Jerkass Woobie/Web Comics

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• The Order of the Stick has a number of these:
  • 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 / Deadly Change-of-Heart / 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/Aw, 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:

"Geez. That Lizard Folk is a jackass, but he doesn't deserve this. It's like watching someone duel their own puppy."

• • 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.
• 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. Behaves like a total jerk, which is partly a facade. Somehow, he hasn't completely driven all his friends away. His backstory is especially troubled.
• 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 Crap Saccharine 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.
• 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.
• 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.
• Yuudai from Sakana may be an absolute Jerkass who makes his coworkers' lives as awful as possible (especially poor Jiro), but Good Lord, does his life suck! Between having a sick mom, a harsh relationship with his dad, having grown in poverty all his life, and especially being subjected to a five year long abusive relationship by a particularly awful Bastard Boyfriend, which only ended recently when the bastard slammed a bottle into his face (which explains how he got his scar); many fans just want to give him a hug. Thankfully, he gets better when he meets Taisei, whose unrelenting kindness causes him to defrost a little and even gain a huge crush on him.
  • While not as extreme, "Angry Lady" aka Mori Yamamoto also fits. She Used to Be a Sweet Kid, until she caught her fiancé cheating on her, and the breakup was so awful she had to move in with her little sister Chie. The trauma led her to become the rude, antisocial woman seen in the present day. It's made clear she's a deeply wounded woman underneath all her anger, as seen when she explains why of her affinity to flowers: "They don't betray you". Sheesh.
  • And then there's the brothers' Jerkass cousin Genji, who suffers from an astounding case of No Social Skills, has a gambling addiction, and definitely doesn't deserve being screwed over by Nishimura and his gang.
• Similarly, Mitch Mueller from Long Exposure. While this hasn't come up much in the comic proper, Word of God confirms he has an horrid Dark and Troubled Past. He comes from a broken home, with his mom and him suffering at the hands of an abusive stepfather, which only ended when he stabbed his stepfather to save his mom, landing him into juvie. This led to him suffering severe PTSD and eating disorders, which he tries to cover behind his fearsome reputation. Worse, his bullying of Jonas is because he has a crush on him but doesn't know how to express it properly. And the origin of said crush? Jonas told him he liked him in one of his lowest moments, being the only one to do so. With all that trainwreck, he's lucky he and Jonas becoming an Official Couple is a Foregone Conclusion.
• 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.
  • Recently, 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.
• 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
  • Fructose Rioflavin, when his origin is revealed. Even prior to that, he could inspire some sympathy for his pitiful desperation over his continual failures.
  • And Galatea certainly has her moments.
• Gwynn in Sluggy Freelance. There's probably a lot of Your Mileage May Vary here, but anyhow...She's ill-tempered, 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.