Follow TV Tropes

This is based on opinion. Please don't list it on a work's trope example list.


Tear Jerker / The Simpsons

Go To

"Your eyes need diapers."
Ralph Wiggum
"At least this time, I'm awake for your goodbye..."

In addition to the laughs, the awesome moments, and the heart-warming moments, Springfield's dysfunctional yellow-skinned family (and the residents of Springfield at large) is bound to put us into helpless tears every now and then.

    open/close all folders 

    Season 1 
  • The very first aired episode "Simpsons Roasting on an Open Fire". After not getting his Christmas bonus, Homer attempts to cut corners at a cheap supermarket. He then sees Flanders buying lavish gifts for his family and chatting with his son about how this could be "the best Christmas yet". Sad music builds up as Homer gazes at the random junk he just bought his family and sheds a single tear at letting them down. And of him coming clean at the end, which is thankfully turned Heartwarming with the introduction of Santa's Little Helper.
    • An earlier scene with Homer and Marge in bed, in which Homer is struggling to tell her that he didn't get his Christmas bonus. He doesn't have the heart to be honest with her, and simply asks if he can do the Christmas shopping instead — which leads to the aforementioned scene at the cheap supermarket.
    • Santa's Little Helper's mistreatment near the end of the episode, before Homer and Bart take him in and adopt him. Sadly, retired greyhounds usually get the short end of the stick in real life.
    • This exchange between Lisa and Patty:
      Patty: Oh, nothing, dear. I'm just trashing your father.
      Lisa: Well, I wish you wouldn't because, aside from the fact that he has the same frailties as all human beings, he's the only father I have. Therefore, he is my model of manhood, and my estimation of him will govern the prospects of my adult relationships. So I hope you bear in mind that any knock at him is a knock at me, and I am far too young to defend myself against such onslaughts.
      Patty: Mm hm. Go watch your cartoon show, dear.
  • Homer nearly being Driven to Suicide in "Homer's Odyssey" after failing to find a new job and being ashamed of himself at raiding Bart's Piggy Bank to try and scrape together enough money for a beer. And this is only the third episode of the series.
    • Just before the suicide attempt, Homer's depression is depicted in a fairly realistic manner; he's listless and has a dazed, tired look on his face, and barely speaks to anyone. And when he finds the cake in the fridge from his family with encouraging words written on it, he pushes it aside.
    • The words in his suicide note are deeply sad to listen to, especially if you've suffered from depression:
      Homer: Dear family. I am an utter failure, and you'll be better off without me. By the time you read this, I will be in my watery grave. I can only leave you with the words my father gave me: "Stand tall, have courage and never give up. " I only hope I can provide a better model in death than I did in life. Warmest regards. Love, Homer J. Simpson.
      • What really makes this scene heartbreaking is when he stops writing and sobs a little bit, brushing back tears before continuing to write.
      • It's implied that the rather stiff "warmest regards" is his first attempt at a sign-off and that he changes it to the more heartfelt "love" upon consideration.
    • The attempt gets as far as the family actually reading the suicide note and running to stop him. When they call out to him Bart even calls him "Dad."
      Marge: Oh, Homer! How could you think of killing yourself? We love you!
  • "Moaning Lisa": Lisa, who has been depressed for days and finds a friend in Bleeding Gums Murphy, is told by Marge to repress her unhappiness and go out into the world smiling over nothing. When Lisa goes to school, boys being using her to do her homework and Mr. Largo (the music teacher) tells her to play the saxophone the way he wants her to play. Marge gets upset, drags Lisa back in the car, and tells her that she was wrong about being a Stepford Smiler and Lisa should be free to express her emotions, with Lisa finally smiling over the fact that someone now understands her. The saddest part is that Marge was really doing her best, the Stepford Smiler advice was the way she was raised by her own mother, and she doesn't know any better way of dealing with sadness.
    • Also, Homer's realization after his nightmare:
      Homer: You know Marge, getting old is a terrible thing. I think the saddest day of my life was when I realized I could beat my dad at most things, and Bart experienced that at the age of four.
  • In "Homer's Night Out", Homer gets caught dancing with an exotic dancer, even placing a couple dollar bills in her underwear. Marge is understandably furious, and is so incensed that she kicks Homer out of the house. But the look on Homer's face is so sad that you can't help but feel sorry for him, as well. He's screwed up and is deeply remorseful.
    Marge: (sobbing, while handing Homer a box of tissues) If you have any soul left, you'll need these. I know I will.
    • And Homer, indeed, uses them.
    • When Mr Burns discovers the picture, he seemingly brings Homer into his office to chew him out for creating negative publicity within the plant. When Smithers leaves however, Burns, in his first sign of vulnerability throughout the series, laments to Homer that, in spite of his financial success, he has lived a rather lonely life, and outright begs him to tell him his secret to attracting ladies.
    Mr. Burns: Simpson, I am by most measures a successful man. I have wealth and power beyond the dreams of you and your clock-punching ilk. And yet, I've led a solitary life.
  • When Bart was about to go to bed in "Krusty Gets Busted", the news comes on and reveals that Krusty the Clown was arrested for committing armed robbery at the Kwik-E-Mart, but it was really Sideshow Bob in disguise to frame him. This shocks Bart massively, and after Homer confirms it due to being there (as seen below), he goes to bed in tears.
    Bart: (Sobbing) Oh, Krusty, how could you?!?
    Marge: (As she comforts Bart) I know it's bad. But who knows, maybe it will turn that he was innocent all along.
    Homer: Earth to Marge, Earth to Marge, I was there. The clown is G-I-L-L-T-Y!note 
    • After Bart went to his room, he pulls his talking Krusty doll.
    Krusty doll: You're my best friend!
    Bart: Thanks, Krusty.
    Krusty doll: Buy my cereal! (laughs) Buy my cereal! (laughs) I didn't do it!
    Bart: I wish I could believe you, Krusty.
    • The despondent, utterly broken expression on Krusty's face as he's led into the courthouse. He looks like he's going to cry.
  • 'Bart the General' has Bart imagining his own funeral. It also features him returning home after being beaten and sobbingly telling Homer he needs help.
    • When Bart comes home he seems to be his usual sarcastic self when saying "I payed the price for helping Lisa", Marge bugs Homer to go check on Bart, thinking he's upset. Homer goes over to find Bart so they can laugh this off, only to see Bart is upset. Poor kid is so scared of Nelson he's crying. He even calls him dad, instead of the usual condescending "Homer".
  • In "Life On the Fast Lane," after Homer finds the glove Jacques gave Marge and realizes she's met another man, he tries to approach her about it while she's making lunch for the family. He doesn't quite manage to say what's on his mind, but his meaning is clear.
    Homer: Marge, may I speak to you?
    Marge: Sure.
    Homer: You know, I've been thinking. Everyone makes peanut butter and jelly sandwiches, but usually the jelly drips out over the side and the guy's hands get all sticky. But—your jelly stays right in the middle where it's supposed to. I don't know how you do it. You just got a gift, I guess. I've always thought so. I just never mentioned it, but it's time you knew how I feel. I don't believe in keeping feelings bottled up. (long pause) Goodbye, my wife.
    (He walks out of the room.)
    Marge: Goodbye, Homer.

    Season 2 
  • "Bart Gets An F": The part where, after Bart goes through Hell to try and pass his history exam (even giving up having fun on a snow day so he can study), he still fails it. He breaks down crying, telling Krabappel that he really did try this time, but he still wasn't good enough.
    Krabappel: What's the matter, Bart? I thought you'd be used to failing by now.
    Bart: [sobbing] No, you don't understand! I really tried this time! I mean, I really tried! This is as good as I can do, and I still failed! Who am I kidding? I really am a failure.
    • It really shows why the slightly rougher animation style worked so much better — just look at Bart's face as he starts crying. It actually crumples up like people do in real life with Inelegant Blubbering and it makes the scene so emotive given the context.
      • Even before this, Bart has a minor breakdown during the Parent-Teach Conference.
        Bart: I know it, you know it, I am dumb, okay?! I'm dumb as a post! Think I'm happy about it?!
    • This episode puts a lot of Bart's trouble in school in perspective: it shows that he is entirely capable of getting good grades and doing well in school, and yet he still chooses to slack off. But the last thing he wants is to be held back, a notion which greatly upsets him when the school propose to have Bart repeat the 4th grade.
    • Fortunately, it gets better when Bart cites that his failure was similar to one George Washington encountered in his defeat in the Battle of Fort Necessity, and Krabappel raises Bart's grade since he showed her that he did learn something. Then it becomes hilarious when Bart kisses Krabappel, shouts to the world that he finally passed a test, then realizes he kissed his own teacher and spits in disgust.
    • From the same episode, Martin discovering that everyone laughs at him.
    • On the Season 2 DVD set, when you select an episode, you'll be brought to a separate menu that has the Simpsons theme playing. For this episode, the theme is replaced with Dr. J Loren Pryor saying that Bart will have to repeat the fourth grade, overlapped with Mrs. Krabappel reading Bart's recent test scores, all while we get to see a lovely image of a terrified Bart. This is the only episode menu on the set to do thisnote . It's clearly FOX's way of acknowledging that this is one of those episodes.
  • Homer losing his hair at the end of "Simpson and Delilah". He seemed so happy to have hair for the first time in years, then the promotions and wealth he gained from his looks all slipped through his fingers. It's no accident that he becomes insanely attached to his remaining three strands after that and bursts into tears whenever they're cut or plucked.
    • Marge tenderly holding Homer in her arms and singing "You Are So Beautiful" to him until he finally smiles is a happy kind of tear jerker.
    • In a more subdued example, the way Mr. Burns recounts his younger years to Homer is pretty depressing- we see photos from his younger years in college, when he had a full head of hair and looked significantly healthier. Then we see a photo of Burns from his mid-twenties, looking very much like he does now.
  • For most of "Two Cars In Every Garage And Three Eyes On Every Fish", Mr. Burns plays the role of antagonist. What sets this up is a Sympathy for the Devil moment however, in which an epically failed safety inspection of the plant leaves him with the ultimatum; bring everything up to code or get shut down, both choices are implied would leave Burns bankrupt. By the end of the day, Burns has drowned his sorrows to the point he staggers out of the building intoxicated, bitterly murmuring "Brother, Can You Spare A Dime".note  Homer later enters the car park to find Burns in his limousine sobbing. Yeah, Burns brought it on himself with his greed and irresponsibility, but the plant is literally his life's work, and as been shown in a few other episodes where he tried to retire or lost the plant, without it he has nothing.
    • Hell, the sight of Mr. Burns crying in his car is so pitiful that even Homer stops to ask if he's alright.
    • The brief shots of a morose Mr. Burns quietly gazing out of his office window at the plant's cooling towers. The scene is nearly silent, save for Burns sniffling a bit and singing softly to himself.
    • It's easy to feel bad for Blinky in the end. Mutated from radiation poisoning, he's captured and used as a prop by both sides of the political war, and ultimately Marge coldly kills and serves him as a means to sabotage Burns.
  • There is something unbearably sad about this exchange in "Dead Putting Society":
    Bart: Hey Lis, what do you call those guys in chess that don't matter?
    Lisa: Well, a blockaded bishop is of little value, but I think you're referring to a pawn.
    Bart: Right, I am a pawn.
    Lisa: Mmm, I know. It's times like this I'm thankful that Dad has little to no interest in almost everything I do.
    • Just the matter-of-fact way she says it; there's no bitterness or longing in her tone, she's an eight year old girl who's already resigned herself to the fact that her father barely acknowledges her existence.
  • "Bart vs. Thanksgiving" has Homer and Marge lamenting Bart running away and blaming themselves for how they acted toward him. This of course, was after Marge screamed at Bart that he ruined Thanksgiving due to him and Lisa arguing over whether or not the centerpiece or the turkey should be front and center in the table (the former fell into the fire).
    • The incident itself is rather heart wrenching. After realizing her art that she toiled over is unsalvageable, Lisa charges at Bart, livid. Unlike most of their comical spats, this is a far more realistic and saddening fight between two children, with both of them furiously shoving and screaming at each other until Marge and Homer restrain them and Lisa runs out of the room crying loudly in pure and utter heartbreak. Ouch.
    • On Skid Row, Bart realizes he can sell his blood for enough cash to get something to eat. He emerges from the blood bank with a $10 bill, a free cookie, and a bandage around his elbow, and starts to say what a great country it is... before fainting onto the sidewalk in shock.
    • Lisa alone in her room blaming herself for Bart running away. On top of that, Bart admitting that he doesn't know why he acts like he does, or why he'd do it again, it just happens. He doesn't set out to be bad, it just comes anyway.
    • Bart playing on the roof and says that "the boy nobody wanted just won the Super Bowl." Than he pauses. Realizing what he just said.
  • For a couple of minutes, "Bart Gets Hit By a Car" deals very harshly with the Surprisingly Realistic Outcome of Marge's honesty causing her to willingly throw a successful fraudulent case against Burns that would have netted the struggling family a cool million: Homer admits to her that he's not sure if he still loves her. Marge's gasp and the way Homer's friends in the pub react really drive it home. Naturally, looking her in the eyes restores his certainty.
    Marge: Oh my lord!
  • "One Fish, Two Fish, Blowfish, Blue Fish" because Homer only had 24 hours to live and wanted to do everything he never got a chance to do which include: Having a man-to-man talk with Bart (and teaching him how to shave, with hilarious results), listen to Lisa play her sax (and singing along to "When the Saints Go Marching In"), and enjoy father-son time with Abe. It didn't help when it really looked like he had died in the middle of the night.
    • And then, the ending finally manages to actually make you cry happy tears, as Marge does when she finds out that Homer is alive.
    • The moment when Homer makes amends with his father and goes out playing with him, and another when he's tucking his kids in for the last time.
    • And again when Marge reads Homer the poem she wrote for him.
      The blackened clouds are forming,
      Soon the rain will fall,
      My dear one is departing,
      But first, please heed this call,
      That always will I love you,
      My one, my love, my all.
    • The family are at the table with Marge looking at the window hoping Homer would come soon. The kids asks why are they all dressed up and using the fine china, she indifferently answers "sometimes it's fun" to do so. When they ask why are they waiting for Homer, Marge says, nearly in tears, because they love him and would want to be with him. After a brief pause, Bart asks why are they really waiting for Homer, Marge silently resumes looking outside.
      • The fact that the kids are Locked Out of the Loop, because Homer didn't want to upset the kids and wants to have his last moments with them to be happy. One can only imagine how they'd take it if Homer did die the next day.
    • Homer listening to the Bible on audiotape as he awaits the end. He isn't a very spiritual person, but even he wants to at least try in his last moments.
    Narrator: In the beginning, God created the Heavens and the Earth...
    Homer: (tearing up) Oh, Marge. I'm gonna die. I'm gonna die!
  • In "The Way We Was", Homer being hopelessly in love with Marge, crying at the prom when she and Artie win prom royalty, and the very end, when Marge picks him up in her car.
    Marge: Why are you doing this? Why can't you accept that I'm here with someone else?
    Homer: (tearful) Because I'm sure we were meant to be together. Usually when I have a thought, there's a lot of other thoughts in there. Some things say yes, some things say no. But this time, there's only yes! How can the only thing I've ever been sure about in my life be wrong?
    Marge:I don't know, but it is.
    • In a combination of this and Nightmare Fuel, Marge is almost molested by her prom date in the back of her car.
    • Flashbacks reveal that Marge was once an ambitious student taking part in several extra-curricular activities and was bound for college and a career. She even has a brief interest in civil activism, as she speaks at a feminist demonstration decrying the housewife. Flashforward fifteen years, Marge is an overworked housewife who often complains of feeling bored and unfulfilled, in essence the epitome of what she was protesting. It's a harsh reminder of how people's lives can veer dramatically from the ideals of their youth.
  • "Principal Charming": Skinner crying on the school steps after Patty (out of sisterly love) turns down his proposal.
    • Selma feeling depressed thoughout the episode. She's always been the more sympathic one.
  • This one line from, "Oh Brother, Where Art Thou?" It sums up all of Homer's feelings in finally finding who he was looking for.
    Homer: "Because... I'm your baby brother, Homer."
    • This just makes the ending even worse. Homer just wanted to help Herbert, he did exactly what Herbert asked him to do; design a car that an Average Joe American type would want, that would appeal to blue-collar guys like Homer... and the result is an ugly, ugly car that cost a disproportionate fortune to make, leaving Herbert bankrupt. His last words on screen are to venomously spit at Homer that he doesn't have a brother, and you can just see how all of this has crushed Homer. It's especially bad if you realize that it was HERB'S fault for giving Homer a job he couldn't handle, and not even inspecting his work.
    • Not helping is Abe coming all the way to meet Herb, until Homer tells him he'll explain everything on the ride home. Abe angrily gets back inside the cab, declaring that he knew Homer would screw it up.
  • "Bart's Dog Gets an F": Bart and Santa's Little Helper having fun for the last time before he is given away. This is happily subverted moments later when SLH shows he can take orders and goes on to pass his final exam, which allows him to stay with the family.
  • "Old Money": The final scenes. Throughout the whole episode, we seem glimpses of the retirement home, and how it's run down and almost in shambles. At the end, Grandpa decides the best thing to do with the money he inherited from Bea was to donate everything to his retirement center so they can have money for better living conditions. Even sadder, Abe originally wanted to use the money to help society's unfortunates, but realized that he simply didn't (and could never) have enough money to do so. In the end, he had to settle for helping the ones he could.
  • A couple from "Brush with Greatness":
    • Marge's flashback, wherein her art teacher from high school mocked and rejected her beautiful painting of Ringo Starr and when Ringo never wrote her back after she sent him the painting, she gave up art entirely. Thankfully it's made better when her new teacher and Ringo Starr himself tell her that they love her art (Starr never answered her original fan letter with the painting because she sent it during the height of Beatlemania, and he didn't have time to read fanmail, much less answer any of it. He's spent his retirement going through 20 years worth of fanmail for the sole purpose of giving his fans their due, and even hangs Marge's portrait in his house. This is very much Truthin Television because at the time the episode aired, he really did answer every fan mail he got and sometimes took a long time to response).
    • The biggest one in the episode would probably be when Marge is busy trying to paint a portrait of a very uncooperative and rude Mr. Burns and Homer rushes in excitedly talking about the progress he's making in his diet (having gone on the diet after a humiliating incident at a local waterpark). Marge praises him, but Mr. Burns responds by mocking Homer's weight, telling him that he's "the fattest thing he's ever seen" and completely shattering his self-confidence in one fell swoop. This prompts Homer to tearfully head into the kitchen to binge on food, while Marge, understandably furious, chews out Mr. Burns and demands that he leave the house. Afterward, she smashes the portrait in fury and rushes to the kitchen to stop Homer from stuffing his face with whipped cream, before declaring that she gives up on seeing any beauty in Mr. Burns, with this whole incident just cementing to her that he's just irredeemably evil and nothing can change that.
      • Adding to this, this almost made Marge completely give up painting again, after spending the whole episode rekindling her talent.
      • What makes this moment especially heartbreaking is that Mr. Burns is essentially mocking the weight of one of his own employees in this scene and Smithers later joins in by laughing at Homer following Burns' comment that "he'd been on safari," which was after he made fun of Homer's weight-loss efforts.
    • It's a minor one, but it's weirdly sad to watch Burns freak out over Maggie hugging his leg. Even people who don't like children generally don't react that poorly, especially not over something so innocent, it's like he's forgotten what a baby even is. Then again last time when Mr. Burns was holding a baby was the one who was a spitting image of his late best friend.
    • A small one occurs when Marge notices all the abuse Burns gives Smithers. She asks the latter why he even puts up with him, but Smithers in a very optimistic tone notes he revels every minute they spend together, seeing him as his best friend. Shortly after Burns throws a cup of singing hot tea at Smithers, to Marge's further disgust.
    • The ending is a mix of this and heartwarming; in the end, 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.
    Burns: Marge, I'm not an art expert, but I know what I hate... and I don't hate this.
  • Four powerful, tiny little words from "Lisa's Substitute": You Are Lisa Simpson.
    • Earlier in the episode, when Ms. Hoover mentions that Mr. Bergstrom didn't follow the lesson plan she'd left and asks Lisa what he taught her, Lisa says, through tears, "He taught me that life was worth living." It can really make you sob, especially if you've had an inspirational teacher of your own...
    • The reason Bergstrom leaves is that he's needed in the projects of Capital City. Lisa tells him she needs him too.
      Bergstrom: That's the problem with being middle-class. Anybody who really cares will abandon you for those who need it more.
    • This line, uttered by a sobbing Lisa just before Mr. Bergstrom leaves:
      Lisa: Thank you, Mr. Bergstrom... If you don't mind, I'll run alongside the train as it speeds you from my life...
    • It's pretty gut-wrenching seeing Lisa screaming at Homer when he didn't seem to care about how upset she is when Mr. Bergstrom left, as if she blames Homer for it. Homer may have had an indirect part of it, since Bergstrom noticed Lisa and Homer don't really connect and probably chose to leave so he wouldn't get in the way of their relationship.
    • The entire ending sequence of Homer cheering up a crying Lisa can bring about happy tears.
      • Struggling to give Lisa the serious talk he wants to give her, Homer finally gets a smile out of her by clowning around. Before that, though, he gets a heartwrenching observation in, echoing Bergstrom's idea that she's destined for greatness (and, therefore, for leaving her humble family behind):
        Homer: Now, you'll have lots of special people in your life, Lisa. There's probably someplace where they all get together, and the food is real good and guys like me are serving drinks.
  • "Blood Feud" has the scene where Burns gets his blood transfusion; he thinks he isn't going to make it and Smithers is almost in tears.
    Mr Burns: Smithers, I'm not going to make it. I want to dictate my epitaph.
    Smithers: (tries not to cry) Go ahead, sir.
    • Saddest part is that Smithers is unable to help his boss; he can only watch him slowly getting worse.
    • Mr Burns' condition turns him into a borderline Jerkass Woobie at the start of the episode. It's strangely poignant to see him weakly reach his hand out to Smithers during what he assumes to be his final moments.
    • After Mr. Burns falls ill, Smithers goes on the intercom at work to inform the employees that Mr. Burns "is at death's door," and outright begs them to come forward and donate blood if they have a compatible blood type. The way Smithers' voice breaks and he has to pause to compose himself as he speaks is just saddening. And nobody is interested in helping anyway because Burns is such a jerk. Even if you feel no sympathy for Burns, it's genuinely sad to see Smithers on the verge of tears because his best friend is dying.
    • The beginning of the episode counts as this, due to its effective use of Mood Whiplash and just from how upsettingly fast things go downhill, all in the span of less than a minute. Smithers rushes into Mr. Burns' bedroom to find him convulsing on the floor, too weak to stand up. As Smithers frantically tries to figure out what to do, Burns sits up slightly and begins to protest that "no quack sawbones will apply his leeches" to him, and then, almost instantly, Burns faints and collapses again. The very next shot shows Burns, with a resignedly pained expression, silently languishing in bed as Doctor Hibbert grimly explains his prognosis to a helpless-looking Smithers. Just... damn.
    • Smithers' intense emotional conflict when he's supposed to give orders to have Homer beaten. He ultimately calls it off, violating a direct order, because he can't bear to hurt the person who saved Burns' life. His admission gives even Burns the closest thing to a Heel Realization he could possibly have, causing him to treat the Simpsons kindly in the end.

    Season 3 
  • From"Stark Raving Dad", Lisa crying and signing "Happy birthday, forgotten middle-child" to herself in the kitchen, accompanied only by Maggie, her birthday completely forgotten amongst all the drama of the episode.
  • In "Mr. Lisa Goes to Washington", Lisa is all set to recite an essay about the birth of America when she sees her congressman taking a bribe and agreeing to level an entire forest (the very same that inspired her essay to begin with). She's so horrified and disillusioned by it that she rips up her essay and runs away in tears. Earlier in the episode, she even hoped that she could vote for him once she's old enough, only to discover that he's just a corrupt pig who doesn't care about anything other than stuffing his pockets.
  • "When Flanders Failed", in general. Homer makes a Jerkass wish against Flanders, leading to him falling on hard times. Eventually, Homer starts to regret it and tries to give back the stuff he bought in Ned's garage sale, only to find that their house has been repossessed and they're spending the night in their car, building up to one of the most depressing conversations in Simpsons history.
    Homer: Flanders, I want to give you your stuff back.
    Ned: Well, there's no house to put it in, Homer. Not since that nice fellow from the bank— who was only doing his job— came and locked it up.
    Homer: You're gonna live in your car?
    Ned: Oh, no. It's just a camp-out tonight then off to my sister's apartment in Capital City. What do you think, kids? The big city. (Kids cheer) Todd, I want to talk to your Uncle Homer. You're head of the car till I get back.
    Todd: Okay, Dad. Gray skies are gonna clear up! (Everyone in the car starts singing)
    Ned: Listen to that singing. Those poor fools. (Voice breaking) Homer, I'm ruined.
    Homer: (Somberly) I know.
    Ned: At times like these I used to turn to the Bible and find solace but even the Good Book can't help me now.
    Homer: Why not?
    Ned: I sold it to you for seven cents.
    Homer: (Guilt ridden) Oh.
    Flander: You know, ever since that barbecue nothing's gone right. It's like there's been a curse on me.
    Homer: (Starts bawling outright) It's all my fault!
    Ned: (Also in tears) No, it's not!
    Homer: Yes, it is.
    Ned: No, you tried to warn me about gambling my family's future on some pig in a poke! I didn't listen. Homer, you were a true friend! (The two of them hug, weeping on each others shoulders)
    Homer: No, I was a swine!
    • The big revelation that starts Homer's regret. He witnesses the Leftorium closing down, just like in his Imagine Spot. Flanders is even sobbing, though far less comically. Homer realizes, he got what he wanted, but it's not what he wanted.
    • Homer rallying Flanders friends throughout Springfield via a phone chain, leading to the Leftorium being saved and lasting well into modern day. An unnamed extra provides the perfect example.
    Woman: It's Homer Simpson!
    Man: *lying on the couch* Tell him I went out.
    Woman: He needs you to help Ned Flanders.
    Man: NED FLANDERS IS IN TROUBLE?!! *rushes out*
  • In "Bart The Murderer", Bart’s day has seen nothing at all go right for him. Homer took the police badge from the cereal box Bart wanted for himself, Santa's Little Helper ate his math homework, he missed the school bus, had to walk to school in the rain, arrived at school forty minutes late, split his pants and got a black eye from a football hitting him in the face. But hey, he’s still got the field trip to the chocolate factory to look forward to. The rug is abruptly pulled out from under him when Krabappel says she trusts that everyone has brought their permission slips to school so they can go on the field trip. Cue Bart screaming in abject horror when he realised that he accidentally left his permission slip at home, followed by a Head Desk and him groaning “What a day...”. For some, that moment can hit very close to home. Even worse, unlike most episodes, Bart has done nothing to deserve any of this. If it hadn’t been for that, the entire rest of the episode, which sees Bart becoming a bartender for the Springfield Mafia and subsequently being framed for Skinner's murder, wouldn’t have happened. That probably makes Bart’s Oh, Crap! Harsher in Hindsight.
  • Krusty mournfully revealing that his father never accepted him becoming a clown and hated him for it, in "Like Father, Like Clown".
    • Later in the episode, after showing an Itchy and Scratchy episode that hits a little too close to homenote , Krusty has a complete meltdown on set and the show has to cut prematurely. The brief silent pause before he breaks down, just gazing with quivering lips and bloodshot eyes, is particularly heart wrenching to see.
  • "Lisa's Pony": Lisa giving up the one thing she loves (a pony) after learning that Homer is taking a second job at the Kwik-E-Mart just so he can pay for the upkeep. Even the stern, British stable master was touched (even though she doesn't express it).
    • Also, the fact that Homer really wanted to make up for not getting Lisa's saxophone reed to her in time for the talent show by getting her the one thing she's always wanted (despite Marge's protests) and working himself to near self destruction is tear-inducing in that "That's very noble" way.
    • His actions were spearheaded further after watching a home video of Lisa as a baby. He at first smiles at seeing his daughter starting to grow, until he notices he didn't pay attention to any of it. He replicates her disappointed mumble after he moves her out of the way of the TV while takes her first steps, and is in tears by the end of the movie, with him again ignoring her as she starts talking (for extra Fridge sadness, she's saying "Da-da").
    Homer: No wonder she hates me. Oohhh, I never even noticed she was alive.
  • "I Married Marge" has a lot of this. Homer tries and fails to get a job and support himself, Marge and their baby (Bart), and the real kicker comes when the baby's things are repossessed. And Marge's wedding ring. The letter Homer leaves behind for Marge is also incredibly sad, reducing Marge to tears (and Lisa in the present), but the last line is really heartbreaking. "You will not see me again until I am a man." Just think about that. Homer doesn't believe he is good enough for Marge or even worthy of being called a man, no matter what he does to try and show it.
    • Possible happy tears may be shed when Marge and Homer reunite at the Gulp 'N' Blow, which only happened because Selma felt sorry for Marge. She may have hated Homer, but she still wanted Marge to be happy, even if it was with someone she personally disapproved.
    • Homer's line to Bart, Lisa and Maggie at the episode's close is both this and Heartwarming: "You know son, the day you were born, I received the greatest gift a man could have. As the years went by, your mother and I were blessed twice more, and not a day goes by that we don't thank God for all three of you."
  • "Radio Bart". Sure, Bart took the town for a ride when he concocted the "Timmy O'Toole" shtick to explain why he fell in an abandoned well, but the town immediately dropping any and all support for him as soon as they found out about it was crushing. Mayor Quimby's press conference, where he told the media "Let him stay down there!" certainly didn't help matters.
  • Marge having a complete mental breakdown at the beginning of "Homer Alone". What causes her to snap is Maggie accidentally spraying her with her bottle, causing Marge, already on the verge of a meltdown, to scream "NOOO!!!" and park her car in the middle of the bridge. She remains silent and unresponsive for a while, until Homer eventually finds her and coaxes her out of the car.
  • "Separate Vocations" features a Role Swap Plot where Lisa has her dreams dashed by an Inept Aptitude Test and starts to underachieve and act out at school, while Bart, who was assigned the potential career of "policeman," becomes a overzealous hall monitor, striking up a friendship with Principal Skinner and even improving his grades as a result. He throws all of this away by Taking the Heat for an expellable offense committed by Lisa. Feeling that Lisa is the more likely to succeed in life out of the two of them, he does what it takes to preserve her chance, even though it means confirming everyone's worst opinions of him (keeping in mind that even Bart would have drawn the line at a deed that could get him expelled, and that he had no real reason for breaking Skinner's trust) and erasing all his progress toward being anything other than the school delinquent. He only misses being expelled into the bargain because Skinner cuts him a break in light of his recent service.
    Lisa: Bart, why'd you take the blame?
    Bart: 'Cause! I didn't want you to wreck your life! You got the brains and the talent to go as far as you want, and when you do, I'll be right there to borrow money.
  • "Dog of Death" hits especially hard for people who know exactly what it's like to lose a beloved pet. None of Santa's Little Helper's condition is played for laughs and, at one point, he even looks at Homer and whimpers with an expression of, "Am I going to die?"
  • At the end of the episode "Colonel Homer" after Homer leaves Lurleen Lumpkin, she goes on the TV and sings:
    Lurleen: (singing) His name was Homer, he's quite a man, I tried to kiss him, but Homer ran, Sure wish I could say that I was his, I hope that Marge knows just how lucky she is.
    Marge: I do.
    • Gets even worse when it's revealed what happened to Lurleen afterwards; Homer's rejection shattered her, she lost most of her money in divorces to husbands who all resembled Homer, and it's eventually revealed that it all tied back to her father abandoning her as a child. Even fame and fortune wasn't able to fix her and she lost all of it. Thankfully she does get better in "Papa Don't Leech"
  • "Bart's Friend Falls in Love": When Samantha Stanky's strict and overprotective father discovers his daughter and Milhouse kissing in the tree together. Not only does he berate her, but he carries her away, as he tells her that he will place her in an all-girl school and that she will never see Milhouse again. The true stinger occurs when the two cry out each other's names. The music that plays when this happens only makes it that more heartbreaking, as Mr. Stanky angrily slams the car door shut and drives off, while Samantha presses against the window screen.
    • But it doesn't end here. Milhouse's depression carries on through the rest of the episode, up until he snaps out of it to beat the crap out of Bart (who tells that he was the one who told Samantha's father about them). The next day, Milhouse and Samantha's brief reunion at her new convent school is cut short when the class bells rings and the girls have to go back in. After sharing one last kiss (in an all-girl Catholic school where the punishment for kissing a boy is 50 rosaries, this means a lot), Samantha is never seen or mentioned again, while Milhouse harbors a hopeless crush on Lisa throughout the rest of the series.
    • In the subplot, Lisa becomes worried about Homer's health after a watching a video about the dangers of obesity that she has an Imagine Spot of Homer's funeral. Granted its Played for Laughs with the family being crushed under Homer's casket, but the fact that Lisa is worried about her own dad's health makes it all the more heart-wrenching.
  • ''Saturdays Of Thunder":
    • Homer and Bart having a falling out after Bart agrees to drive Martins soap box racer, the Honor Roller, due to his injury, especially after the two bonded so closely while building their own car Lil' Lightning. This is one of the few times, especially this early in the show, where you can tell that Homer is genuinely hurt. To add insult to injury, Lightning falls apart again when Homer sits in it.
    Homer: I'll just sit here in Lil' Lightning, and remember that for one brief, shining moment... I had a son...

    Season 4 
  • Lisa being upset over her appearance in "Lisa the Beauty Queen" will affect those who have had self-esteem issues over their appearance. Homer tries to boost her self-esteem by entering her in a beauty pagent, but it temporarily backfires when he sends the same picture that broken her spirit in the first place.
    Lisa: (in tears) How could you? I won't do it!
  • If you have any recollection of what it's like to want something as a kid, "Itchy & Scratchy: The Movie" will be hard to watch. After a lifetime of Pushover Parenting, Homer finally puts his foot down just in time to forbid Bart from seeing the fiercely-awaited and much-hyped Itchy & Scratchy movie, and manages to keep the moratorium up over an 8-month theatrical run, while all of Bart's friends see the movie repeatedly and gush about how great it is. Even Marge and Lisa think he's taking it too far!
  • The ending of "Lisa's First Word", in which Maggie says her first word, "Daddy". For context on why it's heartbreaking: all throughout the story, Bart and Lisa (as babies/toddlers) never called Homer "Dad" or "Daddy" and the one time a Simpson kid does call Homer "Daddy," he misses it (and right after telling her "I hope you never say a word").
    • Bart feeling totally rejected throughout the episode could really bring to light how insecure he actually is. Especially since Marge and Homer never once take the time to try and spend more time with him or even tell him that they still love him, even though Lisa is getting the lion's share of the attention.
      • Before Lisa is born, it's shown that Patty and Selma get a kick out of Bart's singing and even pay him to perform for them, to the point where it's become a routine. When they're fussing over newborn Lisa, he tries to sing "Alouette" for them and just gets snapped at for being irritating.
  • "Homer's Triple Bypass":
    • As Homer and Marge discuss in bed that they don't have the money to pay for Homer's potentially vital surgery, he ultimately just goes into one of his off-tangent one liners. The episode has been good so far at playing the subject light heartedly....but then Marge just abruptly breaks down in tears. It really hits here that Homer could die.
    • Homer praying to God (before the nurse shushed him and pointed to the "No Praying" sign) to look after Marge and make sure Bart, Lisa, and Maggie grow up right should the worst happen to him.
  • Selma feeling sad that she's not mother material after her bad day at Duff Gardens on "Selma's Choice" (even Homer of all people holds her hand in sympathy when she laments that she couldn't care for Bart and Lisa during their disastrous trip), and the ending where she finally gets a "little version" of herself to love and care for — the pet iguana, Jub-Jub (that was originally given to Marge's mom, Jackie, but she tried to stab it with a hat pin.) For all post-classic Simpsons fans: this was before Selma adopted the Chinese baby on season 16's "Goo-Goo Gai Pan"
  • "I Love Lisa" is Ralph Wiggum's Moment of Awesome. After Lisa humiliated him at the Krusty the Klown 29th-anniversary special, he prepares to play George Washington for the President's Day show, with Lisa as his Martha. He tosses the valentine she gave him into the fire...and gives the performance of his friggin' life. It even moves Groundskeeper Willie to tears.
    • George's final words:
    Ralph: (as George) Dear wife, if I could take but one treasure with me to the next life, it would be your tender kiss. (He kisses Lisa's hand and "passes on" as she weeps.)
    Selma: Mmmhmm... now THAT'S a man.
  • Even though it's Played for Laughs, the scene from "Marge Gets a Job" where she and Mr. Burns use the security cameras to spy on three upset coworkers (one who is crying, another who is an alcoholic and the other is obviously mentally unstable and wielding a shotgun) is both heartbreaking and bothersome. Plus, her "solutions" to cheer them up, consisting of funny hats and Tom Jones music, does nothing to solve their problems.

    Season 5 
  • In "Homer's Barbershop Quartet," Skinner is looking through Herman's stall at the swap meet and finds his exact Vietnam POW helmet. He says that he wore it for two years at a Viet Cong internment center, and is amazed that it still fits. Herman, in what is perhaps his only time of concern, says "small world huh?" with Skinner agreeing. It is just one of those moments that reminds you of the hell Skinner went through.
  • In "Rosebud," there's the scene near the ending when Mr. Burns fails to get his beloved childhood teddy bear back from Maggie, and in an uncharacteristically somber way, just gives up and lets her have it. What he ultimately says to her, before sadly walking away, further emphasizes his somewhat Lonely at the Top nature:
    Mr. Burns: Okay, Maggie. You win. But I want you to do something for me. Hang on to that bear. Don't make the same mistake I made. (sighs)
    • It's easy to miss, but when Mr. Burns angrily tries to attack Smithers and eventually collapses in his arms, he's actually crying a little bit.
    • The ending, when Maggie eventually gives Mr. Burns back Bobo, is tearjerking in the heartwarming sort of way. Mr. Burns's smile and happy sigh as he hugs his old teddy bear is just precious.
  • Homer coming to the defense of Flanders in "Homer Loves Flanders," after inadvertently causing the townspeople to turn on him. Having just loudly cussed Homer in church, - the climax of spending the episode trying to ward off Homer's new-found admiration. Flanders himself is openly moved and humbled to tears by this unusually tender speech from his neighbor.
  • In "Sweet Seymour Skinner's Baadasssss Song" Skinner, after being fired from Springfield Elementary, stares at the school and sobs at the memories of the students. Even sadder is that it convinces him to re-enlist in the army because it was "the only thing besides school that has ever given my life meaning."
  • "Lady Bouvier's Lover:"
    • When Smithers helps Mr. Burns write a love letter to Marge's mother, he comes up with something very heartfelt. Mr. Burns asks Smithers how he was able to come up with such an amazing love declaration on the spot. Smithers reveals that he wrote the exact same thing for Burns. Heartbroken that Mr. Burns doesn't remember (or possibly never even read) his love letter, Smithers runs away in tears.
    • Mr. Burns is in such a good mood after finding love that he announces to his employees that "everyone who has found true love may leave early today". Everyone cheers and leaves...except for one man who's standing there on the brink of tears.

    Season 6 
  • A small but heartbreaking gag in "Sideshow Bob Roberts": Bart hastily tries to one-up Lisa's class project by saying he's doing a class project on "fireworks"—grabbing the item closest to him. Marge chides him for lying and throws the fireworks out. Turns out he really had been slated to provide a fireworks display as part of a public sendoff for some visiting Chinese principals, and when he shows up empty-handed, Skinner is angry with him and Edna gives him his latest and least-deserved F. He can only hang his head in response.
  • "Lisa On Ice": The episode involves Bart and Lisa discovering they have a talent for hockey, and as a result their Sibling Rivalry gets wrenched up to eleven. They spend the whole episode viciously competing against each other. Eventually, they reach the end of an important match, and both teams are tied. As Bart is heading over to the goal to make the winning shot, the crowd starts yelling "Kill, Bart" (or "Kill Bart", for Lisa's supporters), baying for blood. Bart and Lisa look at each other, and both remember happier times - Bart remembers helping Lisa reach for the cookie jar, Lisa remembers Bart giving her a scoop of his ice cream after she dropped hers. Both decide to throw down their sticks in the final seconds of the game, which results in a tie. Marge sheds tears of pride for her children, while Homer sobs, exclaiming "They're both losers!" As a result, Chief Wiggum incites a hockey riot while Bart and Lisa peacefully skate around the rink.
    • There's also this:
      Snake: Those kids are, like, so sweet. If only they had had pee-wee hockey when I was a lad. (sniffles) Oh well! (grabs a crowbar and joins the riot, wrecking the arena)
  • "And Maggie Makes Three": Homer quitting his beloved job as a Pin Monkey and going back to the Power Plant. Most heartwrenching is the guys at the alley pitched in and bought Homer a nice jacket as a going away present but the acid rain near the plant dissolved it immediately after he got it.
    • In the same episode, Bart asks Homer what he does with photos of Maggie, since there never seem to be any around the house. Homer responds that he keeps them, "where I needs them the most." The scene then cuts to the reactor where Homer works. Above his workspace is a plaque that reads, "Don’t Forget, You’re Here Forever". That itself is tearjerker enough as it is for a different reason, but at present day of the series, Homer has partially covered the letters with pictures of Maggie in such a way that the plaque now reads, "Do It For Her." That's enough to make any dad tear up.
  • In "A Star is Burns", there's (the unfortunately named) Pukahontas, the film Barney did about how his alcoholism has ruined his life (even worse when you remember that Homer unintentionally ruined his best friend's life by pressuring him to drink in the first place). Despite the funny part where he mistakes Lisa's Girls' Scout meeting for an AA meeting, the rest of the film is very depressing and shows a dark side to Barney's alcoholism. Made worse by the fact that the prize Barney receives is a lifetime supply of Duff Beer.
    Barney: My name is Barney Gumble. I'm 40, I'm single, and I drink. There's a line in Othello about a drinker - "Now a sensible man, by-and-by a fool, presently a beast". That pretty well covers it.
    Barney: Don't cry for me. I'm already dead...
  • Homer's speech to Lisa before her wedding, in "Lisa's Wedding":
    Homer: Little Lisa, Lisa Simpson. You know, I always felt you were the best thing my name ever got attached to. Since the time you learned to pin your own diapers, you've been smarter than me.
    Lisa: Oh, Dad...
    Homer: No, no, let me finish. I just want you to know I've always been proud of you. You're my greatest accomplishment and you did it all yourself. You helped me understand my own wife better and taught me to be a better person, but you're also my daughter, and I don't think anybody could have had a better daughter than you...
    Lisa: Dad, you're babbling.
    Homer: See? You're still helping me.
  • Whether you love or hate Bleeding Gums Murphy, "'Round Springfield" is one of those episodes that would make you cry a lot if you were Lisa. The "Jazz Man" song can also make one burst into tears.
  • On "Who Shot Mr. Burns? Part One", after Mr. Burns fires Smithers for disobeying his orders, Smithers becomes a drunken wreck. He even mentions how Mr. Burns was the closest thing he had as a friend and sobs pitifully.

    Season 7 
  • On "Who Shot Mr. Burns? Part Two", a depressed Smithers walks down streets as he tries to put his memories together and he then comes in conclusion that he was the one who shot Mr. Burns.
    Smithers: Oh, Mr. Burns! What have I've done? (cries in agony)
    • Lisa blocking the police when they try to nab Homer.
      Lisa: STOP! Don't shoot my dad!
  • In "Home Sweet Homediddly-Dum-Doodily," the kids get taken by CPS due to a series of misunderstandings, and it's startlingly not Played for Laughs. The scene of Marge trying to run after them and having to be restrained is especially heartwrenching. Even the fact that they've just gone next door to the Flanders' doesn't help matters, as they're forbidden to communicate and both parents and children feel the pain of being separated by a mere 10 feet. At one point Homer and Marge recognize Bart's obnoxious doorbell ring and run eagerly to the door but find nothing there but a pretend newspaper the Flanders kids had been creating earlier, on which Bart had printed the headline "TODD SMELLS." Homer is disappointed, but Marge tells him to turn it over and we see another headline: "SIMPSON KIDS MISS MOM & DAD."
  • Near the end of "Bart Sells His Soul," Bart tearfully begging God for his soul back. At this point he's aware that Comic Book Guy sold the paper representing the transaction to an unknown customer, and he's terrified he'll never get it back. He's also scared that without a soul, God might not even be able to hear him. It's about as desperate as Bart gets.
  • On "Mother Simpson", the above ending image of Homer sitting alone on the boot of his car for hours, well into the night, is possibly the saddest image ever seen (beaten only by the end of Futurama's "Jurassic Bark"). Definitely a Bittersweet Ending.
    • There was also this fact. At that time, Fox started ending shows with split-screen credits with ads for Fox shows playing over it. The Simpsons staff had to fight tooth-and-nail to have the full studio credits play over that beautiful shot — and they got it.
    • What makes this ending sadder is that they give credit to Jackie Banks, a member on the show, who died fifteen days prior to the episode's airing.
    • This exchange between Homer and Marge, targeting how, even after over two decades years, some part of Homer has always wondered if he was the reason his mother left him:
    Marge: I just don't think you should get too excited about the woman who abandoned you for 25 years. You could get hurt again.
    Homer: First, it wasn't 25 years — it was 27 years. And second, she had a very good reason.
    Homer: [pause] I dunno. I... guess... I was just a horrible son and no mother would want me.
    Marge: Oh, Homey, come on. You're a sweet, kind, loving man. I'm sure you were a wonderful son!
    Homer: (unhappy) Then why did she leave me?
    • When Mona told the family about when she had to leave and the scene where she gave a sleeping Homer one last kiss on his forehead and walked away saying she'll miss him was just heartbreaking. We flashback to the present, with Homer saying he remembers her kissing him, but thought it was a dream.
    • As Mona and Homer say their goodbyes before she heads back living low:
    Homer: At least this time I'm awake for your goodbye.
    • Before Mona gets in the van, when she says "You'll always be a part of me", you can tell that she's trying not to break.
    • When Homer says "Don't forget me!", as Mona heads to the van, if you look closely, you can see tears in her eyes.
    • The way Mona and Homer meet for the first time in decades. While trying to clear his name from faking his death, Homer discovers that the town's records list Mona as being alive. Mona by chance visits Homer's gravesite, only to see Homer in the ditch.
    Mona: You awful, awful man! Get out of my son's grave!
    Homer: I'd hate to rain on your parade, lady, but this is my grave! (pauses) Hey, wait a minute... Mom?
    Mona: Homer?
    Homer: I thought you were dead!
    Mona: I thought you were dead!
  • In "Marge Be Not Proud", after Bart is caught shoplifting the video game Bonestorm, Marge freezes him out of family activities (such as tucking him in at night; even though Bart never looked forward to it, he immediately feels how crushing it is when she doesn't do it). That alone would qualify, but at the end of the episode, Bart comes in with a mysterious item under his jacket. Marge suspects he's shoplifted again... but Bart went back to the store to take a Christmas portrait of himself (that he actually paid for). Marge is touched and forgives him by giving him his Christmas present, a video game. Although he's internally underwhelmed that it's Lee Carvallo's Putting Challenge and not Bonestorm, he's just happy to have her love again and thanks her.
    • The entire part where Marge cuts Bart off from all family activities was depressing (except maybe for the part where Bart puts a marshmallow in his cocoa and it turns into a cocoa-soaked loaf that he has to eat with a knife and fork, with Grampa asking him for a slice) for anyone who has felt like his or her parents don't love them anymore.
    • The build up to this from Marge's perspective is equally tear jerking. She looks upon her life with Bart and that somehow he managed to slip out of her arms, wondering if her coddling has ruined him.
    • The credits scene showing gameplay of Putting Challenge becomes really sweet if you assume it's Bart who's playing. He's so glad Marge is paying attention to him again that he decides to simply play the game Marge bought him instead of complaining.
    • Marge defends Bart when he's accused of shoplifting, stating that he "may not be perfect" but she knows in her heart that he's not a shoplifter. When Brodka whips out the security tape, she tells him to go ahead and play it so that everyone will see he's got the wrong kid. At this point Bart fesses up, but stands in front of the monitor because he doesn't want her to have to actually see it.
    • The scene in which Bart asks Luann, who's kicking him out of the house as usual, if he can hang out with her while she does "mom stuff." She softens and lets him help stamp Christmas cards:
      Bart: Who are Dan and Sherry Adler?
      Luann: Just friends of ours.
      Bart: Oh. And who's Warren Burke?
      Luann: He used to tune our piano before we got rid of it. He grew up in Mechanicsburg.
      Bart: (badly feigning interest) Oh, really! (Luann looks at him.) Tell me I'm good.
  • In "Scenes From The Class Struggle In Springfield", Marge buys a new dress that earns her a bunch of wealthy, snooty new friends. She tries to take her family with her to the country club. On the way there, Homer says he's going to tell a rude anecdote that got him "bleeped" when he tried to tell it on the radio, Bart says he's going to get an old lady to leave him all her money, and Lisa is going to ask all the rich people if they even know their butlers' names. Marge gets angry, thinking the family are going to make her look bad, and scolds them all. She even gives Maggie a Death Glare for sucking on her pacifier! They all hang their heads and say sorry. The real Tear Jerker moment, though, comes when Homer says this, which is so sad it makes Marge realise how horrible she's been:
    Homer: You kids should thank your mother. Now that she's a better person, we can see how awful we really are...
  • From "Lisa the Iconoclast", there's the scene after Homer's job as town crier is taken from him, and he's just sitting at the kitchen table swinging a clock back and forth. He really wanted that job, and he was good at it, and it gets taken away from him just because Lisa wanted to tell the truth.
    Lisa: I'm sorry, dad. I know how much you wanted to be in the parade.
    Homer: It's okay, Lisa. I'm supposed to be the responsible one. I shouldn't have let you let me get carried away.
  • "A Fish Called Selma" is very funny but it is also clear that Selma is terribly lonely, willing to go through a sham of marriage just for the appearance of being happy. Troy himself comes across as just as alone and the last glimpse of him sadly watching Selma walk away might be one of the saddest in the show's history. If the shows implication about his sexual inclinations is true (its all but stated that he's sexually attracted to fish), a normal relationship with a real family might be all but impossible for him.
  • In "Much Apu About Nothing", Apu faces deportation due to being an illegal immigrant. In desperation, he buys a fake ID and tries horribly to act American, only to feel ashamed at rejecting his Indian heritage, and breaks down and cries over being deported. Homer is so shaken he stops his support of the Proposition.
  • Pretty much the whole of Lisa's story through "Summer of 4 Ft. 2". The hits start coming when her yearbook gets passed around by the other students and no one bothers to sign it, and keep coming through Lisa trying to reinvent herself and gain actual friends, only for Bart to ruin it because he's jealous that Lisa's made friends with the cool kids. The tears get to be joyful when the kids reveal that they still like Lisa and that they've attached all this stuff from the beach to the Simpsons family car so she can remember them when she leaves.
    • On the night before they leave on the trip to the Flanders' vacation house on the coast, Marge tells Bart to remind Milhouse of the departure time, and tells Lisa to go ahead and invite a friend along. As they pack for the trip, Marge asks Lisa which one of her friends she invited, and Lisa sadly tells Marge that she's only bringing books on the trip because none of the other kids at school likes her enough to be her friend. After Marge gives the "Be Yourself" advise, Lisa angrily tells herself that being herself is the reason why she's so unpopular.

    Season 8 
  • "Burns Baby Burns" has Burns' lost long son, Larry track him down and the two for a while manage to bond. But then Larry's uncouth tendencies wear on Burns' nerves, leading him to make coldly clear he's done with him:
    Larry: Dad, what's with you tonight? I mean, I'm getting frostbite over here.
    Burns: I'll tell you what's "with me"; the humiliation of having a coarse, boorish ignoramus for a son! *storms off*
    Larry: *gutted* What's the matter, Pop? Don't you love me anymore?? *door slams*
  • After his house is destroyed in "Hurricane Neddy", Ned heads into the church at night and pleads with God for a reason as to why he's lost everything. While not exactly a tear-jerker per se, it's arguably one of the show's most powerful quiet moments, in that there's no humor in it at all. It's just a despairing man trying to make sense of events beyond his control.
    Ned: Why me, Lord? Where have I gone wrong? I've always been nice to people. I don't drink or dance or swear. I've even kept kosher just to be on the safe side. I've done everything the bible says, even the stuff that contradicts the other stuff! What more can I do? I...I feel like I'm coming apart here! I want to yell out, but I can't just can't dang diddily do dang do damn diddily darn do it! I...I...I...
    • The scene where he finally snaps (after the neighbors make a total pig's ear out of rebuilding his house) and shouts everyone down is undeniably funny but also a little scary and a little sad. Ned is being a jerk, true, but none of his accusations are wrong, and the townsfolk are clearly a little ashamed of pushing him over the edge. The worst part is that while most of Neds accusations are true, they came at exactly the wrong moment, when the neighbors only crime was not being good enough, which is hardly their fault. It was just the straw that broke the camels back.
    • Then immediately afterwards, Flanders stoically barges into the mental institution, and declares he must be committed specifically for turning on all his neighbours in spite of their well meaning attempts. It took that quick for Flanders' conscience to kick in and insist on such a heavy punishment.
  • From "The Itchy & Scratchy & Poochie Show" where Homer is trying to keep them from killing Poochie off, and he makes a speech: "Hello Itchy. I know we kind of got off on the wrong foot, and that there are a lot of people who don't like me. I know that I can come off as a little proactive sometimes, and for that, I'm sorry. But if you can find a little place in your heart for the little dog no one wanted, I know we can make people laugh, and cry, as we grow old together."
    • Which gets blasted down when the episode featuring this speech gets hastily edited to make it look like Poochie was really an alien who returned to his home planet and died on the way back. In fact, that part is more heart-breaking than Homer's speech, as Homer poured his heart and soul into supporting something he liked, but no one else did ("rooting for the underdog," so to speak) and, in the end, it was all in vain.
  • In "Grade School Confidential", Principal Skinner and Mrs. Krabappel attend Martin's birthday party, talking about their hobbies (Principal Skinner spends his Saturdays preparing his clothes for the following week; Mrs. Krabappel collects matchbooks from nightclubs). They go silent for a second, and then Principal Skinner asks, in a defeated tone, "Is this what you imagined your life would be, Edna?" Mrs. Krabappel replies, "Yes. But then again, I was a very depressed little girl." It's a beautiful little moment that makes them both seem remarkably human.
  • "The Canine Mutiny" is an uncomfortable watch for any dog-owner, with Bart neglecting Santa's Little Helper in favor of a newer and more impressive dog attained through mail fraud, cumulating in giving Santa's Little Helper away in desperation to keep the new dog from being seized by the repo man. What makes it worse is that up to the point where this happens, Santa's Little Helper isn't even upset, but waits patiently for Bart to pay attention to him again with his tail wagging in anticipation, having no idea that he's been replaced in Bart's affection. From there Bart has the expected My God, What Have I Done? moment and even admits that he probably doesn't deserve Santa's Little Helper back.
  • "The Old Man and the Lisa" features the Mood Whiplash of the grocery store scene. It starts off funny enough, with Mr. Burns struggling to do the basic task of grocery shopping. Things go downhill when a grocery clerk mistakes his confusion for genuine senility, and has the police send him off to a retirement home entirely against his will. He's clearly confused/distraught by this and asks "Where are you taking me? What's happening?" After he's taken there by the cops, he can only say, "But... I'm shopping!" pitiably. He then comes very close to crossing the Despair Event Horizon, retreating into a back room of the retirement home to ignore everyone else and sulk quietly, watching the leaves fall off of a tree outside the window.
    Mr. Burns: So this is how the Monty Burns saga ends... (sighs despairingly)
  • In "The Secret War of Lisa Simpson," when Bart is forced to stay in an all boys' Military School, Lisa decides that she wants to stay too because she finds the curriculum challenging. Being the New Meat, both Bart and Lisa are hazed by the other boys, however they deem Bart worthy of being accepted and he fits in rather well. Lisa, because she's the only girl, is isolated and alone, ignored by the other cadets, or actively bullied. The saddest shot of the episode is when Lisa invites Bart over to listen to a tape Marge sent on a care package, but he turns down her offer because he fears the other cadets will bully him as well. Lisa lies on her cot in the girls' barrack, as she is the only girl in school, completely alone as she plays the tape that has Marge singing "You are my Sunshine," while Bart spies trough his barrack's window, clearly having a "My God, What Have I Done?" moment.
  • In "A Milhouse Divided", the Van Houtens marriage is revealed to be on the rocks. It finally comes apart and they divorce at Marge's party. Kirk ends lamenting how much of a lousy husband he was.
  • In "The Twisted World of Marge Simpson," Marge starts her own pretzel business after she was kicked out her women's investment club. However after some setbacks, she takes Lisa's advice to give out some free pretzels at a baseball game so that people can taste them, and buy their next pretzel. At the baseball game, when Mr. Burns wins a new car, the crowd throws their pretzels at him in frustration, instead of eating them. Following the baseball game fiasco, the family tries to cheer up Marge by telling her to not give up and keep going, only for Marge to sadly admit defeat, and advises Bart and Lisa to not have any lofty hopes and goals, so that if they do succeed it will be easy to do, and is they fail no will care or notice if they do.

    Season 9 
  • Skinner's story in "The Principal And The Pauper" (even though it's heavily criticized for screwing with Skinner's continuity and being a "gimmicky, nonsensical" episode, it does have a lot of heartfelt scenes showing that people do care about Skinner, even the woman whom Skinner calls "Mom").
    Real Skinner: You've led quite a life, Tamzarian.
    Armin Tamzarian: It's your life. I just kept it warm for you.
    • There's also when Skinner makes his spur-of-the-moment decision to pose as Agnes' son, having been sent home from Vietnam to deliver her the news he was MIA and presumed dead. Skinner's voiceover posits he thinks Agnes knew deep down he was not Seymour, but couldn't deal with the idea that her son was dead and accepted the fiction as fact instead. Her sending Skinner to his room and inmediatly clarifying where it is in the house strengthens that theory.
  • "Lisa's Sax" shows the story of Bart's first day at school, where his kindergarten teacher almost immediately manages to crush his enthusiasm for school with a single sentence ("Added extra clap, not college material"), and the discovery of Lisa's intelligence comes at a meeting with a school psychologist, where Homer declares Bart effectively hopeless, at the age of five. Just seeing Bart being given up on so casually by his first teacher is heartbreaking, but to also see his parents doing the same in favor of Lisa. The episode subtlety implies that all of Bart's pranks and antics, it's all just a coping system, so he wouldn't be depressed anymore.
  • Homer briefly mourning the loss of his family in the first segment of "Treehouse of Horror VIII" (The HΩmega Man), after a neutron bomb wipes out all of Springfield.
    Homer: Oh my God... EVERYONE'S GONE!! (crying) Little Bart... (imagines Bart swinging a baseball bat) Little Lisa... (imagines Lisa also swinging a baseball bat) Little Marge... (imagines Marge doing likewise, then imagines Maggie, Santa's Little Helper, Snowball II, and the TV all floating around) ...And the Rest... (sobs) Oh, I've lost everything! I can't go on...
  • The excised lyrics from the original version of "Trash of the Titans"' "The Garbageman" has these lines:
    Milhouse: Who can take my daddy, and my mommy too? Make them get along like moms and dads are supposed to do? The Garbageman? I hope the Garbageman can.
    Homer: The Garbageman can't, but he's got a giant stack of horror comics for you.
  • "Lisa the Simpson," the episode that deals with the infamous "Simpson gene," which supposedly makes all Simpsons lose their intelligence around age 8, as evidenced by the prior cases of Abe, Homer and Bart. Lisa resigns herself to losing her intelligence until meeting other members of the family offers a hell of an Esoteric Happy Ending: the gene only affects the male line, and Simpson women are all intelligent and successful. She's unashamedly thrilled, but Bart is less so.
    Bart: So wait a minute. This means I'm gonna be a failure?
    Homer: Yes, son. A spectacular failure.
    (Bart considers this sadly, then shrugs and goes back to the dangerous head-butting game he was playing with all his male relatives.)

    Season 10 
  • Homer experiences one hell of a Trauma Conga Line in "The Wizard Of Evergreen Terrace". First he has a Heroic BSoD when he realizes he's lived half of the average male lifespan and has nothing to show for it. Then after his family tries to cheer him up with a film of his accomplishments which fails. He then decides to be an inventor after he hears about Thomas Edison, but the only things he can come up with are terrible or dangerous. The only good thing he comes up with is adding extra legs to a chair so he'd stop falling backwards, and then it turns out that Edison had already done it. At the end of the episode, the chair is discovered in Edison's museum along with Homer's electric hammer. In the end, Homer has nothing to show for his efforts.
  • The scene in "Bart the Mother", when Bart tells Marge that even though everyone thinks the lizards are monsters, he still loves them. He thinks Marge won't understand, but Marge whispers "run" and then blocks the door so Bart, Chirpy Boy, and Bart, Jr. can escape. Similarly, the scene when Bart accidentally shoots a mother bird with a pellet gun and Marge finds out-
    Marge: What's the point, Bart? I punish, and I punish, and I punish, but it never sinks in. So you know what? Do what you want. You wanna play with little hoodlums, fine. Have fun killing things.
    • Most mothers wouldn't be particularly proud of their children killing birds, but that was a little too blunt. To flat out give up on Bart like that? Jesus...
    • Mind you, this is after ten years of trying to raise her son right, a son who has spent his entire life fighting her every step of the way. On the other hand, after deciding to ignore him from now on, she then does the opposite of that and meddles with what Bart is doing in his treehouse as if to spite him. Jeez, Marge.
    • The exchange that causes Marge to help Bart escape with his lizards despite the fact that federal law demands they be killed. Bart, in describing his feelings about the lizards, accidentally describes Marge's situation as his mother.
      Bart: Everyone thinks they're monsters, but I raised them, and I love them! I know that's hard to understand.
      Marge: Not as hard as you think.
    • The end tribute to Phil Hartman, making his last Simpsons appearance as Troy McClure (the episode originally aired 3 days after what would have been his 50th birthday). For many people, The Simpsons was never the same without him.
  • Pinchy's death in "Lisa Gets an "A"" is deceptively sad. After spending the episode growing attached to his raised lobster, Homer adopts it and treats it like an equal in the family, even giving it a place on the family table despite vigorous protest from the others. The poor thing even had something of a personality, whimpering and even wagging its tail like a timid little puppy. Then comes the revelation that Homer accidentally boiled Pinchy to death, after which he decides to finally eat him ("Pinchy would have wanted it that way"), sobbing uncontrollably throughout the entire meal.

    Season 11 
  • "Alone Again, Natura-Diddily": Maude's death, and Flanders' reaction.
    • Rod and Todd's reaction too. Especially when they're solemnly playing ball after their mother's funeral.

    Season 12 
  • "HOMR". When the crayon is removed from Homer's nose, he learns that being a genius isn't all it's cracked up to be. The poor guy gets alienated from his friends.

    Season 13 
  • "The Blunder Years":
    • Waylon Smithers Sr.'s Heroic Sacrifice of going into a heavily irradiated reactor to shut it down and save the town and his baby son. It parodied the infamous Window Love scene from Star Trek II: The Wrath of Khan.
    • It's also a rare Pet the Dog moment for Mr. Burns. After Smithers Sr.'s death, he becomes the closest thing Jr. has to a father.
      • A bit of Unfortunate Implications though, seeing as Smithers is revealed to be gay for Mr. Burns.
      • That last bit was hinted in the same episode to stem from Mr. Burns telling Smithers his father was killed by a tribe of Amazon women.
    • While Mr. Burns is far from a nice guy, it's still tearjerking to see how depressed he is when Waylon Sr. dies.
      Mr. Burns: Smithers Sr. gave his life to save the plant.
    • Homer revealing that his being a fat slob can be traced back to him getting a lapfull of dead guy, and that he's struggled with necrophobia (pathological and irrational fear/dislike of corpses) ever since.
  • Bart reveals some inner conflict in "Jaws Wired Shut."
    Bart: So the substitute teacher comes in and says her name is Mrs. Doody. And everyone's lookin' at me like, "Take it, Bart, run with it!" ...Then it hits me. I've become a clown. ...A Class Clown, and it sickens me!
  • "The Frying Game". While inevitably Homer and Marge were going to survive, the whole episode basically shows their lives gradually going downhill after they are framed for murdering an old lady. The trial process ultimately ends up ruling them both guilty despite their best efforts, they're not even given a lie detector or DNA test and they're both sentenced to death. Homer ends up confessing that he did it in order to spare Marge, who is released. Then it cuts to Homer's execution by electric chair, where Marge vows tearfully that she'll always love him, while Patty and Selma are openly rejoicing. It's a setup, of course, and Homer is let free, but that doesn't make the scene any less heartbreaking.

    Season 14 
  • "How I Spent My Strummer Vacation" has Homer when he's black out drunk and has said that he loves his family and can't imagine his life without them. Then he mentions that there's other days where he regrets how his life turned out, that he struggles with being a husband and father and hates his job and that he's grown fat and bald. His family is understandably upset and he feels awful for hurting their feelings.
  • "Barting Over" (the alleged 300th episodenote  where Bart gets emancipated after Homer admit he blew all of Bart's money that he made as a commercial actor): Bart's absolutely terrified while spending his first night alone in a dumpy apartment. The way he says, "I'm gonna die in my jammies!" when riding the elevator is particularly heartbreaking.
  • "Strong Arms of the Ma":
    • Marge develops extreme agoraphobia after a chance encounter with a mugger. It escalates to the point where she ends up living inside her own basement. Fortunately, she eventually overcomes her fear...but it then goes too far in the other direction once she starts taking steroids.
    • This culminates in a rampage at Moe's that would give She-Hulk pause, and the only thing that stops her is Homer, who is audibly on the verge of tears. Leave it to The Simpsons to bring one of its most tender moments after an episode of violence, paranoia and steroid abuse.
      Homer: Somewhere in that sea of bull hormones is the sweet, wonderful girl I married. The woman who, instead of swatting a fly, would give it a bath and send it on its way. (voice breaking) I'd sure like to go home and have Jiffy Pop with her!
  • "I'm Spelling as Fast as I Can": Lisa losing the spelling bee. The look on her face when she realises that she just lost her chance of going to a dream college for nothing is heartbreaking.
    • Turns into a heartwarming moment when Springfield still recognizes her as a winner, as the town hasn't had anyone famous since that woman who once dated Charles Grodin.
  • In "Moe Baby Blues", Moe decides to commit suicide after being rejected from Springfield Botanical Gardens which is holding the blooming of the Sumatran Century Flower because, in Chief Wiggum's own words, "his feelings have been trampled on so many times that once more won't make any difference" and finding out that even street-dwelling hobos have a better life than him. While preparing to jump off the bridge, he accidentally saves Maggie from falling into the river after flying out of the Simpsons car to a faulty safety lock. The townspeople applaud him and laud him as a hero for this act. Because of this and the adorability of Maggie, his monstrous frown gradually turns into a smile then he says "Heh. Life don't seem so hard no more." It's not ruined by a dumb joke either, it cuts to commercial after the line.

    Season 15 
  • Mona returns in "My Mother the Carjacker" has three major moments. The first one is when Mona is arrested for using an alias for a federal park and admitting to it and Homer trying to chase after the car to get her back, with the FBI agent constantly braking every few meters just for a laugh. The second one comes after Homer steals the prison bus she's on and Mona stuns him and throws him out of the bus. She then attempts to escape and the bus falls off the side of a cliff and Homer can do nothing but watch. The third part is her funeral and Homer's speech about how at least he can't lose her again and then the casket slides down the hill, Homer then spends the next scene desperately try to find evidence that she's ok and misses it completely.
  • In "I, (Annoyed Grunt)-Bot," Homer tries to enter a Robot Wars-style competition with Bart in order to win his respect but winds up controlling the "robot" from the inside after it becomes clear that he doesn't have what it takes to build a functioning robot. He successfully makes it through multiple rounds of the competition while injuring himself repeatedly in the process, leading to this line when his arm gets sliced open:
    Homer: Doin' it for the boy. Doin' it for the boy. Pain is love. To bleed is to care!
  • "Milhouse Doesn't Live Here Anymore":
    • The episode opens with Nelson being humiliated on the school bus for having an effeminate lunchbox, then being thrown off for being too poor to afford the fee for the field trip. He looks at his reflection in a window and sees himself wearing a top hat and tails.
    • Bart gets depressed at Milhouse moving away and cries watching home movies of them. To anyone who's lost contact with childhood friends in this manner, this hits hard.
    • In Milhouse's absence, Bart and Lisa become best friends and discover an Indian burial ground that they have as their own secret. Then Milhouse comes back and Bart tells him about the ground. Lisa is aghast, but Bart says that he's his best friend. Lisa understands and starts to cry as they leave.
  • "The Wandering Juvie":
    • Bart getting thrown into juvenile hall. Yeah, he did pull a prank to deserve it, but seeing Marge cry as he is being taking away strikes a chord with any parent whose child has been in legal trouble.
    • Juvenile hall is pretty rough on Bart, where he is bullied constantly, especially by a girl named Gina. Then we see her alone and crying, and Bart learns that she doesn't have a family.
  • Seymour and Edna breaking up at their wedding in "My Big Fat Geek Wedding", spelling an end to an iconic classic-era pairing. Made even worse with Edna moving on to marry Ned Flanders a few seasons later, meaning their relationship never recovered, and with Marcia Wallace's (and Edna's) death, likely never will.

    Season 16 
  • "Sleeping with the Enemy":
    • Nelson really misses his father. The scene when he sings "Papa Can You Hear Me" really drives it home.
    • The B-plot, which revolves around Lisa struggling with anorexia. She even explains in the Bittersweet Ending that while she's willing to eat again, her body image issues are not gone and likely never will be. Even worse, her body image issues only began to surface after some bullies fat-shame her out of nowhere by making fun of her supposed "big butt". It really hits home for people who have been mocked for their appearance in real life.
  • The first act of "Fat Man and Little Boy" deals with Bart being forced to come to terms with growing up. He's definitely depressed about the fact, even giving his old toys a viking funeral.
  • In "Midnight Rx" when Smithers gets sick from having not taken his thyroid medications, he says to Mr. Burns that before he dies he wants to say something and raspily manages to say "I love you," and then he faints.
    • Hearing Mr. Burns of all people saying that he "would move heaven and earth" to save Smithers was strangely moving.
  • "Pranksta Rap:
    • This one is made more tragic in hindsight. During the Credits Gag, Superintendent Chalmers is being paid by Alcatraaaz to do hip-hop. As the hip-hop artists laugh at him, Chalmers confides to Skinner, "I think they're making fun of me, but my wife is very sick." Seven seasons later, we learn that by "Bart Stops to Smell the Roosevelts", she is dead.
    • When Bart calls his family, pretending to be his kidnapper, Marge pleads with him to return Bart and bursts into tears. This guilts Bart into briefly dropping the charade and telling her not to worry, which makes Marge cry even more.
  • Bart having a heart attack in "The Heartbroke Kid". What makes it even more difficult to watch if his family rushing over to him to see if he's okay. This scene can definitely hit home for those who've had or have a loved one who suffered a heart attack before.

    Season 17 
  • In "Milhouse of Sand and Fog," Milhouse's Imagine Spot set to Crosby, Stills, Nash & Young's "Our House" when his parents tell him they're going through a "trial unseparation" and might get back together shows how much the divorce affected him, depicting scenes like Luann spending time with other men and a Bungled Suicide attempt on Kirk's part. It ends with Milhouse landing softly in his parents' arms and Lisa appearing all dressed up for their wedding at the line "Now everything is easy 'cause of you."
    Milhouse: I haven't daydreamed in color in so long!
  • "Marge's Son Poisoning" - the scene where Marge is riding through town on her own and she sees a billboard saying "Give Your Mom a Hug Today".
  • "We're on the Road to D'ohwhere" - Homer, when driving Bart to a juvenile camp causes him to miss a trip to Vegas with his friends, he's stuck in a car with Bart and states "I’m 38 years old, driving a crappy car with a son who doesn't respect me, and I'm one Snickers Pie away from losing my foot to diabetes!" This is very out of character for Homer, and shows he realizes how many misfortunes are in his life, but never complained or mentioned it until this point.
    • What prompts the above is Bart's admission that he thinks playing pranks might be the only thing he's good at. Homer's retort is that at least Bart is good at something.
    • This exchange, after Homer has chained Bart up in the passenger seat to prevent him from escaping again, makes you feel for both of them.
      Bart: Dad, I think you actually enjoy seeing your own son suffer!
      Homer: I don't enjoy it! Being a father is just a job! Long hours, no pay, and at the end, all you get is someone yelling, "You screwed me up"!
      Bart: Well, maybe if you enjoyed me more, I wouldn't be so screwed up!

    Season 18 
  • "Springfield Up": We see the origins of Eleanor Abernathy aka "the Crazy Cat Lady", and it's downright heartbreaking. At age 8, she was a bright student who was already aspiring to be both a doctor and a lawyer, and by age 24, got her degrees for both fields. But by age 32, she was already beginning to feel burned out, and began drinking and acquired her first cat. giggling a little maniacally at that point. Skip ahead to age 40, and we see that she's become the broken/disheveled cat lady, shrieking and wailing incomprehensibly.
    • Why did Homer lie about being a millionaire? He desperately wanted to not be the guy in the documentary that makes everybody else look good.
  • Seeing the whole town shun Bart over a mistake in a championship baseball game in "The Boys of Bummer" is really harsh. Bart hasn't been the nicest kid but he really didn't deserve to have the town turn against him over such a petty thing. He eventually snaps and almost kills himself during a delusional attempt to save face with the townspeople. Marge manages to talk some reason into everyone but it's still pretty sad to watch the citizens destroy his self-esteem so thoroughly.
    • The lead-up to the sequence in which Bart throws himself off the town's water tower. The family wake up to find that the words I HATE BART SIMPSON have been spray-painted all over the houses on their street and watch a news report revealing that the graffiti is all over town.
      Marge: Who would do this to Bart?!
      Lisa: (solemnly) The person who hates Bart more than anyone else. Look!
      (She points out the window to where Bart himself is painting the phrase on the water tower.)
  • "Stop! Or My Dog Will Shoot":
    • When Santa's Little Helper becomes a police dog, he ends up becoming tense, and as a result bites Bart on the leg when he inadvertently startles him. Bart's left shaking and crying, wondering why his dog would bite him.
    • You can't help but feel bad for the snake when Bart has to reject him for Santa's Little Helper.

    Season 19 
  • Most of "He Loves to Fly and He D'ohs". After Homer saves Mr. Burns from drowning while he tries to pick up a penny in a small water fountain (It Makes Sense in Context), Mr. Burns takes Homer to Chicago on a private jet and after a fantastic night in Chicago, Homer spends most of the episode depressed because he's had one of the greatest experiences of his life and can never do it again. After Marge hires him a life coach who discovers that Homer's at his best when he's bowling and inspires him to always wear his bowling shoes, Homer applies for a Safety Inspector job that would let him fly on a private jet and he fails miserably at getting it and spends his days just sitting at Krusty Burger more depressed than ever before.
  • In "Midnight Towboy", we have the following line of dialogue from Marge:
    Marge: Oh, Maggie is getting so independent. At least you still need me, sack of potatoes...
  • Basically the whole entirety of "Eternal Moonshine of the Simpson Mind":
    • For the majority of the episode, Homer is under the impression that Marge has cheated on him, that he has assaulted her, and has chosen to forget about it, while Marge and the kids have all left home. We see Homer become gradually more depressed as the episode tolls on, to a point where Homer is almost driven to suicide. It all gets better, of course, but the lead-up is just depressing.
    • We also get a parody of an internet video, where Homer takes a picture of himself for 39 years in his flashback. While done for the puns, in the background of some of the scenes, we see Abe and Mona arguing, with the latter leaving, and the former gradually sinking into a depressive state. To add a bit of Fridge Logic, Homer seems oblivious of all of this. Perhaps his obliviousness is his coping method, as we know that his parents have always had a tough marriage from previous and future episodes.
      • The sequence also implies that Homer became a Big Eater to cope with losing his mom and shows him receiving abysmal grades in school and his alcoholism seemingly worsening over the course of his marriage to Marge with her hauling increasing numbers of beer cans out of the yard.
  • "That '90s Show":
    • The scene where Homer and Marge are dividing up their belongings. Marge brings out a Beanie Baby octopus and says, "Who gets Cutie-pus?" Homer tells her, "I just want a tentacle." He proceeds to pull one off, and all the beans flow out of the octopus as "Bittersweet Symphony" by The Verve plays in the background.
    • Homer's song "Marjorine" (a take-off of Bush's "Glycerine." The music video is even said to be just like it), to let Marge know he still loves her after she almost leaves him for her professor.
  • In "Papa Don't Leech", after Lurleen finally reunites with her father after 30 years, we get to see her celebrate with a new song about it. Then we see Royce creeping out of the house with his boots.
    Royce: Daddy's a deadbeat, he's leaving his daughter again
  • Nelson's film in "Any Given Sundance". Much like Barney Gumble's film on "A Star is Burns" about how being an alcoholic has ruined his life, Nelson's film on "Any Given Sundance" shows that living with a negligent mother and not having his father around is the reason why he's a bully:
    Nelson: I come to the ocean because only there do my tears seem small.
  • "Mona Leaves-a":
    • Homer goes to apologize to his mother for not believing that she's changed her ways and will stick around, only to find that she died of natural causes in the middle of the night. Made all the worst that it aired as a Mother's Day episode (though it could be taken as an Aesop of, "Love your mom, because you'll never know when the day comes when she won't be there.")
    • And then, at the end, it turns out that Mona's final request for Homer to spread her ashes was just one final plot against Burns. To the very end, Mona only ever saw her son as a tool to be used in her feud with Burns. Homer's genuine anger and disappointment when he realizes the truth is palpable.
    • The flashback that Homer has been trying to fill the void his mother left with food, even before she disappeared, as she started putting her activism ahead of him even before she had to go on the run, leaving him with food as the only substitute. No wonder he overeats...
      Homer: I've been trying to fill the hole you left ever since! *sobbing, clutching a bucket of KFC* But I'm never full...

    Season 20 
  • "Eeny Teeny Maya Moe":
    Moe: Who'd have thought such a little woman could make me feel so big?
    • Not to mention Homer's speech before that:
    Homer: You'll remember that somebody loved you once. And somebody could love you again! And that'll make you smile.

    Season 21 
  • Bluella the whale beaching and later dying in "The Squirt and the Whale".
  • Treehouse of Horror XX from Don't have a cow mankind; Dr Hibbert's final words to the Simpsons; if they see his wife tell her that he loved her. If you listen closely, Hibbert is almost sobbing.

    Season 22 
  • Mr. Largo singing about his life sucking so bad in "Elementary School Musical"
    Mr. Largo: My country 'tis of thee
    My job is misery
    Life disappointed me
    I'm 53!
  • "The Fool Monty" has Mr. Burns receiving grave news; he will die in a week. And when he founds out that no one (expect of course Smithers) is going to miss him, he tries to kill himself.
    • Smithers crying his heart out when he saw Mr. Burns jumping of the ledge to his demise.
  • Homer's guilt over causing Fat Tony's death in "Donnie Fatso", even accepting death from his cousin Fit Tony for causing the whole tragedy.
  • "The Great Simpsina" had Lisa learning magic from an older, retired magician. There were two points that were sad: The magician and Lisa are talking about his late wife, and he says this: "The only magic we couldn't make was a child." At the end of the episode, he's huffing ether (as a painkiller) and sees his late wife as she looked in her youth. He says that maybe he's had too much, but as her apparition fades, he (paraphrasing) says: "Aw, the hell with it," takes in more ether so his wife stays, and they dance as a very sweet song plays.

    Season 23 
  • "Exit Through the Kwik-E-Mart":
    Homer: What's the point? When a man isn't a hero to his son, he's nothing.
  • "How I Wet Your Mother", Homer believing he's responsible for his parents divorce, cause he got too excited and tipoed over the fishing boat.
  • Bill Plympton's couch gag from "Beware My Cheating Bart", which shows the couch falling for Homer, getting pregnant by him, getting dumped, and forced to strip and whore itself out in order to support the baby couch it had, then nearly commits suicide until Homer rescues it and the baby couch (which is now Maggie's play chair). That couch gag alone was considered more heartbreaking and interesting than the actual episode.
  • "A Totally Fun Thing That Bart Will Never Do Again". Though Bart was borderline sociopathic in his attempts to keep the family vacation from ending (by trying to convince everyone that the world was ending back on land because of a viral pandemic), the fact that he wanted to spend time with his family (and he was willing to do something crazy and criminal just to keep it going) shows that he does love his family underneath his sarcastic, prankster ways. Also, the ending where an elderly Bart looks back on the good times with his family and acknowledges that he did have a good life.
    • A little Fridge Logic when old Bart smilingly hugs the picture he's holding with the whole family sliding down the cliff. Homer and Marge would be long dead by this point. Out of all the pictures he has, he's specifically remembering a moment when his parents were with him.
      Bart: What a great ride.
  • "Lisa Goes Gaga": Lady Gaga telling Moe there's no hope for him and then he gets run over by a train.
    • If it helps at all, Moe takes it remarkably well.

    Season 24 
  • In "To Cur With Love", Abe Simpson reveals how he had to give Homer's beloved dog Bongo away to a farm run by a Lesbian couple when he was six in order to protect him from Mr. Burns whom the dog had bitten protecting Homer. At first the dog doesn't want to leave Homer but Abe gives the new owners Homer's sweater to get him to stay with them. Homer then reveals months after he went to get Bongo back but saw that he was already happy in his new home and was no longer his. Since then he's been unable to get close to dogs including "Santa's Little Helper" because they were "disloyal". Abe then shows Homer a photo Bongo's new owners sent of him sleeping on Homer's old sweatshirt, showing that his dog never stopped loving him.
  • Herb Powell, Homer's half-brother, makes his first appearance in twenty years in "The Changing of the Guardian" (though only his voice is heard) should be consider heartwarming if it weren't for the fact that he is poor again.
  • "Love is a Many Splintered Thing" has Bart once again reuniting with Mary Spuckler (his most recurring love interest, not counting his eventual ex-wife Jenda from several possible futures and Jessica Lovejoy's cameos). They actually hit off a proper relationship, but they break up. Bart is actually told that Mary's the best he could get, and he shouts cynically at Marge, only for her to kick him out of the house along with Homer. Bart and Homer spend some time at a hotel, where other men are having relationship problems. As a big grand gesture, Bart gets the other men to sing a musical number for their wives and girlfriends. Mary is present but doesn't take Bart back, as she has already moved on to a new boyfriend.
    Boyfriend: Everyone has a story. Welcome to mine.
  • "Dark Knight Court". The realization that Mr. Burns has a Freudian Excuse as to why he's so evil (his father forbade him from reading comic books and even burned down a comic book publishing company to prove his point), though that's if you believe that Mr. Burns grew up poor, only to be adopted by a loveless, yet rich family a la Charles Foster Kane from Citizen Kane. If you believe that Burns was rich all his life (as seen in "Last Exit to Springfield" and "Burns' Heir") and became Rich in Dollars, Poor in Sense because of his wealthy upbringing, then this doesn't count. Either way, the fact that he had a father like that does explain why Mr. Burns is so evil (besides the fact that he runs on pure bile and hate, which will never go away, technically making Mr. Burns immortal).
  • In "The Saga of Carl", Carl Carlson seemingly ditches his friends. It is later revealed that he needed the lottery money they won to buy a historical document that he can use to prove the innocence of his adoptive ancestors in Iceland. The sad revelation is that while the Carlsons were revealed to not be cowards like the other Icelandic think, they also turned against their own people and even killed and tortured a few of them. Even worse is that Carl admits he never saw any of them as friends, which leads to Lenny trying to kill him.

    Season 25 
  • In the first episode after Marcia Wallace's passing, "Four Regrettings and a Funeral", the blackboard gag was this.
    • What really makes this scene even sadder is that it can hit close to home for those who had close relationships with their teachers as kids but the teachers they were so close to died later on.
    • During the Primetime Emmys' 2015 Really Dead Montage for the celebrities who died the previous year, a slightly modified version of the chalkboard gag was used as the backdrop for Sam Simon's picture, with "Mrs. K." being replaced with "Sam".
  • "Yellow Subterfuge": Bart spends half the episode being on his best behavior so he can go on a school trip on a submarine. However, Skinner is unusually stricter for this trip and finds a petty reason to put Bart on the bad list. Bart does everything to appease Skinner and even resorted to begging because he wanted to go on this trip. Regardless, Skinner refuses to let Bart on the sub.
  • At the end of "The Man Who Grew Too Much", Ned Flanders has a dream of dancing with Edna Krabappel before awakening to remember how much he misses her, a sentiment shared by a near tearful Nelson.
    • To make things even worse, Ned and Nelson say all of this all the while the two look at a photo of Edna on a table, which is right next to a photo of Ned's first deceased wife, Maude (who was killed off when Maggie Roswell quit after the producers refused to increase her pay to cover travel).
    • Again, to make things even worse, there's no music playing directly as the end credits start like there usually is.
    • The episode pays a tribute to Marcia Wallace.
  • In "Diggs", Bart makes a new friend who is pretty lonely. This is best demonstrated where, after Diggs breaks his arm, he says he signed his cast with people he wishes would sign it.
    • When Bart finds out that Diggs is mentally unstable after thinking he could fly and hurting himself. Bart wants to help him but Marge tells him the mental hospital he's going to isn't a good place for him to go alone and likely won't let him visit.
  • "The Yellow Badge of Cowardge" tells us why Homer loves the 4th of July fireworks festival so much: Because it was the only time he couldn't hear his parents arguing.

    Season 26 
  • Don Hertzfeldt's couch gag from "Clown in the Dumps" makes a not-so-subtle statement of the show becoming so dependent on shock humor, non sequiturs, and merchandise shilling, it doesn't have as much heart as it did at its golden age. Homer in a far-distant, super-deformed future recalls relatively less distant and deformed episodes. The memories show that even as the series became more surreal to keep up with the times, Marge still tried to tell Homer she loved him, the Simpsons still considered themselves "a happy family", and Marge assured Homer that she would never forget him. Homer then sees the latest incarnation of Marge spout dystopian propaganda, while Bart and Lisa shout broken catchphrases, and Maggie commands viewers to purchase merchandise. The apparent lack of familial love causes Homer to utter a glum "D'oh." with a sad face. While this couch gag can be confusing and/or disturbing, if one were to think about it, it can be really sad, since it represents the Simpsons when their quality is at their all time worst.
    • The piece that accompanies this couch gag? Fryderyk Chopin's Nocturne Opus 9, No. 2. A bit depressing at least.
    • It's not just the Simpsons. This couch gag could be symbolic of a show that has run WAY, WAY past its prime and no longer has as much heart as it did during its height of popularity.
    • Lisa's broken catchphrase of "I AM SIMPSON" becomes sadder when you take "Lisa's Substitute" into consideration.
    • The death (and resulting impact) of Rabbi Krustofski.
  • In "Simpsorama", (the crossover with Futurama), Seymour makes a reappearance. This could bring back sad memories of "Jurassic Bark" episode, especially with the music.
  • The Simpsons team's tributes to Jan Hooks (who played the recurring role of Apu's wife Manjula from Seasons 9-14), Leonard Nimoy (whose appearances in "Marge vs. The Monorail" and "The Springfield Files" are considered memorable and hilarious moments for the show in its glory days) and Sam Simon (one of the three main executive producers/creators of the show, along with Matt Groening and James L. Brooks) this season.
  • In "Bart's New Friend", while hypnotized into believing he's 10 years old again, Homer tells Bart he doesn't want to have a wife and kids.
    Bart: Wow. He doesn't want to be my dad, he just wants to be a kid like me.
  • In "Peeping Mom", Marge decides to follow Bart everywhere much to his dismay when the police reports to her that a part of the city have been destroyed by a bulldozer and he could have been involved, and Bart keeps on insisting he had nothing to do with. Eventually, Bart becomes so stubborn that Marge becomes fed up and decides to ignore him not unlike in "Bart the Mother".
    Marge: You're in charge of yourself. Get home whenever. My parenting stops now.
    • And then it turns out Marge was right and Bart had been plotting to use the bulldozer for a prank to turn the Springfield sign into the words "FIE". He also acts like he doesn't care that his mother is no longer being involved with him, until a lunch packed by her causes his conscience to act up.
    Marge: (in Bart's imagination when she sees the result of Bart's prank) I failed as a mother!
    • Ned giving up his new puppy Baz to Homer as they had been bonding for the whole episode and he starts thinking she loves Homer more. Luckily, Homer gives Baz back to Ned, telling him that he'll be a better owner.

    Season 27 
  • Lisa in "Halloween of Horror". At a haunted house she looked forward to, she's scared so much she goes into the fetal position. She becomes so scared, she can't even stand Halloween decorations and holds onto her childhood crutch for most of the episode.
  • "Barthood," which really delves deep into Bart's inferiority complex when compared to Lisa. This episode reveals that he felt closest to Abe, which takes a sad turn when it flashforwards to when Bart is 15 and he is talking to Abe's headstone.
    • Homer usually gets on pretty well with his son when he's not acting up. Here Homer blatantly wants nothing to do with his son. He bluntly refuses to spend any time with him and doesn't believe he will amount to anything. While high Homer admits that he's so distant to Bart because his son is like him. Bart is somewhat touched and willing to reconcile with his father...right up until Homer tells his boy that Bart being like him means he has one child who will amount to nothing. It's doubly sad as this statement means Homer is reinforcing Barts's feelings over Lisa, and that he believes he himself has wasted his life.
    • Homer's weed-induced confession to Bart about how becoming a father was the moment he realized he was truly an adult and could never go back to being a kid again. It scared him so much he ducked the responsibility as much as he could, leaving Abe to be the actual stable father figure in his own son's life. Dan Castellaneta actually drops out of Homer's voice and speaks naturally during this scene, and whether it's just to show that Homer is for once being completely serious or he was getting emotional himself reading the lines, the effect is heartbreaking.
    • Another example would be when Bart is turning 12. The celebration is interrupted by yet another one of Lisa's accomplishments and taking attention. Bart then writes Lisa's name on the cake, implying a good deal of bitterness in regards how his celebrations get overlooked and overshadowed by Lisa.
  • "The Burns Cage" has Smithers singing about his feelings for Mr Burns.
    Smithers: Is there a half life for hope and I know the answer is nope.
    • And after the song, he breaks down in tears.

    Season 28 
  • The ending of "Trust, But Clarify" where Kent Brockman regains his job as anchorman after a credibility scandal with Lisa's help, and he approaches his replacement Arnie Pie, who graciously tells him, "Go ahead, take your chair. Do what you do best." Brockman then announces the lottery numbers and ebulliently announces "I'm back!" Brockman's replacement and sometimes rival Arnie Pie being so kind to Brockman and the look of joy on Kent's face at the end makes this a happy tearjerker.
  • "The Great Phatsby" begins with a rather bleak image- Mr. Burns, looking tired and pale, seated in his armchair at home and getting two simultaneous blood transfusions. A somewhat sad reminder that the cruel, downright monstrous Mr. Burns is also a frail, sickly man.

    Season 29 
  • "Flanders' Ladder":
    • Bart having a flatline.
    • Lisa realizing that what she's been doing to Bart in a coma will kill him and she desperately begs him to come back, even telling him she loves him.
    • The Plot Parallel between Lisa begging Bart to wake up and Bart, in his coma dream, begging Homer's ghost not to Ascend to a Higher Plane of Existence.
      Lisa: No, Bart, you have to stay with me!
    • The montage of everyone dying in the future is played for laughs, but still can be very sad:
      • Smithers is Driven to Suicide after Burns marries Angelina Jolie.
      • Poor Homer is murdered by Chief Wiggum just for a sandwich.
      • Marge marries Flanders but then dies of old age, leaving him alone yet again.
      • Lisa seemingly dies of despair after transcendental meditation reveals that her life has been a waste of time.
      • Maggie Ascended to a Higher Plane of Existence, but it's still quite sad that she's apparently no longer human, and has had to watch all her friends and family die.

    Season 30 
  • In "Girl's In the Band" Lisa is scouted by the Capitol City Philharmonic and her family crumble under the pressure of long daily drives in heavy traffic to bring her to rehearsals and back (with Bart and Maggie in tow) and Homer being forced to work a night shift to afford the fee. At one point, Bart—who's been spending his time with the other overshadowed siblings of the children in the youth orchestra—asks Homer point-blank if his feelings matter and Homer, heading off to work another shift, gives him a hasty goodbye without listening to the rest of what he has to say. Sobbing, Marge then utters this line, which Lisa overhears:
    Marge: There's nothing worse than being the parent of a child with promise.

    Season 31 
  • "Todd, Todd, Why Hast Thou Forsaken Me?" Hoo boy, where to begin?
    • Well, how about the premise? Todd Flanders, the younger of Ned's boys, has a crisis of faith and blames God for the death of his mother, who is slipping away from his memories. Shocked by this, Ned casts him out to live with the Simpsons to scare Todd back into Christianity.
      Lovejoy: What would you say to Jesus?
      Todd: I'd say... thanks for nothing! My mommy's dead and she's never coming back and I don't believe in God anymore!
    • Homer tries to have a heart-to-heart with Todd, but it ended up with Homer reliving the night his mother left, before running off to Moe's in desperate need of a drink.
      Homer: My mom is gone! And so is my ice cream! And so is my hair!
    • Much to Moe and Homer's surprises, Ned also shows up at the bar, in need of booze.
      Moe and Homer: What the...?
      Ned: I'm losing everything. Just give me a drink.
    • Hans Moleman runs over Homer and Ned, rendering them comatose. Nearly all of Springfield hold a vigil for Ned outside the hospital.
      Chorus: We need you now O God on high, so stupid Flanders and Homer don't die...
    • Bart prays for Homer's safety, but Todd...
      Todd: I can't pray. I don't think anyone's listening anymore.
      Marge: Oh sweetie, prayer doesn't have to be to God. It could also be an honest conversation we have with ourselves. Just do what your heart tells you.
      Todd: I'm not really sure what's happening, and I'm really sad, and I need help.
      Todd's Prayer: Dear lord. Save my daddy. 🙏. CC: Jesus. And Buddha, just in case.
    • Bart's prayer deserves a mention in itself.
      God, this is just you and me, so I'm gonna tell you a secret. I love my dad, so please don't take him!
    • For another kind of tearjerker, Homer and Mona finally reuniting in Heaven, just for a moment.
  • Bodie getting kicked out of Springfield at the end of "Warrin' Priests: Part 2" and Lisa's sadness at having yet another moment of happiness yanked from her.
  • In "Way of the Dog", Santa's Little Helper reuniting with his mother after having a lot of traumatic flashbacks from being split from her. The ending suggest the Simpsons family take her in for the holidays.

    Season 32 
  • "Burger Kings": Mr. Burns getting depressed after learning that when he dies, nobody is going to mourn him. He even sheds a tear and is about give up entirely by pulling his plug off.
  • "The Last Barfighter": It’s largely Played for Laughs, but the episode provides pretty sad insight into Homer’s alcoholism. Moe reveals Homer drunkenly admitted he spends more time at a bar than at home because he’s so terrified of being a bad husband/father that he thinks it's better to not even try. Later, when Homer’s injected with a serum preventing him from getting drunk, his family cheers. In just three months, a sober Homer gets promoted at work and becomes a more attentive husband and father. When offered an antidote to the anti-booze serum, Homer is the only one of the group who doesn’t immediately throw away his improved life and instead tries to return home… Only to be hunted down and injected by Springfield’s bartenders.

    Season 33 

    Season 34 
  • Homer being humiliated for his lack of intelligence in "Habeas Tortoise". He begins to hear mockery everywhere he goes, even when people aren't talking about him. It's also why he joined the conspiracy group, because he wanted to be with people who didn't keep laughing his ideas out of the room.
  • The cruel treatment of the talk show workers in "The King of Nice". Most of them are scared stiff by the end of the episode (due to a combination of being constantly screamed at and having things thrown at them), and Marge has a massive My God, What Have I Done? moment when she realises that she's acting just as badly towards them as her superiors are and quits on the spot.
  • "Bartless":
    • Homer and Marge both have a My God, What Have I Done? moment: while they saw yet another 'Bart Simpson-like' prank in their eyes by vandalizing school library books, Mrs. Peyton and the librarian actually showed them that Bart actually inspired the younger children to want to read. Bart had actually said as such, but his own parents didn't believe him, leaving them to the realization that they've been unable to see any good in their son, and the real possibility that they hate him.
    • The bulk of the episode deals with a Shared Dream between Homer and Marge in which they never experienced their first unplanned pregnancy, had more time to figure things out, and now live a happy and comfortable life with just Lisa and Maggie. Bart doesn't exist for them until they hit him with their car and end up taking him in while the police search for his family, since he has no memory of who he is or where he came from. Although confounded by his bad behavior at first, they grow increasingly attached to him as they begin to appreciate the fun and unexpectedness that his personality adds to their lives—and then the police come back for him, having decided that Homer and Marge can't keep him and that he needs to be put in an orphanage. As the police car is taking him away, Homer and Marge are struck by the truth that they really do like Bart and chase after the car shouting to Bart that they care about him and begging Wiggum not to take him. Upon waking up in their own bedroom with their normal memories, they run to Bart's room to assure themselves that he's still there and still their son.

    Season 35 


Video Example(s):


Mr. Burns mocks Homer's weight

During "Brush with Greatness", Homer is attempting to lose weight after being humiliated on the news when he got stuck at Mount Splashmore's H2WHOA! slide. After losing 21 pounds, which brings his weight down to 239 pounds, his wife Marge congratulates him for his achievement, only for Mr. Burns to cruelly mock his weight-loss efforts by calling him "the fattest thing he's ever seen", which completely shatters his self-confidence in one fell swoop and causes Homer to start binging on food again. Meanwhile, a furious Marge kicks Mr. Burns out for his mockery of her husband's attempt at losing weight and says that she can finish the portrait by herself and have it finished in time for the unveiling.

How well does it match the trope?

5 (9 votes)

Example of:

Main / KickTheDog

Media sources: