The episode "Bart's Friend Falls in Love" from season three: 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.
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.
Four powerful, tiny little words from season 2's "Lisa's Substitute": You Are Lisa Simpson.
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).
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.
This exchange between Homer and Marge:
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: [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?
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.
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 DVD commentary 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).
Krusty mournfully revealing that his father never accepted him becoming a clown and hated him for it, in "Like Father, Like Clown."
Maude's death, and Flanders' reaction.
"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.
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.
The season 2 episode "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.
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.
Bluella the whale's death in The Squirt and the Whale.
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).
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.
"I Love Lisa" is Ralph Wiggum's Crowning Moment of Awesome. After Lisa humiliated him at the Krusty the Klown 29th anniversary special, he prepares to play George Washingtom 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.
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.
"Home Sweet Diddly Ho Dum Doodly": Just the premise of Homer and Marge having their kids taken from them because the social workers mistook them for negligent parents. If the Simpsons writers were trying to make this funny, then they failed miserably. Save that stuff for South Park or Family Guy, where they actually have writers who may or may not be sociopaths (or make it funny without making it depressing).
"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.
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.
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.
Barney: "Don't cry for me. I'm already dead..."
"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) is tear-inducing in that "That's very noble" way.
"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.
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.
The death of Bea and it's 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.
From the same episode, 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.
One episode 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.
Nelson praying to God for Lisa to be safe: "God, if you don't bring my Lisa back safe, ants will burn tonight!" It was very sweet...in a warped way, considering that Nelson is a bully, but it still shows that he does have a heart for Lisa (even after they broke up in "Lisa's Date with Density")
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.
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 and really wanted the bowel obstruction that killed Great-Aunt Gladys, not a pet reptile). For all post-classic Simpsons fans (if any): this was before Selma adopted the Chinese baby on season 16's "Goo-Goo Gai Pan"
Homer nearly being Driven to Suicide in "Homer's Odyssey" after failing to find a new job.
"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. Fortunately, it gets better when Bart cites that his failure was similar to one George Washington encountered in a failed battle and Krabappel raises Bart's grade since he showed Krabappel 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.
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.
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.
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...
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.
Season 19's "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's song "Majorine" (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.
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.
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. 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.
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.
Lady Gaga telling Moe theres no hope for him and then he gets run over by a train.
"Bart vs. Thanksgiving" has Homer and Marge lamenting Bart running away and blaming themselves for how they acted toward him.
Lisa alone in her room blaming herself for Bart running away.
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...
"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.
"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 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.
In "Mr. Lisa goes to Washington", Lisa is all set to recite an essay about the birth of America when she sees a congressman taking a bribe and agreeing to level an entire forest. She's so horrified and disillusioned by it that she rips up her essay and runs away in tears.
"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".
Twice in "One Fish, Two Fish, Blowfish, Blue Fish". Once when Homer makes amends with his father and goes out playing with him, and the second when he's tucking his kids in for the last time.
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 Greenland. The sad revelation is that while the Carlsons were revealed to not be cowards like the other Norwegians think, they also turned against their own people and even killed and tortured a few of them.
In "And Maggie Makes Three", the thirteenth episode of Season Six, Bart asks Homer what he does with photos 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, "Donít Forget, Youíre 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.
"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).
"Homer's Triple Bypass": 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.
In the first episode after Marcia Wallace's passing, "Four Regrettings and a Funeral", the blackboard gag was this.◊