Satchel Pooch from Get Fuzzy. He's constantly being abused both verbally and sometimes physically, particularly by Bucky the cat. Also, let's not forget the fact that Satchel's father is ashamed of him.
Bucky's British cousin Mac Manc McManx counts as an Iron Woobie. He's an Ugly Cute cat whose dialect almost no one can understand, his girlfriend Julie (who may or may not be abusive) beat up on him (giving him one nasty head injury), and he was mistaken for a terrorist and detained by airport security for a month. A MONTH? Someone give that poor cat a hug! He's a real Sad Clown, that's for sure!
Charlie Brown from Peanuts, obviously. Charles Schulz often described Charlie Brown as a wishy-washy, self-pitying sad sack, like him, and as a result, was insulted and laughed at by many of the characters in the strip.
Linus becomes this the second you take his security blanket from him.
Linus is this even WITH the blanket, especially in the first 15-20 years of the strip. When he's not hanging out with Charlie Brown, Linus can usually be found being emotionally and physically abused by his older sister, whether it's being clobbered for being sarcastic, or being forced to do a church pageant against his will, or trying to deprive him of his security blanket. That's probably why Linus is such good friends with Charlie Brown - woobies flock together in hopes of staying alive.
For Better or for Worse: John's cousin Fiona was one for years. Her backstory tells us that her father was abusive and told her to steal and lie, before he left the family and Fiona ended up in foster care. Fiona developed a gambling addiction as an adult, and she couldn't attract men unless they were shady somehow. And it was only after she found a job at a pool hall after staying for a while with the Pattersons, that she could get a relatively good life as an adult.
During her time as a correspondent on The Daily Show, Kristen Schaal made a career out of being one of these. See here what happens to her when she learns the truth about Chinese female babies. In another segment, she was forced to strip off an article of clothing for every baseless accusation made against a presidential candidate. Needless to say, that episode, everybody found out that Kristen wears a Wonder Woman costume under her suit. Bizarrely enough, her stand-up act runs on this as well.
Myths and Religion
Aboriginal Australian Myths: Gnowee, the Wotjobaluk sun goddess, was once a mother who lived in an age where the world was dark. Having gone to fetch yams, when she returned she found her child was gone. She then lit a torch and now desperately searches for her missing child every day.
Romani Mythology: Ana, the queen of the Keshali, caught the eye of the King of the Loçolici (humans cursed by Satan). She refused him, prompting him to hunt down her people and devour them. To protect her people, she agreed to marry him, but still had some dignity enough not to consummate their marriage. The King circumvented that fact by drugging her and raping her, producing the hateful Melalo, who then goaded his father into raping Ana more times; each time she bore a monstrosity that embodies a specific disease. She was also tricked by Melalo into impregnating herself with animals on separate attempts to cure herself and sterilize herself. With the attempted assassination of the King by Ana's fellow Keshali, he allowed her to divorce him but only if she kept herself immortal, drinking the blood of three of her kind forever. As soon as she dies, all Keshali will belong to the King and will be killed. Now, Ana lives as a recluse in the mountains, killing any encroachers with avalanches. Fortunately, she does her best to protect her worshippers from the evils she bore.
Lucifer from a Satan is Good perspective. Specially if God Is Good as well. Note that this perspective is actually from Paradise Lost. While there is indeed the word "Lucifer" in Isaiah 14:1215 of the King James Bible translation, it means "morning star" and it addresses to the king of Babylon (presumably Nebuchadnezzar II). Satan in the canonical account is internationally a Hate Sink for being Always Chaotic Evil.
Isaac. His own father almost killed him. Later, his wife Rebecca and son Jacob conspire against him to trick him into giving Jacob the blessing.
Hagar becomes Abraham's concubine with his wife Sarah's consent and bears him a much-desired son, Ishmael. Later, once Sarah herself conceives and gives birth to Isaac, she has Abraham evict Hagar and Ishmael, who have to wander around in the wilderness before God intervenes.
Joseph. Lived a destructive relationship with his father and brothers, sold by his brothers to slavery, then wrongly accused of adultery, imprisoned and almost forgotten. It takes a while before he earns his happy ending.
Moses: He was forced to flee his homeland and came back to destroy it, abandoned his family to serve God, roamed around with the Isrealies for 40 years and finally died without making it to The Promised Land. Although in Gospels, Jesus is seen with Elijah and Moses on Mount Tabor during the Transfiguration. Yay! It took several hundred years, but the guy finally made it there!
Job had a good life overall, but there was a time when he lost everything, and then things went From Bad to Worse — he lost his children in a freak disaster. Then, his wife had only bad advice for him. And as if that weren't bad enough, his closest friends believed suffering to be karmic in nature, leaving him bewildered and wondering what he'd done to deserve all this. And it was all a test of character, which he passed, and his fortunes were restored. He must have been able to patch things up with his wife, too, because they had ten more children. Even Worse, this was a bet between God and Satan, to see if Job was genuinely righteous, or only because of all the stuff God had given him.
The Blessed Virgin Mary is sometimes this to Catholics. While they believe that She is very powerful and strong, having even Satan himself fear her, you can't possibly read about Her apparitions at Fatima without crying and wanting to spread devotion towards Her so that She may be loved. And then we find out that very few people actually listened to Her, thereby hindering her chances at having more children and bestowing graces upon them. She also had to watch her son die a painful and humiliating death for something he was innocent of. She also grew up in poverty.
Jesus's path to the cross included a kangaroo court, beatings and insults, scourging with a whip, a crown of thorns pressed into his scalp... and that was prior to the cross, the details of which you can easily find elsewhere if you're not squeamish. And on top of that the unimaginable non-physical pain of his first and only separation from God the Father and the bearing of the penalty for every single sin ever committed by humanity, past, present, and future. He suffered three kangaroo courts, one of them simply to mock him, and then further his punishment. Especially since The Bible presents him as knowing exactly what was going to happen. It's easy to think 'He's God, he could take it, right? He knew it all in advance, probably wasn't even afraid!" But then you consider that in the Garden of Gethsemane he was sweating blood and desperately praying to his father, asking if there was any other possible way, that he would take anything else if he didn't have to die like this...and his father said No. So he said "not my will, but your's be done" and went off to die, completely abandoned; "My God, My God, why have you forsaken me?"
The first Nephi of The Book of Mormon. Chosen by God to retrieve the brass plates, his older cynical brothers, Laman and Lemuel several times berate him. After he does retrieve said plates, he sees a vision of the coming of Jesus, and the fall of his nation. When all is well and done, his father dies, leaving him to be the leader of his family. Obviously, because of their jaded views of their second younger brother, they try to kill him, forcing him to relocate and eventually have to face his brothers and his descendants.
Orpheus is the premier Woobie of Greek mythology (if not in fiction in general). If he expressed such sadness after his wife's death that even Hades wept for him.
Hephaestus needs a hug. Stable, hard-working guy who's horribly ugly. Hera gave birth to him just to spite Zeus, and when she decided he was too ugly he was thrown off a cliff by his own mother. To top it off, he was married to a goddess who never cared about him and cheated on him regularly.
Played straight in God of War III. Even Kratos was disgusted by the Olympians' treatment of him and his "daughter."
Medea has a bit of this going on. She was a princess of a foreign country, and when Jason arrived to get the Golden Fleece, she fell in love with him and used her magic powers to help him accomplish his quest on the condition that he'd marry her. They wound up fleeing the country to escape her father's anger, and in a lot of stories Medea had to kill her brother to distract the king long enough for them to get away. Okay, all well and good. But fast-forward a few years, and now she's a foreigner alone in xenophobic Greece aside from her husband and two children, estranged from her family and friends, and her husband has just announced that he's leaving her to marry the (younger, prettier) princess of Corinth for political gain and oh, by the way, she's going to have to be exiled from the country now but Jason is totally going to try to let her come back to be his mistress. Medea was not pleased at all and poisoned the princess before fleeing the country... so the Corinthians killed her kids.
Some versions of Medusa are this in a nutshell. When you're punished by being made a gorgon because Poseidon couldn't keep it in his pants and raped you in the temple of Athena, let's just say you definitely deserve a hug, even if the hugger is likely to get poisoned or turned to stone for his or her trouble.
Let's not forget Ariadne. Some versions have Dionysus force Theseus to abandon her, while others claim he did it willingly. But either way, poor girl! On the other hand, her sister Phaedra had it maybe even worse...
And oh yeah, there's also Hercules. While we can understand that Hera hated Zeus's infidelity and Hercules had his own anger issues, it was really terrible how she persecuted Hercules like that. It's not like he could help that he was her husband's illegitimate son...
Another good contender and also a bastard child of Zeus is Dionysus. His mother burnt to death while pregnant with him because Hera tricked her into asking to see Zeus' true form, to start with. Then after his second birth, his father hid him at relatives of his mother's, who tried to throw Hera's scent off by passing him as a girl, which went well... for all of three years, when Hera drove them insane, made them kill their own son, and when they got to their senses, they killed themselves in despair, all the while Dionysus watched, only narrowly saved by his father turning him into a goat. Next he was sent to Mount Nysa, had some friends among the satyrs and nymphs, till one day a satyr died when trying to get him a new plant, which after his death Dionysus promptly made the first grape. Then when he tried to spread his knowledge, the king of the first place they went to killed many of his followers and almost killed Dionysus himself. After this Dionysus changed his tune from "let me teach you about wine" to "I WILL teach you about wine or I will make you insane or turn you into whatever I feel like right now. Your pick."
Osiris from Egyptian Mythology. The poor guy was tricked and murdered by his brother, and later had his corpse torn apart by him too.
Martin Crieff in Cabin Pressure. The poor guy lives in an attic, lives in Perpetual Poverty and doesn't get paid to fly, but he does anyway because it's the only thing he's wanted to do since he was six years old. His father always disapproved of his dreams, and passed away four months before Martin got his pilot's license and proved his father wrong. Oh, and what does he actually do to support himself? He does removals with the van his father bequeathed him in his will, rather than the 5000 pounds each of his siblings got. So, even though he did become a pilot, his father was still right about him. All of this is played for laughs.
While quite a few characters from Animamundi Dark Alchemist end up with surprising and sympathetic development that gives them a touch of Woobieness, poor St. Germant fits the trope right down to the E. Despite being completely kind and sincere (and let's stop beating around this shonen-ai bush: cute) - or perhaps because of such - he's arguably the most tormented soul of the entire game, subjected to such horrors as being coerced, tortured, drugged, molested, dominated, and brainwashed by the disturbingly-psychotic Big Bad as a means of getting back at the protagonist.
Doki Doki Literature Club!: Sayori, the preppy vice president of the Literature Club, is the childhood friend of the player character. Revealing her optimism as a front for her depression, Sayori commits suicide regardless of the player's choice. Possessing the chance of becoming insane and deleting the game without Monika's influence, Sayori's depression is conveyed realistically and serves as one of the first true scares of the game.
There are those who find Shirou Emiya from Fate/stay night a woobie, though it's a little odd. In the present, his life seems mostly normal but as a child he was the sole survivor of the battlefield that destroyed a large section of Fuyuki. His parents were killed and he saw hundreds of people die in front of him before being saved by Kiritsugu. In the present, this has left scars on him that even he is only marginally aware of that drive his entire life leading him to have a rather casual attitude towards death and having no sense of self preservation at all. Whether or not this is truly pitiful is a matter of opinion: The manner in which he deals with his life is much more proactive than the standard woobie.
And there's Saber. She gives up any chance of a normal life, and spends 12 years fighting constant wars on the front lines and ruling Britain flawlessly. She doesn't develop a personality because she decides Kings shouldn't be swayed by them. And then she's betrayed by everyone and left to die alone by her own kingdom for being too good a ruler. AND THEN she becomes a Servant to erase herself from existence because she doesn't think she did well enough. Girl really could use a hug.
And then there's Sakura Matou, who is probably the most woobie of all of the cast. She's separated from her family and adopted by a family of former Magi against her will, and is "trained" to become the successor by being sent into a room full of horrible worms every night implant themselves inside her every night since she's five years old. Her adoptive brother Shinji Matou, who's not quite right in the head himself, physically, mentally, and sexually abuses her every day. This all comes back to haunt the cast in the route she is Heroine in, Heaven's Feel. Lets just say that karma is a bitch...
Aeka of Yume Miru Kusuri is the least popular girl at her school. The Alpha Bitch and her friends torment her constantly, humiliating her and attacking her with tasers. Her classmates refuse to get involved, the teacher ignores everything, and the main character's love for her is the only thing keeping her from committing suicide.