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I figured that Woobie Entries should be no more than 300 words, they may need to be shorter. If you ever come across a woobie entry that's 300+ words, may you please add it here if it hasn't already?

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  • Ayane from Dead or Alive qualifies. She was born from her biological father, Raidou, raping her mother to get back at one of his enemies, and was hated and mistreated by her village of origin as a result, with the only two that ever treated her well being her friends Hayate and Kasumi, and her adoptive father Genra. Though she and Kasumi are friends and she's crushing on Hayate, the rest of the village tries to keep her away from them due to associating her with Raidou. Then she finds out from her mother that Kasumi and Hayate are her half siblings, and that while they're treated like ninja royalty, she's outcast because her mother didn't claim her due to the trauma of her birth circumstances. Then Raidou comes back to the village seeking a technique they guarded, and while she's beaten aside easily, Hayate is crippled when she fails to protect him. Kasumi then leaves the village to seek revenge, and Ayane is assigned to kill her for breaking the code of secrecy surrounding the village. And this is all before leaving the backstory! She proceeds to have to face off with both her best friend andher amnesiac love interest when Hayate is brought back by DOATEC as Ein as part of Project Epsilon. Then in the third tournament, she finds out that her adoptive father has been kidnapped by DOATEC and turned into the monstrous bioweapon known as Omega, forcing her to enter the tournament, whereupon she defeats and kills him to set him free of DOATEC's slavery. And past that, with Hayate back as of the fourth game, Kasumi is still marked for death due to Honor Before Reason, and Ayane is still loyally serving her clan to take her down. And through all of this, the only hint of the pain we ever see going through her is a single tear when she's cremating Genra's body after he dies. One really wonders how Tecmo could hurt her worse if the series had gone on.(Over 300 words.)
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  • Becoming one of these is the entire journey of Lucas, the hero from MOTHER 3. The game begins with his life utterly falling to pieces after his mother is killed brutally by a Mechanized Drago, his twin brother disappears while trying to avenge her and is assumed to be dead, his father is driven partially mad from the resulting grief and gets thrown into prison after a rampage, the wildlife around him are all transformed into horrifying Cyborgs that are violent, and everybody in the village he lives in slowly begin turning into self-seeking, cold-shouldered hedonists after the bad guys who are responsible for all this start planting Artifacts of Doom in their houses. All in the span of two days. Before all of this happened, he was already very sensitive and timid, but now he's an absolute wreck. Three years later, one things leads to another, and his adventure begins. During his quest, he faces countless more dangers and traumatic events, including discovering his mother's ghost but finding himself unable to touch or even talk to her, but with the help of his strange but loyal and true new friends, he holds up his head and presses on. And, by the end, how much has he grown? Well, he eventually finds out that his brother isn't dead and finally finds him. However, he's been turned into a Cyborg as well and has been completely stripped of his memories , being sent by the Big Bad to kill Lucas. After one of the most heartbreaking I Know You're In There Somewhere Fights in the history of fiction, his brother realizes who he is and, unable to break the control on himself any other way, commits suicide and dies in Lucas's arms. And, after all this, does Lucas still have it in him to pull the final needle and save the world? Well, you might not, but he sure does.(Over 300 words.)
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  • Kingsman: The Secret Service: Harry. He may be a very well-to-do, smooth badass who gets to wear cool suits, but let’s take a good look at what happens to him throughout the course of the movie. At the very start of the film, he loses his protégé, and instead of getting any particular sympathy from his colleagues, he’s mostly shown getting flack for “making a poor choice.” Then he tries to comfort the dead man’s family with little success, and has to deal with the widow sobbing and yelling at him. All of this is of course made worse by his guilt for having missed the grenade that killed Lancelot. Seventeen years later, the new Lancelot dies, so he loses another colleague, is reminded of his grief and failure, and if that weren’t enough, his boss is still giving him crap over “picking the wrong sort of guy” for the previous Lancelot seventeen years ago. As he puts it in the bar, he’d “had a rather emotional day.” He then is able to take Eggsy under his wing, which must give him some happiness, but shortly afterwards he goes to investigate Professor Arnold and is drugged with an unknown substance and nearly blown up for his trouble. He spends weeks in a coma, and when he finally wakes up he then almost immediately goes back to work, which is apparently his entire life, as he is never shown to have any sort of relationship outside of the Kingsmen – no friends, no family members, no significant other, nothing. Granted, none of the other Kingsmen are shown in relationships either, but Harry seems to be a bit of a misfit among them, given his progressive attitude and lack of snobbery, so he’s isolated even at work. Indeed, his best friend appears to be his deceased and stuffed pet. Then he has to deal with Eggsy failing his final test, just when he’d been so close, and his very next act is to visit the church, where Valentine’s device drives him into a killing frenzy along with everyone else, and when he comes out of it he reacts with horror to what he just did right before he dies. To top it all off, even if he didn’t know it, his boss was one of the people behind his death! Does this guy need a hug, or what?(Over 300 words.)
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  • Castiel on Supernatural. He rebelled, was hunted by his brothers, saw his friends die, discovered God had abandoned the world, is caught in the middle of a Heavenly civil war, has had no discernible success in convincing his fellow angels to respect humanity, has to deal with those whiny Winchesters who expect him to be at their beck and call and do anything they ask with never a word of thanks and the closest thing he has to a friend is a hedonistic asshole of an angel who ran away during the apocalypse and left him to deal with it all on his own, then had the gall to say he was following Castiel's example. To cap it all off, he's been blown up twice. Fans would give anything to see him get that damn hug, but at this point most of them would settle for someone, anyone, showing him some genuine gratitude. And Sam denies him a hug in 'Like a Virgin', not so subtly sitting down as soon as Castiel opened his arms. Comes to a heartbreaking head in The Man Who Would Be King Castiel finally gets his gratitude from Bobby, Sam and especially Dean. Too bad it's 1. Not (knowingly) to his face and 2. Too little too late. Castiel made a deal with Crowley and chose to keep fighting alone rather than go to the Winchesters for help in order to protect them and it seemed like the best plan at the time. When this gets found out the boys are quick to judge and quicker to claim had Cas come to them for help they could have fixed it. It's clear from the conversations that follow and from Castiel's surprise at being told he's like family to them, Castiel had no idea he meant that much to them. And with the way they treated him during the season he had no reason to think it. "The Man Who Knew Too Much" finally has him snapping. Namely, in that he absorbs all the souls from Purgatory, blows up Raphael, kills Balthazar (the aforementioned hedonist), restoring Sam's memories of Hell, and at the very end, after absorbing the souls from Purgatory, declares himself the new {{God}}, saying that anyone who doesn't profess their love to him will be destroyed.(Over 300 words)

  • Final Fantasy VII: Vincent Valentine. Let's start: he never got along with his father. We know that because said father tells Lucrecia, who accidentally killed him by experimenting too much, to apologize to his son for not being a good dad. Next, we have Vincent being employed as the girl's bodyguard. Well okay, the girl is hot, he falls in love with her. Then Vincent finds out that Lucrecia worked with and watched his father die. He's all "Whatever, I still love you", it seems like an unrequited feeling, but why is she flirting with him? Moving on: Lucrecia is in fact Hojo's assistant. Hojo is old, ugly, creepy and downright EVIL. So she sleeps with him. Vincent says that he doesn't care, as long as she's happy. Turns out, they needed a child to be conceived, to experiment on it. Remember Sephiroth? Yeah, this one. That's the child. Still being pregnant, Lucrecia falls ill and Vincent loves her too much to just watch. So he confronts both of them. Hojo kills him because he's 'noisy'. Lucrecia puts him in a tube and brings him back to life by making him the host of Chaos. And then she goes into a cave and seals herself in a Mako crystal, apologizing a lot. Vincent wakes up, discovers he's a bit different than before (no way?) and goes into rage mode. Then he closes himself in a coffin for 30 years (by the way, his body is now nearly indestructible and he never ages), saying that it's the punishment for his sin. Apparently, his sin was doing nothing, but watching the experiment. Then Cloud and co. wake him up in the basement of Shinra Manor and greet him with some great news - Lucrecia's child has become pretty homicidal and is about to destroy the world. And then, when the heroes finally kill Hojo in the game, he tells him to rest in peace. So? Want to hug him yet?(Over 300 Words)

Ryo Bakura lost his mother and sister in a car crash at a young age. He spends almost the entire series under the control of a sadistic ancient spirit. He had to constantly change schools, living with the guilt and negative stigma of having his friends fall into a coma whenever they played a game with him because of Dark Bakura. After Yugi and his friends free him of the Ring's influence, he puts the Ring back on to escape a maze at Duelist Kingdom, becoming an unknowing pawn for the spirit thereafter. At Battle City, as part of a plan to help Marik, Yami Bakura stabs Bakura's arm so badly he had to be hospitalized. Even then he can't get rest, as his body's dragged out of bed to duel Yugi and Dark Marik, the latter of whom killed him temporally. At the beginning of the Millennium World arc, Bobasa refuses to let him into the Pharaoh's mind, despite his desire to help his friends, because of the darkness within his heart, which is the evil spirit of the ring. He puts on a smile and runs away in tears, and any peace he could get from being free of the Ring isn't shown. The anime does very little to make it better and greatly reduces his screentime, omitting him entirely from non-manga adapted adventures. Yu-Gi-Oh! The Dark Side of Dimensions shows even more tragedy in his life, as he was possessed by the Ring when he was young and had it fuse into his chest, with the Ring also attacking his father when he tried to wear it. Dark Bakura then kills Shadi, and Aigami wants to kill Bakura for the incident. Ryo mentions not wanting to talk about the Ring at all and suffers headaches when pressed, then becomes trapped in another dimension for the last third of the movie. The Ring itself also tries to kill him at one point.(Over 300 words)

  • Jerk Ass Woobie: Dante from Devil May Cry. In the main timeline, he is constantly making snide remarks, complaining about money, extremely lazy (only works once a week), is in debt to all of his friends (and makes it clear that he won't be paying anyone back anytime soon), and is a major jerk to just about everyone. Then again, he consistently turns down payment (does the job anyway because it is the right thing) and refuses payment from the poor, saves the world on several occasions, takes care of Patty (to a certain extent), is shown to spare demons who are able to love and refuses to kill humans, and is shown to have a compassionate side as well as a kind side (he'll just give you a hard time). The jerkass act is to cover up the fact that he is miserable (it can be seen basically everywhere, especially in the anime; really, he never smiles except when he is slaughtering a demon or when he does a good deed!). The Woobie part is that he witnessed his mother being slaughtered while she protected him at the age of eight and believed his brother to be dead as well. He also believes that his father abandoned them at a young age and it is assumed that he basically raised himself. He finds his brother completely insane and is forced to defeat him, which leads to Vergil's apparent suicide (or so Dante believed), and forced to finally (all the while not knowing that it was Vergil) kill a possessed Vergil ten years later. His friends constantly take advantage of him (manipulating him, forcing him to pay for clothing, etc.), he is forever hunted and hated by the entire demon world (and most humans hate him because of his demon heritage), and he has no hope of ever having a normal day (let alone a normal life). During everyday life, he is constantly being shot at (Lady shoots him point blank through the forehead twice and later through the stomach...in a period of six hours!), impaled (a Running Gag to be stabbed through the chest or stomach), and other things. Capcom really wanted to make sure that Dante had the worst possible upbringing and life possible, didn't they?(Over 300 words.)

  • The title character of Merlin (2008). Just look at the last half of Series 2. Forced to tell your best friend that magic is evil in order to spare a man who would have you slaughtered? Check. Your best friend kills your girlfriend? Check. Forced to poison one of your friends for the greater good? Check. Finally meet your father only for him to die saving you two days later? Check. And while this is a compilation of the worst things to happen to him, they certainly aren't limited to just lining up in a row and hitting him. Only one person has learned his secret, accepted it, and lived. Everyone else is dead.
    • Oh, and did we mention that these are just specific events? His normal life is being called an idiot and distrusted despite always being right, getting abused and belittled by Arthur despite constantly saving his life, and if he's ever discovered saving all of Camelot, he will be killed. Why? Because he was born magical and thus must be evil. And it would most likely be Arthur who gives out the order.
    • He has never gone into Heroic B So D, rampaged, broken down, or sunk into depression. He cries, sure, but he'll get back on his feet and keep trying with the same episode. Even on the one occasion when he truly felt his cause was hopeless after accidentally killing Uther and possibly turning Arthur against magic forever, he stuck around because Arthur needed his emotional support. He's not even that emotional towards Gaius, the one person who he can rant to. He's had one rant (early series two, before all the above happened), and the rest of the time he just takes comfort in the fact that there is one person who knows how much he's done for Camelot. Forget iron, this guy is an Adamantium Woobie.
    • Oh and his final fate? To Walk the Earth, immortal, until he's needed again. As most fans have noted, this is a curse to see everyone he cares about die, but he's still waiting for Arthur.
      • (Over 300 words + Illegal Indentation)

  • Oswald the Lucky Rabbit, as we get to see in Epic Mickey was abandoned by his own father over a budget dispute with Charles Mintz, and when Walter Lantz took over the cartoons, Walt openly approved of Lantz using Ozzie. And it only got worse when Oswald's half-brother Mickey Mouse usurped his original popularity, which, coupled with Lantz's change of the character, as well as the gradual rise of Screwy Squirrel characters over cute funny animals in the early 1940s (including Universal's own new character, Woody Woodpecker) sent Oswald to his grave in 1943, after limping by for the last several years. You would think that in the world for forgotten Disney characters, he would have finally gotten the happy ending he deserved. But nope, things got even WORSE for him — said half-brother just happened to accidently spill a jug of paint thinner onto Yensid's world, which would up ruining the whole place by turning it into a savage wasteland, as well as unleashing the Shadow Blot upon the place, which would lead the entire world into even more mayhem and ruin, forcing Oswald and any remaining resistance underground—the lowest point of his life would be seeing his own wife, Ortensia the Cat, frozen into stone, the experience eventually degenerating him into a distrusting, bitter Antihero. And on top of that, he's manipulated by the Blot into becoming jealous and hateful of Mickey so he can be used to its advantage. That said, he DOES finally get his happy ending when Wasteland is restored and he finally bonds with Mickey. Things are getting better for him in Real Life as well. In 2004, Japan had a gigantic craving for rabbit and toy companies began churning out Oswald plushies which were insanely popular. Not to mention in 2006, Disney literally traded a human being (sports caster Al Michaels) to NBC in exchange for Oswald, showing that they still truly care for him and that they want him to return home. And if you haven't yet cried for Oswald after hearing his story, try watching this and see if you can keep a dry eye.(Over 300 words)

  • Overlord (2012):
    • Jerkass Woobie: The Captain Remedios Custodio from the Paladin of the Holy Kingdom Arc might be an even bigger Woobie than Climb. While Remedios has many character flaws and can be, quiet frankly, a bitch, none of this was ever really an issue until Demiurge started the demi-human invasion of the Holy Kingdom. Indeed, in spite of her flaws, before the war she could be genuinely friendly and was very idealistic. She cared deeply for her people, queen, and sister. Word of God stated that she was even more pure of heart than Gazef Stranoff the warrior captain and greatest fighter of the E-Estize Kingdom. She did her job well and she was seen as a national hero with the Holy Queen and her Sister helping her by making sure that she didn't have to focus on more complicated matters that she was not prepared to deal with. She had respect, admiration, close friends, and a good life. And then Demiurge enacted his plans to invade the Holy kingdom and make it perfect for conquest by the Great Tomb of Nazerick. Instead of a straight forward conflict, the whole war was simply a way to eliminate troublesome elements in both the Albion Hills area and the Holy Kingdom and change the cultural and political landscape to make it easier to take the Holy Kingdom. Suddenly, Remedios' world is turned on it's head when some of the key figures of the country (the holy queen Calca and her sister, the high priestess Kelarts) being disposed of and Remedios suddenly thrust into a command position that she was neither prepared for nor can handle. It's even heavily implied by the end of the story arc that Demiurge intended to ruin Remedios' life and reputation. He would have gathered detailed information on everyone of importance in the Holy Kingdom. He knew that Calca's charisma and Kelarts intelligence would be a threat so he takes them out first. He makes sure to leave the chaotic situation of the kingdom in the hands of the grossly under-qualified hands of Remedios who is so in over her head she can barely keep what remains of the Northern Holy Kingdom's army together. The pressure and stress of the situation start to break Remedios and she constantly lashes out or berates others. After Ainz gets involved and starts single handedly winning the war on his own, his newfound PR coming at the expense of the paladins and Remedios in particular by making them look like incompetents and weaklings that cannot protect their own people. Later Demiurge has the Wrath Demon posing as Jalabaoth humiliate her in combat by striking her and splattering the remains of her Holy Queen Calca all over her body while defeating her in one stroke all the while Remedios' power and skills, which she takes pride in, can't even hurt the demon. After being brought the severed head of her sister, whom she loved dearly, and without whom the Holy Queen could be resurrected, Remedios goes berserk and from there becomes a mass of seething rage and bitterness cutting herself off from everyone and causing people to distrust and even fear her. Finally dopple-Caspond intends to demote and reassign her and later use her as a scapegoat for why things got so out of hand in the Demi-human invasion as she is the only survivor of the high command of the previous Holy Queen. Through no fault of her own, Remedios was used as a pawn, her life torn apart, her friends and family either dead or turning their backs on her, losing the respect of the people and the position she held with pride when she was considered the hero of the nation while becoming a bitter Broken Bird from the whole experience. Remedios may have been a bit of a Jerkass in the beginning but she certainly didn't deserve what was done to her.(Over 300 Words)

  • Mobile Suit Gundam Age: Two words: Kio Asuno. At the tender age of thirteen, he becomes a Gundam pilot. Because he spent much of his childhood playing battle simulators under the watchful eye of his grandfather, however, he has no idea of the realities of the war he's entering into. His Wide-Eyed Idealist nature and Chronic Hero Syndrome causes him to undergo one of the most painful Trauma Conga Lines in entire Gundam franchise. To start, he takes lessons with his mentor Shanalua, who, as a war orphan who hates killing, is horrified by the poisonous beliefs Kio learned from his grandfather about the enemy. Later, he finds out that she is The Mole for Vagan, but believes that explaining about how she's a nice person to the crew would bring her back. Shanalua flatly refuses because she would be executed for treason and sacrifices herself when Vagan mobile suits attack. Not long after painfully losing his mentor, he finds out that his father is alive as the Captain of the Bisidian pirates. Even so, Flit tells his grandson to forget it ever happened and believe his father is still dead, sowing his gradual detachment from his grandfather. But the poor kid can't even rest then. In Episode 35, having barely avoided death from his sheer lack of experience, Kio gets caught into a Vagan trap while the Diva was en route to retrieve the EXA-DB. While he did escape an episode later, he saw his grandfather try to shake off the Vagans in his outdated AGE-1 and, due to his tendency to follow his heart than his orders, dives right back in to save his grandfather. What ensues is him being captured by Zanald and being brought to Second Moon. But what truly seals the deal are Episodes 37 and 38. Upon his arrival, he gets transferred to Lord Ezelcant's palace, if only because he resembles Ezelcant's dead son Romy. Even with his fairly luxurious imprisonment, Kio realizes that Vagans are forced to deal with rampant poverty and/or the traumatic and deadly diseases from Mars Ray exposure. This is brutally driven home when he is brought to Deen's house after being pickpocketed. Kio finds that Deen's sister Lu (who is a woobie in her own right) takes an immediate liking to him. Not long after a simple dinner, however, he also learns that she is terminally afflicted by the Mars Ray disease and that she wants nothing more than to have something remotely close to a normal life, such as going outside, in the little time she has left. Growing close to her, this realization triggers a Heroic BSoD. This causes him to bring the condition that he could receive medicine for Lu (even though it only relieves the symptoms and doesn't actually cure the disease) when Ezelcant asks him to unlock the AGE system's security protocols. Having grown attached to Lu and having won her brother's trust, Kio found happiness during his imprisonment in Vagan, so it seems like the kid's finally going to get a break, right? Nope. In the middle of his father's rescue attempt, Kio returns to Lu's house one more time to deliver more medicine. What he finds instead is her brother mourning her peaceful death and a diary of all the memories she could have had with Kio. And as he escapes Vagan in his damaged AGE-3, he breaks down and finally realizes that there are others in Vagan that are just like Lu.(Over 300 Words)
  • RWBY: Qrow Branwen, for many of the same reasons like Taiyang: He's had his sister abandon him to go lead their tribe of bandits, whom he's distanced himself from, lost Summer Rose, the leader of his team, watched as his brother in law and close friend Taiyang go through a Heroic B So D, nearly lost his nieces twice, with the second time leaving them worse for wear. While his situations here aren't as bad as Taiyang's, seeing as Qrow has some form of contact with Raven and he chooses to leave Taiyang behind, he still has to deal with Cinder's rise to power being partially his fault and the loss of his dear friend Ozpin. And with Volume 4's reveal that his name and Semblance are rumored to bring bad luck, he's most likely blaming himself for what's happened above. Oh, and he also gets poisoned, leaving him unable to walk, unconscious and deliriously calling out for his teammate, with the possibility that his presence would become more and more of a danger to RJNR with each passing episode due to his aforementioned misfortune Semblance. Yikes. Thankfully, he gets better by the end of the volume, but by the next volume he's disappointed that his and RNJR's meeting with Professor Lionheart, who unbeknownst to them is secretly deep under Salem's thrall, turns out to be fruitless, to the point that he bitterly heads to the nearest bar to drown his sorrows. It's clear by that point that Qrow finds himself unable to function without some guidance from Ozpin, which makes his drunken giddiness and relief that he managed to find the latter all the more disheartening. When tasked with forming a crew of huntsman to oppose Salem, he's thoroughly unsuccessful; this later turns out to be not due to his Semblance, but because Lionheart used his position in the Mistral Council to access the info on Mistral's huntsmen and huntresses, some of them who Qrow knew well, and give it to Salem so that she could dispose of them. Qrow's realization of this after Lionheart's treachery is revealed is full of sorrow and anger. He also has to deal with the fact that Raven, his own sister, set him and his allies up to be ambushed by her and Salem's crew so that she could sneak away with the Relic of Knowledge in the confusion. Qrow is so full of anger at this that he declares that he declares that he and Raven are not family anymore. Yet, after the fighting is over, he still shows concern over Raven's status after Yang's confrontation with her in the vault.(Over 300+ Words)
  • Tenchi Muyo!:
    • Stoic Woobie: Katsuhiko/Yosho in the Universe version instead of leaving due to discrimination on his half human lineage and "women" in the OVA; he had lost his first true friend, a child eating monster who was about to change her ways, till the Jurai force came and beat the hell out of her, then calling her a freak when she revealed her true form and running away. Then in his adulthood, her's forced to kill his best friend who had become power-hungry and killing everything in site, next wanders across the galaxy out of guilt and finding a place for his lover who wasn't royalty, so that they can love each other without being social class discrimination. She up and dies before they even arrive there. His daughter's (Achika) lifespan was greatly diminished as result of most of her Jurai power passing onto Tenchi, when she gave birth to him. She passed away when her son was very young, causing Katsuhiko and Tenchi's father, Nobuyuki to hate winter for a while, being the time she died. Then we get the present where that power-hungry friend has literally come back from hell to use his identity and frame one of his relations for treason, leading to a long chase until he finally meets him again and is understandably distraught about killing him again, to the point that he considers double suicide as a solution. After that mess, that first friend has returned to being a bratty trickster who's now a Yandere for him, to the point that she creates a clone with her and his grandson's DNA and have that said clone rape and take him to her dimension till he comes over himself. And that lover's ghost manipulates his grandson's memories and uses him as a substitute for her former lover. But he continues on being solemn and sometimes cheerful.(Over 300+ words)
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