Azula becomes this via Villainous Breakdown. As evil as she was in the series, the reveal of the reasons behind this and the showcasing of the full extent of her screwed-up mind caused many to pity her, including her foes, Zuko and Katara, in-show, and series creators, Mike and Bryan, outside of it. Her final scene can even qualify as a Tear Jerker.
Zuko himself was also this in the first season, in which he was the chief villain (though his villainous objective got hijacked by Zhao in the end), but lost much of his villain status in the following two seasons and became a straighter example of The Woobie.
Demona in Gargoyles, both very evil and very sympathetic all at once.
Moral Orel: this trope is arguably one of the main internal rules of character writing for this show. No one questions that many characters in this show are repulsive people who do and say repulsive things, which is more often than not used to portray the hypocrisy of religious fundamentalism. However, special attention is paid to make it clear to the audience that disgusting people have feelings too.
Given the events in "Help", Clay's breakdown in "Sacrifice" almost makes you pity him, even if you still hate him.
Joe is also an example. When we're introduced to him, he's pretty much a violent, sociopathic homophobe, but the episode "Dumb" makes it clear that he's terrified of growing old and weak like his elderly father, and it's implied that he feels insecure for not having a mother. Even Orel feels sorry for him.
Orel's little half-brother, Shapey. It's only when he says his first real sentence, articulating how he equates feeling thirsty for his mother's breast milk with feeling lonely, that it's made very clear that he's more than a spoiled, loud, pushy, sometimes violent brat, and there were already implications that parental neglect was a huge factor in why he was so mentally and socially stunted for a seven-year-old.
The Riddler in The Batman, whose abusive father, unfair boss, and treacherous girlfriend all drove him to a life of crime, and in the end, he was denied revenge on any of them.
In Batman Beyond, Willie Watt becomes this:he was bullied in school, picked on especially by the resident Jerk Jock and the gym teachers, and his own father is just as harsh on him. He has no friends, and even the Alpha Bitch only took him out to the prom to piss off the Jerk Jock who bullies him. So he steals his dad's giant construction robot called the Golem to act out revenge. After being arrested and sent to juvenhile hall, he undergoes a Training from Hell and gets Psychic Powers from the accident with the Golem, pretends he's the ghost of a dead student, and attacks the people who wronged him, even trying to steal a kiss from the Alpha Bitch with his psychokinetic abilities, until Batman arrives. In the end, he's defeated by tricked into knocking himself out with a tree sent flying by his own powers. As he lay unconscious, all everyone present could do is give him pity. It's later revealed that he was sent back to juvenile hall, where no-one will visit him, not even his father, out of fear.
In Transformers, a large part of Starscream's attraction is that he is both a horribly abused character and a narcissistic asshole. The ratio of him being beat with his own dislodged arm should be equal to the times he backstabs someone else.
In Big Picture Show, it turn out that Eddy has been physically abused by his own brother for his entire life and his jerkass personality was a desperate cry for acceptance and his way to mask his inferiority complex. The other kids found out his secret, much to their horror. Thankfully, they helped him by standing up to his brother, but the damage had already been done: when his brother is defeated, Eddy's mask cracks and he admits that he had been lying about everything his brother did because he believed that he would be "cool" if he did, only to find out that it just made him more hated. This also allowed him, and the other Eds, to finally be accepted by the other kids.
May has shades of this, mainly in the Valentine's Day special.
Hercules from the new 3D Garfield cartoon The Garfield Show is a mean Chihuahua with a spiked collar who is one of the bully dogs in the neighborhood, but he's just lonely and wants a friend, which is why he stole Pookie in one episode.
William Murderface is this. He's rude, swears, objectifies women, pees on things, doesn't bathe, and is an all-around asshole. His parents were killed by chainsaw in a murder-suicide in front of him while he was a baby, and he just wants someone to pay attention to him. It's made explicit that this hatred for everyone around him pales before his hatred of himself.
While not as big jerks, the other Dethklok members also qualify.
Hey Arnold!'s Helga Pataki. She may be violent, rude, and Tsundere-ish, but pretty much every scene set in her house is a testament to how messed up her life is. Absent-minded, alcoho—ahem, Smoothiholic mother? Check. Corrupt Corporate Executive father who treats her more or less like a piece of furniture? Check. Being The Unfavourite to her Stepford Smiler sister? Check. It's fortunate that the one person she latches onto as her savior, Arnold, is kind and patient enough to see through her facade and gives her the hope that she can change one day.
Rugrats: Angelica could be seen as this. Although she spends most of her time mistreating her baby cousin and his friends, there are episodes that show that she does care about them. Also, her mother concentrates more on her job than her own family, and her father spends most of his time doting on her, which causes her to grow up spoiled. Also, she has very few friends outside of Suzie, whom she treats as a rival, but does ultimately see her as one of her only friends.
Possibly Ren from The Ren & Stimpy Show. He often acts like an abusive asshole towards his friend (and life partner) Stimpy, but he does have his rare moments where he treats Stimpy with kindness, and if he's feeling upset, he usually goes to Stimpy for comfort. He's also just as much of a Chew Toy (sometimes literally) as Stimpy. It's just that Ren is so psychologically screwed up that he doesn't know how to act any other way and you can't help but feel sorry for him. It's also implied that while he does appreciate Stimpy for always sticking by his side and being his friend, he's still pretty lonely. His abrasive personality has the unfortunate effect of driving away potential friends. Let alone the fact that the first thing he felt in life was "UNSPEAKABLE PAIN!" (a slap on the butt by a midwife).
Raven. She does become nicer to her teammates in the later seasons, though, particularly Season 5, which takes place after the season in which the problem that caused her to be so messed up is dealt with.
Timmy Turner. Yes, he can be an insensitive jerk at times, especially in the later seasons, but when you consider what his parents and babysitter are like, it's kind of understandable why he would act in such a way, and it makes you want to hug the poor guy. Not to mention, he has a villainous Sadist Teacher(who, despite his ineptitude, would be a more nurturing parent than Timmy's own), is constantly belittled for his appearance, is constantly beat up and bullied at school, and lets not forget the small fact that he was shown with explicit detail how pretty much the entire world would be far better off without him, which was reality essentially giving him a Reason You Suck Speech. Oh, and the episode "Bad Heir Day" has him injured several times while trying to find Poof. Uncharacteristically, Wanda gives him No Sympathy despite the fact that Timmy is a Badly Battered Babysitter. Sheesh.
Remy Buxaplenty, too. He is a spoiled rotten Jerkass...who suffers even worse parental neglect than Timmy, almost to the point of Parental Abandonment. The reason Remy even has a fairy godparent in the first place is because he has Woobie traits. Even Timmy ends up feeling sorry for him.
The show Invader Zim tended to blur the line between protagonist and antagonist - making both characters (Zim and Dib) hilarious, adorable Woobies with jerkass/sociopathic tendencies.
The Delightful Children from Down the Lane are extremelycreepy children who are bent on the destruction of the Kids Next Door Organization and the supremacy of adults over children. They seem completely unsympathetic until you consider who they actually are and what happened to them. They used to be Sector Z but they were captured by Father himself, whose delightfulization device went haywire and delightfulized them permanately, to the point that it's quite literally impossible to turn them back (any attempts are just temporary). To think that such honorable members of the KND have been turned into such monsters is very unsettling. Which leads to major Fridge Horror when you think about their parents...
Also, Father himself, after "Operation Z.E.R.O." (and minor moments in "I.T." and "C.A.K.E.D.-F.I.V.E.").
Uncle Ruckus. The guy is an over-the-top racist, but he's also a lonely old man who has no family and virtually only one friend. He seems to genuinely hate himself for being black and tries all he can to hide it with delusions like Irish ancestry and re-vitiligo. And if the events of the first season's finale are interpreted, even God hates his guts. Being a walking cultural paradox does absolutely no favors for him. He also had a terrible childhood. His dad and grandma hated him and treated him like crap, his dad kicked him out of the house when he was a kid, while dragging him into objects that damaged his face, and onto a bear trap. His mom's internalized racism leads her to constantly wear a blonde wig and contacts. She told Ruckus that he was adopted and had "re-vitiligo" so he can feel better about himself.
Uncle Ruckus's father arguably would also qualify, due to the constant racism and abuse that he suffered from outside his home, which he took out on Uncle Ruckus to prepare him for a harsh world.
Dr. Doofenshmirtz from Phineas And Ferbhimself also counts as one. He wants to take over THE ENTIRE TRI-STATE AREA, but his backstories makes one wonder whether it's because he's truly evil, or if he's just a confused individual. For example, when he was younger, he used up the allowance he had saved up for a year to get his mother a teddy bear, which she immediately handed to his younger brother, Roger. As a matter of fact, when he makes a Least-likely-inator, he mentions in passing that one of the things he could do with it is 'make my father love me'.
Many members of the Total Drama Island cast (Heather, Duncan, Courtney, Alejandro, etc.) qualify.
Generator Rex: Breach gets this status in her titular episode. Sure, she's an evil, possessive kidnapper, but when her pocket dimension is being trashed by Rex and the Creepy Girl, they're essentially tearing her mind apart. Regardless of the situation, you had to feel sorry for Breach there.
Gwen's Evil Counterpart, Charmcaster, in Ben 10. Most specifically, it's third series, Ultimate Alien, in which it's revealed that, all along, she just wanted power to free her home dimension from an evil tyrant that had enslaved it and murdered her father. At one point, a magical chasm tries tricking her into jumping into it by casting an illusion of her father's voice, at which point, tears flow down her face and she says "...Daddy." At that point, her woobiedom is secured.
It Got Worse as the show has progressed, with her being put through such soul-crushing pain that she's become more of a Broken Bird than ever, and a very large portion of the fandom is hoping and praying for a happy ending for her by the time it's all through.
Ice King:(Unconscious, floating through a cosmic dreamscape) Why do people not like me? Is it because I'm a magic-user? Or is my beard too shaggy? [Sigh] I try so hard to be a good husband for girls. What's wrong with me? The Cosmic Owl: Hoooo! You're a sociopath.
Holly Jolly Secrets shows that the Ice King was once a normal guy that was driven insane by his crown and the loss of his fiancee, whom he called "His Princess". This makes you realise that he's been a Woobie since episode one.
All the enemies from Guardians of the Sunshine wanted was sunlight...and to kill Beemo for imprisoning them inside him for so long.
Lemongrab? Sure he comes across as one of the biggest jerks on television- always screaming at people and punishing them for petty reasons. But he might be the biggest woobie in the show. First of all, as soon as he was born, he was so terrified all he could do was scream and panic, and his eyes rolled back into his head. We didn't see Princess Bubblegum trying to help. He has so many emotional, mental, and psychological issues it's downright depressing if you think about it for too long. And yet, even though he's angry and isolated, he's stuck with the job of ruling a kingdom. He tries his best, and is only punished for it, even though he's obviously not used to being alive. Jesse Moynihan, Lemongrab's creator, recently said that Princess Bubblegum is his mother. Which makes all of those scenes of her verbally and physically abusing him not very amusing, and almost paints her as a complete monster. The guy's not evil- he just has problems with his head, and is constantly punished for having problems that not only aren't his fault, but problems he can't fix! Oh- and by the way, his mother doesn't love him and is ashamed of him, and according to Jesse Moynihan, he doesn't have any friends. His whole sucky, terrible life may make the earl of Lemongrab a bigger woobie than the Ice King!
Flippy from Happy Tree Friends. He's an adorable bear who suffers from severe post-traumatic stress disorder due to his time in war. While his "good" side tends to be one of the kinder and more sociable of the Tree Friends (aside from moments of cannibalism), his "evil" side will emerge whenever he sees or hears something that reminds him of war or death. Once in his evil state, he turns into an Ax Crazy killing machine, slaughtering everyone around him in sadistic glee. One episode had him getting some therapy in an effort to overcome his disorder but the doctor was the Too Dumb to Live Lumpy who's stupidity prevented him from effectively helping Flippy. He's also just as much a Chew Toy as the rest of the cast (meaning that he tends to get killed in horribly gruesome ways if he's not the one doing the killing) and is shown looking terrified every time he comes out of his Ax Crazy states to see the violence that he's committed against his friends.
Daisy Dingo. Most of her jerkishness seems to come from her upbringing. However, she seems to be the second least cruel Dingo (after Shifty). This is expored more toward the end of the first season, with Daisy allying herself more with Shifty than the others.
Also, Shifty, who started off as one of the series' badguys and eventually became a friend of Blinky's and part of the gang. It is debatable whether Shifty even counts as a Jerkass, despite being a dingo. He's actually a real sweetheart compared to Marcia. Shifty's just a little morally confused and a little eccentric, is all.
Homer Simpson. He's a Jerkass, yes, but he has attempted suicide numerous times, was raped by a panda, and all of his innocent buffoonery (and alcoholism) is actually an expression of his deep-seated self-destructive tendencies.
Bart also qualifies in plenty of episodes, as does the current incarnation of Nelson Muntz.
Lisa: It's amazing how I can feel sorry for you and hate you at the same time. I'm sure there's a German word for it.
Sinedd from Galactik Football: a friendless jerkass and probably the most unlucky character in the show (from being a war orphan and getting sick and injured to being used by numerous villains). As he said himself "Do like everyone else. Don't care about me and forget that I even exist."
The eponymous Sterling Archer: an abusive, womanizing, and egotistical secret agent barely tolerated by all those around him...but every indication points that it was a terrible childhood that made him what he is.
Jackal from Tinga Tinga Tales. He kicks other animals out of their homes and steals food from cubs, but then the animals make him a honey addict, and he only gets to taste one drop, and he starts whimpering for it for the rest of his life. Poor guy will never get his moon-honey and he's become so obsessed with it, he's become a total Cloud Cuckoolander.
Aladdin: Mozenrath. While he is undeniably one of the darker villains the series had to offer, he was raised by a man so ruthless that even Jafar feared him, and the source of his power is literally making his body decay, putting him at death's door at a very young age.
Brandy & Mr. Whiskers: Brandy Herrington. Many characters in the show dislike her for her bitchiness, but keep in mind, she's struggling to adjust to her environment and she must really miss her family.
My Little Pony Friendship Is Magic: as it turns out, Princess Luna gets like this when she's upset - it's not that she's a particularly bitchy pony, but she is a bit too thin-skinned for her own good.
Spike as well, at least during Owl's Well That Ends Well and Secret Of My Excess.
Dan Vs: Dan. He's a Jerkass who pretty much hates everything. The 'Woobie' part of Jerkass Woobie comes from the fact that everything seems to hate him back.
Cartman of South Park at times. He is a pretty big Jerkass to Complete Monster levels and he does deserve punishment for a lot of things. However, there's a few scenes where one feels bad for him like in 1% one by one, all his favorite toys are destroyed. The kicker is that his Polly Prissy Pants doll turns out to be the one who killed off his other toys and asks Cartman to kill her. He, with tears in his eyes, complies.
Velma in Scooby Doo Mystery Incorporated. She's a Control Freak to Shaggy, snarky and nearly came to blows with Scooby over Shaggy. But when Shaggy chooses his friendship with Scooby, Velma bursts into tears. And now she has the burden of sharing responsibility for the dissolution of Mystery Incorporated. She's all alone now, save for her parents.
Plucky of Tiny Toon Adventures. Just look at the torture Hamton's family puts him through in the movie.
Quagmire in Family Guy. Sure he can be a womanizing jerk but in the episodes "Screams Of Silence" the shot of Quagmire laying in his bed with an extremely sad face while he listens to his sister get abused is very disturbing.
Peter too at times. Sure he's a Jerkass but you could say he doesn't deserve some of the crap he goes through like that time he was raped by a bull, or the time Meg raped him with a loofa, for example.
Hell, almost EVERYBODY counts at one point. Brian's a narcissist and, according to the fans, the "Liberal Douche", but he has to deal with idiots on a constant basis. Lois can be vile and almost as bad as Peter, but dealing with a Jerkass husband and a Jerkass father may have turned her into a jerk.
