- The Order of the Stick has a number of these:
"Geez. That Lizard Folk is a jackass, but he doesn't deserve this. It's like watching someone duel their own puppy."
- Vaarsuvius, especially after using some very nasty black magic to save hir family, and all they do is look at V in utter disgust.
- The Scrappy, Miko Miyazaki, however, takes the cake. She's a fanatical Lawful Good paladin who takes many morally questionable actions (but doesn't lose her Paladin status until she kills Lord Shojo), and has a holier-than-thou attitude that causes her to be almost universally disliked even by her own allies. It's not until her Heel Realization / Heel–Face Door-Slam / Alas, Poor Scrappy moment that she becomes The Woobie, but she doesn't even get a Died Happily Ever After end. "Redemption isn't for everyone"? Ouch!
- Redcloak. Though it doesn't come across as much in the online strips, Start of Darkness reveals that he has some pretty sympathetic motivations, but has made some absolutely horrible choices.
- Gannji and Enor are amoral bounty hunters who attacked the main characters, but get a Tear Jerker/Aww, Look! They Really Do Love Each Other moment during the Gladiator Games, when they're scheduled to fight each other and try desperately to get out of it. To quote Roy:
- Tsukiko has no patience for living beings, only the Undead, and positively bullies Redcloak. But the Monster in the Dark knows that at least half the reason for this is that she's always been treated badly by the living, and she can trust the Undead. As he comments after Redcloak has her killed and eaten by her "children" Tsukiko just wants to be loved.
- In the end, Nale only wanted to be his own man.
- Drowtales seems to like this one, half the cast seems to suffer symptoms of this. Perhaps most notably:
- Syphile, Ariel's abusive older sister.
- Sil'lice, who suffers from acute Fantastic Racism.
- Her mother, the Val'Sharess Diva'ratrika, is, by most counts, not an especially nice person, but very few people think that she deserved to be betrayed by three of her own daughters and left to die in her throne room.
- Shinae, Chrys' "protector twin".
- Given that this is a Crapsack World where even small children are expected to know how to fight to death if need be...
- Jamie in Khaos Komix is homophobic, a bully, and just all around mean. It's hinted at in some of the earlier stories, but it's not until his chapter (the last one) that the reader finds out that he was sexually abused by a neighbor when he was a child and physically and emotionally abused by his mother. He doesn't think of this as a Freudian Excuse, though, insisting in his internal narration that he's just a jerk.
- Dan and Mab's Furry Adventures: Abel. He is strongly implied to have driven all of his previous roommates to insanity, feeds off of misery, and never leaves Sarcasm Mode. On the other hand, he has a lot of bad luck and his backstory is tragic even for a Crapsaccharine World.
- Candy from Girls with Slingshots: a petty, nasty little (un)professional dominatrix, who was (is?) the closest thing the strip had to a villain...until Jameson (her best and only friend) tells her off due to the increasingly mean pranks she was playing on Jameson's fiancée, Maureen (up to and including replacing their wedding rings with baby seal leather cock rings at the ceremony). You can't help but feel sorry for her when Jameson tells her to go pound sand. And doubly so when guest star Davan - possibly the king of this trope among webcomic characters - calmly but brutally lampshades her stupidity.
- Veser from Hanna Is Not a Boy's Name. Conrad also sometimes counts, but he volleys between Jerkass Woobie and The Chew Toy.
- String Theory has Dr. Schtein, who is an absolute Jerkass. The revelation that his mother abused him, his emotional failings, and the fact that he spends the majority of chapters 2 and 3 either ill or beaten up launch him into Jerkass Woobie territory.
- Speaking of Something*Positive, the fact that Mike holding this status can be considered Character Development tells you what an utter asshole he used to be.
- Sakana: Yuudai is a jerk that often makes his life to make the work of the main characters as awful as humanly possible, and it's not up until way later that we learn that he's actually very lonely and sad, has a hard relationship with his family and up until recently, was in an abusive relationship. He starts growing out of his jerkiness after meeting Taisei.
- Check, Please!: revelations made by Jack in Year 3 makes Kent's character look like this looking back. While his original actions on the Epikegster made him look like a Bitch in Sheep's Clothing, when Jack states that his relationship with Kent was, from his eyes, merely physical, and doomed to end while Kent is still very much in love with him, that besides the fact that Kent is a closeted professional player who his only and biggest friend cut relationships with after a overdose with no explanation, really makes his actions seem to come from sadness and loneliness.
- Jack himself was this on the start. He was a jerk to Bitty for seemingly no good reason to the point where even Bitty disliked him, but he is also a Recovered Addict with severe self esteem issues and that the media and popular rumors insist on picking on. He does though, grows out of his jerkiness after he starts befriending Bitty, by the time they start dating, Jack is a completely Nice Guy.
- Gunnerkrigg Court
- Zimmy, who viciously lashes out at random people. But then, she's constantly under strain, never sleeps, and stuck with an uncontrollable ability she expects to last until she dies. And there are two other students she cares about.
- Ysengrin, of all forest people, was moved close to it.Fan: God, I just want to pet the poor murderous bastard. It's nice to see him evoke an emotion other than fear or anger.
- Jeanne. She's separated from her lover and turned into a human sacrifice by her friends, meets her lover again only for him to be murdered right in front of her, lies at the bottom of a river alone until she dies, and is forced to guard the river as a ghost until her soul rots away. Her reaction to seeing a genuinely happy teenage girl is to assume she's mocking her and try to kill her.
- Anthony Carver has been a largely absent parent, is regarded by just about everyone as cold and emotionless, and the one time he contacted Antimony in-story it was primarily to relay a message to Kat's father, Donald. When he arrives in the flesh, it's as one of Annie's teachers, during which he quickly dismantles much of her character development, takes Reynardine, and forbids her from the forest. He starts to fall into the Woobie side of this trope in the chapter "Annie and the Fire", where its revealed that much of his time away was trying to find a way to bring Annie's mother Surma back from the dead. He was so desperate that he let otherworldly beings trick him into sacrificing his right hand to bring back Surma's soul, remembering too late and to his horror that, due to their etheric ancestry, Surma's soul is Annie's soul. He's grateful that Zimmy's appearance stopped him. After that pushed him past the Despair Event Horizon, he only came back because Annie was threatened with expulsion. But seeing Annie, and her resemblance to Surma, pushed him over the edge, causing much of the bad treatment.
- Monster Lands has a few.
- Eren Lorry is the evil queen of the Monster Lands, but her backstory shows she was born into poverty and was raised to think violence is the only way to enforce her rules as the new ruler.
- Exris is Eren's second-in-command who raised her to be the violent ruler she is today. He's a cruel enforcer of her will. However, he was the abused slave of the previous ruler and it's shown that violence is the only way he knows to solve a problem, he pretty much had no choice but to be evil.
- Luka of The Meek is a vengeful badass dictator who comes from an extremely misogynistic and warlike culture and has a tumultuous relationship with his wife and children. At the same time, his life has been one long string of Break the Cutie that's left him physically mutilated, and despite the above, he does seem to genuinely love his family.
And unfortunately, as if to prove that things really CAN get worse, his beloved wife dies a horrific death right before his eyes. This not only sent his Woobie points through the roof, but also seems to have final broke him, and he seems well on the way to taking the step to being a Woobie, Destroyer of Worlds.
- Most of the trolls in Homestuck have some degree of this, considering what they went through during their game session and the consequences of it, but Karkat definitely takes the cake out of all of them. He's unfailingly violent and egotistical, but tends to beat himself up just as much, especially when he fails to get Sollux into the Medium before the Vast Glub hits.
- Then he sees an alternate universe version of his mentor destroy Prospit right after he finally wakes up, watches his team fall apart, eventually culminating in Eridan killing two of Karkat's friends and blinding another, and the nicest troll of them all goes insane and decides to kill everybody. The poor guy really needs to be cut a break. (His comments about certain elements of troll romance make it clear that he thinks no one will ever be able to hate him as much as he hates himself.)
- Vriska is another big one. When she's introduced, she's the Token Evil Teammate, a sociopathic Smug Snake who does horrible things and seems to have few to no redeeming qualities. Then we find out how she got that way. Even her obnoxious demeanor can traced back to repressed guilt and self-loathing.
- The Inexplicable Adventures of Bob!
- Gwynn in Sluggy Freelance. She's ill-tempered, humorously violently abusive, petty, and selfish, and usually has a kind of love-hate relationship with even those who are the closest to her. But as time passes, we also get to see her uncertainties, weak moments, and regrets over being so selfish as well as so aggressive towards others when she was really being defensive because she knew she was in the wrong. She has some really rough times, too, as the story goes on; there was a time when she may have had it harder than the other characters, though by now, almost everyone's gone through enough hell to surpass even that.
In 2014, the picture next to the comic title at the top of the page was even changed to a sad Gwynn after years of it being of the evil rabbit Bun-bun.
- Flask in Endtown. Her Dark and Troubled Past almost excuses her nasty treatment of everyone. Almost.
- When we first meet Kieth from TwoKinds, he is kind of a jerk to everybody. The 'Hero' is justified, since he has a reputation for being evil, but Flora seems to be a target of Fantastic Racism. Turns out he Was bullied and looked down on by his father for being weak. Was framed for killing his mother and father when he was a child, which had him exiled from his homeland. After that, he met up with the Catfolk, fell in love with one of them, only to be stood up on his wedding day. All of this is revealed to the audience and resolved in the course of two days. Suddenly, his Jerkass behavior seems a lot less mean spirited then it did three hundred comics ago. Did we mention that in those two days he had to watch two people he cared about die (one of whom he killed), and tried to kill his new love interest? Guy has had a really bad day.
- Black from Grey is... definitely fits the bill—however, the comic plays its cards very close to the chest in the beginning, so before readers know anything about him, he just looks like a Jerkass.
- Ferret from Scooter and Ferret has shades of this. He's a Grumpy Bear but you have to feel for him at times.
- Nin Wah from Commander Kitty. She can often be quite an abrasive snarker to anyone other than the Velvet Knight crew. But she goes through hell during the early parts of the comic as she loses her entire crew and winds up put through a Kangaroo Court after being framed for their disappearance. And then there's her insecurities over her cyborg arm...
- And in a rather odd example, there's the Big Bad Zenith herself. She's a Bad Boss who inflicts copious amounts of Body Horror on her victims in the name of creating her own perfect mate...except she also apparently has no idea she's actually a robot, and that all her plans for galactic conquest are pretty much a pipe dream. And shortly after her Face–Heel Turn... she suffers a catastrophic breakdown.
- The eponymous Kev from Alice And Kev is a selfish, sexually-aggressive bully and abusive father. He's also literally, factually insane and doesn't really seem to understand why nobody can stand to be around him.
- Hui, the titular monster fromThe Art Of Monstersmay not be the easiest being to get along with, but she genuinely cares for her master and it’s hard not to feel sorry for her in the end.
- Benni from Forest Hill is a school bully who gets into a fight with Tanya after she refuses to kiss him and when Kaleb came to try to save her, he gave Kaleb a serious head injury that put him in the hospital for days and causes him to start having seizures. Then it turns out that Benni has an extremely abusive and neglectful father who forces him to have sex with men for money (which seems to be the only reason he cares for Benni at all), and poor Benni doesn't even realize that this isn't normal.
- Wayne from Two Guys and Guy is a Played for Laughs example. As the comic's Butt-Monkey he is often on the receiving end of the two other protagonists' Comedic Sociopathy, but whenever we see him interact with people outside the group, we are reminded that he, too, is a horrible person.
- Housepets!: Tiger Arbelt. Despite being mainly portrayed as a secondary comic relief character, he has some serious psychological issues to work though. He's been a victim of bullying and is basically a social outcast among the dogs simply because he has a catlike name. This in turn has made him irritable, aggressive and temperamental to the point of being borderline Ax-Crazy at times while at the same time, struggling with binge eating and depression. Tiger may have a short fuse and a big mouth but he could also really use a big hug and a shoulder to cry on. As one forum member put it: "Tiger is an emotional wreck and responds to his problems by being a jerk."
- When you factor in the fact that King used to belong to PETA, he stops being The Woobie and starts being this.
Jerkass Woobie / Webcomics