GOB from Arrested Development. He's a total ass to everyone in the family, selfish, and aggressively stupid, but his parents hate him and nothing ever goes right for him. As much of a jerkass as he is, it's hard not to feel sympathetic towards him. Pretty much every single awful thing he does is done in an attempt to make someone love him, appreciate him, or even notice him.
Maeby. Yes, she's manipulative, greedy, and sometimes doesn't get how wrong or stupid her behavior is, but her own parents forget she exists when they're not using her as leverage in their failing marriage. Much like GOB, a lot of her bad behavior is really a cry for attention.
Lindsay is a bad bordering on neglectful mom, but she still manages to be sympathetic thanks to her abusive mother Lucille and criminally stupid husband Tobias.
Michael may have become this in Season 4: He was The Woobie in earlier seasons even if he wasn't as kind or competent as he thought he was, but after unethical tactics to get releases from the rest of his family, blowing up George Michael's relationship, and possibly murdering Lucille 2 he's not a good guy anymore and probably falls under this trope.
Lucille in Season 4, when she realizes her kids really do hate her or just don't care.
Londo Mollari of Babylon 5: He's an abrasive, racist, manipulativeham. He effectively condoned genocide against the Narns (rendering the Narn homeworld largely uninhabitable may not have been his idea, but he was certainly defending the invasion and occupation). Still, losing his first wife, and implied true love, because of his family's disapproval, losing Adira because his love for her made her a target, and then realising that the one thing he always truly served, the Cantauri republic, is under the control of a lunatic who's going to bring it down around all their ears...it's hard not to feel bad for him sometimes. Doubly so during his occasional Pet the Dog moments.
Also in the running is G'kar, Londo's personal nemesis, who seems more of an Iron Woobie most of the time, but he has a nasty temper and, in the first few seasons, he appears to be one of the more ruthless of the ambassadors (not that he doesn't have reason). Then there's the part where he Mind Raped Londo to extract information. (After his prison sentence for that crime and the accompanying revalation from Kosh, he's pretty much straight Iron Woobie.)
A MUCH less extreme example is Kara Thrace, aka "Starbuck" (at least in the Jerkass department, in The Woobie department she easily matches anyone in the show). She can be a real bitch a lot of times but seeing her backstory and what happens to her, it's practically impossible not to want to give her a hug MANY times throughout the series.
Battlestar has a lot of these, given the huge number of horrible things that happen to its characters. Gaius Baltar is another good example. He has an insufferably large ego, he is inadvertently responsible for enabling the Cylons' genocide of humanity, he is a serial womaniser, and the series seems to present him with a never-ending Trauma Conga Line. Felix Gaeta also qualifies. By the time he is executed, his life had gotten so shitty that it almost comes as a relief.
Leonard from The Big Bang Theory often makes stupid and selfish decisions to get what he wants, and often tortures Sheldon, but he has an entire family that treats him like he doesn't exist, his mother Beverly has a better relationship with Sheldon than she does with Leonard, and has been treated like shit by Sheldon numoreous times, it's hard to believe the guy hasn't committed suicide by now.
Wolowitz is also a prime example. He always thinks his decisions matter than his own friends', and has always done many relentless things, but he was always turned down by every woman he tried on until he met Bernadette, has an overbearing Jewish Mother who frequently treats him like a child, has a father who abandoned him when he was 11, and even has a good side, so it's really hard not to side with him sometimes.
Sheldon also qualifies to some extent. He's always really hard to deal with, has a huge lack of patience, and is always saying and doing mean things to everyone, but nearly everyone he knows in Pasadena, even his girlfriend borderline hates him, his own mother has a better relationship with Leonard than she does with Sheldon, and he simply doesn't even know better when he does bad things, along with a somewhat Jerk with a Heart of Gold persona, it's hard to not feel at least tiny bit of sympathy for his whole character in general.
Big Time Rush had Sandy, who had an obsessive crush on Kendall but did terrible things, including spreading lies claiming that she was his girlfriend, refusing to let him get a word in to Jo, and using him to lie to her real boyfriend. While she has an Alternative Character Interpretation, she did just want Kendall to herself. Then again, if you were in a boy band, you'd probably run into at least one girl who would probably be like that to you, but still.
In spite of how hilariously misanthropic and needlessly cruel Bernard Black is, he's bizarrely cute and his girlfriend faking her own death to get away from him or his friends casually turning on him tends to inspire more sympathy than Schadenfreude.
Avon of Blake's 7 acts like a complete git for much of the time, refuses to trust anyone and points out repeatedly that anyone who trusts him is stupid. Then we learn that his lover died under torture, protecting him. Still later, it turns out that she wasn't actually dead, but had been working for the authorities all along. At the beginning of Season 4, the woman he maybe even liked a bit, who liked him back, dies. He spends two years searching for his lost leader, going through failure after failure and gradually losing his grip on sanity. This man needs a hug.
Troels Höxenhaven, the scheming, back-stabbing minister from Danish political drama Borgen, who among other things manipulates his own party leader into sabotaging his political career in order to position himself as a future prime minister. But not even a Smug Snake deserves to be outed by a homophobic journalist after 16 years in a sham marriage and as a result be Driven to Suicide. It helps that the actor is very good at pulling tragic faces which pull at the heartsrtings.
Jesse Pinkman from Breaking Bad: He's a meth dealer and starts out as the closest thing the show has to a bad guy, but as the show progresses, the only people he cares about end up dead or injured, and it becomes clear that he's a scared and fundamentally decent kid in over his head. Crosses into regular Woobie in season 5, when Todd enslaves and tortures him.
Skyler White has cheated on Walt, had an on-again, off-again relationship with his meth business, and blackmailed him about it in the earlier seasons, but it's hard not to feel bad for her: In Season 2, she gets a lot of undeserved hate for kicking Walt out of the house, and has to just sit there and let Walt Jr. curse her out because she can't tell him that his father is a drug dealer. In Season 5 Walt's Heisenberg (read: pure evil) alter-ego begins to show up in their domestic life and she's forced to leave her kids with Hank and Marie for their own safety, again opening herself up to hate from her son with no way to defend herself.
Marie is a Know-Nothing Know-It-All, refused to apologize for accidentally getting Skyler arrested, never shuts up, and generally gets involved in things that are none of her business, but in Season 4 it becomes clear she really loves Hank and wants him to get better after he's left paralyzed from a shootout with the Cousins. Her reward for all of this is constant verbal abuse from her husband.
Hank himself. He's rude, obnoxious, could use a refresher course on the 4th Amendment, and not above making incredibly racist jokes around his Hispanic partner. But between his nervous breakdown in Season 2 and getting paralyzed in 3 he becomes actually quite sympathetic, especially when it becomes clear that his obnoxiousness is an act to cover up the uncertainty he feels about whether he's doing the right thing and his fear of getting shot or killed on the job.
This was the second stage of Walt's transformation. He started off as a regular Woobie, and then became this as his character darkened. After crossing what many consider his Moral Event Horizon at the end of Season 4, he left this territory behind as well. He reverts to this in "Ozymandias": He has fled the state and done everything in his power to protect Skyler from prosecution, but Hank's death is his only regret. This continues in "Felina", where he reveals he's still a cold-blooded killer but tries to make everything right with his family before his death.
Say what you like about Faith's brash, tactless attitude, her willingless and lack of shame at using people like tampons and her psychotic murderous qualities, but even her most zealous of haters (as well as her most dedicated fans) admit that it must of sucked to be her. To have abusive, alcoholic parents who are strongly implied to be dead, to see your watcher die in front of your eyes and to never of had a real father figure must of stung pretty badly. And of course, there's the whole being stuck in a coma for months thing, before awakening to find the only person who ever cared for you is dead. Truly the cherry upon the crappy cake that is Faith's life.The real question among the fandom is whether Faith uses all her misfortune as a excuse to be a heartless, violent bitch or if she is genuinely a victim who has been pushed off the rails and needs all the support she can get. Of course, then there are the people who argued that she was offered support, but chose not to take it, preferring to resume her sociopathic, reckless lifestyle for her own selfish benefit. Or even if she was so unused to being offered friendship and understanding that the poor mess couldn't process it. Either way, definitely a Jerkass, definitely a woobie.
Spike spent most of his human life as a ridiculed introvert, rejected by the woman he loved. Then he was turned, and turned his mother out of love and devotion. She promptly tried to molest him, and implied that he was Oedipal, forcing him to stake her. He then spent twenty years or so in the company of three of the most evil vampires in history, often considered bottom of the pack as the youngest, and had to see Drusilla, who he adored, screw Angelus. Then he lost Drusilla and was essentially neutered and mocked, used as a source for information and occasional meatshield by the Scoobies. Despite this, he retained a capacity to feel love (even if he was phenomenally bad at expressing it in a remotely human manner) and affection (e.g. Dawn and Joyce), making him nigh on unique among vampires. After that, Buffy essentially yanks him back and forth for most of series 6. Then he gets driven mad by the First and dies after being re ensouled in a Heroic Sacrifice. The Woobie part is very definitely there, especially as the universe is clearly still kicking the crap out of him, judging by Series 5 of Angel and the Season 8 comics.
This quote sums it up pretty well; "The chip. It won't let me be a monster. And I can't be a man. I'm nothing." Did Spike get what was inevitably coming to him? Did he deserve this? Did he bring all or at least most of his suffering on himself? Well, yeah. Does that make him any less ashamed, lonely and conflicted in a way a lot of the audience really connected with? Not one bit.
And from the Spin Off, we have several, but one of the most noted is Connor. This is the kid that grew up in a hell dimension, his father figure lied to him about the nature of his real father, he was driven mad with revenge, and was seduced into the service of an Eldritch Abomination. Sometimes, you just want to give the little guy a hug, but he was also known for being unbelievably Ax-Crazy...
Cheers: Cliff Clavin gets a lot of abuse for his Know-Nothing Know-It-All attitude. Mostly from Carla, but after a while, Sam also had difficulty hiding just how much he depises Cliff.
Cold Case: Katerina from Season 4 episode Cargo. On one hand, she lied to a vulnerable girl about the girl being abandoned when she was not, murdered the victim and sold his boat to make money. On the other hand, she'd been raped for years, and was about to watch what may have been her only chance at freedom slip away.
Pierce Hawthorne in the second half of season two of Community. He is shown to be insecure about how his age is creating a barrier between him and the rest of the group, and much of his attention seeking behavior is an outgrowth of his dysfunctional relationship with his father.
Chang in season 2. All he wants is to be part of the group, but he keeps getting shot down. Especially when you consider that they were planning to let him in from the beginning. Though he did spend most of Season 1 tormenting them, so it's understandable.
Leanne Tilsley. Despite being a manipulative opportunist, a cheat, a homewrecker and usually a total bitch, things have really stunk for her in her life. Her mother abandoned her at birth, she's forced to abort the child she created with the husband she loves, she gets addicted to drugs and works as a prostitute to pay for said addiction, she suffers a miscarriage with her second husband, who then cheats on her and eventually marries the other woman, her next husband (who was also her first husband) cheats and slept with his sister-in-law on Christmas day, possibly impregnating her, watches her one-time fiancé die in an explosion and her stepson, who used to love her like his own mother, verbally and physically abuses her.
David Platt hovers between this and regular Woobie. For years on the show, he went from a nasty Troll who just tried to get a rise out of people for his own amusement, to a deranged, violent criminal who attacked his own mother and was sent to prison, until he got better (somewhat). Yet things have sucked for him pretty hard. His mother tried to abort him, and then as a child Richard Hillman tried to murder him and his family. He then spent years being The Un-Favourite to his older brother and younger sister. His first girlfriend aborted his child behind his back (which his mother kept secret from him), and his brother sleeps with his wife on Christmas Day (which David's family also plots to keep a secret from him). He was then kicked out of his own house, denied access to his kids and treated like a complete monster in late 2013. All for 'trying to kill' his brother (which was a genuine accident). Just when he seems to be getting his life back on track, his family is terrorised by his wife's drug dealer and his wife is then murdered.
One hopes this trope doesn't apply to the Real Life Larry David, but the Larry David character on Curb Your Enthusiasm exemplifies it. He's a legitimate Jerkass and extremely self-centered...but the Universe seems determined to make him seem even worse than that. He also endures a lot throughout the series and some of it isn't even his fault.
Degrassi has a few, mostly due to having to have antagonistic main characters who can be protagonists at other points in a given season:
Craig has a lot of it too, usually involved with his improbable trouble with girls or his more probable trouble with family.
Holly J., when her act of pretending to be a jerk comes into play during Season 8, when we see both her Jerkass and Woobie side by side (it's there during late Season 7 and early Season 9 too.)
Riley's Gayngst causes some of this, mostly during Season 8 and 9 while he tries to date beards.
Degrassi Junior High: Kathleen is a snooty bitch, but her life is such a wreck - alcoholic mom, absentee dad, abusive boyfriend, anorexia...
The First Doctor was a contemptuous and evasive Grumpy Old Man who liked to do Malicious Misnaming and could occasionally be really ruthless, and was usually very rude even to people he liked. The longer his tenure goes on the more we realise that he's secretly very scared and insecure and must nevergo back.
Is it really any wonder the Third Doctor tends to pick on the Brigadier and Jo when he's been abused as a Boxed Crook by the Time Lords for centuries, had TARDIS travel stripped from him and is being forced to co-operate with a military organisation that committed a genocide in its third on-screen story? His rudeness towards his friends is really the only power he has.
The Fourth Doctor starts out as a sparkling and hilarious Mad Hatter (with occasional moments where his madness would make him a bit disturbing) but by the time of "Logopolis" seems to have segued into a more realistic portrayal of mental illness. He appears skeletal, temperamental and brittle, barks at his companions and makes insensitive comments to Tegan about her aunt dying - and makes awkward, disjointed plans based on paranoia that make no sense and in a few cases are actively suicidal. He gets over it, but only by making a big change in his life.
The Ninth Doctor is much more abrupt and jerkish than his past incarnations. However, most of this is because he thinks he is the Last of His Kind and he killed his own people to end the Time War.
The Tenth Doctor could be mean and petty; not only is he still dealing with trauma from the Time War but also the loss of the woman he loved.
The Twelfth Doctor is can be mean spirited, insulting and is less likely to weep over the deaths he sees. This is partly because he knows grieving will not help anyone and is likely to get more people killed and partly due to being racked by insecurities and having lost so many people already.
Omega, one of the early Time Lords, a deranged megalomaniac who only became that way after aeons of isolation and who just wants to return to our universe. The Doctor treats him more with pity than anger or contempt.
Eldrad in "The Hand of Fear" possesses Sarah Jane, and accidentally causes an innocent man to die by possessing them into a murderous frenzy state in which they fall off things. She tortures the Doctor for little reason and tortures other people with an Agony Beam - but at the same time it's difficult not to feel sorry for her due to her (apparently) unjust exile and physical beauty. Upon regenerating into a male form he reveals he's actually just a genocidal megalomaniac, but still inspires pity due to his despair about the other Kastrians cheating him out of his victory.
Turlough is this, at least for his first few episodes. He's an alien criminal trying secretly to murder the Doctor, but his boyishness and conflicted nature makes him rather sympathetic.
Topher from Dollhouse, by the series' end. Especially after Bennett, the only girl he could have truly loved, was killed right in front of him
Thomas Barrow from Downton Abbey. He's a sly, smug snake of a schemer, happily willing to throw anybody under the bus if it will help him further himself and be mean for the fun of it, yet, good lord.
His plan of running off to valet for his lover is dashed, he's right in the thick of WW1, he goes back to Blighty with 1 person pleased that he's not dead, he connects with a wounded soldier who promptly commits suicide, he nearly doesn't get his old job back, his business venture ruins him, that friend of his hates him now, 1 of approximately 3 people who've been kind to him dies, he falls for someone whom he is told fancies him back, said person explodes when Thomas kisses him, that fellow then tries to ruin Thomas's life at the behest of said ex-friend, he's facing either prison or complete destitution, and who has to help him? The one person Thomas hates more than anyone.
And now in Season 5, he's apparently self-medicating to "cure" his homosexuality. Fans are speculating that he's using Apomorphine, which is a powerful emetic (induces vomiting). Poor, poor baby. No wonder he's been looking like death (barely) warmed over for the last few episodes...
And let's not forget his suicide attempt in Season 6.
Ari Gold from Entourage. He becomes one in "The Beginning Of The End" - when Mrs. Gold tells him that she's started seeing someone else, he looks utterly crushed.
Lauren in Faking It. In any other show she would be the Alpha Bitch but in the pathologically liberal atmosphere of the school she attends she's the outsider. Throw in the fact that she's intersex and a couple of Pet the Dog moments and she easily fits into this trope.
Scorpius from Farscape gets into this territory at times- at least, when he's not knee-deep in his plan. Despite the fact that he'd spent most of his tenure of the show hunting, torturing and terrorizing Crichton and the others for the secrets of wormhole technology, he still manages to achieve a certain degree of sympathy when his backstory is unveiled: the son of a woman abducted and raped by the Scarran, he was raised by them as part of an experiment to determine if the Sebaceans could be used as breeding stock. The first eleven years of his life was a virtually non-stop torture session, enduring beatings, dehydration, and a whole host of other techniques designed to punish him for being born sickly; at one point, he was even forced to watch a video recording of his mother being raped. After over a decade of this treatment, he escaped and joined the Peacekeepers; however, it later becomes clear that this wasn't because he wanted power, but because he wanted revenge for what was done to him and his mother. It is literally the only thing he really wants: even when Crichton finally manages to defeat him at the end of season three, Scorpius wearily declines all opportunities to take revenge on him- either by letting his I-Yensch bracelet kill him or by destroying Earth- simply because there'd no point in it now that the vengeance he really wanted was out of reach.
Before him was Captain Bialar Crais, who doggedly pursued Crichton across an implausibly large portion of space because of an honest-to-goodness-accident that lead to his brother's death, repeatedly refusing to believe it was an accident and, even when he does come to terms with that fact, doesn't care and continues the hunt anyway. This hunt goes further and further against his direct orders, eventually leading to his expulsion from the Peacekeepers and replacement, Scorpius dubbing him a fugitive as well. A prolonged Enemy Mine with the crew of Moya turns out that his ENTIRE purpose in hunting down Crichton so dutifully was because, as a child, he'd sworn that he would do anything to protect his little brother; in the end, Crais simply couldn't accept the fact that- after all the years he spent looking out for Tauvo, he died because of a simple accident that nobody, not even Bialar, could have planned for. All the speeches about revenge were just a cover for the brotherly love he felt that was considered a weakness by his people and he was never able to properly express. He finally makes up for all the hardship he caused the crew by performing a suicide maneuver in order to allow the people he finally considers friends, who he forgives and who forgive him, to escape capture.
Harry Wells, introduced in season 2 of The Flash (2014), comes off as a rude, arrogant jerkass who has very little regard for the feelings of those around him. However, it turns out that the Big Bad has kidnapped his daughter and the resulting Adult Fear and Heroic BSoD has done a number on his people skills. Add to that the fact that his wife died when their daughter was very young, and it's hard not to sympathise with the way he lashes out at people and pushes them away so he doesn't have to deal with losing anyone else.
Frasier Crane from Frasier. Sure, he's a pompous, arrogant, overbearing, snotty jackass a lot of the time, but deep down, he's a very insecure and sensitive man whose deepest desire is to be liked by everyone, whose controlling behavior towards his younger brother Niles and best friend Roz is often symptomatic of a fear that they might stop needing (and therefore stop liking) him, and who desperately wants a meaningful romantic relationship but he keeps getting slapped in the face by luck over and over and over again.
Daniel from Freaks and Geeks is manipulative, lazy and seems set on doing as little as possible in life. But his father is sick, his mother obviously doesn't think much of him, his teachers seem set on making sure he never succeeds, he's thought of by everyone as a failure by default and even his closest friends can't see him with any type of future. He seems caught in a vicious cycle: Everyone assumes he's a screwup, he tries to prove them wrong but it doesn't work, he becomes indifferent and complacent, and everyone thinks he just doesn't care.
Kim Kelly also qualifies. When We first meet her, She is rude, cold, and utterly horrible to almost everyone especially Lindsey who always tries to be nice. But her family and home life is so horrible you're just amazed She hasn't turned out a lot worse.
From Fresh Meat, JP is such a dick, being smug, completely self-absorbed, and unrepentantly looking down on everybody. However, he also suffers incredibly throughout the show, with his father dying, his mother selling his house without telling him, and his so-called "friends" manipulating him all the time while he desperately struggles for their approval. And he has twocrying steps.
Emily. She turned into a Control Freak and Clingy Jealous Girl only after Ross humiliated her in front of her family and friends at her wedding, the most important day of her life.
Ross can also be this sometimes.
Phoebe. She already has a Dark and Troubled Past (living on the street, a mother who killed herself) and apparently became more of a bitch by the end of the series because of the revelations about her family. Makes perfect sense when you realize that she found out she had a brother her father didn't bother telling her about, her grandmother didn't tell her how to get in touch with her father, she lost a year when she found out she's a year older than she thought, doesn't even know her full name because her sister sold her birth certificate, and found out her mom isn't her mom, but her mom's girlfriend. She probably started being such a bitch when she realized her entire family lied to her almost all of her life.
The George Lopez Show: Benny was a horrible mother to George, no bones about it. But her parents were much worse, and she had to raise a kid on her own without help.
Ricky was Max's delinquent friend who talked Max into a lot of stunts that damaged the Lopez house and drained their finances. But his childhood was pretty much the same as George's, maybe even worse, so George was willing to take him in and give him a better life.
Veronica was a spoiled brat who tested George's patience more than once. But her father was a manipulative conman who stole her quinceanera money and abandoned her, and returned again just to steal her trust fund money, her mother died, and it's implied that her spoiled relatives were also poor role models, since her mother Claudia made George a the trustee to her inheritance, and one of them later sued Veronica for her money, forcing her to live with the Lopez family.
Zack Powers is a subversion. He may have had a difficult childhood (a negligent father and an alcoholic mom), but his embezzlement of company money, trashing the factory just to spite his father, and his manipulation of Carmen into running away and having sex with him shreds all sympathy you can have for him.
Kurt. He's pretty manipulative and borderline Stalker with a Crush on Finn (which was not condoned), but he's victimised and struggling for acceptance and it's hard not to just want to jump through the screen and give him a cuddle.
Rachel. She's conceited and demanding, yes, but she has almost nothing to hold on to besides her dreams of stardom. A lot of her arrogance is compensating for her insecurities and loneliness.
As of "Never Been Kissed", Dave Karofsky, one of Those TwoJerk Jocks, joins the club when he's revealed to be struggling with his own sexuality and is most likely full of self-hatred. He becomes a card-carrying example after his A Day in the Limelight episode, "The Sue Sylvester Bowl Shuffle". Also, in On My Way he tries to kill himself.
Sue. Let's see, her mom abandoned her when she was little, her dad passed away, and she was left to take care of her mentally disabled sister, who later heartwrenchingly dies. On top of this, she was bullied because she stood up for her sister. Yes, she's a complete bitch most of the time, but she really does have a heart underneath it all.
Santana as of "Mash Off". After constantly bullying Finn, he finally got fed up and called her out about being in the closet, humiliating her in front of the whole school. Then, one of Sue's opponents in the run for congress outs her in one of their campaign videos, not just to the rest of the school, but to everybody. Furthermore, Finn also made her question Brittany's feelings for her. This is made all the more poignant by the Troubletones' song choice. Their mash-up of Adele's 'Rumor Has It' and 'Someone Like You' involves love lost/unrequited and secrets being outed (duh). This parallels Finn's claim that Santana's afraid that Brittany doesn't love her back and her fears about what people will say behind her back when she's outed being realised. Also, in "I Kissed A Girl", Santana gets kicked out of her grandmother's house after coming out to her and is driven to tears.
Quinn: she's kind of bitchy but she's also an intelligent but insecure girl who lost everything she had.
Gossip Girl's Chuck Bass may be a pseudo date rapist, Magnificent Bastard, Chess Master, and ruthless force who will crush anybody just because he feels like it and sell his soulmate for a hotel...But he's also put through more heart-wrenching pain than all the other characters. He's the only male character that's been driven to tears and that's happend four times over the course of three seasons.
Blair Waldorf will destroy you if she wants to, or even if she's just in a bit of a bad mood. However, with her low self-esteem, bulimia, neglectful parents, being sold for a hotel, her failed marriage, and her miscarriage, it's hard not to feel bad for her, especially what with Leighton Meester's talent for using her big brown eyes to show agony.
Alex from Grey's Anatomy is a Jerkass, but he also grew up in and out of foster care, had an abusive, drug-addicted father and an alcoholic mother, had a girlfriend breakdown, and when he finally started to trust someone, she got cancer and left him with her hospital bills over a stupid miscommunication. And he was shot. And he had to commit his brother to a psych ward after he had a psychotic episode and tried to kill their sister.
Dr. Frederick Chilton in Hannibal is a smug, slimy administrator who manipulates Gideon into believing he's the Chesapeake Ripper. Despite his many sins, it's difficult not to feel pity for him after all of his trials and tribulations. In season 1, Gideon kidnaps him and vivisects him. The ordeal costs him a kidney and leaves him with a limp, requiring him to walk with a cane. In season 2, when he realizes that Hannibal is a serial killer, Jack Crawford refuses to take him seriously when he begs for FBI protection. Hannibal then frames him for three murders he didn't commit. Finally, a traumatized Miriam mistakes Chilton for her captor and shoots him in the head.
Elle Bishop also qualifies. Essentially imprisoned for most of her life, a subject of cruel experiments, constantly belittled by her father, lonely, and socially oblivious, she's got a whole raft of psychological issues that spawned her love of Electric Torture. ("When I was eleven years old, the doctors diagnosed me as a sociopath with paranoid delusions — but they were all out to get me because I threatened to kill them.") And then she loses control of her powers and is in constant agony...and then Sylar murders her. Poor Elle.
Randy Taylor on Home Improvement was a wise-cracking Insufferable Genius, but a handful of episodes either shed a glimpse on or were devoted to his insecurities over his small size or feeling like The Un-Favourite now and then. Plus, there's "The Longest Day" in which he had to cope with the possibility of cancer.
Chase is a womanizing pretty-boy who kisses up to House and badmouths patients when he's not meeting with them, but between his Abusive Parents, dad's death in season 2, nervous breakdown and divorce from Cameron in Season 6 and general abuse and disrespect from his boss and coworkers, it's hard not to sympathize with him.
Foreman has a God complex, insists that everyone recognize his authority whenever House steps out of the room and generally has a severe case of Small Name, Big Ego, but his mom barely remembers him anymore due to advanced-stage Alzheimer's, his father is cold and unsympathetic, his one attempt to get away from House and have a normal life blows up in his face, and it's revealed in later seasons that a lot of his egomania is because he's very insecure about his abilities and feels he didn't deserve his medical career.
Patricia, mostly in the first season. She's a Deadpan Snarker with jealousy and temper issues. However, she does care about her friends, and seems to have insecurities about a few things- which is probably the two things that are what cause her to act badly in the first place.
Jerome is manipulative and has a tendency to be rather selfish. He was also a victim of Parental Abandonment, unrequited love, and loneliness, as well as a target of Rufus Zeno for two seasons. He also has tried to get better, but has trouble shaking his bad habits and is an Anti-Hero at best.
Joy. While she was relentless in getting Fabian to like her and also was a Control Freak with an It's All About Me streak, she also went through a lot in her life. She genuinely felt ignored by all of her friends and replaced by Nina, as well as unfairly shut out of Sibuna despite everything that happened in the first season.
Barney Stinson. Most of the time, he comes off as an unrepetant, petty, womanizing Attention Whore, but not only is he an actual person, but he's a pretty pathetic and frail one. Especially in regards to his relationships with Robin or his absent father.
Billy Zabka. He's a Woobie, because everyone hates him just for playing the bad guy in The Karate Kid, but he's also a Jerkass, because he tries to take over Ted's position as the best man at a wedding, out of nothing but jealousy.
Sam in the episode "iSpeed Date". A case for a Jerkass becoming a Woobie in that episode.
Even more so when you remember that her mom is not the most competent parent, her father abandoned her, and most of her family is or was in jail.
Nora. She was a psychopathic kidnapper who tried to outright murder Gibby, but it's hard not to feel sorry for her. The girl's parents left her alone on her birthday (the way she said it implies that this is a common occurence), she had no friends except her chicken, and her insanity was likely because of it. In-universe, Carly actually feels sorry for her.
I'm Alan Partridge: Alan Partridge, absolutely insufferable and yet, sometimes, his haplessness is pitiable. He's an utter twat but, sometimes, you want to give him a mug of hot cocoa and a hug.
The Inspector Lynley Mysteries: DS Barbara Havers starts out as this in the pilot episode. The woman cannot take a compliment to save her life, nor can she comprehend the idea that someone might actually respect her for her abilities. As a result, she is bitchy, snappish, and defensive, and rather tends to make viewers (and Inspector Lynley himself) want to smack her across the face. But the storyline makes it very clear just what cause she has to be this way, and as a result, the aforementioned viewers are torn between wanting to slap her in the face and just giving her a goddamn hug already because she needs one so badly. By the end of the three-hour, two-part pilot, the mask has cracked, and she begins to open up to her partner instead of shoving him away. She becomes progressively less bitchy and defensive as the series goes on; although she never loses it completely.
Ben. Definitely a villain, Manipulative Bastard, unrepentant liar, and murderer, yet his Freudian Excuse and the fact that the writers seem to enjoy having him constantly get the pulp beaten out of him (even though most of the time, he deserves it) have the side effect of making him somewhat sympathetic. It also helps that he was redeemed in the episode "Dr. Linus".
Also, Sawyer, at least for the first three seasons. After that, the jerkass part tones down.
Locke, at times. He's not a bad guy, but he definitely comes across as one to his fellow survivors on several occasions, most notably after attacking Sayid, killing Naomi and becoming slightly tyrannical once assuming leadership of a group of islanders. He only does all of this, however, because he knows that the Island is special and he feels he needs to protect it at all costs. It's the first time he felt he had a real purpose, as his life before the Island was one big heap of misery.
Malcolm from Malcolm in the Middle. He is an arrogant dick at times, but he is abused by his parents, bullied by his brothers, is an outcast at school and loses most of his friends in High School. When you realize all this, you want to just hug him and make him feel better.
The fact that his increase in dickish behavior coincides with both mid-adolescence and the onset of a pileup of steadily worsening familial problems, combined with the finale strongly implying that his dickish phase was a prelude to an epiphany that inspires him to dedicate his life to working his ass off to use his intelligence to do good, qualifies as something of a Freudian Excuse in hindsight.
Reese as well. He's a violent, stupid, uncouth bully, but the sheer number of horrible and patently unfair things that happen to him and the number of times he's been exploited and dumped on due to his low intelligence over the course of the show - and which no one except Malcolm and Lois seem to care about due to his status as a "thug" - is enough to make you want to wrap him up in blankets to keep him safe.
Even the boys' mother Lois qualifies (in her more humane moments). She's far from being an ideal mother but dealing with several rambunctious sons and a doormat of a husband has definitely left its mark on her. Not to mention her own mother Ida was even worse towards her.
Al Bundy from Married... with Children is mean, egoistical, and hates everyone and life in general, but considering how practically everyone and everything, from his wife who constantly picks on him and refuses to do anything worthwhile around the house to the fat women who make his shoe salesman job hell to the universe yanking his chain whenever anything begins going slightly right for him, craps on him, you can't really hate him and even have to admire him for refusing to give up even in the face of everything in his life conspiring against him.
"...But I'm not a loser...And the fact that I haven't put a gun in my mouth, you pudding of a woman, makes me a winner." (The full speech delivered by Al - https://www.youtube.com/watch?v=jyLmSAnoR6g - is even more impressive.)
His successor at the 4077th, Charles Winchester, occasionally was one of these as well. Particularly in the final episode. Although he's generally a lot less of a jerkass than Frank Burns was as well.
Howard Moon from The Mighty Boosh. He's a pompous, deluded, self-absorbed misanthrope who seems to cause more trouble than he's worth, but is put through hell in the course of most episodes, to the point where he more than wins the audience's sympathy. At least once in most live shows, there's a scene where he's cruelly picked on or gets incredibly depressed, and the accompanying sympathetic "Awww" from the audience is loud enough to warrant a response from Howard.
Howard: So alone... Random Girl from Audience: Come back to my place! Howard: I'm not that lonely.
Nathan in Misfits (E4 Channel, UK) is very much shaping up to be a Jerkass Woobie. While he started off as a pretty straightforward jerk, moments in which he reconnects with his Mum, has a fight with his Dad, and we see him shell-shocked after barely surviving an attack by his rabid probation officer in an alterna-present (it's complicated. Watch the show. No, seriously, watch the show) all point squarely at him being a classic example of a Jerkass Woobie. The fact that they have cast the rather pretty Robert Sheehan in the role also indicates that this is exactly the effect the programme makers wanted. But the main factor of his Jerkass Woobie status — aside from some very effective Pet the Dog moments, and the casting of a ridiculously charismatic actor with big puppy dog eyes — is probably the fact that the writers seem to just delight in punishing him. Although he is a genuine jerkass, the viewer barely has time to hate him before some kind of amusing karmic retribution (often in the shape of Kelly's fist) comes along to knock the crap out of him.
Rudy seems to have taken over this position rather nicely, though in a different way. Sure Rudy is a jerkass with little regard for how he hurts people, but the secound his other side comes out(rather literally) it's impossible not to feel sorry for the guy.
Adrian Monk from Monk moves back and forth between the status of The Woobie and Jerkass Woobie. While he's a nice and caring man who's crushed under a debilitating amount of phobias and compulsions, his inability to connect with others on an empathic level makes him an insufferably demanding boss and an outright jerk at times. It should be hard to feel sympathy for a guy who would take candy from a baby if it wasn't unsanitary, but he suffers from a socially debilitating disorder, was basically abandoned by his parents, and his one remaining relative is more neurotic than he is. Not to mention that his beloved wife was murdered in the one crime he can't solve. Of course, it helps that Monk can show his heart of gold while being a total Jerkass.
C.C. Babcock on The Nanny. She may be a horrible, greedy, selfish person and a massive Rich Bitch, but considering all the crap she takes, you can't help but have a tiny bit of sympathy for her.
Nashville's Juliette Barnes is this in spades - difficult and can be inconsiderate but a genuinely talented performer, and with a rough upbringing at the hands of her drug addicted mother who ultimately sacrificed herself and a penchant for falling for/into bed with any man who gives her the slightest positive attention, not to mention how every time something good happens to her it's always tainted, it's hard to outright call her a beeyotch. Although that hasn't stopped some people... even after she married Avery and had his child.
Ryan Harper and Rachel Culgrin from Night and Day. Both seem to delight in being absolutely vile to everyone they know, but neither is deprived of moments of vulnerability or humanity. Ultimately, they have loneliness in common. In-universe, Josh Alexander recognises both of them as Jerkass Woobies and befriends both in an attempt to encourage them to be better people. That's until he himself goes nuts and gets demon-eyes.
Michael Scott. He may be an insensitive Jerkass with no internal filter and a massive lack of self-awareness, but when you consider his horrid relationship with the bitchy Jan and his depression after his roast over how much fun he'd have instead of what really happens at a roast and his short-lived romance with Holly (and he still holds a torch for her), it's hard not to sympathize with him. Also, in general, his lack of social skills can be a downer sometimes.
Even further than that, throughout the show, it's clear that most of Michael's decisions (becoming a salesman being a big one) are made with the intent of either making friends or finding romance. Unfortunately, failure seems to be the only option for him, as bad luck tends to break up any chance at either that Michael's own thoughtlessness, childishness, obliviousness, or generally self-centered nature doesn't drive away first. It gets really woobie-ish at the brief points where Michael actually realizes this, such as in "Bring Your Daughter to Work Day".
Once Upon a Time: Both Regina/The Evil Queen and Gold/Rumpelstilstkin have signs of this, both being jerk-hearted jerks who have a tendency towards being cruel to the few people they actually care about. But seing their excuses for their behavior (Regina had a cruel, controlling mother who murdered Regina's fiance, while Rumple gained magic to save his son, was corrupted by the magic until his son left their world in disgust, and was manipulated by Regina into believing that his Love Interestkilled herself after he made her leave under the suspicion that she was working for the Queen.) make them both sympathetic to varying degrees. (Note that Rumple seems to fit this trope the best, as Regina has so many Kick the Dog moments with other characters, Kick the Son of a Bitch / Kick the Dog (depending on the day) moments with Rumple, and Moral Event Horizon moments that even he tends to come off as having the more sympathetic background.)
Really subject to analysis, as it was Rumple who first intentionally manipulated Regina into her Start of Darkness for his own plans, so things she does to him later on are kind of karmic considering he started it. In any case, they both give as good as they get to each other, so whose background is more sympathetic is merely viewer's preference.
Orange Is the New Black: Most of the cast counts, given that they have committed crimes but have also led fairly harsh and disadvantaged lives. Several of the prison staff as well:
Mendez. One of the big causes of his jerkassery is that he's just really, really lonely; he's a jerkass because he's lonely and he's lonely because he's a jerkass.
Also Caputo, who is a total asshole to everyone save for newbie officer Fischer, whom he has a blatant crush on. He then buys her flowers right before she introduces him to her boyfriend. The fact, that he is the least apathetic of the workers and wants to improve the prison's condition also earns him redemptive points.
Alex when she tells Piper that the latter broke her heartand then her speech about heroin being "the perfect girlfriend."
Despite turning his back on Piper when she could be getting stabbed to death, Healy comes across like this when more of his background is revealed. He hasn't got any real friends, his wife is a mail-order bride who mostly ignores him and he looks genuinely heartbroken when he overhears Soso mentioning that none of the girls like him. Like Mendez, a lot of Healy's jerkassery appears to come from the fact he really is a very lonely person. It's also revealed that Healy had a troubled childhood, and that his issues with women stem from the fact his mother was clinically insane, and he had to try to take care of her from a very young age. Later, we have him calling Katya and leaving a heartfelt message because he just wants someone to talk to. Then he proceeds to walk deeper into the ocean as if he's ready to kill himself, only to be stopped when he hears his phone ring. He goes back, probably thinking Katya is answering him, but it's just work. He may have done some shitty things before, but after witnessing how crappy his life was growing up and how lonely he is, you really can't help but feel bad for him.
All of her corruption and callousness towards the prisoners aside, even Figueroa had a woobie moment when it was revealed that her husband is gay and is having an affair with his campaign manager. It is also implied that when she had originally started her job, she was idealistic and optimistic like Caputo, but the years of the prison system's corruption and incompetence that she faced eventually turned her into the cold-hearted bureaucrat that she is now.
Pennsatucky in season two, when her former clique shuns her and she struggles to become a better person, and also in the first season when she landed in Psych - due to actions she committed genuinely believing she's helping people. Plus in season 3 it's revealed that she was raped as a teenager. And at Litchfield, she's assaulted again, by CO Coates.
Many fans found themselves feeling sorry for Piper despite her jerkass tendencies in season 4 when she genuinely tries to make things right between her and other inmates and she's left on her own with no one to spend time with at a dance before the Hawaiian girl turns on her and sells her out to the Spanish gang who brand her with a swastika in retaliation for her framing one of them with contraband underwear. The scene was disturbing and tearjerking especially when we see Piper's face contorted in pain and her anguished screams.
Piper showed these tendencies before that, it was helped by her Cry Cute moments and while some fans thought she complained too much about her first world problems there are many things she experienced that are genuinely worth crying about.
The next episode shows Piper crying in her bunk and when the Hawaiian girl asks her if she's okay Piper responds brokenly "Not even a little bit." She also looks unwell physically as well as mentally.
Outnumbered: While Angela starts out as easily the least sympathetic character in the show — abandoning her father after she promised she would look after him, and generally acting spiteful and vindictive toward Sue and her family — it's hard not to sympathize with her when she thinks she's finally found true love, only for her new husband, Brick, to turn out to be a manipulative, psychologically abusive sociopath who drove his last wife into an institution. She attempts to flee from him and to protect his daughter, Misty, from his cruelty, only for Brick to respond with a two-fold attack — first sending his very expensive lawyers after her, then, once she is cornered, calling her up to convince her that he can change and everything will be fine. Even after she finally breaks free from his control, her life doesn't get a great deal better, as she becomes stuck in a cycle of disastrous relationships that inevitably end in heartbreak for her.
Chris Keller. Despite how terribly manipulative he was to practically everyone and the fact that he was an insane murderer, he truly did love Beecher in his own twisted way and suffered horribly (and willingly).
Shirley Bellinger. She is a criminally insane woman who deliberately killed her daughter with no remorse, racist, and sexually promiscuous. But the scene where she is to be hanged, in which she freaks out, struggles against the guards, has to be tied up, and fervently prays to God for forgiveness while sobbing uncontrollably is nothing short of heartbreaking.
Every Woobie in the show did something that landed them in prison in the first place.
Both Mark and Jeremy from Peep Show. You could count the times things have worked out for either of Them on one hand. Jeremy stands out more though. He's a complete dick with practically no morals, motivation or loyalty to his friends and is happy to sponge off everyone around him. But His dad abandoned him, his music career is going nowhere, he doesn't seem to have any other friends aside from an equally pathetic crack addict, he can't form a meaningful relationship and the only woman he loved used him to get a green card and left him, his best friend and roommate sees Him as the living definition of a fuck up and the universe seems set on viciously crushing whatever optimism he can scrounge up around him.
Not to downgrade Mark either. He's neurotic, selfish, never thinks of others and is constantly coming up with excuses for his behaviour. Still his life seems determined to crush anything good that comes his way while also putting him in terrible and awkward situations beyond his control. He is also The Un-Favourite of his family, his father is emotionally abusive, his mother had an affair, and pretty much everyone he meets seems to think he exists solely to be treated like crap and be their personal whipping boy.
Astronema from Power Rangers in Space. Being kidnapped and raised by the "Master of all Evil", fighting your own brother and being brainwashed into becoming a ruthless warlord does not make a happy person.
Frax from Power Rangers Time Force. He was a kind scientist who saved Ransik from poisoning, who repaid his kindness by insulting and attempting to kill him. Fran rebuilt himself as a robot and joined Ransik with the intent to get his revenge. Near the end of the series, Frax gets a chance to talk with Nadira, who has been conflicted about her father's hatred of humans. In the end, Frax is reprogrammed and destroyed.
Camille from Power Rangers Jungle Fury. Camille has Undying Loyalty to Dai Shi, and is greatly attracted to his host's body. However, he doesn't return her affections and continuously treats her as nothing more than a pawn. While Jarrod grows to care for her, Dai Shi sees her as nothing more than a servant, breaking her heart despite how much she's willing to do for him.
Miss Parker on The Pretender is a tough as nails Action Bitch and Smug Snake rolled into one hot package, until you remember what happened to her mother.
And of all people, Mr Raines breaking down in tears at the end of "Blue Moon" when he receives his daughter's locket and finally learns her fate at the hands of a sadistic serial killer.
Theodore "T-Bag" Bagwell from Prison Break certainly fits this. He's an unrepentant Ax-Crazy psychopath, murdered children, is a racist, and is a Depraved Bisexual of the highest order who will get it on with Anything That Moves. But his horrible childhood (being the product of incest and rape, being molested by his father, and forced to memorize entire dictionaries) combined with some of the horrible things that happen to him in the series (having his hand cut off, for starters) really stirs up some pity for the bastard. It becomes more apparent in the fourth season when T-Bag slowly starts Becoming the Mask after taking on a fake identity, genuinely wanting redemption, only for it to just not work out in the end. Robert Knepper (who played him) noted this pretty well.
"Around episode 6 or 7, I got so many letters from people saying, 'When I first started watching this show, I absolutely hated you and I wanted you dead. Now I still want you dead, but I'm starting to feel for you.' I think there's something in my eyes, a childlike thing in there. There's still an innocence. There's still a bit of hope."
When his character breaks out of prison again in a crossover episode of Breakout Kings, it turns out that his monstrous actions during the episode were motivated solely by getting revenge on the orderlies who sexually abused his comatose, dying mother. During the final chase scene, he is not trying to escape but is actually running to his mother's hospital room so he can see her before her death. Even the marshalls who witnessed his horrendous crimes are not able to refuse him that last moment.
Charlotte on Private Practice is a horrible, thoroughly unpleasant person. And then she was brutally beaten and raped and it became impossible not to feel sorry for her.
Red Dwarf: Arnold Rimmer. It's a comedy series, so his problems are usually treated light-heartedly, but given everything, is it any wonder that he's a mess? In particular, he would have turned out like Ace Rimmer (what a guy!) had he simply been held back a year instead of being allowed to progress. Even when he gets a break, it turns out for the worst. Of course, the series also takes pains to point out that the Woobie part doesn't automatically excuse or justify the Jerkass part; he's still, in many ways, a loathsome, repellent, hypocritical coward, for the most part.
Perhaps no episode highlights both the Jerkass and Woobie portions of his personality better than "Me2", when we are faced with a second Rimmer Hologram. The second Rimmer is every bit the Jerkass the original was, except he seems to delight in focusing all of his worst qualities against the original Rimmer hologram. Under the belief that he has been chosen for deletion, the original Rimmer hologram shares a deeply personal, and painfully embarrassing, moment from his life with Lister and Cat. It's revealed after he's finished that Lister had already deleted the second hologram as he'd exited the room. What helps further highlight Rimmer's Jerkass status is that, as Lister points out, this is all his own fault: he was the one who stole and hid all of the other hologrammatic disks, going to the extent of replacing the disk for Kristine Kochanski with a second copy of his own, then refused to own up even after Lister had come up with a plan for creating a second functioning hologram.
Another good example is Terrorform. Anthropomorphic Personifications of Rimmer's self-hatred and inner demons are bearing down on the ship, which is unable to drag itself out of a swamp representing his despair. His friends take this opportunity to tell Rimmer that, regardless of their past differences, he is a member of the crew and they care about him. This briefly brings back to life the personifications of Rimmer's good-qualities, like his nobility and self-confidence, which hold off the demons and frees the ship from the swamp. Upon escaping the planet, Rimmer asks the crew whether all of the things they said were just to escape and if they meant any of it. The crew's response? A unanimous and immediate "No!"
Revenge: Emily Throne. It's hard not to root for her after all the Graysons have done to her father, and her by extension. Their actions, however, have led to Emily becoming a Tragic Monster who's hellbent on making sure they suffer, and she cares very little for collateral damage. At first, anyway.
Tyler Barrol has a bit of this, when you remember that he's genuinely mentally ill (and when you find out that he only got violent because Emily was deliberately pushing him into a breakdown to get rid of him).
Guy of Gisborne from Robin Hood stabs unarmed women, leaves babies in the woods to die, burns down houses, and sells his sister to a rapist. He's also arrogant, selfish, and has a vicious temper that causes mass suffering to him and everyone around him. And yet, whenever anyone shows him a shred of kindness, he blossoms like a delicate little flower in the sun...the fact that he's a Draco in Leather Pants doesn't hurt either.
Sherlock often comes off as cold and unfeeling, but in "The Blind Banker" it's hard to watch him try not to show that hearing how everyone at school hated him upsets him without wanting to give the guy a hug.
George's status as a Jerkass Woobie is brought home in the Season 8 episode, "The Andrea Doria." There, George is competing with a survivor of the sinking of the S.S. Andrea Doria (a 1956 maritime disaster) for a new apartment. After the survivor tells his story to the apartment board, George follows by telling the board the long list of misfortunes he's suffered over the course of the entire series (such as suffering "shrinkage", being tied up by a woman and robbed for eight dollars, being confused for a Nazi by an angry mob, getting caught holding a marble rye in front of his future in-laws, and his fiancée's death from licking poisonous wedding invitation envelopes). The board unanimously chooses to award him the apartment over the shipwreck survivor (until he himself loses out on the apartment to Elaine's former boyfriend whom she stabbed for making fun of the size of her head).
Mini from the third generation of Skins is turning out to be this. Yes, she is the Alpha Bitch with major Machevellian tendencies and is bitchy, passive aggressive, and very Sugar and Ice. On the other hand, she has an insane longing for control and stability in her unstable life, eating disorders (and probably some sort of anxiety problem), her best friend slept with her boyfriend, her boyfriend took her virginity (painfully), and she generally just seems like a sad, sick girl playing at confidence. On top of it all, her friendship with Franky - the one truly authentic person in her life - has gotten complicated because Mini has developed a crush on her while Franky only has eyes for Matty. YMMV, though. Some people just see her as a jerkass.
And, of course, this is thanks to her abusive childhood due to abandonment by her father, Lionel.
Even Lionel qualifies. Born and raised in the slums, where his mother was an alchoholic and his father was a thief and murderer, he has to claw his way to the top of the financial spectrum (which he starts by murdering his parents). Loses his younger infant son, Julian when (he thinks) Julian's older brother Lex accidentally kills him. Loses his wife, Lillian, who dies while Lex is still a pre-teen. Then Lex is rendered permantly bald by the meteor shower. When an adult Lex discovers what Lionel did to his own parents, Lionel's forced to drive Lex into insanity and erase his memory. Lionel actually feels a great deal of remorse about it. He then learns, long after it's too late to do anything about it or make it up to Lex for it, that Julian was actually deliberately murdered by Lillian. He undergoes a HeelFace Turn right around the same time Lex does a FaceHeel Turn, ensuring that he and his son will always be at odds. Falls genuinely in love with Martha Kent (and she even seems to return some of that affection, even if she's a bit freaked out by it), but can never fully win her over because he has to reveal to her that he's indirectly, unintentionally responsible for her husband's deathDetails Lionel staged a meeting with Jonathan Kent to reveal he knew Clark's secret. Lionel's intention was to form an alliance with the Kents, but his arrogant demeanor combined with Jonathan's quick temper resulted in Jonathan physically attacking Lionel. While Lionel didn't strike back, the strain of attacking Lionel brought about Jonathan's fatal heart attack.. After being knocked out while trying to help Clark defeat Bizarro, is then kidnapped and tortured for several weeks by Lana Lang. He meets Grant Gabriel, the adult clone of his dead son Julian, and starts to bond with Grant...only to witness Grant being murdered on Lex's orders. He can never fully let go of his manipulative tendancies, so when he gets several cryptic threats about Clark, resorts to kidnapping him to keep him safe. Clark shuns him for this, since Lionel's not LanaLang. Patricia Swann tells Clark that Lionel killed her father, further deepening the rift between them.note And the very fact that Patricia's accusation makes no sense since her father died sometime after Lionel's HeelFace Turn, only makes Lionel even more sympathetic than was perhaps intended. Lionel desperately tries to warn Clark and Chloe about the looming threat of Lex and the coming Apocalypse, but they'll now have nothing to do with him. Is finally cornered by Lex, and when he refuses to divulge Clark's secret, is murdered by his own son, dying friendless and alone.
Really, being a Jerkass Woobie seems to be a Luthor family trait. You want to hug all three of them, Lex, Lionel, and Tess, then slap them in the face and say, "Stop being such bastards, guys! Even being Magnificent Bastards doesn't make up for all the crap you go through for being bastards!"
A (milder) example would be Oliver Queen. The fangirls apparently find him Troubled, but Cute, especially in season nine with his self-destructive spiral. However, other than being a jerkass towards Clark, he also murdered Lex.
Armus from "Skin of Evil", especially if he ever got free. He's a black liquid of pure evil made of the discarded negative emotions of an ancient race of highly advanced aliens, but he had no choice in his own creation and his constant state of undirected rage and hatred actually pains him as well. He wants nothing more than to be reunited with his creators for leaving him on a dead planet for millennia, but he will never get the chance. Both Picard and Troi express their pity for him while acknowleding his malevolence, but he angrily rejects it.
Gul Madred, Picard's Cardassian torturer in the two-part episode "Chain of Command", grew up on the streets as a poor boy, once beaten up over some food. Picard, however, calls him out on it in light of how he became a brutal torturer:
Picard: When I look at you now, I won't see a powerful Cardassian officer... but a small boy weeping because he was powerless to protect himself.
Apollo in Who Mourns for Adonais is a family-friendly version of the Jerkass he is in Greek Mythology, and goes on a power trip. However, one's heart still aches for him in the end when resigns himself to going the way of the other Olympians.
Jonah of Summer Heights High. He's undeniably a Jerkass (just look at the way he treats a lonely kid assigned to be his buddy for confirmation), but one can't help feeling at least a little sympathetic for him in the final episode when he is humiliated in front of his entire class by his teacher, and expelled from the school.
Dean Winchester. He can have a nasty temper and is a cocky, self-righteous, judgmental, always-wisecracking Jerkass manwhore with such low self-esteem that he thought he deserved to go to hell, has an almost obsessive devotion to his family (and he really wanted them back together again, which is never going to happen) and especially his little brother, an unwillingness to actually stand up for himself (when it came to Missouri, John, and sometimes Sam), has shown an honest willingness to sacrifice himself and his own happiness for perfect strangers, and all that wisecracking is just to "mask all that nasty pain". Not forgetting that he's also the show's favourite bitch, so you've got to give him some sympathy.
His brother, Sam. He's self-absorbed, doesn't seem to think much of Dean sometimes even though he'd give anything for him, can be incredibly cruel at times ("You were four when Mom died. How could you possibly know how I feel?", anyone?), and is prone to self-pity by the bucket-load. He knows just how to twist Dean around his little finger, but he tries a hell of a lot harder to make Dean feel better than John ever did, he falls apart trying to save Dean in Season Three, he's using his demonic powers for good, he really did try to make it up to his father after "In My Time Of Dying" by focusing on the hunt, and much of the bitchiness is leaning towards the affectionate Deadpan Snarker style and not the unsympathetic Jerkass style. His violent streak isn't quite natural in origin and, much like Dean, he endures a lot of crapthroughout the series.
Gabriel/the Trickster. Yes, he screws with people and likes to torment Sam Winchester even more than the other antagonists, but he left Heaven because he couldn't stand to watch his brothers kill each other, only for the fight to begin again and to be dragged back into the fight. He then fought for the humans, believing them to be better than the angels, because they at least try to be better, and gets killed by his big brother, Lucifer, who he loved. The look on his face when he's stabbed◊ will break your heart.
Castiel is turning into this. He has always been a Woobie but, in season six, he starts becoming a Jerkass. He is fighting a civil war against other angels in Heaven and chose to make a Deal with the Devil in order to get the power needed to win the fight. Despite that, he still helps Sam and Dean and tries to keep them safe until he sacrifices even his friends.
Owen Harper from Torchwood. He's undeniably a jerkass, misanthropic and womanising, but just tell me you don't want to give him a hug in the flashback scenes after his fiancee dies, or in "Adam" finding out how his mother treated him. No wonder he's out to make the whole world hate him.
Charlie Harper from Two and a Half Men is this. Despite all of his Jerkass behavior (Womanizing and mistreatment of women, his treatment of his brother in later seasons, etc.) that makes you want to rip him a new one, his narcissist of a mother is an Abusive Parent who throughout the years abused and neglected him and shows up all the time to guilt trip him. His brother becomes a sponge who happily mooches off of him without remorse, he has a stalker who people try to pair him with. Said stalker ended up murdering him and even after death, he's still treated like crap by his mother.
Charlie's brother Alan counts too. Sure, he's a pretty shameless sponge and very cheap moocher, and becomes more of a Jerkass in later seasons, but he hasn't had an easy life either. Aside from their aforementioned Evil Matriarch mother, Alan also has to deal with his incredibly bitchy and hypocritical ex-wife Judith wringing out every last drop of happiness from him for no reason other than her own personal amusement, a Dumbass Teenage Son who constantly tries his patience, a string of failed relationships, and the fact that Charlie tends to be a Karma Houdini who coasts through life rather easily (the occasional Humiliation Conga notwithstanding) while he's had to work tirelessly for anything resembling happiness and having next to nothing to show for it.
Logan! "Obligatory psychotic jackass" or not, his life just sucks so much. Dead girlfriend and mother, horribly abusive father who was also the one who killed his girlfriend, falsely accused of murder, and generally, his friends and loved ones keep dying/being evil/breaking his heart/fleeing the country/any combination of the above.
Even Dick starts crossing into this late in season 3, when he has something of a Heel Realizationabout the way he treated his brother, blaming himself for everything Cassidy did, including his suicide.
Robbie. He gets a few episodes where he is clearly the 'villain' of the piece, then we get episodes like Rex Dies and the one where he gets his car stolen, where he's woobie-tastic.
Also, Jade, to an extent. Sure she's really mean when she wants to be, but it's known that she and her father have a poor relationship and it's implied she has a bad relationship with the rest of her family as well. Sure, she's controlling and jealous to Beck, but once you realize how easy it was for him to kiss Tori as well as how he barely seems phased with other girls flirting with him, it's understandable.
Ingrid from Young Dracula may be one of the evilest characters on the show, with several murder attempts to her name, but when you look at the way her father (and nearly everyone in her family) treats her it really makes you want to give her a hug.