The Sopranos was packed with this type of character. There's Tony, Carmela, Christopher, Paulie, Bobby, Eugene, Pussy, Vito, Patsy, Johnny Sack, Uncle Junior, Jackie Jnr, AJ, etc. - even Ralfie had his moments.
Dino Ortolani, Donald Groves, Miguel Alvarez, Nino Schibetta, Peter Schibetta, Schillenger's son, Andrew (and occasionally Schillenger himself), and James Robson.
Also, 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.
Almost every murder in Cracker fits this trope. Albie Kinsella (Robert Carlyle) and Janice (Elizabeth Estensen) being particularly strong examples. Jimmy Beck becomes this during the second series as well.
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.
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
Turlough is this, at least for his first few episodes.
No one saw it coming, but in The End of Time, the Master evokes this response during the confrontation with Rassilon. At first, he's being all megalomaniacal-whackjob as usual, and then Rassilon wipes out the Master's control over humanity with a flick of his finger. The Master then finds out that he's been manipulated his entire life by Rassilon, been knowingly driven insane and used as a tool for the rest of the Time Lords who followed Rassilon to "ascend to a higher state of being". The Master was not invited, but don't worry, he teaches Rassilon a fun counting game.
The Doctor himself has this a bit, particuarly in his later incarnations.
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.
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.)
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.
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.
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. Than 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 Heel-Face Turn right around the same time Lex does a Face-Heel 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 Heel-Face 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.
Say what you like about Faith's brash, tactless attitude, her willingless and lack of shame at using people like tampons and her pyschotic 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...
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.
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.
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.
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.
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.
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 someone with so angelic an appearance as Robert Sheehan (yes, of course I am being totally objective about this. How could you possibly suggest otherwise?) in the role also indicates that this is exactly the effect the programme makers wanted.
Oh Lord, Nathan epitomises this trope. 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.
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.
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.
From Degrassi Junior High: oh, Kathleen. You're such a snooty bitch, but your life's such a wreck - alcoholic mom, absentee dad, abusive boyfriend, anorexia...
Degrassi has a few, mostly due to having to have antagonistic main characters who can be protagonists at other points in a given season:
Sean spends a while wearing this coat, during his time in the Candy Bandits.
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 Jerkass Façade 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.
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.
Tyler Lockwood and Caroline Forbes before characterdevelopment set in.
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 Listen 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!"
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.
James Cook from Skins, according to some fans. And Tony Stonem from Season 1 and 2 has his moments.
Malcolm Tucker, a spin doctor from The Thick of It whose job description is Magnificent Bastard, has become one of these by season three. He treats the politicans he has to police like crap (although... well, Acceptable Targets and all...) and speaks in Cluster F Bombs (when he's not talking of Country Matters), and, as one character notes, he pretty much "thrives on being disliked". He has a Morality Pet in the form of his secretary Sam, and one of the series' very, very few crowning moments of heartwarming comes when he leaps to her defence and comforts her when she's crying (bear in mind that he takes the time to do this in the middle of his sacking from Number 10. Glimpses into his personal life are very rare, but when we do see him at home, he's just lying forlornly on his sofa, eating crisps alone.
Season 3, episode 6: as Terri offered him a hug, many viewers wanted to give him a hug too. As inexplicably loveable as he is, in season 1, this would have been unthinkable.
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.
Also, 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 be 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 Jerk Ass. 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.
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.
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 Unfavourite 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.
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.
Most characters on My So-Called Life have had been mean to each other but remain sympathetic in various different ways.
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.
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.
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.
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.
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.
Hell's Kitchen: Gordon Ramsay initially seems like a pompous, foul-tempered Jerkass, at least until you see what some of the contestants on his show put him through and you understand just why he's so cranky to begin with.
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.
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 - http://www.youtube.com/watch?v=jyLmSAnoR6g - is even more impressive.)
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.
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.
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.
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.
The Office (US): Michael Scott. He may be a Jerk Ass, 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 sympathise 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, oblivity, 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".
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 Unfavourite now and then. Plus, there's "The Longest Day" in which he had to cope with the possibility of cancer.
Gul Madred, Picard's Cardassian torturer in the two-part Star Trek: The Next Generation 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.
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.
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.
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.
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.
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, she goes from this trope to a Woobie with a Jerkass Façade that isn't much of a facade at all.
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.
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.)
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.
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.
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.
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.
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 WW 1, 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.
Katerina from the Cold Case Episode Cargo. On one hand, she lied two a vulnerable girl about the girl being abandoned (when she wasn't) 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
Once Upon a Time: Both Regina/The Evil Queen and Gold/Rumpelstilstkin have signs of this, both being Jerk with a Heart of JerkMagnificent Bastards 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.)
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).
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.
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.
Charlie Harper from Two and a Half Men is this. Despite all of his Jerk Ass 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, a Dumbass Teenage Son who tries his patience more than once, 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.
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. Gets even worse 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 basically 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 seems to be moving back towards this as of "Ozymandias", as he has fled the state and claimed to be the sole mastermind of the meth empire, even implying that he killed Hank, so that Skyler and Marie won't face charges.
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, it's hard to outright call her a beeyotch. Although that hasn't stopped some people...
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.
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.
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.
House of Anubis. Pretty much everyone has their moments, however a few people stand out.
For starters, you have Patricia Williamson. She did some pretty nasty things, such as the fake initiation for Nina, complete with locking her in the attic, throwing away the key, and nearly getting her in trouble with Victor twice. However, she was also the one who was desperate to save her best friend, Joy, when everyone else was willing to just forget about her; She was betrayed by nearly everyone she trusted before Sibuna came along; Kidnapped by a person she had rescued just a few episodes before...and that's just scratching the surface.
Joy Mercer. Oh, poor Joy. She's been relentless in trying to attract Fabian's attention, and wrote an incredibly nasty article in the school paper trying to get Nina to leave. But there's no denying her life is a MESS- kidnapped by her father just for it to turn out that she was not the chosen one, coming back just to realize Nina basically took her place in the house, ignored by Sibuna even when she wasn't doing bad things...
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.