Let's face it: Harry Potter is one DEEP, DARK PIT crawling with woobies.
Many fangirls are under the misguided notion that Severus Snape from the Harry Potter series is a delightful, cuddly chap. His actual backstory doesn't help, since he alternates between Woobie and Jerkass with surprising ease.
He is without a doubt a Jerkass Woobie, an integral and popular member of the Woobie family
Remus Lupin. His argument with Harry in Deathly Hallows was woobiedom encased in a few lines of dialogue. How can anyone not feel sorry for a kind, fair-minded, good-natured bloke shouting about how their in-laws are disgusted at his marriage to their daughter; how he feels he's dragged his wife down; how most people he meets can barely look at him and how his unborn child must always be ashamed of him, all because of his lycanthropy? Then add to that the notion that being a Werewolf is more or less treated as having AIDS, and that Greyback - the werewolf who bit him - purposely goes after children because he's just that demented. And to top it off, JK Rowling kills both him and his wife.
Not to mention that he didn't have any friends at all until age 11, when he made 'three great friends'... who he automatically assumed would abandon him if they ever found out his secret. They didn't, but he still lost them all, one by one.
Harry himself. Remember Dumbledore in OOTP? "My only defense is this: I have watched you struggling under more burdens than any student who has ever passed through this school, and I could not bring myself to add another — the greatest one of all."
Or the end of GoF, when Harry is already in a state of complete shell shock after being assaulted and nearly murdered, and witnessing the pointless murder of a friend, by Lord Voldemort... and then, while he's still reeling and vulnerable, another villain gets Harry alone under the guise of helping him, and promptly attacks him.
"Harry had no memory of ever being hugged like this, as though by a mother." That is all.
Harry's an innocent teenager who carries the world on his shoulders. All the grief of losing every single person he loved. Of being fated and knowing you have to battle the greatest dark wizard of all time. Seeing your friends die around you. No one should have to go through those horrors, but he did, and he has a heck of a lot more coming.
This is really driven home in the last book, when Harry arrives at Hogwarts and is searching for the last Horcrux in a frantic race against time to defeat the Big Bad and prevent anyone else from being killed, but it's right then that everyone he loves shows up at the school and basically volunteers to throw themselves into a meat grinder just to buy him more time. He then has to watch his friends die left and right as they fight the Death Eaters, knowing that they're dying for him.
Let's not forget Andromeda Tonks. She loses her husband Ted Tonks and a couple of months later loses her daughter and son-in-law in the same battle. And she's expected then to care for her grandson by herself (Well, with some help from Harry) in all her presumed grief.
Let's not forget the loss of her sister as well. They might've hated each other, but there'd still be a bit of sisterly connection from Andromeda, surely?
And then there's Sirius, whose entire life has basically been a total hell for him. His parents were pureblood supremacists who disowned him after he ran away, and though he had a few happy years at Hogwarts, he shortly loses James, his best friend. And then Sirius gets betrayed by another friend, who frames him and gets him imprisoned in the worst jail imaginable with no trial and the whole world thinking he's an evil murderer. Then he gets stuck in the place he hates most, Grimmauld Place, feeling trapped and utterly miserable.
Poor Luna Lovegood who enjoyed being in the D.A. because "it was like having friends". And she's not even sad or angsty about this — she's just completely accepted that she will probably always be a social outcast and never experience true friendship.
The scene in book 7 when Harry sees the portraits in Luna's room was a powerful woobie tearjerker. Basically, the five closest people to friends she's got are Harry, Ron, Hermione, Ginny and Neville who all think she is a bit bonkers, but the thing is they don't make fun of her and treat her with respect. I mean Hermione is there, and she and Hermione don't really agree on anything!
The House Elves! Every one introduced was an immediate woobie, from their species' history to their eventual fates. Hokie is thrown into Azkaban. Kreacher is used and abused by Voldemort and has to deal with the loss of those who cared for him; Dobby is abused by The Malfoys and dies an early (if heroic) death.
Winky. Out of the house elves, she's the biggest Woobie of 'em all.
Hagrid constitutes as a woobie- forever a bit of an outcast, loses his mother and his father before he's 16, gets expelled unjustly, and supposedly never even gets together with Madame Maxime. He got sent to Azkaban for several months simply because the government wanted to look like they were doing something, and he was a suspect.
Dumbledore is a near woobie. Loses most of his family early on, then one of his best friends/crush turns out to be a real monster, and is basically isolated by his intelligence for a century and a half until he is killed after being tortured by drinking a toxic potion. One that forces him to relive all his worst memories.
Moaning Myrtle. Killed by a monster, constantly bullied before and after death and forced to haunt the bathrooms forever. And no-one could ever hug her, because they'd just go right through her.
She is somewhat better off later in the series...
Pius Thicknesse. Under the Imperius Curse throughout his term as Minister of Magic. Imagine achieving your lifelong dream only to be Not Yourself and a Mind Raped slave.
Draco Malfoy goes from Jerkass to Woobie in the sixth and seventh books. For the first five he's a solid Jerkass, but in the sixth he becomes a Death Eater. However it's pretty obvious that Voldemort is using him to get revenge on his father Lucius, and knows Draco will likely die trying to complete his "mission" which is to kill Dumbledore. Draco breaks down, but survives the mission thanks to Snape, but then his whole family is embarassed in the first chapter of the seventh book, he's forced to witness tortures and murders, and he's even forced to torture other people. One of his goons dies horribly in the Final Battle, and he nearly gets attacked by his fellow Death Eaters. It gets to the point where even Harry, who absolutely hated Draco for six books, starts to feel bad for him and wonders what sick crap Voldemort's going to put him through next. Draco definitely isn't a nice guy, but it's hard not to feel bad for him in the last book.
Merope Gaunt is probably the most pathetic character in the whole series. She only wanted to be loved and Mrs. Cole, whom she met in about the last ten minutes of her life, may well be the only person to ever treat her with anything resembling kindness. Her family abused her and the local townspeople thought she was a freak. Consider nearly everyone else on this page has at least someone they're friends with or is at least decent to them. Merope crossed the line by effectively date-raping Tom Riddle, Sr. into marrying her, but at that point you really couldn't blame her if she decided Humans Are Bastards and went on a murderous rampage.
Her son was more than happy to take up that particular task.
An essay that further explores Merope's woobieness.
Subverted with Quirrell. The guy spends most of the book as prime woobie material - A smart but naive young professor who went off to experience the world... and was so traumatized by his experiences that he is constantly trembling and stuttering. Even worse, because of this he is mocked by his students, despite having a "brilliant mind". He also appears to be one of the kinder professors - at one point he 'rescues' Harry and his friends from Filch. The poor guy is even bullied later on by Snape. Of course, then we find out that it was an act and he was the villain all along. Wasted sympathy.
Another good subversion comes with Peter Pettigrew: In Prisoner of Azkaban, he was revealed to have been the least of the Marauders, physically and intellectually; even the teachers were harsh with him, something McGonagall admits regretting after he confronted Sirius Black and was killed by him. Subverted by the teensy little fact that he betrayed the Potters to Lord Voldemort, blasted apart a street filled with Muggles, and framed Sirius for both crimes. Oh, and uh, he wasn't dead. Also, he's a Dirty Coward and The Quisling, especially in Deathly Hallows.
George Weasley in the final book. First, his ear is cut off by a stray curse, then his twin, partner in crime, and best friend Fred is tragically killed in the final battle. He lives, but must go on physically and emotionally maimed for life.
Professor Trewlaney in OOTP. Harassed by colossal Jerk Ass Dolores Umbridge for no other reason than she has the authority to. Fired and humiliated in front of the entire school. Forced to leave her only home (though Dumbledore does help her out on the last one). Emma Thompson's performance borders on Tear Jerker.
Even Professor McGonagall who has criticized her subject again and again feels sad and comforts her.
Hermione Granger. Her first half year she was completely shunned. Not only that, but she also has to memory wipe and ship off her own parents knowing full and well that her chance of survival is slim. She's the one who has to keep the group together, despite everything they go through. Especially after her scene in Half-Blood Prince, crying with Harry, you just want to pick her up and just hug her forever.
Regulus Black. Turns out he was a good guy in the end, and he was killed for trying to destroy the locket Horcrux. However, Sirius only ever knew him as a jerk and a Death Eater. Which is sad.
Filch might qualify. We learn in the second book that he's a squib. So he's an outcast, wizards never treated him as an equal and he was probably mocked as a child. As an adult, he works with young wizards who continuously show off their magic in front of him and he's deadly afraid that one of the kids discovers his secret and makes fun of him. Oh, and apparently, his only friend is a cat. Who gets petrified for several months.
Ron Weasley is normally the series Chew Toy, rather than woobie - his repeated embarrassments stemming from his lack of money, being Overshadowed by Awesome, or both, are typically played for laughs (along with his tendency to react with deadpan snark). But the funny Chew Toy moments are increasingly interspersed with serious ones as the series goes on, and eventually leading to a heartbreaking scene in book seven when the horcrux spins his lifetime of self-doubt and insecurity into a nightmarish hallucination, bringing Ron perilously close to crossing the Despair Event Horizon. He manages to resist and destroy it, but is a complete wreck afterwards. When the guy who normally tends to brush things off with snark or self-deprecating humor, instead breaks down sobbing in anguish? Yeah, his woobiedom temporarily went off the charts.
For a while in Books 4 and 5, Cho Chang. Poor girl; her boyfriend died just because he was in the wrong place at the wrong time. Her bouts of crying, especially when she began to realize she liked Harry and couldn't figure out if she was okay with that, could very easily have come off as pathetic; given the situation, I'm sure plenty of readers just wanted to hug her.
While Tom Riddle is not a remotely sympathetic charecter, his identity as Lord Voldemort is created by a series of tragedies. His Mother, who was mistreated all her life, became pregant out of a desperate bid to be loved, and then died just after giving birth, then Tom was raised with no one to teach him about his powers, and he therefore felt detatched from his fellow orphans. When he went to Hogwarts his feelings of superiority caused him to abuse his incredible intellect, he also found out more about his father abandoning him and his mother, and was angry. This spirled into a hatred for muggles, and muggle-borns. While any sympathy one could feel for him stops at Tom's terrorizing his peers at the orphanage, one could feel sorry for him in the way Dumbledore feels sorry for Dudley.
Petunia Dursley for the Jerkass Woobie variety. Sure she is crappy to Harry, and he doesn't deserve her taking her issues with her sister out on him, but it's not like she had a nice life either. She grew up in her younger sister's shadow in everything. Her parents fawned over Lily's magical talent, and it's strongly implied that while Lily was pretty, confident and happy, Petunia was plain and insecure. Her envy begins with Lily's magic and admission to Hogwarts to the point that she desperately writes Dumbledore pleading to be admitted to Hogwarts herself, and then again when Lily grows up to happily marry a handsome and apparently very rich James Potter, while Petunia is relegated to depressingly dull life with an idiot for a husband. Then has a magic baby so special that he defeats the greatest villain that ever lived as a toddler, while his mother dies and he is forced on her to care for as a constant, 11-year-reminder of everything he is, her sister was, and that she didn't get to be. Yeah.
Professor McGonagall is revealed to be this in her Pottermore-provided backstory. When she had just graduated from Hogwarts, she fell in love with a young Muggle farmer and cheerfully accepted his marriage proposal. However, a combination of knowing what happened when her own father unknowingly married a witch and a Career Versus Man dilemma (for a job at the Ministry she later found out she didn't even enjoy) forced her to break off the engagement without being able to tell him why. After becoming a teacher at Hogwarts, she later found out he married another woman, driving her to tears. On top of that, when she had much later gotten over it, she got Happily Married with an older man, only for him to die only three years into the marriage. As Pottermore puts it, "few people - excepting perhaps Albus Dumbledore - ever realised how much she suffered."