encourages her to go through with it, loses control of her Semblance, and is tricked into killing Penny in front of a worldwide audience]]. Everything turns out to [[ShaggyDogStory be for naught]] when [[spoiler:Cinder kills the Fall Maiden, and uses her power to burn Pyrrha from the inside out]].
** You'll definitely want to give Yang a hug by the end of Volume 3. [[spoiler:She gets suckered by the villains into an incident that leaves her disgraced in the eyes of the whole world on live TV, she finds out that her MissingMom doesn't really care about her and wouldn't bother helping her if she finds herself in harm's way again, her best friend abandons her without a reason or so much as a "goodbye", she ''loses her right arm'' in a CurbStompBattle against Adam (moreso than other Hunters, both of her arms are integral to her weapons and fighting style), her school gets destroyed, and what's worse, she probably even believes that the destruction of Beacon was all her fault (the sheer amount of negativity the audience felt after seeing the event that disgraced her was a catalyst in attracting Grimm to the Amity Colosseum). In the epilogue, she's left bedridden and under her father's care, a depressed EmptyShell of a girl far removed from her usual cheerful and humorous self.]]
** Ruby watches her sister, Yang, [[spoiler:brutalize Mercury, a person she considered her friend, discovers that the entire incident was a setup, and the people she considered friends were responsible for it]]. She watches another friend, [[spoiler:Pyrrha, dismember Penny, a close friend of hers, and was too late to save Penny]]. After giving her all to reach the top of Beacon's tower in time, she helplessly watches [[spoiler:Cinder kill Pyrrha]]. Out of grief, she [[spoiler:unlocks a rare, previously unknown power that makes her a special person]], a thing she complained about on her first day arriving at Beacon Academy. Her team completely falls apart; [[spoiler:Yang becomes too despondent to care about anything, Weiss was forcibly taken back to Atlas, and Blake ran away without saying anything to anybody]]. [[IronWoobie Despite all of this]], she still soldiers on with [[spoiler:what's left of Team JNPR]] to find Cinder and take revenge.

* ''WebAnimation/AlfredsPlayhouse'' is about a traumatized, mentally ill dog named Alfred Alfer, who tries to forget about his abusive childhood by [[ThinkHappyThoughts imagining himself in a happy fantasy world.]]

* From ''Main/EpicsGameshows'', contestants "[=TheWaddlerMC=]" and "Jacaljt10" from Epic's Minecraft Survivor Season 2 ended up being victims to "[=DevinwithDevin=]"'s bullying. Some of Devin's comments weren't aired due to how bad they got.
* From ''Main/KawaiiVinnysMinecraftSurvivor'', some examples include Radiant_Oblivion, Michael918, Emperor_Vayne and Blockie. Things didn't go right for them in their respective seasons to put it lightly.
* ''WebAnimation/TheMostPopularGirlsInSchool'': If she wasn't such a DeadpanSnarker, Bridget Tice would be one. She has a pretty depressing life, when you think about it.
** Ashley Katchadourian due to the DisproportionateRetribution she suffers in episode 11 and 13.
*** [[spoiler: It gets even worse because of Episode 31 when we learn she was specifically set up to be blamed by Jenna Darabond so she could get Ashely's then-boyfriend Justin and has been TheChewToy for the whole series. In episode 32 she asks to be left out of the ongoing strife between Mackenzie and Jenna, and Trisha speaks on her behalf. In episode 33, we learn from Ashley's little sister Brooklyn that Ashley has been depressed for a while and their mom is trying to help her.]]
** Jenna Dapananian- she just wants ''someone'' to make out with her, among other things. [[ThrowTheDogABone She eventually gets her wish, though.]]
* The WebVideo/ScootertrixTheAbridged version of at least a couple characters fit this description.
** Rarity is a [[spoiler: changeling who had to defect to Equestria, due to her own species intolerance to her artistic mind. Only for Equestria to force her into being TheMole, to her own race.]]
** Luna was imprisoned on the moon for one thousand years, only for no one to even recognize her when she came back. She also has to deal with her JerkAss sister, Celestia who constantly makes selfish, reckless, and irresponsible decisions regarding the protection of their subjects, only for herself, to be constantly proven wrong, while Celestia is constantly rewarded with success.

* FeliciaDay's character, Codex, in ''TheGuild''.

* 80% of the protagonists of various [[SlenderManMythos Slendyblogs]] tend to come across as Woobie-ish. Most notable are probably Noah from TribeTwelve, [[DamselInDistress 'Damsel']] from EverymanHYBRID and [[spoiler:the young Vincent from the Bag in the same ARG]].

* The ScootertrexTheAbridged version of at least a couple characters fit this description.
** Rarity is a [[spoilder: changeling who had to defect to Equestria, due to her own species intolerance to her artistic mind. Only for Equestria to force her into being TheMole, to her own race.]]

* Quite a few characters in EquestriaChronicles but [[{{Moe}} Scribble Quill]] [[TastesLikeDiabetes takes the cake.]]

* Gino Gambino is the king of this trope on ''GaiaOnline'', subjected to neglect and [[WeirdnessMagnet shenanigans]] by his father for years, yet unwilling to so much as protest this treatment.

* ''WebAnimation/{{RWBY}}: