Jerkass Woobie/Comic Books

Examples of Jerkass Woobie in Comic Books.

Donald Duck.
Emma Frost from X-Men. As a kid, she was raised by a heartless father and a doormat mother. Her older sister was a queen bitch. Then, the headaches started. After losing several friends and lovers, suffering Fantastic Racism, nearly being a victim of sororicide, et cetera, it's not surprising that Emma Frost acts coldly even after joining the good guys.
- It Got Worse since she joined the good guys, what with her students dying and all. She's something of a Mama Bear now, though she's still as cold as ever.
Watchmen
- Rorschach. He's a disgusting psychopath who falls somewhere in between Anti-Hero and Anti-Villain, but his backstory combined with the awfulness of his entire existence just makes you feel immense pity for the guy. It's perfectly intentional that people should feel sorry for him -- unfortunately, some admire him and consider his nihilistic, absolutist worldview to be correct.
- Dr. Manhattan cheats on his wife with the second Silk Spectre, eventually alienates Silk Spectre too, and cares nothing about the course humanity takes, letting the Comedian murder the mother of his illegitimate child in front of him. On the other hand, his backstory reveals that he, as a result of being able to see the future, has lost the ability to relate to people or even decide his own fate.
  - In other words, he knows he's going to cheat on his wife with a girl whom he hasn't even met yet. It's insanity to even think about it, but he fully comprehends and accepts it, which sets him apart from everyone.
  - He gets better after his ability to see the future is disrupted and he sees the value of life.
- The Comedian may be another example. While his actions can be downright horrifying, he is entirely aware of how awful a person he is and desperately wants to change but can't. The only people he seems to care about view him as a Complete Monster, and he is full of self-loathing. Stopping Ozymandias would bring some form of redemption, but he knows that it is too late. Although the Comedian seems more like the guy who has lost hope in humanity and doesn't want to make it better. He doesn't even try stopping Veidt and he only does "superheroic" things because he enjoys the chaos.
  - The closest thing he has to a friend is his former Arch Enemy. Even the Comedian realizes how pathetic that makes him.
Arguably, Rayek from Elf Quest. Megalomaniac, drama queen, Troubled but Cute Jerkass, and still somehow sympathetic.
Superboy Prime. Many of the things he's done are monstrous, true. On the other hand, his superhero career started with his universe getting destroyed, followed by spending a few years with nothing to do but watch either his past life or the worst of the Dark Age. His first superhero fight after getting out went horribly wrong after he accidentally punched just a little harder than he meant to and knocked a heroine's head off. His life since then has mostly been an attempt to hide from his inner pain by using his vast power on anything that reminds him of it. Oh, and he's aware of the writers doing all this the whole time.
Batman: sure, he acts like a total jerk at times, but, hey, you'd be pissed too if your parents were gunned down in a dark alley.
- Same with his son Damian. All the kid wanted is to follow in his father's footsteps and for his mother to love him -- although now, since he chose Dick and his father's ideals over his mother, she pretty much abandoned him. And, since he was born, he was trained as an assassin and never got a chance to interact with society properly as a normal kid. And he was spoiled rotten and always got his way, without really knowing things like morals.
- Jason Todd/Red Hood. Considering that he grew up on the streets, had his foster mother (drugs), his father (Two-Face), his real mother (Joker), and his adopted father (Batman, really lost in time but he doesn't know that) all die on him, had his real mother betray him to the Joker when he tried to help her, was brutally beaten and then blown up by the Joker, was resurrected without his memories and forced to dig his way out of his grave and live on the streets, was dunked in a Lazarus Pit to regain his memories, found out that his adopted father had failed to avenge his death, was "betrayed" again when Batman attacked him to stop him from killing the Joker...
The Flash villain Captain Cold. He'd hit the ceiling if you called him any sort of woobie, jerkass or otherwise. This dude personifies the cold-hearted, unpleasant, pitiless SOB. Of course, his trailer-trash background, complete with a horribly abusive father who beat the snot out of him for saying, "I love you", might explain some of it. Cold spent his childhood trying to protect his little sister from their dad's rages. His mom was just another punching bag. His grandpa--the only good thing in his and his sister's life--died when he was 12. And then his sister followed him into crime, became the Golden Glider, and was murdered by one of her boyfriends. Cold's a genuinely tragic villain. Don't believe me? He reveals that he hasn't shed a tear since his grandfather's death. Then, he tracks down, tortures, and murders his sister's killer. A few panels later, he's at home, tears running down his face, saying, "Much as I hate it, my heart's not always cold."
Sometimes, Victor Von Doom falls in this trope. On the other hand, this is the guy who brought every bad thing that has ever happened to him down on his own head because he was too much of an arrogant prick to listen to Reed Richards' advice, opting instead to try to maliciously destroy the latter's life because he accidentally bruised Doom's ego by daring to be smarter than him. So he's basically crossed over the line to Woobie, Destroyer of Worlds.
Iron Man. Tony Stark. He's an arrogant, smarmy, womanizing jackass; but his life has been one long Trauma Conga Line, and due to his awareness of his flaws, he's a deep, dark pit of The Atoner bordering on Death Seeker, to the point where he feels that all his teammates' lives are always more important than his own.
Black Alice from The DCU isn't a nice girl. At all. She's petty, cruel, ruthless, and she has a strong case of Protagonist-Centered Morality. Her moral compass isn't very good either -- she once sold out fellow magic users to demons in Hell in a bid to fix her own powers and she briefly teamed up with the Secret Six. On the Woobie side of things, her entire life has been one long Trauma Conga Line that started with discovering that her mother was a suicidal junkie after she found her body in their pool. Then she had to watch her father lose himself in alcohol and depression. Then her boyfriend cheated on her with her best friend. She was the victim of a particularly cruel scheme of Talia Al Ghul's. Her disastrous attempts to master the Helm of Fate nearly got her father killed. Her powers got nerfed when she got mind raped in Hell. Most recently, she accidentally gave her father cancer. The poor girl is a miserable person with an even more miserable life.
Johnny the Homicidal Maniac. A little heavy on the jerkass, perhaps, but when we find out that he was a talented artist driven to insanity after being made into a flusher for the world's evils, it's impossible not to pity the guy.
Jezebel in Blacksad, book two, Arctic Nation. Her father literally left her mother to die while pregnant. She lived and raised her twin daughters before dying young. Our Jerkass Woobie plotted out revenge on that father over the course of decades -- a true Xanatos Gambit verging on Xanatos Roulette. She's cruel as hell to that man, and arranges for his death by lynch mob -- but she also loves her sister more than anything and wants just to be happy with her sister and her niece. And then, at the end, she's achieved her revenge, but her sister is dead, too, and Jezebel herself has nothing whatsoever to show for it. Try to not feel bad for her.
Doctor Who Magazine comic companion Destrii. She's a total Jerkass in her first appearance -- especially since she betrays then-current companion Izzy -- but when she returns later on, we find out about her childhood, which, among other things, involved being painfully and viciously tortured by her mother. Then her Affably Evil uncle, the only person who seemed to show her any real affection, beat her to a pulp for spoiling his plans. Even the other characters find themselves wanting to treat her like a Jerkass Woobie.
In Archie Sonic Universe issue 29 only, this is Scourge the Hedgehog-pretty much every single audience member was along with his pity party in that they wanted to see him get hurt more for one reason or another. Some people thought this. He's back to normal by the next issue, which subverts the trope.
According to his Christmas special, Larfleeze. He may be a greedy asshole, but he misses his family above everything.