* ''Webcomic/TheOrderOfTheStick'' has a number of these:
** Vaarsuvius, [[spoiler: especially after using some very nasty black magic to save hir family, and all they do is look at V in utter disgust.]]
** TheScrappy, Miko Miyazaki, however, takes the cake. She's a fanatical LawfulGood paladin who takes many morally questionable actions ([[spoiler: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 [[spoiler: her HeelRealization / HeelFaceDoorSlam / AlasPoorScrappy moment]] that she becomes TheWoobie, but [[spoiler: she doesn't even get a DiedHappilyEverAfter 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 TearJerker[=/=]AwLookTheyReallyDoLoveEachOther moment during the GladiatorGames, when they're scheduled to fight each other and try desperately to get out of it. To quote Roy:
-->"Geez. That LizardFolk 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 [[spoiler: 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:
** [[http://www.drowtales.com/mainarchive.php?order=chapters&id=67 Syphile]], Ariel's abusive older sister.
** [[http://www.drowtales.com/mainarchive.php?id=0 Sil'lice]], who suffers from acute FantasticRacism.
** Her mother, the Val'Sharess Diva'ratrika, is, by most counts, not an especially nice person, but very few people think that [[spoiler:she deserved to be betrayed by three of her own daughters and left to die in her throne room]].
** [[http://www.drowtales.com/mainarchive.php?id=1646 Shinae]], Chrys' "[[http://www.drowtales.com/mainarchive.php?id=1326 protector twin"]].
** Given that this is a CrapsackWorld where even small children are expected to know how to fight to death if need be...
* Jamie in ''KhaosKomix'' 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 [[spoiler: 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 FreudianExcuse, though, insisting in his internal narration that he's just a jerk.
* ''DanAndMabsFurryAdventures'': Abel. He is strongly implied to have driven all of his previous roommates to insanity, feeds off of [[BadPowersBadPeople misery]], and never leaves SarcasmMode. On the other hand, he has a lot of bad luck and [[DeusAngstMachina his backstory]] is tragic even for a CrapsaccharineWorld.
* Candy from ''GirlsWithSlingshots'': 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 [[http://www.girlswithslingshots.com/comic/gws786/ replacing their wedding rings]] with [[DudeNotFunny 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 [[Webcomic/SomethingPositive Davan]] - possibly the king of this trope among webcomic characters - [[http://www.somethingpositive.net/sp09292009.shtml calmly but brutally]] {{lampshade}}s her stupidity.
* Veser from ''HannaIsNotABoysName''. Conrad also sometimes counts, but he volleys between JerkassWoobie and TheChewToy.
* ''Webcomic/StringTheory'' 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 JerkassWoobie territory.
* Speaking of ''Webcomic/SomethingPositive'', the fact that Mike holding this status can be considered CharacterDevelopment tells you what an utter asshole he used to be.
* ''Webcomic/GunnerkriggCourt''
** Zimmy, who viciously lashes out at random people. But then, she's constantly under strain, [[TheInsomniac never sleeps]], and stuck with an [[PowerIncontinence uncontrollable]] ability she expects to last until she dies. And there are two other students she cares about.
** Recently, [[spoiler:Ysengrin, of all forest people]], was moved close to it.
-->'''[[http://gunnerkrigg.proboards.com/index.cgi?board=general&action=display=843=1#32975 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. [[spoiler: 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 ''Webcomic/TheMeek'' 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 BreakTheCutie 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 [[FromBadToWorse things really CAN get worse]], [[spoiler: 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 [[spoiler: taking the step to being a WoobieDestroyerOfWorlds.]]
* Most of the trolls in ''Webcomic/{{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 [[ItsAllMyFault beat himself up just as much]], especially when [[spoiler: [[MyGreatestFailure he fails to get Sollux into the Medium]] before the Vast Glub hits.]]
** Then he sees [[spoiler: 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 [[FoeYay 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 TokenEvilTeammate, a sociopathic SmugSnake who [[KickTheDog does horrible things]] and seems to have few to no redeeming qualities. Then we find out [[AbusiveParents how she got]] [[TraumaCongaLine that way]]. Even her obnoxious demeanor can traced back to [[spoiler:repressed guilt and self-loathing]].
* ''TheInexplicableAdventuresOfBob''
** [[BigBad Fructose Rioflavin]], when his [[http://bobadventures.comicgenesis.com/d/20100831.html origin is revealed.]] Even prior to that, he could inspire some sympathy for his [[http://bobadventures.comicgenesis.com/d/20070327.html pitiful desperation over his continual failures.]] His status as Jerkass Woobie is [[http://bobadventures.comicgenesis.com/d/20101218.html Lampshaded here]]
** And Galatea certainly [[http://bobadventures.comicgenesis.com/d/20080719.html has her moments.]]
* Gwynn in ''Webcomic/SluggyFreelance''. She's ill-tempered, [[PlayedForLaughs 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 ''Webcomic/{{Endtown}}''. Her DarkAndTroubledPast almost excuses her nasty treatment of everyone. Almost.
* When we first meet Kieth from TwoKinds, he is kind of a jerk to everybody. The [[AmnesiacHero 'Hero']] is justified, since he has a reputation for being evil, but [[CatGirl Flora]] seems to be a target of FantasticRacism. Turns out he [[spoiler: 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 ''Webcomic/GreyIs'' 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 ScooterAndFerret has shades of this. He's a GrumpyBear but you have to feel for him at times.
* Nin Wah from ''Webcomic/CommanderKitty''. She can often be quite an abrasive [[DeadpanSnarker snarker]] to anyone other than the Velvet Knight crew. But she goes through hell during the early parts of the comic [[http://www.commanderkitty.com/2009/06/12/the-tagged/ as she loses her entire crew]] and [[http://www.commanderkitty.com/2009/09/19/no-doug-llewellyn/ winds up put through a]] KangarooCourt after being framed for their disappearance. And then [[http://www.commanderkitty.com/2009/05/03/lefty/ there's her insecurities over her]] [[ArtificialLimb cyborg arm]]...
** And in a rather odd example, there's the BigBad [[MixAndMatchCritter Zenith]] herself. She's a BadBoss who inflicts copious amounts of BodyHorror on her victims [[http://www.commanderkitty.com/2010/04/25/plot/ in the name of creating her own perfect mate]]...[[http://www.commanderkitty.com/2011/08/07/enemy-among-us/ except she also apparently has no idea she's actually a robot]], [[http://www.commanderkitty.com/2011/08/28/process-of-elimination/ and that all her plans for galactic conquest are pretty much a pipe dream]]. And shortly after her FaceHeelTurn...[[spoiler: [[http://www.commanderkitty.com/2012/09/09/she-dun-goofed/ she suffers a catastrophic breakdown]].]]
* The eponymous Kev from ''Webcomic/AliceAndKev'' is a selfish, sexually-aggressive bully and abusive father. He's also literally, factually insane and [[IJustWantToBeLoved doesn't really seem to understand why nobody can stand to be around him]].