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* Charles Montgomery Burns (Mr. Burns for short), on occasion. "[[Recap/TheSimpsonsS10E21MontyCantBuyMeLove Monty Can't Buy Me Love]]" has him trying to do good things for people to gain everyone's respect. In "[[Recap/TheSimpsonsS14E15CEDoh 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.

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* Charles Montgomery Burns (Mr. Burns for short), on occasion. "[[Recap/TheSimpsonsS10E21MontyCantBuyMeLove Monty Can't Buy Me Love]]" has 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 trying to do good things for people water, polluting the water, constantly neglecting and abusing his assistant Smithers, and selling arms to gain everyone's respect.the nazis during WWII. However, the image that is painted of him is slowly unveiled to be a sad, pathetic old man."[[Recap/TheSimpsonsS5E4Rosebud]]" 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 "[[Recap/TheSimpsonsS14E15CEDoh 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.meltdown. "[[Recap/TheSimpsonsS2E4TwoCarsInEveryGarageAndThreeEyesOnEveryFish]]" 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. [[Recap/TheSimpsonsS10E21MontyCantBuyMeLove 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 "[[Recap/TheSimpsonsS2E18BrushWithGreatness]]", 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.


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

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For [[WesternAnimation/TheSimpsons a show show]] that's supposed to make you laugh, there are some instances where you [[TheWoobie feel sorry for the characters.
characters]].


* 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, and has probably got his heart crushed more than any character on the show. He was even nearly [[DrivenToSuicide driven]] to suicide for the [[SarcasmMode heinous crime]] of missing a [[FelonyMisdemeanor fly ball]] in a baseball game. In one episode, it's even revealed he has ADD. If all this doesn't make you want to hug the poor little guy, despite his {{Jerkass}} tendencies, then you may have no soul.

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* 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, and has probably got his heart crushed more than any character on the show. show, and has ADD according to another episode. He was even nearly [[DrivenToSuicide driven]] driven to suicide suicide]] for the [[SarcasmMode heinous crime]] of missing a [[FelonyMisdemeanor missing a fly ball]] in a baseball game. In one episode, it's even revealed he has ADD. If all this doesn't make you want to hug the poor little guy, despite Despite his {{Jerkass}} tendencies, then you may have no soul.it's not hard to feel for him considering all the above.


** 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 [[WesternAnimation/FamilyGuy Stewie Griffin]]) go even further and in "[[Recap/TheSimpsonsS21E14PostcardsFromTheWedge 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.



* 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, and has probably got his heart crushed more than any character on the show. He was even nearly [[DrivenToSuicide driven]] to suicide for the [[SarcasmMode heinous crime]] of missing a [[FelonyMisdemeanor fly ball]] in a baseball game. In one episode, it's even revealed he has ADD. If all this doesn't make you want to hug the poor little guy, despite his {{Jerkass}} tendencies, then you may have no soul.

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* 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, and has probably got his heart crushed more than any character on the show. He was even nearly [[DrivenToSuicide driven]] to suicide for the [[SarcasmMode heinous crime]] of missing a [[FelonyMisdemeanor fly ball]] in a baseball game. In one episode, it's even revealed he has ADD. If all this doesn't make you want to hug the poor little guy, despite his {{Jerkass}} tendencies, then you may have no soul.soul.
** 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 [[WesternAnimation/FamilyGuy Stewie Griffin]]) go even further and in "[[Recap/TheSimpsonsS21E14PostcardsFromTheWedge 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.


* Bart, if you look closely. 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, and has probably got his heart crushed more than any character on the show. He was even nearly [[DrivenToSuicide driven]] to suicide for the [[SarcasmMode heinous crime]] of missing a [[FelonyMisdemeanor fly ball]] in a baseball game. In one episode, it's even revealed he has ADD. If all this doesn't make you want to hug the poor little guy, despite his {{Jerkass}} tendencies, then you may have no soul.



* [[Recap/TheSimpsonsS8E23HomersEnemy 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.

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* [[Recap/TheSimpsonsS8E23HomersEnemy 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.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, and has probably got his heart crushed more than any character on the show. He was even nearly [[DrivenToSuicide driven]] to suicide for the [[SarcasmMode heinous crime]] of missing a [[FelonyMisdemeanor fly ball]] in a baseball game. In one episode, it's even revealed he has ADD. If all this doesn't make you want to hug the poor little guy, despite his {{Jerkass}} tendencies, then you may have no soul.


* Waylon Smithers, who craves for acknowledgment and sexual attention of an evil old man who rarely cares about him, regardless of Burns's sexuality. His father died when he was just a baby, and we know nothing of his mother so it can be assumed ''she'''s dead too.

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* Waylon Smithers, who craves for acknowledgment and sexual attention of an evil old man who rarely cares about him, regardless of Burns's sexuality. His father died when he was just a baby, and we know nothing of his mother so it can be assumed ''she'''s dead too.


* Charles Montgomery Burns (Mr. Burns for short), on occasion. "[[Recap/TheSimpsonsS10E21MontyCantBuyMeLove Monty Can't Buy Me Love]]" has him trying to do good things for people to gain everyone's respect. In "[[Recap/TheSimpsonsS14E15CEDoh 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.

to:

* Charles Montgomery Burns (Mr. Burns for short), on occasion. "[[Recap/TheSimpsonsS10E21MontyCantBuyMeLove Monty Can't Buy Me Love]]" has him trying to do good things for people to gain everyone's respect. In "[[Recap/TheSimpsonsS14E15CEDoh 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.

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** 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 [[WesternAnimation/FamilyGuy Stewie Griffin]]) go even further and in the episode "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.
* 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 embarassed 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 [[ArsonMurderAndJaywalking 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 Crosswords"). The entirity 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.

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** 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 [[WesternAnimation/FamilyGuy Stewie Griffin]]) go even further and in the episode "Postcards "[[Recap/TheSimpsonsS21E14PostcardsFromTheWedge Postcards from the Wedge" 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.
* 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 embarassed embarrassed for. Matt Groening Creator/MattGroening 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 [[ArsonMurderAndJaywalking 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 "[[Recap/TheSimpsonsS14E8TheDadWhoKnewTooLittle The Dad Who Knew Too Little" Little]]" and "Homer "[[Recap/TheSimpsonsS20E6HomerAndLisaExchangeCrossWords Homer and Lisa Exchange Crosswords"). Cross Words]]"). The entirity 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 Music/TheMonkees 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 and Scratchy and Marge, Treehouse of Horror IX) but those are few and far between. There was even an episode [[OffscreenMomentOfAwesome where]] [[TookALevelInBadass Scratchy]] finally got even with Itchy, and it wasn't shown because of Homer's college friends.
* For one-shot characters, [[{{Tsundere}} Gina]] (from The Wandering Juvie, not Sideshow Bob's kid - that's Gino) is one too. Unlike Bart's other [[FilleFatale well-known]] [[BitchInSheepsClothing girlfriend]], she has a [[JerkWithAHeartOfGold 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.

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* 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 "[[Recap/TheSimpsonsS18E3PleaseHomerDontHammerEm Please Homer, Don't Hammer Em", 'Em]]", not having the best physique in another episode, and so on. Plus she was teased at school for liking Music/TheMonkees 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 [[WesternAnimation/TomAndJerry 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 and ("[[Recap/TheSimpsonsS2E9ItchyAndScratchyAndMarge Itchy & Scratchy and Marge, & Marge]]", "[[Recap/TheSimpsonsS10E4TreehouseOfHorrorIX Treehouse of Horror IX) IX]]") but those are few and far between. There was even an episode [[OffscreenMomentOfAwesome where]] [[TookALevelInBadass Scratchy]] finally got even with Itchy, and it wasn't shown because of Homer's college friends.
* For one-shot characters, [[{{Tsundere}} Gina]] (from "[[Recap/TheSimpsonsS15E16TheWanderingJuvie The Wandering Juvie, Juvie]]", not Sideshow Bob's kid - that's Gino) is one too. Unlike Bart's other [[FilleFatale well-known]] [[BitchInSheepsClothing girlfriend]], she has a [[JerkWithAHeartOfGold 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.



** 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 [[EvilerThanThou 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 HotBlooded Scot we see today. When you find this out, all his jerkish behaviour seems justified.

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** Even though we already knew this from "The "[[Recap/TheSimpsonsS9E2ThePrincipalAndThePauper The Principal and the Pauper", 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 "[[Recap/TheSimpsonsS21E6PranksAndGreens Pranks and Greens" Greens]]" is any indication. It's revealed in that episode that there was an [[EvilerThanThou 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 HotBlooded Scot we see today. When you find this out, all his jerkish behaviour seems justified.



* T-Rex (yes [[AwesomeMcCoolName 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 [[AllAnimalsAreDogs 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 TheRival 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 ChildProdigy. 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.

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* T-Rex (yes [[AwesomeMcCoolName that]] is his real name) Terrence's son from "[[Recap/TheSimpsonsS24E7TheDayTheEarthStoodCool The Day The the Earth Stood Cool.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 "[[Recap/TheSimpsonsS10E7LisaGetsAnA Lisa Gets An A".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 [[AllAnimalsAreDogs 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"."[[Recap/TheSimpsonsS6E2LisasRival Lisa's Rival]]". Despite being TheRival 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 ChildProdigy. And Lisa can only think of getting revenge on her. Thankfully after the diorama incident, they become friends. And "Lard "[[Recap/TheSimpsonsS10E1LardOfTheDance Lard of the Dance" Dance]]" shows Alison in the group with the other girls.
* Krusty in "Like "[[Recap/TheSimpsonsS3E6LikeFatherLikeClown Like Father, Like Clown".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.



* Charles Montgomery Burns (Mr. Burns for short), on occasion. The episode, "Monty Can't Buy Me Love" has him trying to do good things for people to gain everyone's respect. In the episode C.E.Doh, 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.
* 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 the episode "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 [[FreudianExcuse 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.

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* Charles Montgomery Burns (Mr. Burns for short), on occasion. The episode, "Monty "[[Recap/TheSimpsonsS10E21MontyCantBuyMeLove Monty Can't Buy Me Love" Love]]" has him trying to do good things for people to gain everyone's respect. In the episode "[[Recap/TheSimpsonsS14E15CEDoh C.E.Doh, 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.
* 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 the episode "Lisa's "[[Recap/TheSimpsonsS8E7LisasDateWithDensity Lisa's Date with Density": 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 "[[Recap/TheSimpsonsS22E18TheGreatSimpsina The Great Simpsina". Simpsina]]". It's not just Lisa, either- he befriends a blind kid in "Stealing "[[Recap/TheSimpsonsS21E15StealingFirstBase Stealing First Base" 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 "[[Recap/TheSimpsonsS23E9HolidaysOfFuturePassed Holidays of Future Passed": 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.''WesternAnimation/{{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 [[FreudianExcuse 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.



* 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.

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* [[Recap/TheSimpsonsS8E23HomersEnemy Frank "Grimey" Grimes.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.



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* 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.



* Sideshow Bob is both a ButtMonkey 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. And all he really wanted to was 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.

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* Sideshow Bob is both a ButtMonkey 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. And all he really wanted 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.


* 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. 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, 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.

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* 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.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, 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.


* 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.

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* 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 Music/TheMonkees and has to deal with two {{Jerkass}} sisters and a {{Jerkass}} husband.



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* 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.


* Homer could also qualify when he's not being a {{Jerkass}}. 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.

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* 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'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.



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* Alison Taylor from "Lisa's Rival". Despite being TheRival 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 ChildProdigy. 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.

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