Woobie / The Simpsons

For a show that's supposed to make you laugh, there are some instances where you feel sorry for the characters.

Normal Woobies

• Ol' Gil Gunderson, who is constantly shown to be struggling, gets fired or is unemployed in most episodes he appears in and generally has the demeanor of someone who just can't be happy anymore although he would naturally be cheerful.
• And Hans Moleman who ends up in life-threatening situations over and over again. Poor guy.
• Before Flanderization set in, Ned Flanders used to be a Woobie too. A happy, helpful, non-judgemental Christian man who wants to help everyone, but is constantly bullied and mistreated by Homer out of petty jealousy. He is also twice widowed, his house was destroyed, his stuff is always getting destroyed or messed with by Homer (and in one episode, Bart), and if the flashbacks are to be believed, the only reason Ned is an overly religious zealot is because, possible retcon aside, it was a coping mechanism for his first wife's death or mental problems as a child. Homer's Jerkass antics got so bad in one episode (where Ned was made the laughingstock of Springfield), he left to go to Humbleton, PA.
  • His sons Rod and Todd, too, for the same reasons. Even their parents could be cruel to them sometimes (Flanders wishing Todd didn't have "the devil's curly hair" and Maude calling her son's hands "small and girlish"), when they weren't being wildly overprotected. And just when they have a parent who encourages them and tries to help them out of their shells? She dies, too! Plus, they're pretty unpopular with kids their age.
• Waylon Smithers, who craves for acknowledgment and sexual attention of an evil old man who rarely cares about him, regardless of Burns's sexuality. He is espicially a woobie in episode "Blood Feud", because he can do nothing to help Mr. Burns and is visibly holding back tears when it seems that Burns will die.
• Milhouse doubles as this and the Butt-Monkey, mostly played for laughs. Milhouse is always bullied at school, his only friend is Bart who always takes advantage of him, and his parents gotten divorced at least more than once while they always fought in front of him. It's pretty much safe to say that Milhouse is pretty fragile after all he went through. Season 25 was pretty much a "The Reason You Suck" Speech to poor Milhouse where he's been eaten, killed (in the intro of the Treehouse of Horror special), and even beaten up several times. Season 26 seems to be treating Milhouse better though some argue he Took a Level in Jerkass especially with the apathy he has towards his dad having to sell his house to pay for his expensive birthday party. (Played for Laughs of course.)
• His dad, Kirk, doesn't get off much better. Ever since he lost his job at the cracker factory and Luanne left him, Kirk's had to live in an apartment with little to no money making him the epitome of a deadbeat dad. "Just a statue? This country makes me sick" indeed. He even has a very cheesy Stylistic Suck song that he wrote in a desperate attempt to get money. There's one episode where he accidentally kills a bunch of animals with a flag. When he does get thrown a bone, it usually goes away because Status Quo Is God. When Luanne remarries him in the 17th season, he's a lot better. And so is Milhouse. Kirk even sells his house in a Season 26 episode so that Milhouse can have the best birthday ever. Then Season 25 hits and let's just say Milhouse doesn't get off too well in this season. Season 26 was Kirk's Butt-Monkey season having something bad happen to him in almost every episode. It must run in the family.
• Lisa too. She seems to be the only both highly intelligent and compassionate person in Springfield, but feels alienated by everyone. She has no real friends at school and has a brain dead father she often feels embarrassed for. Matt Groening once said she is the only character that provides hope, because she "might" be able to escape that horrid town in the future. She's also been mocked for her beliefs on many different occasions and has to deal with a brother who has tried to ruin her life on many different occasions and is doomed to marry Milhouse. With that said, Bart still loves her and has helped her many a time. Also speaking of her father, he knows absolutely nothing about her, even when he tries to care, he ends up hurting her (Biggest example is "The Dad Who Knew Too Little" and "Homer and Lisa Exchange Cross Words"). The entirety of these two episodes was basically Homer saying he knows nothing about his own daughter and doesn't care, besides the fact she plays the saxophone. In a few episodes, Lisa has been upstaged by girls younger (or in Meg's case, older) and she even lost a (rigged) spelling competition. Yet even in her worst moments, Lisa can usually find something good about it.
• Marge can be a woobie too. Being an overworked housewife with little to no thanks from any of her family, except for when the plot demands it, being judged for being a woman handyman in "Please Homer, Don't Hammer 'Em", not having the best physique in another episode, and so on. Plus she was teased at school for liking The Monkees and has to deal with two Jerkass sisters and a Jerkass husband.
• Scratchy, who's always getting brutally murdered by Itchy for doing absolutely nothing wrong. Unlike Tom who at some points can be Jerkass and deserve his punishment, Scratchy's just a normal nice cat. There's a few moments where he and Itchy team up ("Itchy & Scratchy & Marge", "Treehouse of Horror IX") but those are few and far between. There was even an episode where Scratchy finally got even with Itchy, and it wasn't shown because of Homer's college friends.
• For one-shot characters, Gina (from "The Wandering Juvie", not Sideshow Bob's kid - that's Gino) is one too. Unlike Bart's other well-known girlfriend, she has a hidden heart of gold much like Bart. Growing up alone as a bitter orphan, she soon went into juvenile delinquency. Although she does try and hurt Bart emotionally a few times and physically, and gets him in trouble, she is nonetheless a tragic figure who deserves sympathy over not having a family and turning to delinquency as an outlet. When she cries near the end, you just want to hug the poor thing.
• Moe Syszlak is either this or Cosmic Plaything, or both. Whenever he gets a glimpse of success, it's taken away from him because Status Quo Is God. (The worst example of this being Pygmoelion where the Duff corporation put several stickers over his face because he's that ugly forcing him to get plastic surgery and becomes handsome until the end of the episode.) He's a hideous Gonk because of boxing, he's tried to commit suicide so many times that the suicide hotline blocked his number and Reverend Lovejoy tells him he's got nothing to live for. Is it any wonder why he's so bitter?
  • Luckily, Moe proposed to Maya years later.
• Principal Seymour Skinner. When he isn't being tortured by Bart, he's getting his heart broken by Edna, humiliated by Chalmers, or abused by his mother. And when none of those four things are happening to him, he's telling us about the horrible things that happened to him during Vietnam that still give him nightmares.
  • Even though we already knew this from "The Principal and the Pauper", Skinner didn't used to be an uptight tool as Bart puts it. He used to be a fairly nice guy if the flashback in "Pranks and Greens" is any indication. It's revealed in that episode that there was an even worse prankster than Bart, who pulled a prank that almost killed Skinner and successfully killed his enthusiasm as a teacher. It also made Groundskeeper Willie, who was also a pretty nice and laid back guy, into the cynical Hot-Blooded Scot we see today. When you find this out, all his jerkish behaviour seems justified.
• Edna Krabappel. Her first husband cheated on her and put sugar in her gas tank, she fell victim to a love letter prank by Bart, and she's clearly dissatisfied with her career as a teacher. Even her romance with Skinner didn't stay a case of Throw the Dog a Bone very long, when she realized he wasn't that passionate about her and didn't love her enough to spend the rest of his life with her. Is it any wonder the poor woman smoked so much? Even when she finds happiness by marrying Flanders and is able to be a good mother to Rod and Tod (better than Maude ever was) this doesn't last because she is Killed Offscreen because her voice actress died. Ouch.
• Gary Chalmers, yes the Large Ham No Indoor Voice Superintendent of Springfield becomes one in the episode Bart Stops to Smell The Roosevelts. Being the only teacher to successfully teach Bart something (and made him passionate about learning, something that seemed impossible for every other teacher) it's revealed he's a cynical hardass because his wife passed away and he's been beaten down whenever he's tried to teach anyone. When he takes Bart, the only student he was ever able to successfully teach, along with Milhouse, and the bullies out on a field trip to find Teddy Roosevelt's spectacles, Nelson falls and breaks his arm causing Chalmers to lose his job, causing him to realize it's ok to cry given that he grew up in a very different era from most of the other characters on this list. In another episode it's revealed he has high blood pressure. Is it any wonder why he's always bellowing "SKIN-NER!"? Though the episode ending is bittersweet (Chalmers doesn't get to return to teaching, but he gets his old Superintendent job back) it's one of the more heartwarming moments in the newer episodes.
• Selma Bouvier. Every time she tries to land a man, it doesn't work out. One of the men (Sideshow Bob) she married ended up trying to kill her, another (Troy McClure) was presumably into fish instead of women, and there was also the time Homer tried to set her up with a man, only to have the man (Principal Skinner) end up falling for Patty instead. She has moments of being a Jerkass like her sister, but they are substantially less than what she's been through. Season 16 threw her a bone by giving her an adoptive daughter, though, even if said daughter only appears infrequently.
• Lenny. He may seem to have it going on, but the poor guy is always getting his eye injured, getting beaten up, or being compared unfavorably to Carl by everyone, including his own family.
• T-Rex (yes, that is his real name) Terrence's son from "The Day the Earth Stood Cool". His parents are insufferably judgemental hipsters, and he's not allowed to watch TV or do anything "normal" kids do which has made him very jaded. He's essentially what Bart would have become if he was raised by hipster parents. He calls Bart's dad a "poser" but that's because he was envious of Bart's relationship (despite how abusive Homer can be) with his father, which he never had with his parents. His smile when Bart offers to let him watch TV at his place is pretty cute. By the end of the episode, the two families get along and it's pretty sweet.
• Pinchy from "Lisa Gets an "A"". Homer raised the lobster for the purpose of eating him as a plump adult. But then it started showing a personality, acting meek before threats and even wagging it's tail happily at Homer, leading him to get adopted as a pet. He still meets his horrible fate however, as Homer accidentally boils him alive when giving him a hot bath. Homer eats him, but sobs uncontrollably throughout the whole meal. He genuinely loved him.
• Alison Taylor from "Lisa's Rival". Despite being The Rival to Lisa, she's a good-hearted girl who only wants to be friends. She never does anything maliciously, and even invites Lisa over to her house to play. Not to mention that she gets picked on for being a Child Prodigy. And Lisa can only think of getting revenge on her. Thankfully after the diorama incident, they become friends. And "Lard of the Dance" shows Alison in the group with the other girls.
• Krusty in "Like Father, Like Clown". His backstory reveals that he wanted to be a clown but his stubborn rabbi father would not let him do so, and when he found out Krusty was doing it anyway behind his back because the lure was too strong, he disowned him and didn't speak to him for twenty-five years. It was so bad for Krusty that merely thinking about his father can reduce him to tears, and after showing a father-son Itchy and Scratchy episode and probably wishing he had moments like that with his own father, he was reduced to a sobbing mess on TV, causing Bart and Lisa to do all they can to reunite Krusty with his father, which they are eventually able to do.
• Sideshow Mel is essentially Sideshow Bob, but without the backbone to turn nasty, meaning in spite of his own desire for a more dignified role in entertainment, he's stuck being Krusty's mistreated sidekick, getting put through horrific slapstick onstage, and frequently getting lambasted offstage.
• Ralph Wiggum. He may be a total ditz who tends to tell people Too Much Information about his medical ailments and inner thought process, but deep down, he's a sweet kid who just needs a friend. In the Valentine's Day Episode "I Love Lisa", no one in his class bothers to give him a valentine except Lisa, who flat-out admits she only gave Ralph a valentine because she felt sorry for him.

Jerkass Woobies

• Charles Montgomery Burns (Mr. Burns for short) pushes the Jerkass portion near the breaking point, constantly engaging in horrific actions such as blanking out the entire sun in an attempt to force the town to pay him for water, polluting the water, constantly neglecting and abusing his assistant Smithers, and selling arms to the nazis during WWII. However, the image that is painted of him is slowly unveiled to be a sad, pathetic old man."Rosebud" reveals he was groomed to become the heartless wealthy sociopath he was by his wealthy grandfather for the purposes of perpetuating the former's business. In "C.E. D'oh", it's revealed that Burns' entire family and friends died out while he worked at the nuclear plant. You've got to feel some sympathy for the man after that, regardless of how evil he is. He also lost his dear friend Waylon Smithers Sr, when the latter sacrificed himself that Springfield (and his baby son) wouldn't get destroyed to nuclear meltdown. "Two Cars In Every Garage And Three Eyes On Every Fish" demonstrates that he's invested so much into his blatantly hazardous nuclear power plant that he can't cope with the concept of leaving it, as it's all that he has and what he's devoted his life to, to the point that he get severely drunks and stumbles into his car, where he impotently weeps until Homer finds him. Monty Can't Buy Me Love" has him trying to do good things for people to gain everyone's respect. His body is in a constant state of near-death, with it being shown that he's only alive because he has every disease at once and they counter themselves while leaving him pathetically frail. He's so isolated from the concept of human compassion that when he sees Maggie, a small, innocent child, his first move is to panic in horror. It's summed up best in "Brush with Greatness", Where after desperately trying throughout the episode and nearly concluding him to be a lost cause, Marge does find some inner beauty in Mr. Burns, that underneath his cruel personality and evil actions is a frail, tired old man, just as mortal as any other creature. Mr. Burns realizes this to be true and compliments the portrait in one of his few positive gestures.
• The current incarnation of Nelson Muntz. True, he can be (and often is) a violent brute who finds amusement in others' misfortune. However, he does have a soft side. Take "Lisa's Date with Density": although he doesn't appear to return Lisa's feelings for him until the end, he was willing to go along with her attempts to bring out the nice guy in him throughout the whole episode (he even wore clothes he felt uncomfortable in just to make her happy), and he reveals at the end this was because she was the first person to think he had a softer, more sensitive side. He continues to show signs of harboring some romantic feelings for her afterwards, such as begging God to not let "his" Lisa get hurt in "The Great Simpsina". It's not just Lisa, either- he befriends a blind kid in "Stealing First Base" and acts surprisingly polite and grateful to Marge for taking him into her house in "Sleeping with the Enemy". And yet his life is pretty terrible, even by Springfield standards: his father left him for a pack of cigarettes, his mother's constantly dating someone undesirable (and has been implied to have a job as a stripper), and he's dirt-poor. He doesn't even get the girl in the end, as revealed in "Holidays of Future Passed": Milhouse is the one who ends up married to Lisa.
• Jeff "Comic Book Guy" Albertson is this when he has a cardiac episode, and claims he has no friends at all. Except Superfriends. As much of an ass as he is on a daily basis, when he says he has no friends, you can't help but feel bad for him. Plus he's been a victim of bullying himself, that's probably why he's such a Jerkass. They threw him a bone in the newer seasons by giving him a lovely Japanese manga artist wife.
• Sideshow Bob is both a Butt-Monkey and this to an extent as well. He may want nothing more than to kill a 10 year old boy, but come on! At first he was a regular Jerkass villain, but later on, motive decay happens. Especially in the episode with his brother Cecil where all Bob wants to do is reconcile with Bart and Lisa and yet he's the one taken to jail. Not to mention his provocation for framing Krusty for robbery was to escape being his mercilessly abused sidekick and provide quality children's programming. Which he did before Bart caught him. Some fans however, take this way too far and make both him and Snake into innocent woobies who would never harm anyone.
• Artie Ziff, going from riches to rags all because he cheated the shareholders of his company. He also gets Homer arrested for his own crime. And he's really, really selfish. Sounds like a real scumbag, right? But he's been a homeless bum for quite a while and if what he claims is true, he's been living on nothing but the moisture in the attic of the Simpsons attic. And he does come to a Heel Realization and starts thinking of others. Plus, no matter what he does, he can never get the girl of his dreams (Marge) and is doomed to be forever alone. That, and he's tried to kill himself. With that said, he's still a huge flirt with No Sense of Personal Space when it comes to Marge. And he calls Homer's friends losers.
• Frank "Grimey" Grimes. A good portion of fans also felt sorry for him: he was abandoned by his own parents when he was four, had a difficult childhood, had a lot of bad luck in his life. However, he lashed out at Homer, the one person who did feel bad about hurting him, and did anything he could to ruin the man. His failure resulted in him going crazy and electrocuting himself in anger, but due to Homer's antics, everyone laughed when he was lowered in the casket.
• Bart, if you look closely and think well enough about it. He gets abused physically by Homer, Lisa (in one episode especially), sometimes resented by his mother Marge, nearly held back in one episode, abused by some French wine makers and his kindergarten teacher, constantly humiliated, nearly killed by Mr. Burns, Groundskeeper Willie, and Sideshow Bob, and isn't close to being as popular as he thinks he is. His only close friend is Milhouse, who usually only hangs around because he has no other options and leaves when Bart needs him on several occasions. He's constantly teased for lack of intelligence despite being innately clever, has probably got his heart crushed more than any character on the show, and has ADD according to another episode. He was even nearly Driven to Suicide for missing a fly ball in a baseball game. Despite his Jerkass tendencies, it's not hard to feel for him considering all the above. A lot of the time he can be made a Designated Villain in Homer or Lisa focused episodes, even if he does the same thing they do in other episodes, making him Unintentionally Sympathetic. He can be a Bratty Half-Pint, but sometimes his consequences are disproportionate.
  • It doesn't help that Bart only wants to be a petty thug while we see others in many other episodes and other Fox comedy sitcoms (particularly Andy Hamilton and Stewie Griffin) go even further and in "Postcards from the Wedge" where we see Bart at his nastiest, (even called a Sociopath by Lisa) he eventually feels guilt for what he had done and purposely made it so his mom and dad could catch him in the act. He was horrified by Stewie claiming to have raped Moe's sister and wasn't very happy at him kidnapping his arch enemies (and Apu) just so he could have a good laugh.
• Homer could also qualify when he's not being a Jerkass. He's been neglected and abused by his father most if not all of his life, his mother abandoned him as a child and abandons him multiple times as an adult and he ends up finding her dead in his living room after an argument. He found a corpse when he was 12, he's attempted suicide multiple times, been fired from multiple jobs, was molested by a panda, and even had his family leave him as a result of said Jerkass tendencies. It's also revealed the reason he is such a buffoon is because he has a crayon wedged in his brain and drinks his sorrows away. Despite being an abusive parent to Bart (and on occasion Lisa) he's someone you can't help but pity.