Luke Skywalker. He's a Woobie even while he's a whiny kid, since he's got every reason to whine (never knew his parents, all his friends have left his hometown, he thinks he's never going to achieve his dream and wasn't allowed to pick up some power converters at Tosche Station, he sees his relatives were burnt to crisp). Angsting is all part of being a teenager. Once he grows up, he grows out of it. And his father cut his hand off, as well. Like father, like son, as we discover in the prequels (although if someone had just caved in and given the kid a hug or something, deserved or not, we might have averted a lot of suffering in that Galaxy Far, Far Away). In the Star Wars Expanded Universe books, almost every love interest Luke has had has died. The only notable one who hasn't left him without warning.
Oola. Lured into slavery with the promise of stardom, she doesn't believe she's in any danger when Luke Skywalker offers to free her. When she realizes the truth, she tries to hold on, but she runs afoul of Jabba and is fed to the rancor a few hours before Luke would have freed her.
Then there's Obi-Wan Kenobi. His master dies when he's very young and he's plunged into becoming a master when he's not ready. He finally opens up to his apprentice and then his apprentice turns evil and tries to kill him...then he's forced into seclusion and nearly everyone he ever cared for is either dead, a fellow exile or now his enemy. And then, when he comes out of seclusion to try and help the Rebellion... the aforementioned apprentice does kill him - although it was a deliberate Heroic Sacrifice on Obi Wan's part.
Chewbacca. Where do we begin? He's a loyal sidekick to Han Solo and in some ways contrasts the latter's Jerk Ass-ness. Even though he played as big a part as everyone else in the Battle of Yavin, he is infamously denied a medal (though in all fairness R2-D2 didn't get one either, maybe they only go to ship commanders). Even though a lot of people in-universe (and outside of it) dislike C-3PO, Chewie takes great pains to put him back together in Cloud City. Chewie is also as fond of giving Bear Hug s as he is of ripping arms out of sockets-though the hugs are sometimes violent. Early on in life, Chewie was bullied for not being as big and strong as the other Wookiees. His final act was a Heroic Sacrifice in order to save Han Solo's son, and the comics story "Chewbacca" (in which C-3PO and R2-D2 travel the universe to collect anecdotes and stories about the late Wookiee for his Meaningful Funeral) is likely to have you in tears at the end.
Then there's the way that Chewbacca became Han's sidekick. The Expanded Universe holds that Han was once an Imperial officer, but was cashiered with a full dishonorable discharge. His crime against military discipline: striking a superior officer and causing the loss of Imperial property. More to the point, clobbering a superior officer who was fixing to kill a Wookiee slave, then aiding in the escape of said slave... named Chewbacca.
What about Han Solo, eh? Okay, he's a jerk at the beginning (but less of a jerk than a Loveable Rogue by the end of the first movie, and he just got better from there), but come on: He was brutally tortured by Darth Vader (who was using his and Leia's distress to lure Luke to Cloud City), then frozen in carbonite to repay his debt to Jabba the Hutt, then sentenced to die in the Sarlaac pit because Luke defeated the rancor... And how about the times (at least two) when Han risked his own life to save Luke's? Also, when Leia releases him from the carbonite in Return of the Jedi, how could you not want to hug Han as he's shivering, blind and scared, having no clue where he is or (because of Leia's mask) who's talking to him? And those are just his woobie moments from the movies. (His biggest woobie moment in the Expanded Universe? The deaths of Chewie and Jacen.) Also: He's an orphan. Orphans are woobies by default.
The Han Solo Trilogy pretty much explains his jerk behavior by beating the crap out of his life right up to New Hope.
So I suppose forcing to watch as her home planet got blown up, tortured while being interrogated by Darth Vader, who turned out to be her own father, and made a slave by Jabba isn't enough to qualify Leia on the list?
I know nobody wants to hear it (which is sad in and of itself), Jar Jar Binks is a number one candidate for the "Star Wars Woobie Awards". First, he's hated, no he's loathed out of universe simply for being George Lucas's admittedly shaky attempt at making another successful Kid-Appeal Character like R2. He also seems to be almost as disliked in universe (perhaps as a means to appease the fans). The poor guy is mocked in other media as well, where some even wish him dead simply for existing!! Ironically enough, if any character in the series needs a hug, it would have to be Jar Jar.
The Expanded Universe reveals Greedo to be one. He's basically The Chew Toy and the only reason he was a bad guy was because he wanted to become a famous bounty hunter. He promptly got heckled, abused, and tormented due to his incompetence, forced into danger he wanted no part of, and was nearly killed horribly on multiple occasions (including a time he was almost beaten to death with flowers). And of course the time he finally got a notable job, it ended in him getting casually shot dead by Han Solo. Really, given his past, one could almost consider Han shooting him to be a Mercy Kill.
All Clone troopers. Born and breed to fight as a slave army for a Republic where the common-folk views them as nothing more then flesh-droids and where they holds not a singel legal right. Their training(which included live ammunition) started as soon as they could walk and anyone that showed less then perfection were "removed". To makes sure that the army is ready to fight in time they were genetically engineered to age twice as fast as a normal human, so those who lives through the war have effectively been robbed of half their natural lifespan. Anyone who tries to desert are hunted down and killed (by other Clones) and those who are injured severely enough to never return to active service are terminated as "faulty property of the Grand Army of the Republic". Most Jedi treated them with dignity though, which makes Order 66 even more sad.
Zuckess and 4-LOM eventually became this. How? Well the two Heterosexual Life-Partners bounty hunters pulled a Heel-Face Turn near the end of the war with the Empire and worked with the Rebel Alliance. But than on a mission 4-LOM got heavily damaged and a distraught Zuckess had to give him a memory wipe as part of the repairs. This took 4-LOM's personality along with it and resulted in him becoming a cold and ruthless droid who only cared about his next paycheck. This inturn utterly destroyed probably one of the closest friendships in the galaxy. We're treated to a tearful goodbye between the two as their ties are severed, with Zuckuss devastated and 4-LOM walking off without even realizing why this is a bad thing. We don't learn if the two ever patched things up but it's doubtful.
Vua Rapuung, a Yuuzhan Vong warrior who fell in love with a Yandere bioengineer. When this was about to come to light, she denied it and discredited him by making his body reject his implants, considered a sign of divine disfavor in the Vong's death cult.
Tycho Celchu's extremely unfortunate backstory - Pilot for the Empire who had been talking to his entire family on Alderaan when it was destroyed and initially thought it was normal comm breakdown - combined with his near-breaking in a secret prison and his incredible patience when he's believed to be an Imperial double agent and comes under heavy suspicion, particularly being framed for Corran's apparent death, is probably a good percentage of the reason why he ended up being far more popular than his creator ever imagined.
Quietly lampshaded in Starfighters of Adumar, quoted above. By that point, while Tycho's not as tragic as he used to be, having picked up the pieces and made a new life, he still looks sad, and his history is there to see.
You really have to feel at least a little sorry for Lorana Jinzler, a young Jedi from Outbound Flight. She's got a domineering Master with no confidence in her, and so she has little confidence in herself and not much say in what she does and where she goes. A man confronts her and turns out to be the brother she never knew, angrily telling her that the parents who never knew her loved her more than they loved him. She wants peace and acceptance and to get along, but her Master is totally blind to that, starts all kinds of conflicts, and eventually indirectly dooms Outbound Flight despite her efforts. Lorana steals a hand-holding with a Chiss syndic as they sacrifice themselves to save all the survivors. No one ever knows what she did, and the survivors she died to save curse her name for decades.
The Alderaanian contractors on the Death Star. Bad enough that The Empire chooses their home planet to demonstrate its destructive power, but they're on the kriffing station that did it. And then that sergeant comes in and gloats about it. Talk to the Fist, sithspawn!
Scout, poor kid. She's a Jedi Padawan who is the epitome of Weak, but Skilled, having little Force ability but ridiculously determined to make up for it by perfecting all other skills. She lives in fear of being washed out of the Padawan ranks and sent to labor in the less-glorious Agricultural Corps; she was ecstatic when a Master picked her as Padawan... and then that Master died early in the Clone Wars. Scout tried harder, tricking her way into winning a tournament of unattached Padawans, and ended up with a reluctant new Master... who only finally accepted her in the moments before he died. She gets some happiness in the last book of the Republic Commando series, when she becomes the unexpected guest of Kal Skirata and his Mandalorian clan.
"Happiness". Mandalorians, as written by that author, are universally deeply anti-Jedi, and Jedi universally either get proven wrong by them constantly, or don't even protest the vitriol that's chucked at them, tucking their chins and accepting that they're inferior morally, philosophically, and so on. Scout is described as looking and acting very similarly to Etain, a young Jedi who fell in with them and quickly learned her place, that she should never question them, and that they're all smarter than her and should be able to govern her life and body. Scout goes from an assertive girl who Master Yoda says has impressive spirit and determination, and isn't to be underestimated, to someone the Jedi think are useless. In Dark Rendezvous she loves being a Jedi and considers them her family. If she becomes passive and happy with people who hate her family and make jokes about killing them, it's only by destroying a fundamental part of herself.
No love for Jacen? Sure, he turned out to be a horrible, evil Sith tyrant similar to his grandfather, but he did it because he genuinely thought it was the only way to save the galaxy - and his daughter. Really, the only thing his lives for in the end is his daughter. He nearly obliteratesAurra Sing when she tries to kill poor Allana, and, when he finds out about the deadly virus bioengineered to kill Allana and his lover, Tenel Ka, instead of defending himself from his sister'skilling blow, he screams a warning to them through the Force, becoming his old Jedi self the instant before he dies.
For that matter, Allana. She lost her father to the dark side and she almost never gets to see her mother owing to the fact that Allana is supposed to have died in the virus attack, covering up for the fact that Jacen was her father; Tenel Ka had to give Allana up to the Solos to preserve the illusion, yet she manages not to go insane.
The Jensaarai. Coerced into helping a Pirate queen pull her mooks' choobies out of the conflagration (or else their Protectorate will be annihilated), and the Saarai-Kaar herself has lost her (evil, but she didn't know it) mentor to a Jedi team and her son to Darth Vader.
Ferrouz, when Mara gets to him and finds out his reasons for offering the Rebels sanctuary.
Sorro retroactively becomes one when it's discovered that he's only working for who he is because his family was kidnapped and threatened.
Mara Jade, at the end, waiting for the Hand of Judgment to come back, and missing them. Despite the fact that she basically conscripted them and never told them her first name, she trusts them and is unhappy when they don't come back. It's an unfamiliar feeling. There are two constants in her life - the Emperor, who she could never miss because he's always there, and people like Vader, who she could take or leave. It really illustrates how she really does have no other friends or allies - when she later tells Luke that he destroyed her life, she wasn't exaggerating.
Thrawn of all people shows a hint of this when Car'das asks why Thrawn picked him. Thrawn lets his icy stoic exterior crack slightly into a sad smile. "Because you're the only one I trust."
Car'das stared at him, some of his own self-pity fading away into a fresh pool of shame. Thrawn had left everything: his home, his people, his prestige, his life. He'd dedicated himself to protecting the civilized parts of the galaxy against pirates, warlords, and distant, nameless nightmares that Car'das could barely even imagine.
And yet, in the end, all that work and sacrifice had come down to this. The greatest military mind of the age, with only a single, solitary, worthless man whom he could trust.
In Luke Skywalker and the Shadows of Mindor, the Book Ends, taking place after the main story, have Luke hiring a private investigator to build a case that he's committed war crimes, then later finding that the investigator had decided to write a swashbuckling holothriller script based on the events instead. The whole time there's the sense that he's on the brink of despair, as when he describes his 'best trick'.
Skywalker lifted his face from his hands, and his eyes were dark. Wounded. Haunted by shadows. "My best trick is to do one thing - to make one small move, even a simple choice - and kill thousands of people. Thousands."
In the Clone Wars Gambit novels, Obi-Wan is even more of a woobie than he is in the films. In Wild Space, he spends several days on a Sith planet getting tortured by a Sith device with the ability to dredge up his worst memories and make him experience them all over again as if it were the first time. In addition to getting really badly injured physically, he has to repeatedly experience the death of Qui-Gon, Xanatos drowning in acid, the grisly torture of a man called Tayvor Mandirly, the battle of Geonosis, Anakin losing his arm and a multitude of other traumatic memories. Add to that the incessant murmur of die Jedi, die Jedi, die Jedi, die and it's a wonder that he managed to stay sane.
Lara: There was never a time I saw a file labeled 'How to Destroy Talon Squadron' and thought to myself, 'Oh, that's what I want to do.' To me it was just data about occupied territories and interplanetary borders. Then I infiltrated Wraith Squadron, just a ploy to make myself more valuable to prospective employers, and things started happening. All the furniture that made up the way I'd thought and felt about things all my life started coming loose in my head. Nowadays it slides around and breaks into pieces and I have no idea what parts of it are real and what aren't. It hurts, and a lot of the time I don't know who I am anymore. But I know what I have to do. Whoever I am, I'm staying here, like a vibroblade right next to Zsinj's vitals, and when the right time comes I'm going to stab him deep. That'll probably be the last thing I do. I don't have any friends here, except one droid, and I don't have any where you are, or anywhere else in the galaxy, so when I'm gone there isn't going to be anyone to remember me kindly. So I was just sort of hoping you wouldn't hate me anymore. I really can't stand thinking that's the only way I'll be remembered. I wish I'd been someone else. To give you that chance you wanted.
Zayne Carrick from Star Wars Knights of the Old Republic is the woobie for the first 2 years of the comics main story: he's framed for murder, forced to learn that his friends never believed in him, is thrown in prison, and towards the end his girlfriend tries to kill him twice. After proving his innocence to said girlfriend and getting a real lead in clearing his name his luck slowly picks up until he earns his happy ending after the Vindication arc.
The planet Orvax IV is a woobie factory. Especially for those who are sold, or whose loved ones have been sold, to Dezono Qua.
Poor Jorin Sol. A combination of bad circumstances served to utterly destroy the innocent and unassuming man. Jorin was a mathematician working for the Rebel Alliance who had almost nothing to do with the military aspect of the Rebellion, and was instrumental in devising a hyperspace jump algorithm that the rebel fleet used to meet up if they were attacked and had to flee. During a routine mission of diplomacy taken alongside Leia and Luke, Jorin was quickly caught up in a nasty course of events that led to him being turned over to Darth Vader by a traitor. Vader led Sol away for a private interrogation session, and afterwards turned him over to a group of Imperial specialists with orders to turn him into a sleeper agent. Over the course of several weeks, Jorin was tortured almost endlessly to break his will and make him more susceptible to brainwashing. They learned of the hyperspace algorithm and used it to set a trap for the rebels, allowing Sol to be rescued so as to put him in position to assassinate leaders if the chance arose. During the fleet battle that followed, Jorin broke through the mental conditioning long enough to tell the Rebels to make random jumps, lest they continually find Imperials waiting for them. Finally, he managed to fight through the brainwashing in order to initiate the rebel flagship's jump, at the cost of his own life when the badly damaged ship's bridge exploded.
From the same series of comics is Deena Shan, a minor woobie who is, as her father told her, always in the wrong place at the wrong time. One of her first missions after joining the Alliance was to an unknown planet that happened to be infested by a vicious, man-eating plant creature—but she was with the Heroes, so she escaped unscathed. A little while later, Deena was included in a mission to rescue Jorin Sol (see above) and posed as an Imperial officer. During her stay at the base, she helped set a trap for the Imperials, but fell for the dashing young Imperial Captain Kale Roshuir... who soon lost his entire squad to said trap and quickly figured out that Deena was behind it. She barely escaped his vengeful wrath with the other rebels and became alcoholic. When undertaking an unauthorized mission with Luke Skywalker, she heard a door open behind her and turned to find Captain Roshuir flanked by a squad of stormtroopers. She and Luke narrowly escaped that situation, only to be sternly punished for disobeying orders.
Zaalbar from Knights of the Old Republic is a Woobie who is a hairy bipedal humanoid from the planet Kashyyyk. His brother betrays him, his father exiles him, he's sold into slavery, escapes to help out a little girl on a planet which hates aliens, gets captured again, swears the life debt that is the Wookiees' hat when rescued, and comes back to his homeworld only to find himself in prison while corporate scum ravage the planet.
Even the player character, if you go Light Side, is something of this by the end; and the back-stories make almost everyone one of these:
Mission Vao, street-smart teen, was brought to Taris at age 5 by her con artist brother, stowed away on a cargo ship - and then he left her there, to deal with the gangs and flesh-eating mutants by herself.
Worse, after you leave Taris, she doesn't even have a what little she had anymore. The Sith pretty much reduced Taris to rubble. When you meet her she's probably a bit overconfident. When Zaalbar is captured she panics and acts a few years younger than she is, but bounces back once you go after the Wookie. Once you escape Taris, though, she's very quiet. Playing light side you can really help her out both then and throughout the game, but Mission sure had it rough.
Carth Onasi held his wife in his arms as she died in an attack on their home world led by his former mentor, then couldn't find his teenage son. During the course of the game, you can find his son on Korriban - as a member of the Sith.
Juhani. When she was a baby, the Mandalorians started a genocide of the Cathar, decimating her homeworld; her parents fled with her but were only able to get as far as Taris, the same human-dominated cityworld Mission hails from. All of her life, the only other Cathar she's ever known has been those two. The massive Fantastic Racism on Taris, and the stigma of being part of a species believed to be made entirely of violent warriors meant they had to live in the worst slums. Her father turned to stimulants and was shot by a human. Her mother broke inside after that, wasn't able to make enough money to feed herself and her daughter even after turning to a Loan Shark, and died of illness. Immediately after that the loan sharks, settling the debt, took her as a slave, bound her like a beast and treated her like one. She was almost bought by the man who killed her father, who had helped with the genocide on her homeworld. The Jedi came and saved her, and said she could become a Jedi too, but it wasn't over for her.
She made some friends at the Jedi Academy, but one of them ran away and joined the Sith when she couldn't return his feelings. Her Master goaded her into lashing out and allowed Juhani to believe that she'd killed her own Master; horrified, Juhani ran away to lurk in a meditation grove and tried to convince herself that now that there was no turning back, she had to embrace her darkness. The player character can convince her to stop and go back to the Academy, at which point she finds that it was all a lesson, to show her how easy it was to fall. Then, hastily promoted from Padawan to Knight, she is sent to join the player character, partly as a lesson to them about the Dark Side.
Bastila; barely-trained Padawan with the weight of the whole war effort dumped on her shoulders before even finishing her training. Learns that her father, whom she missed terribly when she became a Jedi, has died without ever seeing him again. Reconciles with her mother only to learn mom has a terminal disease so she might never see her again. Has a direct mental link to an ex-Sith Lord exacerbating her existing problems with resisting The Dark Side. Probably scared stiff, and acting like an Ice Queen as a coping mechanism.
The Jedi Exile would have to count. Followed Revan to war to stop the Mandalorians. Malak wanted to kill her. Was led to Malachor V for the final battle where it turns out those who were not loyal enough were to be killed. The pain of the deaths of her allies forced her to cut herself from the Force to survive. She returns to the Jedi only to be exiled. And this is just the backstory. Jump ten years and she is one of the last Jedi. Hunted by the Sith, bounty hunters and criminal organizations. Her mentor turns out to be using her for revenge. The allies she gathers hate each other. She is ultimately captured and forced to work for the crime boss hunting her. Her life is owned by a Mandalorian bounty hunter. One of the last remaining Jedi wanted her dead before she fell to the Dark Side. The remnants of the Jedi declare her too great a threat to be allowed to retain her new found Force sense and intend to sever it. And she still returns to Telos to save it from the Sith after all of that.
Visas Marr as well. Feels her homeworld destroyed around her through the Force which damages her Force Sight in the process and is then taken by Darth Nihilus, the being responsible for the destruction of her homeworld, as his servant. Nihilus then crushes her spirit so utterly that by the time the gameplay starts she is begging him to kill her. When she fights the Exile the implication is that she wants to be killed by him/her. And to cap it all when she joins your crew she seems surprised and confused that the Exile would take the time to show some basic human decency and ask if she's alright.