The Simpsons: 10 Times The Show Broke Our Hearts

With the announcement at Disney’s recent D23 convention that all 30 seasons of The Simpsons will be available to stream from the platform’s launch date, fans of the show are over the moon. Now more than ever viewers will have access to every episode from the long-running comedy and will be able to pour through the yellow family’s back catalog.

While the show itself is a comedy, and a hilarious one at that, The Simpsons was one of the first adult cartoons to really push the boundaries of what animation can be. While maintaining a comedic tone over the years, the Simpsons have experienced real family drama and often learned valuable life lessons in the process. More than any other show of this sort The Simpsons has a way of accessing people’s emotions and playing havoc with their tear ducts. Get the tissues ready.

10 ‘ALONE AGAIN, NATURA-DIDDLY’ – MAUDE’S DEATH

Throughout the course of The Simpsons there have been a number of deaths but none as enduringly sad as the passing of Maude Flanders. For starters, most of the other deaths on the show have been secondary characters, who have only appeared in an episode or two. What was so shocking about Maude’s passing was that, despite being a secondary character, she had been a constant presence. What exacerbates the sadness of her death is the way Ned Flanders has to reconcile with his faith in the face of tragedy. On a show with little to no stakes, when everything returns to normal at the start of each episode, Maude’s death felt like a permanent loss.

9 ‘MARGE BE NOT PROUD’ – BART’S CHRISTMAS PRESENT

In this Christmas-themed episode Bart is in trouble for shoplifting, ruining yet another family portrait. Marge is not angry, she’s disappointed, and for the viewer this disappointment is palpable. It’s easy to empathize with Marge. However, the heartbreaking moment comes when Bart tries to make good. When Marge accuses him of stealing yet again he produces a photo of himself that he’s had taken as Marge’s Christmas present. She is truly touched and their relationship is reconciled. It’s a heartwarming moment between mother and son and one that had viewers reaching for the tissues.

8 ‘THE SQUIRT AND THE WHALE’ – LISA’S WHALE FRIEND

One of the more recent entries on this list, Lisa’s friendship with a beached whale was a return to form for the show. After 30 years of storytelling, The Simpsons can be forgiven for not reaching the dramatic heights of its early years. However, in this episode when Lisa befriends a whale, washed up on the beach and unable to return to the water, the show reached the emotionally charged levels of some of its earlier seasons.

Lisa rallies the town to save the whale and when nothing is to be done she waits with her friend, who she has named Bluella, reading to her and sleeping next to her until sadly the whale dies. It’s a heart-crushing moment and a brutal lesson about the laws of nature.

7 ‘LISA’S SUBSTITUTE’ – LISA’S RECEIVES A NOTE

Lisa has always been the most intelligent and sensitive of the Simpson clan. These attributes sometimes ostracise her from the group and make her feel like an outsider. When a substitute teacher arrives at Springfield Elementary and seems to fill the void in Lisa’s life, she begins to feel validated in a way she’s never experienced before. The heartbreak comes when her substitute’s time at the school is up and he has to move on. Lisa is distraught but the substitute leaves her a note, which simply reads: ‘You are Lisa Simpson.’ The sentiment giving her hope and strength for the future.

6 ‘LISA’S FIRST WORD’ – MAGGIE SPEAKS

This is probably one of the most adorable episodes of The Simpsons as we not only discover Lisa’s first word, we witness a normally silent character utter her first words as well, with heartbreaking sentimentality. In the episode, we learn that despite their antagonistic relationship, Bart and Lisa have a familial bond that runs even deeper. Bart, use to being an only child, hated Lisa for being born and was ready to run away, he stopped when he heard Lisa’s first word ‘Bart.’ The episode is capped off when Homer puts Maggie to bed, telling her he doesn’t mind if she never says a word. When he shuts the door, the usually silent Maggie takes out her dummy and says ‘Daddy.’ It’s a one-two punch of heartbreak.

5 ‘BART GETS AN F’ – BART’S BREAKDOWN

Bart’s grades have never been much to write home about and in this episode he’s threatened with academic purgatory. Bart learns that he will need to repeat fourth grade if he fails his next test. It’s motivation enough for Bart to actually put his head down and study, which is a sharp left turn for the character.

The kicker comes when despite actually trying this time, Bart still fails the test. The lesson being that one bout of studying can’t make up for a lifetime of not trying. Bart has a breakdown in the classroom which is truly heart wrenching and even the stoic Miss Krabappel has a moment of sympathy.

4 ‘ONE FISH, TWO FISH, BLOW FISH, BLUE FISH’ – HOMER SAYS GOODBYE

Homer is usually carefree and empty-headed, however, in this episode his mortality is brought into question with touching results. After a night at a sushi restaurant, Homer believes he’s eaten poisonous pufferfish and is told he only has 24 hours to live, well, 22 hours after being kept waiting by Dr. Hibbert. He attempts to cram in all the things he wanted to do before he died over the course of the next day but realizes too late – he’s not had a chance to spend time with his family. One by one he tucks in his kids and says his goodbyes to them before heading downstairs to listen to an audiobook of the Bible and die. Of course, he doesn’t die but this is one of The Simpsons’ most heart-wrenching entries.

3 ‘MOTHER SIMPSON’ – HOMER WATCHES THE STARS

Homer can barely remember his mother, having been abandoned at an early age, until one day she turns up in Springfield and he discovers she is a fugitive and has been on the run. Homer and his mother are able to spend time together and discover the things they have in common and begin to heal the wounds of their estranged past. However, the time comes for Homer’s mother to leave again. In this episode, Homer is dealing with feelings of abandonment and despite learning that his mother is proud of him he is left grappling with the loss of his mother yet again. The episode concludes with Homer watching the stars. It’s an unusually quiet and contemplative moment for Homer and the show.

2 ‘AND MAGGIE MAKES THREE’ – ‘DO IT FOR HER’

Perhaps the most enduringly heartbreaking episode of The Simpsons, ‘And Maggie Makes Three’ addresses the lack of photos of Maggie in the house. We learn that before Maggie was born Homer quit his job at the nuclear power plant and landed his dream job of working at a bowling alley.

Unfortunately, the new baby meant he had to return to a more lucrative position and when he was hired back at the plant, Mr. Burns put up a ‘de-motivational’ plaque to remind Homer: ‘Don’t Forget You’re Here Forever.’ In heartwarming fashion Homer has used all photos of Maggie to cover up the text of the plaque, changing the message to: ‘Do It For Her.’

1 ‘FOUR REGRETTING & A FUNERAL’ – BART’S BLACKBOARD MESSAGE

Not so much a story point rather a nod to the passing of Miss. Krabappel voice actor Marcia Wallace, one of the most heartbreaking moments from The Simpsons was the message Bart was writing on the blackboard, in the first episode recorded without his adversary and fourth-grade teacher. Instead of a joke line, covering the board, Bart has simply written: ‘We’ll really miss you Mrs. K.’