Lucky. Sure, he has a massive ego and a tremendous stubborn streak. Also, he can be quite the brat as evidenced in "Splishing And Splashing" where he outright refuses to apologize to Lucy for splashing her but then there are episodes like "Lucky To Be Alone" "Watch For Falling Idols" and "Cone Head" where he gets hit with a pretty heavy dose of Break the Haughty.
Mooch. He pretty much has the reputation of a thuggish gang leader and bully on the farm but in "Twelve Angry Pups", he's blamed for a crime he didn't commit and in "My Fair Moochie", Cadpig crushed his heart pretty hard after he tried to make a genuine attempt to change. It's perfectly understandable why he bursts into tears and sobs on Lucky's shoulder after Cadpig dumps him.
Dipstick. Sure, he's part of Mooch's gang but just watching him cry in "Twelve Angry Pups" kind of makes you want to cuddle and pet the poor thing. He also had his collar stolen by Swamp Rat in another episode.
All the enemies from Guardians of the Sunshine wanted was sunlight... and to kill Beemo for imprisoning them inside him for so long.
The Earl of Lemongrab. He's a jerk, (and really annoying) but he's absolutely pathetic, in his social awkwardness, Mommy Issues, constant anxiety, Friendless Background, and perpetual unhappiness. For some people, it's impossible to watch an episode with Lemongrab in it and not want to give him a hug or say something nice to him.
All Dogs Go to Heaven: Killer. In the original movie, he has a bloodthirsty streak and wishes to squeeze Charlie's head with pliers while in the animated series, he's a rude and obnoxious complainer but at the same time, he gets pretty much no respect from his boss, Carface. In the episode "Sidekicked", he's pretty much given up any hope of Carface saving him yet he constantly badmouths Itchy.
Roger Smith is this and a Woobie, Destroyer of Worlds. His Ax-Crazy behaviour is because his species releases a toxic bile that kills them if they don't "let their evilness out". Made worse when it is revealed the reason he is trapped on Earth is that the others of his species wanted to get rid of him (Apparently only Emperor Zing wanted to get rid of him as its heavily implied that he sent Roger to Earth as a crash test dummy and tried to kill him to get revenge of Roger for having an affair with a human man and Zing kept this a secret that only he and the Majestic knew). In addition, there are moments where he really seems to care about his adoptive family. It is implied that Roger only acts that way because he was made to be evil, and not by choice and pure malice, and if you stop to think about it, it's sad and terrible being him.
Stan Smith also counts. It turns out that the reason why he turned out to be a bigoted, impulsive, and arrogant man with anger problems was because he had a very rough childhood. His dad left his mom at Stan's 8th birthday party because Stan's mom had an affair with the party clown and Stan initially believed that his father was fully to blame for leaving him therefore losing all respect for him. Plus Stan's mom forced her own son to kill a dog that he loved so much because she wanted to get into an apartment that didn't allow dogs. Even after all of this Stan had to put up with his mom's antics not to mention the training he had to go through as an agent of the CIA.
Slappy Squirrel becomes this in "One Flew Over The Cuckoo Clock". Sure, she's a grumpy and bloodthirsty Screwy Squirrel who loves harming her enemies with dynamite but in the episode, she suffers from a nervous breakdown and has her own nephew taken away from her. The Single Tear she sheds in the episode really sells this.
Baynarts "Charlton" Woodchuck. He's a very bossy and egotistical actor and director who keeps a list of everyone whose ever insulted him but he goes through a ton of slapstick violence. Getting beaten up by a bear several times, stung by a nest full of bees, getting stuck in a toilet. His cute character design alone kind of makes you want to hug the poor little guy.
AP (the former Captain Atomic) is the epitome of Smug Super and tends to be very rude, but his transformation into a sock puppet has made him extremely unhappy. He's always afraid that his former friends won't take him back, the city's he's protected for years thinks he's abandoned them, and he's afraid of losing Joey, as it'll render him totally powerless (it's almost happened to him a few times). For the greatest superhero Mega City has known, he's pretty miserable as a puppet.
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.
It gets worse. In The Search, one can't help but pity her more. Her mental health is even worse than before, and she agrees to help Zuko find their mother. However, her suspicions about her mother not loving her all that much are confirmed, especially when she learns she has a half-sister, who is a much more playful, sweet, and well-adjusted child.
Zuko was 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.
Mary Dahl, aka "Baby Doll", was an actress who had a genetic disorder which prevented her from aging normally, and hence, leaving her stuck playing the same troublesome tot well into adulthood. All her attempts at breaking out in other roles backfired because nobody would accept her as anything but Baby Doll. It drove her so mad that she abducted her former costars to reenact the show, particularly one episode in which a costar supposedly humiliated her, and she was going to get back at them. Her Villainous Breakdown in the end is one of the most heartbreaking moments in the DCAU.
Mr. Freeze started as a Woobie, Destroyer of Worlds who would do everything to help his terminally-ill wife. Though by the time of "Cold Comfort", he has become merciless, bent upon destroying everything and everyone held dear to the people of Gotham City, because of his wife leaving him and his body having deteriorated entirely except for his head. He does go back to the former personality by the time of Batman Beyond.
Clayface. Unlike his peers, he's genuinely a jerk and little more. Yet the Body Horror he routinely suffers seem to be way to harsh.
Batman Beyond: Willie Watt 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 the Alpha Bitch only agreed to go to the prom with him 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.
Ben 10: Gwen's Evil Counterpart, Charmcaster, is evil because she was raised and trained by an emotionally abusive uncle. In the 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. Things went further downhill 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.
Bonkers: Skunky Skunk from the episode "Is Toon Fur Really Warm?". For the most part, he acts like an insulting jerk and is adamant that he "doesn't do birthday parties" because he thinks it will make him go soft. Keep in mind that the main episode plot is about him being framed for a murder and having to hide out.
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, 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.
Brandy & Mr. Whiskers: Brandy Herrington. Many characters in the show dislike her for her bitchiness, but she's struggling to adjust to her environment and she must really miss her family.
Chester is an interesting case. He's not quite as naturally mean as your typical example but he's known for his scathing sarcasm as well as a tendency to take revenge to the point of becoming a bully. The episode "Chester's Shop of Horrors" especially highlights this where after mercilessly bullying Bunnicula to get back at him, he goes on an emotional rant about just how insecure he really is at the climax of the episode. There's also the fact that he constantly suffers from both physical and emotional abuse and is pretty much a ball of nerves most of the time. In another episode, he tries to put up Bunnicula for adoption to get rid of him but after hearing Mina tell someone a story about him, he's legit moved to tears and feels guilty about attempting to do so.
The ghost of Rusty Bones from the episode "Scaraoke". True, he put a horrible curse on an innocent teenage girl for butchering his song on a karaoke machine but his life was absolute hell before his eventual death.
The Riddler, 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.
Poison Ivy of the same series, though it's far more apparent in the comic spin-off The Batman Strikes (which explores her character in more depth).
Capitol Critters: Jammet is a smartass, extremely irritable and obnoxious jerk who is a notorious Deadpan Snarker but in the episode If Loving You Is Wrong, he falls in love with a female hamster who happens to be a girl's pet. Eventually, they break up and Jammet cries in his mother's arms. It's hard not to feel for Jammet in that episode.
Cat gets beaten up on a regular basis by the greasers, and always gets hurt because of Dog running around and bumping to what ever is in his path, and he suffers the repercussions of whatever Dog does.
Eddie The Squirrel also has his moments. He's by far one of the most obnoxious characters in the show but in a couple later episodes like Shriek On Ice where Cliff tells him to get lost and all he can do is stare back with tears in his eyes, it's enough to make you feel kinda sorry for the poor pest.
The Delightful Children from Down the Lane are extremely Creepy 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 permanently, to the point that it's 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...
Father himself, after Operation: Z.E.R.O. (and minor moments in "I.T." and "C.A.K.E.D.-F.I.V.E.").
Eustace Bagge. His family has been just as bad to him as he's been to everybody else, and his life is practically a study in failure.
Kitty from "The Mask". Her hatred of dogs is perfectly justified when you find out what happened to her best friend...
DC Super Hero Girls does this to Blackfire. Sure, she's snarky, insensitive, and gets way too blinded by ambition, but also consider that she's been pushed by head master Sinestro to essentially be an uncaring person, and the fact she looks fondly on a childhood picture of her and Starfire, clearly wanting to patch things up with her.
There's also Lena Luthor. Sure, she may resort to underhanded means to acquire, but also consider how she went bald from trying to do so from experimentation, and how she's controlled by Brainiac. In the Lego projects for the series, she's much more ineffectual compared to Dark Opal, and while she still goes for underhanded means to get power, she won't resort to destroying the earth to get what she wants.
May Kanker has shades of this, mainly in the Valentine's Day special when she is found in the janitor's closet sobbing because Ed harshly rejected her valentine. All three of the Kankers could fall into this. Yes, they are temperamental, possessive, rude and unhygienic, but there have been moments that show they DO care for each other. They have barely any physical traits in common and it's heavily implied their mother Really Gets Around and they have three different Dads who aren't around anymore, so as such they latched on to the Eds because that's all they know how to do. Notably, after spending most of the series violently pursuing, the Movie shows them actually doing their best to protect the Eds from the wrath of the rest of the Cul-de-sac; it can be inferred that dubious ways of going about it, they do genuinely have feelings for the Eds.
Eek! The Cat: Sharky The Shark Dog. There are episodes where he maims and attacks Eek but he gets abused more than any other character in the show. He was horribly abused in "Shark Therapy", forced into being nice in "A Sharkwork Orange" and bullied by mailmen in "The Gradueek". Most of his translated dialogue consists of sarcastic jabs at Eek or "Why me?" before he receives inevitable harm. Also, his soft, puppylike whimpers when he gets hurt will make you pity him in spite of the fact that he's a bloodthirsty guard dog. The episode "Shark Doggy Dog" even lampshades this trope when he gets put on trial for being a serial mailman biter and pulls the Freudian Excuse card by talking about growing up as the abused runt of the litter.
Timmy Turner. Yes, he can be an insensitive jerk at times, 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. He has a villainous Sadist Teacher(who, despite his ineptitude, would be a more nurturing parent than Timmy's own, barring Timmy having to stop Crocker's magic-related schemes), is constantly belittled for his appearance, is constantly beat up and bullied at school, and he was shown with explicit detail how the world would be far better off without him, which was reality essentially giving him a "Reason You Suck" Speech. It's been explicitly stated he's gone to therapy several times, apparently since he was five (his parent's way of dealing with an imaginary friend). After all the only requisite to be granted a Fairy Godparent is to be the most miserable child in the world.
Remy Buxaplenty is a spoiled rotten Jerkass... who suffers even worse parental neglect than Timmy, almost to the point of Parental Abandonment. Despite being very rich, the neglect is enough to be granted a fairy godparent and maintain it (compare to Timmy dealing with his parents, Vicky the evil babysitter, Francis the bully and Crocker) and it's clear he's pretty messed up. Made more poignant when Timmy points out that despite having a godparent and being wealthy, Remy is still miserable. In fact, his first appearance had Remy compete with Turner with the loser losing their godparents. After being tied and Timmy trying to convince him to let the whole thing go, he confesses that he doesn't understand why Timmy gets loving parents and godparents while he doesn't, meaning his misery has nowhere else to go but envy. Even Timmy's wish to attempt for Remy to spend more time with his parents backfires (they end up on an island; Remy's father discovers oil while his mother opens a hotel, making them richer and Remy lonelier).
Denzel Crocker. Yes, he's an insane lunatic who Would Hurt a Child to accomplish his means, but as we know from "The Secret Origin of Denzel Crocker", he was driven to it by circumstances that were in no way his fault, and he has gone through his whole life ridiculed by everyone including his own mother for trying to spread the truth. The fact that Timmy's attempt at trying to fix it fails and Crocker remains the same makes it worse.
Cosmo (for being lethally stupid, having a sort of All of the Other Reindeer reputation among the other fairies, as well as having a mother who wants to kill Wanda.) and Wanda (for being the daughter of a mafia fairy (who didn't want her to get married at all and actively disapproves of their marriage) who is always dragged into Timmy's zany schemes and has to deal with a husband with the IQ of a coconut. Similar to Marge Simpson). Jerkass because sometimes they encourage Timmy's jerkish behaviour. Though they (and probably Timmy too) on their good days are more traditional examples of The Woobie.
Glenn Quagmire. He's a Casanova Wannabe who became that way when the woman he truly loved (Cheryl Tiegs) broke up with him note Though he had no problem falling for Joan the maid on "I Take Thee Quagmire", has a sister who lets herself be abused by her boyfriend (whom Brian first mistook for one of Quagmire's dates who was Too Kinky to Torture), has a female cousin who is suffering from cancer and has to get chemo (which has her mistaken for a boy), and grew up without a father (until he came back years later and revealed that he was getting a sex change operation). And there have been times where Quagmire actually cares about things other than his own libido (i.e., helping out at a soup kitchen as implied on the epic "The Reason You Suck" Speech on "Jerome Is The New Black," his illegitimate baby daughter note Before he adds that he'll most likely have sex with her when she turns 18 whom he gives up for adoption after realizing that he's not father material on "Quagmire's Baby," the pet cat that Peter killed on "Episode 420," and his father — especially when Brian had sex with him following his sex change operation — on "Quagmire's Dad.")
Peter Griffin. Yes, he's a self-centered sociopath who gets away with virtually anything he does, but violence is probably all Peter knows when dealing with something he can't handle, and when he tries to do another method he usually screws up badly or find himself in a more difficult situation. Also unlike Lois, Quagmire, and Brian who live with the knowledge of how much their Parents love them, Peter's own parents are implied not to be so good to him. It's implied, but never stated outright, that Peter's abusive personality may have came from his own troubled background which includes him being abused by his sister and being humiliated with her making him pee his pants deliberately. This even earns Meg's sympathy. There are episodes which depict him being a frequent rape victim, once by pie steam, another by a bull, another by a worm and a bug, and another time by Lois. He reacts to this with horror making one feel sorry for him and its revealed that when Lois gets fed up with Peter's hair brained schemes she often calls him a stupid man while abusing him physically while he cries.
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 (and on the Very Special Episode, he reveals to Stewie that he's suicidal).
Lois can be almost as bad as Peter, but dealing with a Jerkass husband and a Jerkass father may have turned her into a jerk. A joke from "No Country Club for Old Men" even implies she's bulimic.
Stewie, especially in later seasons. He started out evil and can still be mean sometimes, but considering he's suffered abuse from his parents and the fact that Brian is closest thing he has to an actual friend, it's hard not to feel sorry for him. At the end of "The Simpsons Guy" Stewie tries to show Bart how cool he is by capturing all his enemies, but Bart is less than amused. When Stewie returns home, he says nothing's wrong but runs up to his room and starts copying Bart's chalkboard gag while crying. And then there's the episode where Brian dies (temporarily). Poor guy...
Forest Friends: Danny the fox has a huge ego and often plays mean practical jokes, but his classmates sometimes treat him like trash. In "Big Brother Blues", he has to babysit his little brother Didoo and they have a sand castle building contest. Didoo doesn't like Danny babysitting him and builds a sand castle with Jeff, causing Danny to break down in tears. It's hard not to feel sorry for him.
Bender is a sociopath of the highest order, goes beyond megalomania, has a laundry list of felonies, and is constantly abusing his own friends. He also was born without a backup unit, only got saved because Hermes took pity on him as a baby, is constantly abused by The Professor (being sent on deadly missions), and has a son who cannot remember him, because Bender and his son decided to have the latter's memory card replaced in order for him to go to bending school.
Zapp Brannigan. Yes, he's extremely corrupt, egotistical, and perverted, but he's also a complete and utter failure who is expected by the people of Earth to be a godlike figure, and the only girl he may have actually cared about despises him.
The Garfield Show: Hercules 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.
Gargoyles: Demona, both very evil and very sympathetic all at once.
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.
Gravity Falls: Pacifica Northwest may be a stuck-up Alpha Bitch, but in "The Golf War", she is shown to be pressured by her parents to meet their expectations and not lose the golf game, plus she doesn't understand the concept of sharing. Then it turns out her father controls her every action with a bell, Pavlov style, and she is very afraid to talk back to them.
Fee: She was more than happy to throw Kratz under the bus in "Someone's Been Stealing Our Stuff" and was viciously racist to a ghost in "Ghost Problem" but you can still feel sorry for her when she's being ostracized by the other kids.
Dade: On one hand, he's a very bossy, grumpy, bitter, rude and hot-tempered "tattlepants" who is extremely jealous of Fee and Foo. In one scene in "Old Fashion Dade", he considers poisoning them so he could have Harvey to himself (though he actually wound up manipulating them to get them kicked out of the festival by breaking a ride). On the other hand, Dade is deeply concerned over Harvey's safety and even used to be his closest friend until the imps came along and ruined it for him. Seeing him break down in tears in "Harvey's First Scar" is much Harsher in Hindsight when you find out his past friendship with Harvey in "Old Fashioned Dade". He's also had an unwanted sugar rush forced upon him by Foo in "Nightclub Night". To contrast his irritable and neurotic personality, he looks like a fluffy, pudgy, cuddly bunny. That being said, Dade deserves a big hug despite being a bit of a jerk.
Princess: She's MUCH meaner and more obnoxious than Dade and Randl combined but you can't help but pity her in "Princess Is Better Than You" when it's revealed she only has crystals to play with and actually teared up when Claire gave her an actual doll as a gift.
Randl: The grumpy, bitter bike shop owner. He has to deal with his senile mother and people who steal his bikes and vandalize his shop. Of course, those were part of Harvey's attempt to Dare to Be Badass, but even then.
Hey Arnold!: Helga Pataki. She may be violent, rude, and Tsundere-ish, but every scene set in her house is a testament to how messed up her life is. Absent-minded mother? Check. Corrupt Corporate Executive father who treats her more or less like a piece of furniture? Check. Being The Unfavorite to her Stepford Smiler sister? Check. It's fortunate that the one person she latches onto as her savior, Arnold, is (usually) kind and patient enough to see through her facade and gives her the hope that she can change one day.
Jungle Book: Tabaqui from the 2012 DQ Entertainment CGI series. Yes, he tries to trick, trap, manipulate and lie to Mowgli several times but he suffers more physical and verbal abuse than any other character in the series, often leaving him a shivering and terrified wreck. His Adorkableantics when he actually isn't up to something bad only makes him all the more cute and pitiful.
Mr. Cat from Kaeloo. He may be a jerkass, even to his friends, but he is constantly suffering from physical and/or emotional abuse, one way or another. It's clear he has psychological issues due to having an abusive family, having to deal with the death of one or more loved ones, and running away from home. In addition, he gets beaten up by Kaeloo, who he has a crush on, Once an Episode, and unlike resident Cosmic Plaything Stumpy, he never gets any Throw the Dog a Bone moments.
Snooky Wookums is a bratty, manipulative little backstabber of a kitten but its clear that Mechanikat barely treats him with any respect whatsoever. Even Supercat's fan club admitted they felt sorry for him in the episode "Join The Club".
Ignatius. He's greedy and a massive narcissist but as a villain, he's so utterly pathetic that its hard not to feel even a little bad for him.
Hot Dog. Sure, he's easily the rudest and most temperamental of the Dog Star Patrol but he just can't catch a break and he certainly didn't deserve to be drained of his power in "Bathound Meets The Dog Stars".
Tahno from the Sequel Series. He's a smug Jerkass, but many fans have said they felt sorry for him after the scene in which he lost his bending to Amon.
Tarrlok is now one too. Beneath his exterior of a manipulative jerk, he was broken as the result of an abusive childhood, forced to bloodbend even though he didn't like inflicting pain on the animals who were on the receiving end, and witnessed his brother's Start of Darkness. He Used to Be a Sweet Kid.
Amon/Noatak is this as of the finale too. Him telling Tarrlok that he was to only thing he had left in the world and the single tear that Amon cries right before Tarrlok blows them both up is part of it, along with also suffering an abusive childhood like Tarrlok.
In the early half of book 2, Korra herself had entered this. As much as she means well, everyone she trusts betrays her somehow (Tenzin and Tonraq by locking her up in a compound for her entire childhood and lying about it, Unalaq by imprisoning her father, Mako by telling Raiko about her plans to take his military, Varrick by being a greedy warmonger, etc.) and everyone's trying to use her for something (even Tonraq, as much as he loves her, uses her to gather troops for his war on his brother), and her reaction is violent and often outright terrifying. So far, she's fired Tenzin as a teacher, kicked her father out of her adventuring party, threatened to kill people on three separate occasions (once by sticking a judge's head in Naga's mouth), plotted to get a nation's military sucked into a war that had nothing to do with them when the President wouldn't agree to send troops, and kicked over her boyfriend's desk in the middle of a police station... luckilly, she recieved some character development and moved into Iron Woobie territory.
Lin Bei Fong given what came out of her back story from season 1 and season 3 having been dumped by her former lover Tenzin because she didn't want children, while years before that her own younger sister Suyin scarred her face when Lin, in the early days of her career as a Metal Bending Police Officer, broke up a robbery Suyin was taking part in - although to be fair the scarring was an accident - and their mother, Chief Toph, responds by covering up the incident and sending Suyin away to live with her grandparents. Where are things in the present? Suyin is living happily ever after with a family of her own in a city she helped build after years of walking the Earth, while Tenzin is living it up with his much younger wife Pema and their four air bending kids, and Lin has only her job to keep her going at the end of the day. So while Lin definitely has some Jerkass tendencies it's hard not to feel sympathy for her since it appears that she's worked hard most of her life and has gotten nothing in return for her efforts while being forced to watch while everyone else she ever cared about go off and enjoy their happy endings.
The Grand Finale has both Baatar Jr. and Kuvira become one. Both controlled the Earth Empire with an iron fist, but Baatar Jr. wound up having his would-be-wife Kuvira fire at him with a Spirit Cannon to unite her empire after he proclaimed his love to her and was willing to give up their ambition to be with her and is left feeling like his family will never want him back. And Kuvira, was abandoned by her parents at a young age and admitted to wanting to unite the empire out of fear the Earth Kingdom would be left in the dust and unwanted like she felt. After turning herself in she's met with a cold "You will answer to everything" from Suyin, her mother figure, despite Baatar Jr. being Easily Forgiven
Looney Tunes: Sure that Daffy is a self professed cowardly and greedy egomaniac, and has a plenty moments of assholery, but he's also a HUGE Butt-Monkey, making him one of the most pathetic characters in the Looney Tunes Universe.
More minor character Charlie Dog also qualifies as one. Sure, he forces himself to be Porky Pig's pet and he's very manipulative but he's also clearly homeless and faces constant rejection from several of his "masters". There's also the fact that he can pull off a really adorable Cry Cute.
Metalocalypse: 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.
Pizzaz Miller. In episode five, Pizzaz helps instigate a massive drug epidemic in order to make Mayor Eo Jaxxon more famous, but only because he was threatening to have the entire police force disbanded and folded into the (far more competent and liked) fire department. It's also clear that Pizzaz was willing to do this for A: The sake of saving her police force, and B: That she'd do anything to get the mayor off her back and out of her life for good, as Jaxxon is aggressive, predatory, cruel, and makes it incredibly clear he wants to have sex with her, despite how visibly uncomfortable she is with the idea. Unfortunately for Pizzaz, the drug epidemic plan fails terribly, and she now has to have mostly-unwilling sex with Jaxxon three times a week, in order to keep the police department active.
Episode six later reveals her backstory as one of the five daughters of the laser mogul who helped build Moonbeam City, but her four older sisters squandered the company and resources for their personal pleasure and as a result this is what turned the city into a Wretched Hive. Pizzaz became a police officer after disowning her sisters for the sake of trying to restore the city. When we meet her sisters they quickly reveal themselves as abusive bitches whom even their father admits are pure evil, with Pizzaz being the only one who seems to legitimately care about him.
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. When we're introduced to him, he's 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.
Ms. Sculptham, Orel's teacher who is unenthusiastic about her job and refuses to "teach" outside of school hours. She also takes advantage of Doughy's crush on her so he'll buy her expensive gifts. Then we find out she was raped by Mr. Creepler, the ice cream man who was obsessed with Doughy, which led to her performing an abortion on herself. And she fantasizes about him.
In the episode "Keep Calm and Flutter On", Discord of all characters becomes one when he realizes how much Fluttershy's friendship actually means to him. He had never known friendship until his Heel Realization.
Angel Bunny becomes one in "Just for Sidekicks" while he's being watched over by Spike. He misses his owner Fluttershy so badly that he drags Spike, the rest of the pets and the Cutie Mark Crusaders onto a train just so he can see her again. Once there, Spike foils his plan to catch up to her by creating a diversion with his last gem. Angel nearly blows their cover when they all have to hide from the Mane Six but when Spike finally apologizes for his improper care of the pets, Angel finally cuts him a break.
Starlight Glimmer. As a filly, her best friend Sunburst rescued her from being crushed by books, only to gain his Cutie Mark in the process, running off and leaving her behind. Traumatized by this action, Starlight vowed never to let something like differences and Cutie Marks ruin anymore of her friendships, becoming a powerful unicorn in her own right, creating the village of Our Town and stripping everyone of their Cutie Marks. When the Mane Six put a stop to this, she vowed revenge - a petty one at that as she obtained a time travel spell and modified it to allow her to alter the past, using it to stop the Sonic Rainboom. When Twilight learns of why she's doing this, the princess has to talk her down and convince her to put aside her mad vendetta, asking her to give friendship another try.
Oscars Oasis: Harchi the hyena bullies Oscar just like Popy and Buck, but the episode "Lost" reveals he suffers from separation anxiety. He's also really good at looking like a kicked puppy when he's sad. Plus, he seemed to be a little nicer to Oscar than his two friends, and it's clear that his heart is in the right place. You still have to feel a little sorry for him, regardless of his actions.
Phineas and Ferb: Dr. Heinz Doofenshmirtz 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'.
The teddy bear story doesn't begin to cover it. His parents thought Roger would be born a girl and used all their fabric to make dresses, forcing Heinz to wear them as a child. His father used him as a lawn gnome when their first one was repossessed, meaning he forced Heinz to stand perfectly still, all day and all night, with no breaks to eat or sleep. Despite making Inators capable of blasting lasers into space, he always lost every contest to a paper-mache volcanos (even a poetry contest). Even before Roger was born, his father named his dog "Only Son" and both of his parents didn't show up for his birth. Then he was just flat-out abandoned and adopted by ocelots (who treated him better, other than the occasional maiming) and tricked into moving to a brand-new country that a new life of hopes and dreams. But couldn't go there and moved to America instead. His love life is comical at best (the one girl who actually loved him got accidentally hit by his Anti-Love Inator). His only two friends are Balloony and Perry the Platapus. The former flew away and later popped, while the latter is Heinz' arch-nemesis.
Buttercup. She can be mean and generally rude, but she's never had actually attention. She's not a bad girl or even remotely evil. She's misunderstood and lets her anger take over her, even if her sisters are trying to help.
Mojo Jojo in "A Very Special Blossom", when he almost gets blamed for something Blossom did when he was spending the whole episode not planning on committing crimes, but on wishing his deceased father a happy Father's Day, and in "The Powerpuff Girls Rule!", after he gives up hope for a perfect world due to being forced to quit trying to rule the world.
Boomer is always causing trouble with the rest of the Rowdyruff Boys, but he is constantly picked on by Brick and Butch. To make him even more sympathetic, he is possibly the nicest member of the trio(by comparison, of course) and is the cutest of them to boot.
Oscar Proud may deserve some of the things that happen to him, but he is always emotionally abused by Suga Mama, humiliated by his rival Wizard Kelly, and is sometimes beaten up by his wife and mother. To add insult to injury, his abuse is played for laughs.
Even Sugar Mama is this, in occasions. True, she treats Oscar as The Unfavorite, but it is implied that she is one, too. It's a little hypocritical, but you still have to feel a little sympathy for her
The Real Ghostbusters: Peter Venkman behaves as a womanizing, cocky jerk most of the time who's only in it for the money, but he genuinely cares about his friends and the people he helps and has been shown to be willing to sacrifice himself for them. On top of that, his father is a con man who likes to embroil Peter into his schemes and use his son's fame for his own gain, he grew up in a bad neighborhood and it's hinted that his mother passed away when he was a child.
Regular Show: Benson, despite his Hair-Trigger Temper and harsh nature towards Mordecai and Rigby (although the latter is the one that causes problems), can't live without the park he works at. The reason for his yelling is because his dad taught him that you can't get anything out of life unless you yell for it.
The Ren & Stimpy Show: Ren Hoek often acts like an abusive asshole towards his friend 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 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).
Rick and Morty: Rick Sánchez is one. While he is a selfish guy who takes advantage of living with his daughter and her family while exploiting her own grandson for help on very dangerous adventures, he is shown several times to actually be a sad old man whose life has had many unfortunate twists and turns. In one episode, an entity named Unity who he truly loved, dumps him and he responds by trying to kill himself only to pass out at the last second. He is also heavily implied to have gone through a strained marriage with Beth's mother and is one of the people who fights against the Galactic Federation, which was an oppressive and exploitative dictatorship. In "The Wedding Squanchers" Rick falls deeper into depression after he and his friends and family get betrayed by Tammy. He has been shown several times throughout the show to truly care about Morty.
Rugrats: Angelica Pickles spends most of her time mistreating her baby cousin and his friends, but there are episodes that showed a softer side to her:
She may mistreat the rest of her friends, but 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.
In some episodes, like "Babies in Toyland", Angelica's Imagine Spot involves a figure that she's pretending is there giving her a "The Reason You Suck" Speech; essentially, she's telling herself that she's a selfish brat. This, coupled with her confession in Rugrats in Paris seems to suggest that on some level she knows how awful she can be and absolutely hates herself for it. Poor girl.
Sanjay and Craig: Mr. Noodman. At first his father tormenting him with snakes as a kid appears to simply come off as a Freudian Excuse for his treatment of the titular characters but then came the episode "Family Re-Noodman" where we see that his father still torments him with snakes and has made him the laughing stock of his entire family.
Scooby-Doo! Mystery Incorporated: Velma Dinkley is 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.
Homer Simpson. He is self-absorbed, abusive to Bart, has a very short temper, and often "borrows" from Flanders. However, he has attempted suicide numerous times, was molested by a panda, his family left him in The Simpsons Movie because of his jerkass tendencies and Marge banned him from the house because he didn't show up on Christmas, and all of his innocent buffoonery (and alcoholism) is actually an expression of his deep-seated self-destructive tendencies.
Bart, despite being a Bratty Half-Pint, also qualifies in plenty of episodes. For example, he abused by his father (on a regular basis) and sister ("On a Clear Day, I Can't See My Sister"), was resented by his mother more than once ("Marge Be Not Proud", "Bart the Mother", "Love is a Many Splintered Thing"), had a mean kindergarten teacher ("Lisa's Sax") was nearly being held back ("Bart Gets An F"), trapped in a well ("Radio Bart"), nearly killed by Mr. Burns ("The Curse Of The Flying Hellfish"), Groundskeeper Willie ("Girly Edition") and Sideshow Bob (on a semi-regular basis) and harassed by the whole town several times ("Bart's Girlfriend", "Miracle on Evergreen Terrace", "The Boys of Bummer"). He also had to watch his dog in a wheelchair, and lost his dog multiple times. One of which he was nearly killed by his dog. With all this crap, it's a wonder he didn't commit suicide (he almost did in "The Boys of Bummer").
Milhouse Van Houten. On one hand, he can be a Casanova Wannabe who acts spiteful when Bart abandons him for a new girl, and is relentless in his attempts for Lisa to love him. However, his parents divorced in the 8th season, he is relentlessly mocked, and he is often thrown under the bus by Lisa. That kid just can't catch a break.
Charles Montgomery Burns (Mr. Burns for short), on occasion. The episode, "Monty Can't Buy Me Love" has him trying to do good things for people to gain everyone's respect. In the episode C.E.Doh, it's revealed that Burns' entire family and friends died out while he worked at the nuclear plant. You've got to feel some sympathy for the man after that, regardless of how evil he is.
The current incarnation of Nelson Muntz. True, he can be (and often is) a violent brute who finds amusement in others' misfortune. However, he does have a soft side. Take the episode "Lisa's Date with Density": although he doesn't appear to return Lisa's feelings for him until the end, he was willing to go along with her attempts to bring out the nice guy in him throughout the whole episode (he even wore clothes he felt uncomfortable in just to make her happy), and he reveals at the end this was because she was the first person to think he had a softer, more sensitive side. He continues to show signs of harboring some romantic feelings for her afterwards, such as begging God to not let "his" Lisa get hurt in "The Great Simpsina". It's not just Lisa, either- he befriends a blind kid in "Stealing First Base" and acts surprisingly polite and grateful to Marge for taking him into her house in "Sleeping with the Enemy". And yet his life is pretty terrible, even by Springfield standards: his father left him for a pack of cigarettes, his mother's constantly dating someone undesirable (and has been implied to have a job as a stripper), and he's dirt-poor. He doesn't even get the girl in the end, as revealed in "Holidays of Future Passed": Milhouse is the one who ends up married to Lisa.
Lisa is an insufferable Soapbox Sadie who takes on pet causes for no good reason (though often, but not always, her reasons are good: in the movie she single-handedly delays the eco-catastrophy that the lake becomes) and isn't ashamed to admit she thinks she's better than everyone else in Springfield. She's also completely alone, with a family that doesn't even try to help her or share her interests, and her friends (on the occasion that she has any) aren't much better either.
Frank Grimes is a very divisive character. On one hand, he had a miserable childhood, worked hard for little rewards or pay, and had to work with Homer, a lazy, stupid employee who had no understanding of sacrifice. On the other hand, Grimes' response to this was to lash out at Homer and try to ruin him, and this was after Homer tried to make it up to Grimes. When his attempt to make Homer look stupid fail, he snaps and kills himself. Even his funeral was overshadowed by Homer's stupidity.
Gina Vendetti from "The Wandering Juvie". She is a juvenile delinquent who knocked a woman dressed as Snow White over a parapet. She torments Bart in juvenile hall, uses him for a prison break, plans to make him take the blame, and regularly pushes him around. Then she breaks down crying, revealing she is an orphan, and seeing Bart's family made her tell the truth to the police. Thankfully, she is able to enjoy a taco dinner with the Simpsons.
South Park does have a lot of assholes, but there are some that people can feel sorry for:
Eric Cartman at times. He's a pretty big Jerkass 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. And this is all a result of his insane, schizophrenic mind, which just makes you feel worse for him. This is even more evident in earlier seasons, where he's more of a typical obnoxious bully and implied to be the result of teasing from the entire class (Clyde at one point just barely avoided the same fate after Kyle and Stan berated him mercilessly in Cartman's place).
Scott Tenorman is a manipulative bully who cons Cartman out of $16.12 by selling him used pubic hair, continuously mocks his obesity and stupidity, tricks him into doing a humiliating piggy dance and then shows it to all of South Park, and tries to trick him into eating chili laced with pubes. Then Cartman tricks him into eating his parents, gets his favorite band Radiohead to mock him over his very understandable breakdown, and drinks his tears to rub salt further into the wound.
Squidward Tentacles may be arrogant, rude, self-centered, egotistical and just downright mean, but he's also the Only Sane Man amongst various idiots, his Jerkass boss, Mr. Krabs, and Sandy Cheeks. Sometimes Plankton can be this too, mainly post-movie.
Mrs. Puff. Woobie because she constantly has to put up with SpongeBob and Patrick's (mostly Spongebob's though) incredible idiocy, and SpongeBob's inability to pass his driving test, to the point where she seems to be undergoing Sanity Slippage because of it. Jerkass because she deals with it by attempting to murder them.
If you thought that Darth Vader couldn't be more of a Jerkass Woobie, then wait until you see his adventures as Anakin Skywalker. You can add the deaths of several friends, Clones and Jedi alike, his Padawan leaving the Jedi Order, Fives dying in a vain attempt to expose Order 66, his relationship to Padme damaged by the presence of Rush Clovis, him forced to go undercover as a slaver, etc, is it really a surprise he turned out the way he did?
Peridot. She was effectively the main villain for the latter half of season one, with her boss Yellow Diamond as a presence who only got name-dropped now and then with one appearance later in the series. She knows if she succeeds, Earth is doomed, and she really doesn't care. However, she's a Punch-Clock Villain who gets no respect, and ever since being stuck on Earth, has only wanted to get what she was assigned to do over and done with so she can get off this mudball and go home. As time wears on, she's driven to Sanity Slippage by her repeated defeats and Yellow Diamond being in no hurry to help. On top of that, destroying Earth isn't her master plan or anything; it's a by-product of a larger scheme put in place by others a very long time ago, and she is as screwed as we are if she can't leave, hence her desperation. If that isn't bad enough, we find in "Catch and Release" that she's not a cyborg or a new kind of gem as we believed; all her tools and weaponry come from her suit, and once deprived of it, we find her true self is child-sized and has no powers. By the end, she's reduced to hiding in the bathroom while being terrified that things like toothbrushes or towels are actually weapons the main characters plan to use against her, and clutching the single boot that remains of her former arsenal like a child's security blanket. You just want to hug her.
Amethyst. She's mischievous and frequently shows disregard for the feelings of others, but it's hard not to feel sorry for her once it's revealed that she hates herself due to being a product of the Kindergarten, a Gem site that sucked the life out of the Earth (what exactly is meant by that isn't very clear, but we are shown the results and they are not good) to produce new Gems; this results in her feeling stranded from even her family of 5,000 years, as she assumes they look down her as much as she does. In addition, like the rest of the Crystal Gems, she is still having a hard time coping with the loss of their leader, Rose, who was like a mother to her. Many of her Jerkass moments can actually be chalked up to her trying to shut away or deal with those issues (poorly).
Lars is selfish, lazy, cowardly and petty, despite having great friends in Steven, Sadie and the cool kids, and seemingly a stable, supportive home and family. He's often condescending or even cruel to Steven, and insensitive to Sadie's feelings and needs. But he's shown to be desperately insecure, intensely self-loathing and heart-wrenchingly lonesome. The show strikes a good balance between sympathy and accountability, and Lars has a long arc of self-improvement over the seasons.
Superjail!: The show operates on a cast full of Jerkass characters, although some seem to also exhibit this (or at least in some minds):
Alice is not exactly meant to be the most sympathetic character, with the creators even calling her a sadistic bully and messed up. Even so, she shows a soft spot for children and has her own issues due to having been rejected by her old warden after she started her sex-change (in an attempt for them to be together, only to find out that he was a gay man). Her official profile also stated that she wants men to desire her and find her beautiful, although it's counterproductive as most are horribly put off by her brutality and she does not take that rejection very well.
The Twins somewhat qualify after "The Trouble with Triples" showed that they're The Unfavourite and have abuse heaped on them by their elder siblings, are neglected and looked down on by their father in comparison, as well as being expected to conquer and rule worlds when they hate "real work" and just want to live their own lives (even if said lives consist of them just organizing death and destruction for fun and not some goal of conquering). Then when they do (inadvertantly) manage to impress their father, thanks to the Warden jumping into the fray, he decides to take them home and torture them.
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.
Tinga Tinga Tales: Jackal 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.
The large majority of time in most episodes, the engines either gets themselves into a misfortune or an accident, due to their stubborn refusal to accept help from others.
Henry was this in the end of the episode "The Sad Story of Henry". Earlier on, he stubbornly refused to come out of a tunnel because he was afraid that the rain will ruin his paint. As a result for his disobedience, he is bricked up inside the tunnel "for always and always and always". Henry is left alone, very saddened that no one will ever see his paint again.
Tom and Jerry: Tom is a mean cat that gets put through a lot of pain which is sometimes deserved and his own fault and sometimes happens because he's a huge Butt-Monkey.
Transformers Prime:Throughout the seires, a large part of Starscream's appeal is that he's both a horribly abused character and a narcissistic asshole. The ratio of him being beaten and losing his T-cog for almost the rest of Season 2 should be equal to the times he backstabs someone else.
Trust Me, I'm a Genie: Ziggy is an Anti-Hero genie, somewhere on the borderline of Benevolent Genie and a Jackass Genie due to his It's All About Me attitude. He's selfish, short-tempered, sarcastic, a loudmouth, sneaky, verbally abusive at times and often lies, cheats and steals to help his master Diego fulfill his final wish so he can finally be set free. The woobie part of him comes in when you realize how messed up his magic got from sand being trapped in his can. He tries so hard for the final wish to succeed that it always comes close only for Ziggy to experience a Yank the Dog's Chain because his magic is defective. There are times when he's actually broken down in tears over the failed final wish and in the final episode, he gets treated like garbage from the other genies because of all his failed wishes and when he says his goodbye to Diego in the final episode because his master's wish succeeds, he looks to be on the verge of tears. Possibly, because he's saying goodbye to his best (and possibly one of his only) friends in the whole world. On top of all this, Ziggy looks like an adorable and cuddly purple raccoon to contrast his mean personality.
Watership Down: Hawkbit from the animated series spends most of his time complaining and making sarcastic remarks. In one episode, Bigwig works him til he's exhausted and he lets his anger out on Fiver, calling Fiver a curse to the warren. In a later episode, Hawkbit nearly loses faith in Hazel's leadership skills, almost shoves Fiver off a cliff in panic and has a near sobbing panic attack when he, Hazel and Fiver get lost in the mines. Although he's a jerk and a complainer, it's hard not to feel sorry for the poor bunny at times.
Vervain qualifies as of the third season. He's a mean, nasty Dirty Coward of a scumbag but he pretty much knows that he's universally hated and half of the time, the poor bastard is scared out of his wits.
Panda, if you really think about it. He has more selfish moments and is more quick-tempered than his brothers, (such as destroying his brothers' phones, lying, kicking at a pigeon, etc.) but is very insecure and sensitive, so he definitely has his woobie-ish moments. Panda isn't even a bad bear at all, just one that tends to cause mischief.
Nom Nom could be interpreted as one, such as in "Nom Nom's Entourage", where he says he doesn't know how to make friends.
"Kyle" only furthers this by revealing how extremely lonely he is due to having been separated from his family at a young age.
Dave from "The Island". He was a self-absorbed Yandere who had no qualms with killing baby bears, but he was stranded on the island long before Karla did. Plus Karla and the bears take the supplies for leaving the island away from him, hinting that he'll stay there forever.
Whatamess: Trash from the DiC Entertainment adaptation of the series is a "mean pitbull" stereotype with a reputation as a sarcastic bully but he's been tricked into eating fertilizer to cure a cold, nearly run over by a train, had his birthday forgotten and his owner apparently lives in squalor. Also, in one episode, he and Whatamess are captured by a dog catcher and sent to a pound. When Trash finds out that all his usual escape exits are sealed, he breaks down into a fit of tears, thinking he'll be left to die in the pound. Also, his Ugly Cutecharacter design only serves to amplify his "woobie" factor.
Winx Club: Is Diaspro a Rich Bitch? Damn right! Does she cooperate with supervillains on a regular basis? Of course. The thing is that she doesn't see herself as having a choice in the matter. For one, she can no more see a scenario where she doesn't end up marrying Prince Sky than she can see one in which she spontaneously grows an extra set of limbs....despite the fact that a red-haired usurper who won't listen to reason and refuses to understand the volatile power politics that get in her way seems Hell-bent on disrupting everything for silly and self-serving reasons. Since said irritant is both insanely popular and a possessor of godlike abilities, Diaspro sees herself as being backed into a corner.
Wolverine and the X-Men: Toad, perhaps based on the fact that his incarnation in X-Men: Evolution was one of the show's woobie-characters. On the one hand, his mutations mean he has a deformed, frog-like appearance (webbed hands, gangly limbs, green skin), an Overly Long Tongue, and the ability to hork up gouts of sticky slime. On the other hand, he's an evil little toad of a person who willingly signed up with a mutant supremacist group so he'd be able to commit havoc without fear of punishment; it's implied in his first appearance that Toad is recurrently caught vandalising or mugging people and never gets punished because the Brotherhood always busts him out again. When Quicksilver declares the Brotherhood have decided Toad isn't worth saving any more and so they're kicking him out and leaving him in the MRD Facility, one simultaneously understands where Quicksilver's coming from and feels pity for Toad — it's the look on his face and the quiet way he asks if they're really dumping him.