Rayne, the author of Abstract Gender, also almost qualifies in some people's minds, what with the Curse and all.
Dark Smoke Puncher is about the closest The Adventures of Dr. McNinja gets to having a Woobie. He hides his intelligence behind false idiocy and slang, and his fantasy is apparently having his father hug him while expressing approval of computers. There's also Gordito, whose father was murdered by PETA.
Hell, the doctor himself. His entire childhood was an exercise in Training from Hell, and he's had to lose his mentor to death three times. The same mentor. One of those times involved Ben Franklin II's zombie re-dying in his arms after Gordito shot him. His parents disapprove of his job as a doctor. When all the drug-ninjas he killed came back as zombies, he blamed himself, thinking they wanted revenge. The list goes on.
Mongo the uber-ninja, when he learned all life is precious.
Actually, if all of the characters weren't awesome incarnate, about half of them would qualify as Woobies.
Roast Beef from Achewood, who is "from circumstances" which cause him to suffer from depression and possibly avoidance disorder, and is subjected to a constant stream of bad luck in life in general. This is made all the more noticeable given that his best friend is Ray, who becomes rich without trying and was only prevented from becoming President because of his mother's disapproval.
Alien Dice has Lexx as a main character who grows up in an uncaring orphanage and is forced to fight as a pokemon/gladiator (really). Lisaan, supporting character, gets rejected for being a half-blood and then sold into slavery. Cue much angsting which contrasts nicely with most of the other cast's cheerful attitude and grand stand in society.
Sy, from the Alchemist Muse's webcomic Asylum- Blacklight is a woobie to an extreme (has even been declared so by word of god, when Muse listed the tropes Blacklight follows and subverts. In the OC tournament "The Cure", Sy demonstrates his ability to fight and kill opponents, and yet end up still being the one you feel sorry for in the end.
Archipelago has Blitz. The poor guy has Trauma-Induced Amnesia, Ocean Madness (though there were a few other factors), is missing an eye (which he took out by himself, by the way), and mind is broken completely beyond repair. It's even stated that even if he was 'fixable', he may not like what he finds. Add the fact that he's a total sweetheart who just wants to be helpful, and you can't help but want to give him a hug.
Buni is so optimistic, even though he probably has the worst luck in the universe. The audience wants so desperately for him to be happy... but even when he is happy, it usually remains tainted with some sort of hopelessness, or is immediately followed by some soul-crushing misfortune.
Abel from Dan and Mab's Furry Adventures . Dear God, Abel. Picked on as a kid because he's different; his one friend from his old hometown eventually commits suicide; he gets stuck in a battle alongside two of his former tormentors, both of whom end up dead; his father turns out to be a 'cubi who killed his mom's actual husband and masqueraded as him in order to get a child; said 'cubi-dad proceeds to smack his mom around, kills his friend in a fit of rage, and threatens to kill his mom in order to keep him at SAIA, and the next time he sees her is when she is on her deathbed.
Komiyan from Darken qualifies. He's a cowardly drow with bad eyesight who wears glasses and has a courageous side. He looks absolutely adorable. And he rarely gets to do any badassery for long before being whomped by something. Or stabbed, or shot, or tortured.
Grimal's Furry webcomicDeo succeded in woobiefying the ENTIRE MAIN CAST. Every single one has something terribly, terribly wrong in their personal lives, and you keep reading just in the vain hope that something good happens to em at some point. This is a webcomic where you want to take the entire cast, put them in a room, and give them all blankets and hugs. And some group therapy.
Ed from Digger (pictured... unless they've changed it). Isolated for 17 years? After suffering spousal abuse for some time? And ripping his mate's throat out because she was beating their child because he loved her? Who doesn't want to give him a hug and some tea? At least Digger feels the same way.
Scapegrace from Daddy-Long-Legs has shades of this at times, with his extremely sad and depressing dreams, which indicate his childhood was not exactly nice and his family was dysfunctional and screwed up. Oh and he's probably having the same sickness his dad had, showing the same symptoms, so there's the possibility that his days are numbered. And really, Harvestman and Crane are pretty much his only friends, and even Crane thinks him to suspicious and creepy, such as the scene where he immediately thought Scapegrace to be the cause of his missing son. It's hard not to feel sorry for him.
The titular character of Dominic Deegan, who seems to run into more problems than he knows what to do with, and always thrusts himself headlong into them, to the point where he eventually traded the "crippled" role with his own younger brother. Of course, there's also a good portion of the fanbase who just want to punch him instead.
Rilian, of all people, might count as one. He seems to have had all of three good friends in his life, two of whom he's had to kill to save the world, both times from the same threat while being unable to prevent the death of the third. Nobody else seems to like or trust him because he's a spooky looking necromancer. Then there's the time he spends as "Brian", when he acts friendly and gregarious and just plain likable; followed by the revelation that that's who he actually is at heart. His cold Dog Shooter nature is a facade he uses to deal with his trauma. His woobiedom can be seen here.
Leaflette: You are as cold as always Rilian.
Rilian: My roles requires me to be cold. Otherwise I would be overcome by the immense sadness it brings me to have to kill you, Leaflette.
Luna. Let's see, born with a set of rather unappealing tusks, bullied and belittled by her entire family throughout her entire life as a result, gave her virginity to a man she was in love with who returned the favor by sleeping with her sister the very next day, was rejected by ANOTHER man she had a crush on when he catches sight of her tusks, learns that her own mother set up those last two points in an attempt to get her to KILL HERSELF for MONEY (an attempt that very nearly succeeded, as she was preparing to hang herself with Dominic stumbled upon her), watches as said mother get decapitated right in front of her, learns two days later that her mother left her NOTHING in her will out of pure spite, and tops it all off by trying to kill herself AGAIN. And really, can you BLAME her? Forget one hug, this woman needs, nay, deserves a hundred of them.
Drowtales has several varieties of Woobie, since it's set in a Crapsack World where cuties get broken on a regular basis. There's the main character Ariel, her friend Faen who can't control her empathic powers, Naal'suul, who shouldn't even be alive, and Jerkass Woobie Syphile as well.
Pretty much everyone in El Goonish Shive, to some extent, but Grace and Justin in particular.
Ellen, at least when she's introduced (as an Opposite-Sex Clone who remembers everything the original does... as far as she's concerned, her body was changed, then her life is no longer hers, then it turns out she's probably going to die within a month... she was having a seriously bad week.) From this point on, some think she stays the Woobie, while others think she turns into a Jerkass. Others take a third option.
Recently Susan has been getting another good Woobie streak, not to mention Catalina...
To summarize Susan's Woobieness (which in it's own way is as bad as Grace's), she first sees her father cheating on her mother with a blonde woman, who looks very, very similar to how Susan does when she's older, which causes her to develop a hatred of men and to dye her hair. Next, on a trip to France, she's attacked by a Vampire (well not quite a vampire, but...) because she had the potential to kill it, not the ability. She's then recruited, as a Child Soldier, by a group of Immortals to kill said vampire, which she does, but the event leaves her traumatized. In more present times, she's alienated for her feminist veiws, and when her school brings in uniforms she's attacked by the other students for not trying to completely remove them, but to just make them better. Then, a few years later, when she's started to come to terms with this and open up again, she's then told that she didn't actually need to kill the vampire because there where governmental forces nearby the Immortals could have contacted, which would have been faster, more effective, and not relied on two fifteen year old girls. And then the Immortal who revealed all this kinda dies. Ouch
and to make her woobiness more complete, she's capable of being incrediblycute at times, to cement her need for a hug.
Dan has said that sometimes he wishes he could actually hug his characters, especially Catalina.
Grace. Oh poor, poor Grace. She's watched her "father" (He was from a genderless species, long story) die brutally in front of her at a young age, been abused by her brother ("Only when I was bad"), and, even when she escapes, is still hounded. Dan even draws a sketch where he apologizes. He even titles it "It's my comic, and I'll cry if I want to."
All of the main cast of Alone In A Crowd qualify as Woobies for one reason or another.
Sara lost her parents and now has to look after her little sister, at first on very limited income.
Sara's little sister, Faith, was born with cat ears instead of human ears and is being bullied at school because of it.
Faith's friend and later, adopted sister, Hope was abandoned by her jerkass parents.
Rumiko Takahata in Fans!!, especially regarding her romantic relationships, so often that the rule 'Rumy must suffer' became an in-joke in the fan forum.
Florence in Freefall has been skirting this trope lately, what with the Mad Scientisthaving fritzed her short-term memory, not to mention turning her off (just her consciousness, fortunately) more than once. Somewhat averted, though, because she's approached the situation as a problem to be solved with her usual level-headed good cheer.
The Ecosystems Unlimited security computer made me want to hug it in this strip. It's incredibly incompetent at its job and the humans it works with don't really recognise it as a person, so I can understand why that would have happened, but that was literally the only compliment it's ever received. Poor little buggy AI. It doesn't seem overly bothered by being treated with exasperation, contempt, and the occasional death threat, though. In fact, it's more of a Large Ham than anything ("Security guard: RECOGNIZED! Room 101 door: OPENED! Element of surprise:RETAINED!").
Black from Grey is... every time you hear more about his past you just want to hug him and make it all better. Luckily White is there to do it for us
Zimmy in Gunnerkrigg Court: When she first appears, she seems like the last character you'd want to give a big hug to out of sheer sympathy. But recent chapters, especially this page, have proven that wrong.
Boxbot would be a woobie, but he is disqualified for being terrible.
Annie herself qualifies pretty well. Her mom's dead (and up until then lived most of her life in the hospital with her) and her dad's disappeared without a trace. Comparatively, that doesn't sound so bad until you learn that none of the Psychopompoi were able to lead her mother to the afterlife, so she had to do it herself.
Annie recieves an even worse revelation later on in the story. She was the cause of her mothers death, which is WHY she had to lead her into the afterlife.
Gamma, too. Because of Zimmy, she barely gets any sleep and she thinks everyone hates her (because she doesn't speak English - Zimmy doesn't want her to learn - and Zimmy lies about what other people are saying because she thinks that Gamma would abandon her if she had the chance to make other friends), but she's so sweet and so devoted to Zimmy that she doesn't mind any of it. And when her feelingsget hurt you just want to give her a big hug and tell her everything's okay.
We could save a lot of time and simply say EVERYONE from Homestuck. The universe is not kind to these characters.
The trolls as a whole. While at first they seem like plain old antagonists; they are eventually established as closer to the neutral end (with the exceptions of Eridan and Vriska): Sburb is destroying their home planet as well, and the reason they harass the protagonists is that the heroes' session is so screwed up it breaks their game as well.
Tavros, in this update especially. Basically, an Ineffectual Sympathetic Villain with heavy emphasis on "sympathetic". Andrew just refuses to give the poor guy a break. Accidentally running over his Lusus, forced to jump off a cliff in mockery of his greatest desire, his one attempt to to be assertive and helpful on his own ending up killing the grandfather of the human he had hoped to befriend... He eventually discovers his primary tormentor has actively created the unstoppable monster endangering them all. He finally decides to challenge her, not for his own sake, but for everyone's. As soon as she realizes he means it for once, she promptly kills him for actually standing up to her.
Vriska, despite being nicknamed as a HUGE 8ITCH, still winds up being almost tragic. While she's done a number of really awful things, it eventually becomes clear that she's basically trying to cover up her self-hate and loneliness by turning herself into a Jerk Sue. The bitchiness, hamminess, and attempts to make herself the central character in everything are all because she's trying to live up to what she thinks her ancestor was like, and it's not until after she kills someone she knew well that she starts to realize that she doesn't actually like being the person she's always tried to be. Then, when it starts to seem like she's considering redemption, she tries to go and confront Bec Noir, and Terezi kills her to stop her from leading him back to murder the rest of them.
WV, once we saw what Jack Noirdid to the army that rose up and followed him. It also turned his antics with Can Town into a huge (and hugely depressing) "Funny Aneurysm" Moment.
Karkat. He watches his team is fall apart, killing each other and going insane before his eyes. He watches one of his best friends being killed, and the killer's past self hits on him. He's being mindgamed by a murderous, ridiculously powerful psychopath who knows exactly where he is, could destroy him in one hit, and could even be in the room with him right now. Later on, he watches yet another friend begin to die in front of him, and starts openly sobbing when he finally does die.
Dave, Rose, Davesprite, and Dirk all count as Stoic Woobies, trying to hide their pain.
Mituna, Sollux's Pre-Scratch ancestor. The poor guy has a hard time being understood because of his mental disability, and most of his "friends" treat him terribly. Cronus keeps insulting him and invading his personal space, Kankri gives him lectures about how his helmet makes people with mental disabilities look bad even though Mituna physically needs the helmet to avoid hurting himself, and when Meenah of all people attempts to come to his aid by bitching out Cronus, she gets called out for being a hypocrite.
Calliope, who a major chunk of the fanbase really, really wants to hug. Even death was no escape.
This is how some fans see Eridan. In canon, his situation is not the best ( After a hard breakup with Feferi, he does not take her relationship with Sollux and refusal of his protection well, driving him to kill the love of his life and blind his rival.), but many people try to excuse his actions and paint him as a sad, misunderstood child only longing for his true love. This tends to bother the rest of the fandom, considering that in canon, he's a genocidal maniac, more obsessed with murder of all landdwellers (including his friends) than getting a date.
On a related note, Katia Managan from Prequel is designed to be this trope; "Making a cat cry" is actually in the subtitle. Everything in the universe seems hellbent on making her miserable. She grew up with horrifying nightmares every night for most of her young life, blamed by her family for said nightmares forcing them to live in poverty, never been hugged once, become a homeless alcoholic and generally seen as a slut for her drunken misadventures and, despite her best efforts, never made any money. And that's just the backstory; it gets increasingly worse once she tries reinventing herself. Recently, after a long time when it looked like everything was going to be alright for her, it was all cruelly snatched away.
King from Housepets!. He was once a human who was a member of PETA. Now he's become fate's doormat.
Inhuman has several of these. In the main comic, Kyotoshi and Soshika Lypha, whose parents were murdered in front of them, and (arguably) Grey.
No one here has mentioned poor Dina Sarazu of It's Walky! here? The love of her life dumps her for another girl, she gets ignored and overshadowed whenever she makes an important discovery, a few of the characters hate her because she got saved from being crushed rather than big boss and she ends up in a relationship with a violent Jerkass who is only nice when he's drunk and thinks she's completely useless. And then she gets killed in an explosion. A major factor in why her Dumbing of Age incarnation is so beloved.
Secret from Keychain of Creation is very much the Woobie - though one of the Exalted, she's been given the Black Exaltation, turned into basically a superpowered, Exalted vampire cursed and doomed to bring death and destruction to the world - and she hates it. Worse, she has serious self-confidence issues, and is really kind of a hopeless, lovable klutz when separated from her malevolent, sentient shapeshifting sword in a world where epic heroes do violent things to each other all the time.
Riley Zinc from A Loonatic's Tale. Death of his father... check. Several mental/physical complications from lack of sleep, eating, and anguish from said parental death? Check. Paranoia and extreme superstition? Check.... and he's a musician on top of everything else. Don't you just wanna make him feel better?
Junko has recently been hit with the Woobie stick really hard with her father being revealed to be an alcoholic and coming to her school to quite openly leech money from her. Seeing what up till now was a strong, spunky female character looking like she's about to burst into tears combined with the implication that Junko was practicing Enjo Kosai to sustain this guy has made many people ANGRY.
It is worth noting that Nanasawa Kimiko crosses into Woobie territory in universe as well as out. Not only does one of her senior colleagues ask their boss if a hug would be appropriate, she is later horrified to find she has attracted an army of sympathetic minor characters, calling themselves the Nanasawa Protection Coalition.
A better case can be made for Ash being the Woobie, considering that the condition that has caused so muchangst also makes the impulse to give a hug both stronger andů appealing.
Mika of Mob Ties. Cute little goth waif? Check. Victim of a violent rape so traumatic that it left her in a coma for more than a year? Big check. Hates everything because of all the trauma she has been through? Double check. She will make you want to hug your monitor to death.
Nana's Everyday Life takes this to ridiculous levels as it Crosses the Line Twice. Imagine a comic about Nana from Elfen Lied and Henrietta from Gunslinger Girl constantly suffering undeserved divine punishments, one after another, in a constantly-repeating loop that only ends with the title character dying alone in a cold alley, and everyone she ever loved either sadistically betrayed her or died violently.
Though it must be said that her death resurrects a one-eared kitten who died just a couple pages earlier and fills the alley she died in with flowers. Which, in my mind, makes it that much more tragic.
And now his new girlfriend's Jerkass sister is making his life worse.
And it seems things were awful before Lorna adopted him.
Lorna and Rochelle also have some woobieish traits.
Opey The Warhead is about a boy named Opey... who also happens to (at least appear to) be a nuclear warhead. When the class realizes he doesn't explode on impact, he immediately becomes the victim of the entire classroom (well, three kids, but it's After the End) of bullies. Despite not having a face, Opey is amazingly expressionate and totally woobie material being a generally sweet-natured kid.
The climax of the arc in particular gives us plenty of Woobie moments for Vaarsuvius. It's beginning to seem like the character exists only to be beaten up... Being zapped by runes? Being hit with a frikin' huge rock? Having his/her windpipe slowly crushed by a Lich's bony fingers in a sort of Redemption Equals Strangulation moment? Woobie, definitely.
And it still goes on. Finally recognising the raven familiar as an companion and an equal, only to have everyone else think that the raven is an illusion and that Vaarsuvius is crazy? Having Inkyrius sue him/her for divorce and full custody of the children? V truly cannot get a break.
Haley, at times. Especially when you find out that she is obsessed with money because she wants to save her dad, who is being held captive by a country that will release him only if Haley pays them an outrageous sum of money. The events leading up to her Anguished Declaration of Love also count.
Er, not quite. As we see in On the Origins of PCs, Haley was obsessed with money even before that.
David Andrew Bartlett, protagonist of Ow, my sanity To put things in perspective, he ended up in the possition he's in because when facing an apparently imminent death by Eldritch Abomination, his only wish was that someone had given a crap about him during his life. The first person to do so is said Eldritch Abomination.
Ceasar Wolfe from Pandect would be a normal 17-year-old boy except that he's infected with a Virus that overwhelms him with uncontrollable feelings of lust. Naturally, no one trusts him, no one wants to be around him, and his name has become a synonym for "pervert". When he finally gets a genuine offer of friendship, it takes him completely by surprise.
Charlotte in Penny and Aggie is an interesting case. At first, she seems simply angry and bigoted, but we gradually learn more about her, her woobieness becomes quickly apparent. And then there's the "Missing Person" arc, where she appears to have hit a Moral Event Horizon... only for things to drastically turn around and her woobie status becomes weapons-grade - almost literally, as it led to massive fan outcry for the death of Cyndi, something almost never before seen in the fandom.
Jonas Faulkner of The Phoenix Requiem is not having a great time of it. His friend shoots him after he escapes from an insane asylum. And that's just the start of his problems.
Jeremy from Platinum Grit. And if the abuse he suffers over the course of the comic isn't enough, his backstory involves a childhood of being tormented by his Axe Crazy cousin while the rest of the family shunned him as a simpleton.
Jacob and Vincent share the role in Precocious as they somehow keep optimistic and cheerful in a world of cynicism and cognitive dissonance.
Buwaro from Slightly Damned counts. Something went wrong when he was born, leaving him a bestial, rage-crazed creature that attacked everything in sight. He wears an amulet that clears his mind and calms him down, but if it's ever removed, he'll go back to being a monster. His biological family is dead, and his adoptive father, brother and sister are gone, disappeared, and murdered, respectively. Oh, and one of his closest friends, who he may have feelings for, is now afraid of him because she's learned of his aformentioned rage. Oh, and just look at his childhood
Things have gotten both better and worse for Buwaro. Worse: he found out that both his sister and his brother, who he looks up to, hated him as a baby, and his sister is responsible for the rip in his ear. He also thinks his adoptive angelic father is dead (though he really isn't) and seems to be unable to grasp the basics of combat to defend himself. Better: he is learning, though, and at least he knows he had a father. Also, aforementioned friend has admitted her feelings for him.Repeatedly!
Kieri as well. She's stuck in a completely unfamiliar world, her brother is also lost in said world and she has no way of knowing what's happening to him, and she has no way of getting home. Compounding that, she has serious insecurity problems and believes that she is worthless and troublesome, stemming from her abusive mother. Fortunately, things seem to be looking up for her now that she has some supportive people in her life.
Sluggy Freelance has Oasis being quite Woobietastic, when she's not being Ax-Crazy or Bad Ass. Idiot Hero Torg gets a few moments of this during That Which Redeems. Even Aylee gets it during her visit to the parallel world where her species exists.
Jinx, the Cirbozoid technology officer in Kris Straub's Starslip. He is often put down by Vanderbeam and is unfortunately unable to fight back in most circumstances due to the "natural subservience" of his species. The Cirbozoids' baffling physiology also tends to put off most personal involvement from other crew members, and when it does overlap, the trope is just magnified.
Quentyn in Tales of the Questor. In fact, this trope is specified by the bully, Rahan, of why he picked on Quentyn: everyone feels so sorry for Quentyn that he gets away with everything no matter how outrageous the trouble he stirs up in Rahan's eyes.
Keith Keiser of TwoKinds: Accused of murdering his parents (He did kill his father - in self-defense, his father murdered his mother), exiled in order to protect his father's reputation (he was a high ranking military leader), manages to fulfill the impossible conditions of his exile (capture the Grand Templar, which happens to be Trace), only to be ordered to betray Trace (who he considers a friend) to the Bastians. And along the way, he develops feelings for the Kedrian assassin, Natani... self-loathing, misogynistic, gender-confused, biologically female Natani (Made worse because Bastians are prudish and xenophobic by nature and culture), and has been ordered to kill her to be accepted back into society.
You forget being engaged to a Keidren who then gets cold feet, goes into hiding and avoids him for several days. Her village turns him out saying she doesn't love him anymore. Finally, when he and Natani might have a relationship potential, she shows up, asking for forgiveness. On another note he has just had to kill his longtime childhood friend. Poor, poor, Keith.
Jake Miller in Umlaut House; in the second series, Pierce Lee takes this role up.
Lynn in Union of Heroes but what else do you expect from a superheroine called "The Eternal Victim"?.
The whole basis for Warbot In Accounting is how much it sucks to be the titular death robot. In just a single comic, he sat silently in the corner pretending to eat lunch while his co-workers talked about their families, tried to fill out a profile on a dating site but failed due to his giant claw/gun hands, failed three dates by being unable to perform basic activities, tried to build a robotic child only to have it cry in agony and die, and sat in the corner alone again on "bring you daughter to work day."
There is also Ashton from Winters In Lavelle. It doesn't matter what he tries to do, he still looks like a beaten puppy, either that or in some cases a "sad lil praying mantis".
Jack from Zoophobia is cursed/blessed with immortality, but can still feel pain. This "gift", and his supernaturally incessant bad luck, renders him practically agoraphobic and afraid of everything. Nevertheless, he's an adorableNervous Wreck who just needs love and courage. Awww. What pushes him even deeper into woobie territory is this page. Crying is listed as one of his "hobbies".
Poor, poor Sizemore Rockwell from ''Erfworld. He's a pacifist in a world where nothing but war exists, and he lacks the free will to exercise his beliefs and is forced to kill. He's interested in all sorts of magic, but is only talented in his own field, and his boss considers him useless and can't even remember his name. Did we mention he's one or two deaths away from being the Last of His Kind?.
He's also one of the greatest examples of the Stoic Woobie ever. To sum it up perfectly is this simple quote "when life gives you crap, you make crap golems". He's being very literal...
Terinu himself is more of a Jerkass Woobie, but his best friend Matt is a pure woobie. To put it in perspective, he grew up on a Mega Corp. controlled planet where the workers were kept in debt slavery, then sold at age eight to Space Pirate Mavra Chan by his father to pay for the man's alcoholism fueled debts. That was a step up for him.
Orville was only a Butt Monkey in his titular comic but then a mysterious figure came around and revealed his backstory, Orville was born a regular squirrel and his mother died soon after his birth, later his father died as well and he was adopted by a family of flying squirrels. Poor Orville grew up his entire life believing he could fly only to be crushed when he found out he was adopted years later.This comic strip pretty much says it all. He needs a warm cuddle.
Alice from The Sims 3 blog/webcomic Alice And Kev. She just needs a nice loving family to let her sleep on their couch without kicking her out. What makes it worse is that she's incredibly selfless, giving her paycheck to charity rather than spending it on, you know, food.
Jeremy of Split Screen: A sad sack with an abusive childhood, a best friend/love interest whom he hadn't spoken to in a decade and a dead wife and daughter. All of which combined to give him a bookstore's worth of issues. Still has a vulnerable, chubby charm to him.