History Sandbox / TheWoobieReEvaluationPage12

* In FanFic/MegaManDefenderOfTheHumanRace, Mega Man, Roll, and ProtoMan all have moments of this at times.

* Fanfic/TheMadScientistWars: Chic Geek counts as well, especially with recent developments. Note that she's Cousin to Andrew and Desius — seeing a theme?

Molly Hooper in Fanfic/BeingMollyHooper. She gets trapped in her own subconscious after Irene Adler takes over her body and her life.

Another Homestuck fanfic, Fanfic/{{Hemostuck}} plays it very well with Kanaya, Eridan, and Feferi.

The Psiioniic. Wired into an engine, raped repeatedly for centuries by a crazed Yandere, and forced into having sex with his equally unconsenting daughter.
Tsukey. A member of the sufferist cult and Tavros' former palecrush. Captured and tortured for information, ended up as one of the aforementioned kin.
Gamzee straddles the line between this and JerkassWoobie, but no matter how big an ass he can be you can't help but feel sorry for the guy after everything he's been through.
In FanFic/MegaManDefenderOfTheHumanRace, Mega Man, Roll, and ProtoMan all have moments of this at times.

Nomad is activated by mistake, feels pain almost immediately upon waking, is unable to speak, overhears Wily talking about wiping her memory, and doesn't get a name before running off.
Read any of WesternAnimation/TheRaccoons fanfics by [[https://www.fanfiction.net/u/1423968/Ralph-Jr Ralph Jr.]] and expect Ralph, Melissa and even Bert to all be painted as woobies in them:
Ralph had a crummy childhood, sobbed his heart out in high school for being dateless, got beaten to a bloody pulp and almost killed by a bully who temporarily stole his girlfriend and has low self-esteem issues in general.
Melissa lost her mother, grew up an only child and her uncle was killed in combat. On top of all this, she loses her father to lung cancer in Beat The Clock and has to deal with pregnancy.
Bert is quite the Sad Clown. He wanted to strike it big and become a famous musician only to have his hopes and dreams crushed. On top of all this, in Beat The Clock, Lisa rejects him which actually reduces the poor guy to tears. This title card pretty much says it all.
[[https://www.deviantart.com/ask-the-fazbear-bros/art/Error-5-508922018 Shadow Bonnie also qualifies as this, considering he is a manifestation of Bonnie's depression and fear as well as Clyde's insanity. He's basically insane, full of anxiety and usually has [[http://ask-the-fazbear-bros.deviantart.com/art/Error-3-508825821 tears running down his face]] and is [[http://ask-the-fazbear-bros.deviantart.com/art/Error-4-508829498 abused by Shadow Freddy]].
From Fanfic/MaimDeMaim, we have poor Nui and, unlike Ryuuko, her life was never good to begin with and just as things were starting to look up for her, she gets knocked down pretty hard when her prescriptions were canceled against her will by her own mother. Damn.
Fanfic/PacificWorldWarIIUsNavyShipgirls has two: Arizona and Oklahoma. Both of them are the unlucky ones among the US Navy ship girls, who are both based on the two US battleships lost during the Attack on Pearl Harbor. Especially moreso for the former, who thanks to Past-Life Memories refuses to talk about anything related to the incident.

Any Series/KamenRiderGaimpost-canon fanfics would usually portray Mitsuzane Kureshima as this.
[[https://www.fanfiction.net/s/11772125/1/Metroid-Kamen-Rider-Generations-Full-Series Metroid: Kamen Rider Generations]]: This revolves more of Mitsuzane's habit of Heroic Self-Deprecation, and spends most of his time thinking that that his old friends still hate him. Word of God states that Mitsuzane had a hard time getting over his past. Good thing, he finds a company of a Heterosexual Life-Partner in the form of Gou/Kamen Rider Mach to keep him in check, and a new Love Interest in Samus to confide his insecurities with and help him cope with it.
Zack (to Alain): Micchy screws around... when he cries. When he feels so sad, he starts making jokes at anyone’s expense. It all started two years ago, when the Overlords began to conquer Earth, he aligned himself with them and betrayed all of us, this is the reason why him and Kouta became bitter enemies. Two months after Helheim was removed from Earth, and Kouta, Mai, and Kaito were presumed dead, Micchy is but an apathetic shadow of his former self, ashamed of what he have become. He feels like we shunned him for the sins he committed, though he was given a chance to redeem himself. Since then, his past would come to haunt him, which is the reason why you can hear he jokes around at anyone to hide his pain. In such away that protects him from a relentlessly and unkind world.
This canon divergence fic [[http://archiveofourown.org/works/4222647 Requiem]] by Perditus.
The MLP:FIM story FanFic/HarmonyTheory has several examples:
Rainbow Dash. She wakes up stranded in a Crapsack World and Bad Future for Equestria, on the brink of war, Celestia and Luna are gone, she is thrown in the middle of a conspiracy involving a War Godess and a ruthless criminal mastermind, and with none of her old friends to help her.
When Rarity and Applejack started waking up, they had to face the same problems, but with one sad difference: Their families are gone.
Fluttershy. She comes in on Max Cash's disemboweled corpse, and later sees Rainbow Dash kill Charisma.
The Lucky Star fanfic Fanfic/TheDayEverythingChanged, has Kagami becoming thoroughly woobified during Chapter 4, when she suffers the beatdown of her life at the hands of Sakura Takahashi, the school bully. She might have been killed if Konata hadn't intervened.
Due to her inability to tell Kagami her true feelings and the fact that she suffers more than a few brutal hits trying to protect Kagami from further harm but still keeps fighting back, Konata also qualifies as this, especially being more of an Iron Woobie.
Fanfic/TheMadScientistWars: Chic Geek counts as well, especially with recent developments. Note that she's Cousin to Andrew and Desius — seeing a theme?
From the [[http://strange-tomato.livejournal.com/26887.html Sims 2 story "Strangetown, Here We Come"]]:
Frances J. Worthington III is the epitome of woobie. Especially when 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 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.
WebVideo/ScootertrixTheAbridged: Rarity is a 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 The Mole, to her own race.

Fanfic/AdviceAndTrust: Kaworu also applies for similar reasons. He also has to live with the knowledge that the only way that the world can be safe for sure is if he dies. And like Rei, he's subject to the Mind Rape from Arael.