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- 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.
- 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.
- "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.
- Also, Homer's realization after his nightmare:
- 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.
- 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
Krusty doll: You're my best friend!
- After Bart went to his room, he pulls his talking Krusty doll.
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.
- "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 actually studied and took the assignment seriously.Bart: (In hysterical tears) No, you don't understand! I really tried this time. I really tried! This is as good as I can do, and I still failed... oh, 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.
- This episode puts a lot of Bart's trouble in school in perspective; he isn't just an "underachiever and proud of it" like the early merchandise of the show liked to say, he genuinely lacks the focus and intelligence needed to succeed in school. No amount of hard work and struggling is ever going to make up for that.
- 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.
- 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 can be a happy tear jerker to some.
- 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 a 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.
- "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 realising 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 somber tantrum fight between two children, with both of them furiously shoving and screaming each other until the parents restrain them and Lisa runs out of room sobbing loudly in heartbreak.
- 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.
- "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.
Narrator: In the beginning, God created the Heavens and the Earth...
- 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 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 just says "sometimes it's fun". 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. When Bart asks why are they really waiting for him, Marge is silent and resumes looking outside.
- 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.
- When Homer and Marge first find out that Homer is dying, they hug each other and sob into each other's shoulders. The image is just saddening.
- 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.Homer: How can the one thing I've ever been sure of be so wrong?!
- 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.
- 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.
- "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 have enough money to do so. In the end, he had to settle for helping the ones he could.
- The death of Bea and its immediate aftermath is shattering. Abe loses someone he could genuinely love, and he ostracizes Homer a result, as Homer's disappointing safari trip kept Abe away from the retirement home while Bea died.Abe: You made me miss the last precious moments of Bea's life! I'll never speak to you again! I HAVE NO SOOOOOON!(A Single Tear rolls down Homer's cheek)
- The tragic and crushed way Abe says "They may say she died of a burst ventricle, but the truth is she died of a broken heart." With his borderline sobbing tone, even a cheesy line like that becomes tearjerking.
- The death of Bea and its immediate aftermath is shattering. Abe loses someone he could genuinely love, and he ostracizes Homer a result, as Homer's disappointing safari trip kept Abe away from the retirement home while Bea died.
- A couple from "Brush with Greatness":
Burns: Marge, I'm not an art expert, but I know what I hate... and I don't hate this.
- 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 entirerly. 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).
- 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.
- 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.
- Four powerful, tiny little words from "Lisa's Substitute": You Are Lisa Simpson.
Lisa: "Thank you, Mr. Bergstrom... If you don't mind, I'll run alongside the train as it speeds you from my life..."
- 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...
- This line, uttered by a sobbing Lisa just before Mr. Bergstrom leaves:
- The entire ending sequence of Homer cheering up a crying Lisa can bring about happy tears.
- "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: (in tears) Go ahead, sir.
- "Lisa, It's Your Birthday", for being only a minute long within the episode "Stark Raving Dad", can cause tears of joy out of practically anyone. It's now more depressing than it should be in light of Michael Jackson's death.
- It gets worse; due to the documentary, Leaving Neverland bringing back the controversy surrounding Michael Jackson's child molestation allegations, the episode has been pulled from syndication. The only way to see the episode now is on DVD or online.
- 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. (The two of them hug, weeping on each others shoulders)Ned: 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.Homer: No, I was a swine.
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*
- 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 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.
- YMMV on this one, but in Bart The Murderer, Barts 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, hes 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. If it hadnt been for that, the entire rest of the episode, which sees Bart becoming a bartender for the Springfield Mafia and subsequently being framed for Skinners murder, wouldnt have happened. That probably makes Barts 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".
- "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).
Homer: No wonder she hates me. Oohhh, I never even noticed she was alive.
- 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").
- "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." Awww...
- "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.
- "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.
- "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 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 through out the rest of the series.
- Lisa being upset over her appearance in "Lisa the Beauty Queen" will affect those who have had self-esteem issues over their appearance (ditto for the subplot of "Sleeping with the Enemy" where Lisa purposely starves herself so she can lose weight in her butt, then at the end, tells Homer that her body image issues will never be resolved and that she'll still feel bad about the way she looks).
- 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 (even though the writers on the DVDCommentary said that they had to go through a lot of takes to make Elizabeth Taylor's "Daddy" line sound like something a one-year-old child would say and not a 20-year-old seductress perched on the lap of a squirming, blushing man as she's caressing his face and nuzzling his neck).
- Bart feeling totally rejected thoughout the episode really can bring to light insecure he actually is.
- "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 Groundskepper Willie to tears.
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.
- George's final words:
- Earlier in the episode, when Ralph cries over not getting any Valentine cards, it's so hard not to feel sorry for him.
- 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.
- 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 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".
- From "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.
- "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:
- "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, "Dont Forget, Youre Here Forever". 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 realize that the season four episode "Mr. Plow" revealed that Barney was a Harvard-bound honors student studying for his SATs until Homer pressured him into trying beer, meaning that Homer ruined his best friend's life). Despite the funny part where he mistakes Lisa's Girls' Scout meeting with 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 "Mother Simpson", the 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 Downer Ending.
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.Marge: Which was...?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?
- 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:
Homer: At least this time I'm awake for your good-bye.
- 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:
- 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.
- 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...
- "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.
- 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.
- 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.
- In the same episode, Mrs. Krabappel's farewell speech to her class suddenly got depressing after Marcia Wallace's passing.
- 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.
- "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 episodes shows that deep down, Bart is a SadClown.
- 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 comics for you.
- 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 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 it's 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.
- "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.
- "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.
- "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.
- 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.
- "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.
- Speaking of "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!
- 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.
- "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.
- 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.
- "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.
- This one is made more tragic in hindsight. In "Pranksta Rap", 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.
- "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".
- "Were on the Road to Doh-where - 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 "Im 38 years old, driving a crappy car with a son who doesnt respect me, and Im 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.
- 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.
- "Springfield Up": First introduced in season 9's "Girly Edition", 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.
- "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.
- I can't help but feel bad for the snake when Bart has to reject him for Santa's Little Helper.
- 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 episode 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. Or perhaps I'm just reading too much into this?
- Despite being despised for screwing with show continuity and showing Marge at her most ungrateful (see DethroningMoment.The Simpsons), the scene in the episode That 90's Show 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" 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.")
Homer: I've been trying to fill the hole you left ever since! *sobbing, clutching a bucket of KFC* But I'm never full...
- 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...
- "Eeny Teeny Maya Moe":Moe: Who'd have thought such a little woman could make me feel so big?
Homer: You'll remember that somebody loved you once. And somebody could love you again! And that'll make you smile.
- Not to mention Homer's speech before that:
- Bluella the whale's death in "The Squirt and the Whale".
- "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.
- 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.
- "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.
- 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.
- Love is a Many-Splintered Thing has Bart once again reuniting with Mary Spunckler (who by the way is his most reacurring love interest not counting 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 coldly disown him. 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.
- "The 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.
- Herb Powell, Homer's half-brother, makes his first appearance in 20 years (though only his voice is heard) should be consider heartwarming if it weren't for the fact that he is poor again.
- In the first episode after Marcia Wallace's passing, "Four Regrettings and a Funeral", the blackboard gag was this.◊
- 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 McLeaned 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.
- We'll always have the Bongo comics. (With Edna, at least.)
- 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.
- 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 peak. 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."
- In "Simpsorama", (the crossover with Futurama), Seymour makes a reappearance. This could bring back sad memories from Futurama's "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 "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.
Marge: (in Bart's imagination when she sees the result of Bart's prank) I failed as a mother!
- 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 doesn't care his mother is no longer being involved with him, until a lunch packed by her causes his conscience to act up.
- In that same episode, 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.
- 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.
- 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.
- 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 episode "Flanders' Ladder"
- Bart having a flatline.