- Let's just say Italy is so in Gankona, Unnachgiebig, Unità
because of his past and how it impacted him in present day. Like in canon, he had been abused by Austria for hundreds of years, leading him to develop terrible anxiety that he hides behind brilliant smiles. - Socrates from Calvin and Hobbes: The Series is starting to become this in Season 5, as things start to come to a head and he begins to have a central part in the plot.
- Frank Brainstorm in the 3rd season finale "Thunderstorm", as he spends a good portion of the plot fighting against his once best friend (who was always one step ahead of him).
- Then there's Susie in "Chains", whose bad luck (which may or may not have been a direct result of her ripping up a Chain Letter) goes to incredibly extreme lengths.
- The Parselmouth of Gryffindor: Alastair, who was lastingly injured as a child by Vernon Dursley's carelessness and is barely cared for by the other Acromantulas because he's seen as weak and useless. You could also make a case for Apophis.
- The author behind Tiberium Wars and Forward has a borderline obsession with Woobies, pointing out in one of his author's notes that (paraphrased) "if I like a character, I hurt them. A lot." This is especially prevalent in Forward, where River Tam is regularly put through the wringer, suffering constant mental breakdowns, injuries, and at one point is tortured by Niska.
- Anyone who's read a certain Pokémon fiction involving a boy named Tommy will feel horrible, burning sympathy for pretty much every character. Not only for what's happened in their past, but the fact that once the protagonist manages to escape from the deserted island the story takes place on, he can either leave behind his only friends that aren't dead, or live in ridicule by all other humans who know who he is. But hey, his parents would never reject him. Neither his presumed dead birth parents, or his for sure dead adoptive parents. Gotta catch em all.
- freya_sacksen likes hurting the That Guy with the Glasses cast. A lot. Especially of note is her "In Space" fic, where everyone gets broken but probably the main two suffering in that one are Marz Gurl and the Nostalgia Critic. Marz Gurl is generally like River Tam in an apocalyptic future and as for the Critic? Well, you try being tortured for centuries by Ask That Guy and Dr. Insano, end up failing to save the world and then actually give Ask That Guy the idea to start the whole thing off anyway and see how you feel.
- The Nostalgia Critic, Linkara and Spoony tend to the main woobies of the fanfic fandom, anyway. Spoony seems to suffer the most psychologically, Linkara tends to be the one for bondage and the Critic gets the most humilation and physical torture. Although there is, of course, lots of overlap.
- Fanfiction about Film Brain falls into two categories: Hurt/Comfort Fic and tooth-rotting fluff. In fact, when some of the people from the site found the Kink Meme, Film Brain's woobie status was one of the first befuddled observations they made. I blame Kickassia.
- While The Nostalgia Chick is sometimes causing the woobie-dom in others, she gets this too occasionally: there's a certain Hooker Verse which turned her relationship with Nella around and broke the cutie massively.
Kaorin, Sakaki and Chiyo get a bit of this in Differing Paths, though partially undone by the series' Black and Grey Morality.
- Challenge: step 1 - log into Fanfiction.net, step 2- search National Treasure fics step 3- try to find a fic that IS NOT about Riley Poole tragic past, tragic present or tragic future...mixed with healthy doses of whumpage and comfort.
- Flash and Spyro in the Legend of Spryo fanfic The Broken Line. Flash is close to only his grandmother, who died when he was young, and his brother, who goes missing. Then, after a lot of searching, Flash finds him dying. Spyro, on the other hand, is framed for the massacre of half a village, before being tortured for information by said village. Meanwhile, Nexus, the actual killer, is pretending to be Spyro and attacking the guardians while his mate and friends think that Spyro is attacking them. The actual Spyro enters Warfang while Nexus and the Grublins are attacking it. Cynder is the first to find him, and almost cripples his leg.
- The Yin Yang Yo! Alternate Universe Doorstopper fanfic, Re: Yin Yang Who? or Yin Yang Yo! Forever: Jobeaux - To a lesser extent somehow; thankfully (so far), he gets better, marries Annie, and has a daughter.
- Lind's Back Story in Ah! Archfall! reveals that up until the original Angel-Eater incident, she has had a VERY hard life. Jago isn't much better but somehow he's still smiling.
- The Homestuck bloodswap AU fanfic Red Dead Virgo has a red blooded Kanaya fit this trope very, very well. Due in no small part to copious amounts of well written but heart-breakingly tragic Break the Cutie.
Read this Percy Jackson and the Olympians story and tell me you don't feel sorry for Melanie.
- While he was portrayed as a Butt-Monkey in the canon series, Davis Motomiya is usually portrayed as a woobie in non-canon stories. Two of them which are so excellent written that you would believe that they're canon in the first place. In both of them, he's usually portrayed as a guy with an inferiority complex and behind his boasting and carefree nature is a lonely boy who just pretend this facade in order to cope with his unpopularity within his Digidestined group, at school and at home. These stories developed his character very well, making him an intelligent yet naive person who clearly has issues with himself and the others, and those who were disappointed on the canon's lack of Character Development on him should read these stories.
- The first one is Zero 2 A Revision. In A Revision, he is constantly suffering at the hands of his own comrades, especially Yolei who enjoys picking on him, never seems to appreciate his hard work and is always putting him down for the smallest thing, he also experienced a Painful Transformation when he obrained his own crest as it is carved into his own body instead of being turned into a trinket like the other Digidestined. His jealously and hatred for TK for spending more time with Kari allows Umbradevimon to put him through a Mind Rape which turned him into the homicidal, ruthless fighting- killing-machine Darkheart and he has to watch him assimilate the Digidestined and destroyed entire continents just because he feels like it. And just when you thought he has gotten a break his parents ended up being indirectly murdered by Gravemon resulting him and Jun becoming orphans. Oh, and he also have to share an apartment with Yolei after the series ended whom to him, is the most annoying girl to ever existed and vice versa.
- The second one is Walkabout In Walkabout, he didn't get promoted to Woobie, Destroyer of Worlds but he still kept his woobie status. In this story, he decided to do an "walkabout" through the Digital World in order to search his soul and improve himself so that he could be accepted by his peers.
- In Teenage Mutant Ninja Turtles section on fanfiction.net, Donatello seems to be rather popular with being hurt in some fashion on top of being emotionally abused by Shredder, and in some cases, his own brothers. lion-of-judah is one author that pretty much attacks Donatello at every moment.
- The Metal Gear Solid fanfic Revolution (a side-story to a much longer fanfic that basically lives off the continuity of The Last Days of FOXHOUND) takes Big Bad Extraordinaire Liquid Snake and turns him into the woobiest woobie that ever did woobie. If anything, this is probably the first fic to ever attempt that feat.
- Another Metal Gear fic, The Joy of Battle presents all of the Cobra Unit members with woobie moments but none so bad as the Fury who is injured and emotionally tortured to the point where he breaks, only to be sedated by the End's tranquilizer rifle.
- This is a common Alternative Character Interpretation of Britney from My Immortal. She's cast as a Designated Villain for simply not sharing the protagonists' tastes in fashion and music. Until the very end of the story, she does absolutely nothing else to warrant the abuse and bullying which she constantly receives from the "heroes". Instead, the mere fact that she exists is considered an offense all by itself. And her behavior at the end can easily be interpreted as a response to the abuse leveled at her for the whole story.
- Everybody in the Death Note fic Second Chances — but especially L. The author's putting the poor guy (maybe literally) through hell. Without even going into detail about the way his bad sleeping and eating habits are finally taking their toll on his body, he doesn't make friends easily and knows it, so his habit of losing left and right the few people he comes to care about hits hard.
- In the Kingdom Hearts fanfic Fill the Moon, the author's mantra seems to be, "make the entire cast suffer until they break down and cry. Then sell ringside seats. You think this is an exaggeration? Please. Literally EVERYONE in the cast is given a day as a Woobie, and some of the cast just push down on the Woobie button and don't let up.
- The best example is the little OC Nobody, the Cute Monster Girl Senayax. While being basically seven years old and trapped in a body that's just going through puberty already nets some major Woobie points, the author just will not stop making her suffer. To date, after around one hundred and fifty chapters of fanfiction, she has been both driven to suicide and murdered before being brought back from the dead, been forcibly impregnated on orders from her father by her lover, Zexion—who, as it should be noted, is around five years older than her—been forced to eat her beloved grandfather to survive after murdering him due to being an Unwitting Pawn in one of her parents' schemes to get her grandfather's money, being subject to an incredibly nasty and disgustingly sexual Mind Rape from the giant fucking Eldritch Abomination that lives inside of her body, almost dying due to the consequences of the previously mentioned forced pregnancy, and spending around four months in agony due to treatments designed solely to keep her alive during this pregnancy while the Messianic Archetype completely forgets her existence. To top it off, she watches her lover perform a Heroic Sacrifice to save her life, and thus get murdered by Sora before she decides to follow in his footsteps and commit suicide using the Keyblade as her murder weapon. Despite all this, she remains an eternal cheerful child who is a friend to all living things and tries to put on a happy face for her family, including the father figure who ordered her to be impregnated. Want to hug her yet?
- Considering the above troper's remarks on Xemnas, this troper feels it's appropriate to bring up the fact that the author makes him out to be a woobie on occasion. Sure, she doesn't exactly justify or excuse his impregnating of Senayax, but considering he hadn't been around when the original experiment failed horribly, he wasn't out to murder her. If anything, the author makes him incredibly sympathetic with his My God, What Have I Done? freak outs and habit of becoming The Atoner. ** While what he did is certainly horrible, he's not as much of a monster as, say, Hollowmoon, and it wasn't on purpose. If anything, he's there to represent the consequences of being the leader and Superior. Despite the fact that he's incredibly flawed, this troper firmly believes he's still a woobie, (although definitely not to the extent of the rest of the cast.)
Pff, please. While Senayax certainly gets the worst of it, Demyx is probably the one who gets hit the hardest aside from her. After being emotionally, mentally, and physically abused by an older brother who he was desperate to gain the approval of for his entire life as Myde, he is suddenly and brutally almost-murdered by said older brother, who would have finished the deed had a Heartless not come along. Afterwards, he has such deep emotional and mental scars that he has a major Freak Out-cum-Minor Injury Overreaction on Xigbar's behalf after the other man is mildly wounded on a mission, not to mention a downright suicidal attempt to clean the entire castle using lye. Which is corrosive and leaves behind horrible chemical burns and open sores. And this is all due to his older brother beating him and breaking him down until he was horribly, horribly mentally scarred, enough so to believe that he deserved to be bitten and beaten by Xigbar. Of course, he eventually gets better, but that doesn't change the fact that he still needs hugs.
- Larxene actually might tie for second place with Demyx. Yes, that Larxene. Considering she was raped and abused for three years by her ex-husband, who she brutally murdered in self-defense after he attempted to rape her for a fourth time, and is implied by Word of God to have had many, many abusive relationships, and, due to the fact that the author of the fic is open about being a rape survivor, has very realistic reactions to traumatic triggers or events. Despite this, she manages to maintain her normal Deadpan Snarker-slash-Dark Action Girl personality, albeit with a bit more depth under her sarcastic and caustic surface. She really, really deserved all the Cooldown Hugs from Lexaeus that she got. Poor girl.
Hell, the author just likes taking the strangest of characters, and turning them into massive, massive woobies. Case in point; the next biggest woobie in the story? Xaldin. And because of the way that the Mooniverse's canon works, this makes perfect sense. Let's see...
- Before he finds his "soulmate," Luxord, he is twenty-nine, and quite blatantly a virgin. Now, that isn't a bad thing, per se, but considering his older brother, who he loves more than anyone else in the whole world is implied to basically do anything that moves, the pressure to find a lover wears down on him, especially considering he doesn't have a heart to really experience love. It takes him a long time, but he does finally accept Luxord's love and does end up happy. However, considering the author plans on going into their backstory as Apprentices to Ansem, in which Braig is still a slut and he's still a loveless virgin, expect him to get even more Woobie-fied later on...
- You know who else gets beaten with the Break the Cutie stick? Of all people, once again, Vexen. He's constantly stalked by a lover he doesn't want, well, initially, at least, he's thirty-four and alone, and is shown to be cracking under the strain of having basically raised the other five Apprentices by himself. While he's not tortured as much as some of the other members of the cast, (perhaps due in part because of the author's major PSL for him), when he is hit with the woobie treatment, the author hits him hard.
- You think Vexen being a Woobie is bad? Try Axel. Yes, badass Deadpan Snarker Axel. While the author doesn't turn him into a Draco in Leather Pants, and actually makes him out to be the violent, dangerous, deadly-loyal man that he was supposed to be in Kingdom Hearts, his friendship with Isa/Saix, who is now in love with Xemnas, (whom Axel is not exactly on the best terms with), nets him some woobie moments, especially when he feels like Isa has stopped caring about him. And as of the more recent chapters, his pining for Roxas, who doesn't even exist yet, might qualify.
- Ansem can definitely count as this on occasion. Considering Ansem watched his sons lose their hearts by basically being eaten alive right in front of his eyes, while he was powerless to do a thing, it's no small wonder that he's more than a little messed up by the time he's introduced in Fill the Moon.
- Rain Nook in the Yoshi Egg Series, up until you find out that she's being manipulated through her stone by an Eldritch Abomination-like demon. But you start loving her again in the beginning of Fantendo Chronicles: Episode 1, where she and Unten paired up and "went forward" after the Chaoti swarm, Rain supposedly still alive and not possessed anymore.
- The fanfiction Street Sharks: Redux is basically the result of rewriting a silly cartoon in a way that's actually kind of dark and scary. As a result, the heroes have to go through a lot of nasty stuff, what with being kidnapped and mutated and all. Of particular note are them turning into sharks and flashing back to how it happened, and chapter six, which is the start of a story arc that gives a lot of unpleasant details about how Slamu gets kidnapped again and painfully experimented on a second time.
