Eponine, especially in the musical. She's abused by her parents, is always alone, and falls in love with Marius, who doesn't love her back. After she visits the middle of rebellion to see him, he asks her to deliver a letter from him to the girl that he does love. She ends up taking a bullet during the fighting and dying (although she dies happy because he's there comforting her).
You've got to hand it to Cosette, too, when it comes to woobiedom. First, she gets separated from her mother. Then she gets berated, teased, overworked, starved, beaten, and deprived of adequate clothing by the Thenardiers. At one point, she wraps a small knife in rags and sings to it, pretending that it's a baby doll. Things do improve considerably for her, but still.
Jean Valjean himself. Granted, he dies happy, but throughout the course of the book, all his suffering (and there's a lot of it) is derived from his desire to simply help other people. The man spends nineteen years in jail because he was trying to feed his sister's family (granted, fourteen of those years are his own damn fault) and only gets the law back on his trail because he saved a man's life.
Bung a vote in for Fantine, too... Falls in love, gets pregnant, man goes off and leaves her as a practical joke, ends up sending the child to be looked after, loses her job because she's trying to look after the kid, so she sells everything she has (including her hair and teeth), and, finally, her body. Gets helped out by Valjean, but dies before she ever gets to see her daughter again.
Gavroche certainly counts, especially given that he's identified as a nearly starving, homeless child... many people would love to just give him a huge hug immediately.
What about the boys fighting at the barricade? The fact that they all die helps. Mostly a fanon development, as though they do have personalities in the novel, they aren't explored in huge depth. Extra woobie points go to Grantaire, who's cynical, hard-drinking and emotionally wounded, as well as pretty much enamoured with Enjolras. That the students are fighting for justice, played straight, helps.
Erik (the Phantom). He has huge issues about his physical appearance, exacerbated by being put in a freakshow and beaten by his captors. He eventually escapes and is able to compose his music underneath the Paris opera house until he falls in love with, and gives lessons to, a beautiful young singer who isn't repulsed by him, but, in the words of Cleolinda, "prefers the Missing Hanson Brother to [him]." Granted, he's a bit crazy and kills people, but he has a Freudian Excuse. And he's (sometimes) sexy.
He's only sexy in the movie version with Gerard Butler. In the original novel, the Phantom is ugly as sin and even more psychotic... but still can come off as rather sympathetic.
Although when it comes to Woobiefication, even Andrew Lloyd Webber can't beat the take on the character in the Arthur Kopit/Maury Yeston musical, who literally has lived his entire life under the Opera House, lost his beloved mother at an early age, and only starts getting nasty when an incompetent manager and his shrill-voiced wife start messing things up.
For that matter, fellow protagonist Christine Daaé seems to also qualify completely. As a mere chorus girl having to deal with being an orphan in the shadow of her prominent father, a famous violinist, being suddenly placed into a massive stage role would be extremely stressful by itself. And then having to deal with the twisted events of the musical's plot almost tears her apart, with the audience along for the ride.
While its merit otherwise can be debated (and it being canon is... questionable, to say the least), The Lord of the Rings musical managed to woobiefy Gollum—or, more specifically, Sméagol — largely owing to actor Michael Therriault's performance. Sméagol actually wants to change for the better and physically fights with himself over whether or not to kill Frodo and Sam in their sleep, to the point of holding a sword to his own throat instead of allowing Gollum to stab them, then collapses, sobbing "We changed!" to Gollum's accusation of cowardice, and finally curls up to sleep by Frodo's feet. All made sadder by most of the audience knowing that he will eventually lose out to Gollum... about thirty seconds later.
Yonah from Stephen Schwartz's Children of Eden. Her song "Stranger to the Rain" is especially anvilicious. "I'm a daughter of the race of Cain/I am not a stranger to the rain."
Alfred in Tanz der Vampire is so cute and well-meaning that you just want to pick him up and put him in your pocket, especially after the cutie-breaking sets in. If Herbert isn't played as a Sissy Villain, he'll be played as one of these. There's not a lot of middle ground.
The title character of Benjamin Britten's opera Peter Grimes.
Tobias Ragg. A Victorian orphan, possibly mentally handicapped depending on the production, abused by Signor Pirelli until he's taken in by Mrs. Lovett, for whom he develops a deep and sadly misguided devotion. When he discovers just what's been going into those meat pies of hers, he literally goes mad from the revelation.
The movie version makes it even worse, since the depictions of Pirelli's physical violence were so much more extreme (and bloody) than it generally is in stage productions.
To a lesser extent, the boy who Judge Turpin sends to be hanged for stealing food. In this troper's production, he was played by the directors SEVEN YEAR OLD SON. Then audience as a whole was horrifed by the woobie face he made.
Elphaba from Wicked. Born into circumstances beyond her control, discriminated against since birth, had about 3 people in her whole life (Glinda, Fiyero, Dr. Dillamond) who cared about her, tried to do the right thing and got persecuted for god-only-knows how long for it.
Tracie Thom's portrayal of Joanne in the on-stage version made the character into more of a woobie than she had been previously. It's probably her sweet face. In general, Joanne is more of a Woobie in the stage version than in the movie, simply due to some of the dialog removed from the film as well as because of her helplessly annoyed stage play-only solo "We're Okay".
Mark definietely qualifies, especially if you've seen the stage version of RENT. "Halloween" gives a lot of insight into Mark's character, it reflects on his intimate feelings on the loss of hope, confidence and coping with the harsh reality that he is being faced with in his life. After watching Angel die, he must come to terms that Mimi, Roger, and Collins will eventually suffer the same fate. This also shows how loveless his life is; he was dumped by Maureen for Joanne, and by this point in the show, Roger is leaving for Santa Fe. Not only that, but he is also failing at his filmmaking career, so much so that he resorts to working with Alexi Darling. This is when you realize/are reminded that among all the chaos that is going on in the show, Mark has been in the middle of everything this whole time.
Every single teenager in Spring Awakening, no matter how much of a Jerkass they seem to be or how much teenagerly Wangst they show, makes you want to run down onto the stage and give them a hug. Lots of 'em. It certainly doesn't help any that some of the conflicts of the more minor characters aren't even resolved. The point of the show is that Adults Are Useless, but even as a teenager it was hard not to feel sorry for Wendla's mother too. Fridge Logic ahoy!: Wendla's mother is a woman in the nineteenth century herself- how much preparation do you suppose she was given about matters of sex as a young girl? Isn't it more likely than not that she just told Wendla what she was told years ago?
It's certainly very debatable, but depending on where you stand, Malvolio might well be this, despite having likely been written as a Butt Monkey (understandably, considering how unpopular puritans were at the time). If you're sympathetic to his conservative social views (which really don't seem unreasonable in practice), in particular, you'll likely see him as a very loyal, if somewhat dour, butler who was simply doing his duty in reprimanding his mistress's blatantly rude jester and arrogant drunkard of an uncle...and he gets rewarded by being humilated in front of his mistress, locked up in a mad house (notoriously horrible places at the time, of course), and victimised by his tormentors. And even after his innocence comes out, no one seems willing to offer him any real apology for any of this. May also depend somewhat on how serious or comical the particular production plays his character, but still...
Similarly, many productions make an effort to play up Sir Andrew Aguecheek, another Butt Monkey and the plucky comic relief, as one of these, the key often being his line 'I was adored once, too', combined with an emphasis on the abuse he recieves at the hands of Sir Toby. Some of the darkest and edgiest adaptations have managed to crank him up to an all-out tragic character.
Go see Chicago some time. When Amos finishes singing "Mister Cellophane", listen to the crowd (and probably yourself) as they go "Awwww!". Pure woobie.
Depending on your interpretation, Harry Beaton of Brigadoon. Forced to stay within his hometown for the rest of his life, can't go and get a university degree and make something of his life, and is forced to watch the one girl he likes marry another man. It's no wonder why he snaps.
Pretty much everyone from Avenue Q. Lampshaded in "It Sucks to be Me" and "Schadenfreude".
The clown at the center of the "Snowstorm" act in Cirque du Soleil's Alegria, which tells the tale of a friendship found and lost between him and a stranger that manifests in his coat and hat when he hangs them up.
Kim from Miss Saigon certainly qualifies. She's forced to work as a bar girl/prostitute even though she's underaged, falls in love with an American GI who leaves her and marries another woman, bears his child and eventually kills herself so her son can live with just his father and stepmom.
Toby in The Medium by Gian-Carlo Menotti. Being The Speechless, he suffers in silence.
MacDuff from Macbeth, who has lost his whole family to the title character's paranoia. And in the scene where he learns of this, it is revealed that Scotland is full of woobies.
Horatio from Hamlet. He turns up in Denmark for the King's funeral (presumably partly for his friend Hamlet's benefit, though it appears that he didn't actually get a chance to see Hamlet until Gertrude and Claudius' wedding). Then he gets his whole worldview blown out of the water by the appearance of the Ghost, watches Hamlet's emotional issues (or outright insanity, depending on the interpretation) take him over and can do nothing about it. And at the very end, most of the cast suddenly drops dead around him and Hamlet dies in his arms. No wonder he tries to kill himself.
Hamlet: O good Horatio, what a wounded name
...If thou didst ever hold me in thy heart
Absent thee from felicity awhile,
And in this harsh world draw thy breath in pain,
To tell my story.
Gertrude McFuzz from Seussical. She's in love with her next door neighbor, Horton, although he never notices her. Plus, she is really self conscious about her one-feathered tail.
Blanche Dubois from A Streetcar Named Desire. First of all, she fell in love only to discover that her Husband was gay. Then said Husband killed himself, partially over something Blanche herself said. Blanche becomes slightly unhinged after that, turning to promiscuity because it's the only thing that makes her feel validated and living in a fantasy world because she hates her real life so much. It was her Brother in law who finished her off, though- firstly, by telling her new partner, Mitch, about her past, resulting in Mitch leaving her; and then, finally, by raping her, which caused her yet more emotional damage. When Blanche tried to tell her sister about the rape, her sister chose to disbelieve her and pack her off a mental institution.
Stanhope from R.C Sherrif's play 'Journey's End'. Set in a trench in WW1, the play teems with Woobie's, but Stanhope stands out mostly because the poor thing is so young and so damaged. When he gets drunk and finally breaks down you just want to get a huge orange shock blanket and cuddle him to death.
Love is not always lovely in the end. Often, in the end, there are lawyers.
Beth from Little Women does everything for her family, and dies before they can repay her. Well, except Jo.
Sunset Boulevard gives us Max von Mayerling. He was once a high-powered silent film director, who met the love of his life when she was cast in one of his movies. But she failed to make the transition to talkies, they divorced, and though making said transition would have been easier for him than her, he gave up his job in order to stay in her life... as her butler. By the end of the show, he's the only one of the four main characters who isn't dead, broken, or insane, but that, of course, means he's now completely alone in the world, and all he can do is lead his now-crazed murderess ex to the police by playing the director's role again for her.
Edgar/ the Bat Boy. He practically spent his whole life in a cave without seeing the "light of day" until the local sheriff brought him to the Vet's house after he bit a kid. He then spends the first quarter of the play in a cage starving to death and billed a freak, monster, creep, etc. by everyone except Meredith. After learning to be civilized, he becomes Adorkable and really wants to be accepted by the town while trying to be human and hating his need to diet on blood. He still ends up being blamed for everything that goes wrong and is overall hated by everyone save his adoptive mother and her daughter. Turns out that the Vet is technically his biological father and that the mom really is his mother. Due to a freak lab accident, Dr. Parker raped Meredith, and she was raped by bats due to the same accident. Twins were the result, and repulsed by the baby boy, Meredith had Dr. Parker get rid of him. And then Dr. Parker goes around framing Edgar for murder and incites an Angry Mob against him. Meanwhile, Edgar and Shelley have intercourse. That's ruined when Meredith tells Edgar the truth. Shelly is his twin. This understandably horrifies him. In the end, Edgar realizes that he'll never be accepted, and that there's no room in the world for someone who isn't a beast or a man. He's stabbed to death by Thomas Parker in a Murder-Suicide, and dies with the Tearjerker words: "I am not a boy. I am an animal.'' So major Downer Ending for the pseudo Vegetarian Vampire with a Monster Sob Story and who's clearly Not Evil, Just Misunderstood. The real clincher? The only "person" Edgar really killed was a cow, and he apologized to it. Thomas was the one offing the people Bat Boy bit.
Meredith as well, for the above reasons regarding seriously painful rape. And it's clear that she regrets getting rid of her son and is sincerely trying to make amends with him. She tries taking a stab for him too, but they both end up dying. The fact that it's her husband doing the stabbing makes it even worse.
While we're at it, Shelley. The happy ending she and her mother imagined was completely ruined. The boy she fell in love with and was utterly devoted to by the musical's end turned out to be her brother. And he died in her arms. She had to witness her father lose it and kill himself, along with her mother and lover. Not to mention the fact that the townsfolk now know how messed up her family is and what she did with the Bat Boy.
Vladimir and Estragon from Waiting for Godot are seemingly doomed to stand for eternity in a barren field, waiting for someone who will never show up.
The 2013 musical version of Charlie and the Chocolate Factory has the sweetest, most rounded Charlie Bucket this side of the 1971 film version. He's a Cheerful Child prone to daydreaming who works so hard to make the best of his meager situation — the sort who can look at a trash dump and see all sorts of useful stuff in the rubble that's "Almost Nearly Perfect". He's a light in the lives of his toiling parents, who wish they could give him the life he deserves but just can't (as seen in the "If Your Mother Were Here" sequence), and his bedridden grandparents. A lonely kid who has dreams that he just can't attain is a sad sight indeed, and watching him fall into a blue funk as each Golden Ticket is found — by four repulsive, little brats no less — is heart-tugging. Even when he gets his own golden chance, the poor, shy kid keeps bringing up the rear come tour day, lost in the shadows of the limelight shed on the other finders. Of course, he gets his happy ending, but it's especially touching in this version thanks to a plot twist: The Reveal that all along, the man he admires most in the world — Willy Wonka — was looking out for him. He was the tramp at the dump (a case of King Incognito), and touched by Charlie's sweet, imaginative, appreciative nature, he secretly rigged his own contest to give the boy the chance to become his heir. Seriously, Charlie Bucket's family, especially his mother and father, certainly qualify as much as he does. Although facing serious poverty, they're very much caring parents that want the best for everyone.