Jerkass Woobie/Web Comics

""Geez. That Lizard Folk is a jackass, but he doesn't deserve this. It's like watching someone duel their own puppy.""
 * Order of the Stick has a number of these:
 * Vaarsuvius,
 * The Scrappy, Miko Miyazaki, however, takes the cake. She's a fanatical Lawful Good paladin who takes many morally questionable actions, and has a holier-than-thou attitude that causes her to be almost universally disliked even by her own allies. It's not until  that she becomes The Woobie, but
 * 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:

"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."
 * 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  Tsukiko just wants to be loved.
 * Drow Tales 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.
 * 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 Mabs 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.
 * Veser from Hanna Is Not a Boys 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.
 * 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,, was moved close to it.

And unfortunately, as if to prove that things really CAN get worse,. 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
 * Jeanne.  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.
 * 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
 * Then he sees  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.
 * 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.