10 Saddest Episodes of The Simpsons

10 Saddest Episodes of The Simpsons

As someone who grew up with The Simpsons as a constant companion, I can wholeheartedly say that these two episodes are undeniably among the show’s finest moments. Each one offers a unique perspective on the characters we’ve come to know and love, while also delivering poignant messages that resonate far beyond Springfield’s borders.


Cartoon comedies like “The Simpsons” are primarily designed to amuse audiences and, generally speaking, it adheres to the conventions of its genre. Many episodes center around the characters embarking on humorous escapades within or beyond Springfield, or simply engaging in ridiculous antics. Examples include Bart’s mischievous phone calls and the lively exchanges at Moe’s Tavern. There is no scarcity of amusing moments on this show. Additionally, its numerous parody episodes offer plenty of laughs.

Occasionally, the series delves into somber tones which may provoke brief feelings of sadness in viewers, especially those who tune in for the comedy. Yet, these emotional segments serve a purpose as they add depth to the characters, reflecting the realities of life where humor isn’t always present and difficult times arise. It’s essential to prepare oneself for such moments when watching an animated sitcom.

10 “And Maggie Makes Three”

Season 6, Episode 13

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Destiny seems to have dealt a rough hand to Homer on several occasions, as depicted in the episode “‘And Maggie Makes Three’“. In this storyline, it’s 1993 and Homer is determined to pursue his passion instead of working at the Springfield Power Plant. He leaves his job with a blaze of disregard for future opportunities. However, as Marge becomes pregnant with their third child, Maggie, Homer comes to terms with the fact that his new salary won’t be sufficient to cover the baby’s costs. Consequently, he is left with no choice but to humbly ask for his old job back.

A Father’s Sacrifice

If you’re seeking an outstanding illustration of the quality content that The Simpsons was capable of during its best times, I recommend giving “And Maggie Makes Three” a watch. Although having a baby isn’t inherently negative, it’s touching to comprehend how Homer gave up his aspirations in order to provide a comfortable life for his family. What makes this situation even more distressing is that Mr. Burns mistreats him upon his return, not only making him beg for his old position back but also placing an insulting plaque near his desk.

“Don’t forget: you’re here forever”.

He surely is as brutal as bosses come.

9 “Four Regrettings and a Funeral”

Season 25, Episode 3

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Bart could sometimes be difficult to manage, but for a long period, things generally stayed under control thanks to Edna Krabappel-Flanders, often referred to as Mrs. K, who was always there to keep him in check. Regrettably, the actress voicing her character, Marcia Wallace, passed away due to pneumonia, leading the show to write off her character. The episode opens with Bart writing something on the chalkboard, and it is later revealed that his scribble reads:

“We’ll really miss you Mrs. K.”

Just like that, the show bids her farewell.

One of the Show’s Most Relatable Characters

Without a doubt, one of the lesser-known yet captivating characters from “The Simpsons” is Mrs. Krabappel, who could both irritate and delight fans in equal measure. She was originally designed as a satire of America’s troubled educational system, often appearing grumpy but with genuine goodwill at heart.

A hopeless romantic, Mrs. K was always searching for a lover, yet Cupid never seemed interested in her. The seesaw plots covering her personal and professional lives made for great viewing, hence hearts were heavy when it dawned on viewers that she wouldn’t be a part of the show anymore.

8 “Mother Simpson”

Season 7, Episode 8

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For quite some time, Homer assumed his mother, Mona, was deceased. But in an unexpected turn of events, he encounters her in the show “Mother Simpson.” As anticipated, she comes prepared with a reason for her disappearance. Seems like she and other hippies had clashed with Mr. Burns at a protest against his germ warfare lab. They ended up injuring him, which led to Mona having to hide. She reconnected with Homer’s family, but their bond was cut short when someone revealed her whereabouts to the FBI, forcing her back into hiding. The episode concludes with Homer looking mournfully at the stars.

The Realization That Homer Will Never Have the Kind of Parental Love He Gives His Children

In a somewhat less polished manner than other episodes, “Mother Simpson” stands out due to its sharp dialogue and exceptional voice acting by Glenn Close, propelling it into a chilling trajectory of its own. Drawing inspiration from films about people on the run, this episode thrives on its breathless pace, immaculate animation, and a compact cast. Crucially, it invites viewers to empathize with Homer, who, in a rare twist, is not portrayed as a self-victimizer but rather an individual yearning for parental affection, a longing that will forever remain unfulfilled.

7 “One Fish, Two Fish, Blowfish, Blue Fish”

Season 2, Episode 11

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In a different phrasing: Homer shows an aversion towards advice, which can be quite problematic given his character’s low intelligence in “The Simpsons”. An example of this reckless behavior is when he visits the town’s latest sushi restaurant in “One Fish, Two Fish, Blowfish, Blue Fish,” and orders fugu (a toxic pufferfish) despite being cautioned about its danger. He believes the head chef will safely remove all the toxins, but finds himself in trouble when the chef is preoccupied with romantic pursuits, leading a less experienced worker to handle Homer’s meal instead. Consequently, Homer falls ill and learns he has only 22 hours left to live at the hospital.

Rushing to Make Things Right

In a manner similar to Homer in an episode, viewers are led to believe that the main character is on the brink of death. Consequently, the narrative becomes filled with poignant moments as the character rushes to accomplish everything they’ve ever wanted. They compile a schedule, but find certain tasks take longer than anticipated (like making amends with their father). This added stress only intensifies, and when night falls, they bid farewell to each family member and settles on the couch. To everyone’s relief, come morning, the character is alive and well.

6 “Dog of Death”

Season 3, Episode 19

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In “Dog of Death,” Santa’s Little Helper, the perfect pet for any family, transforms into a terrifying creature. The Simpsons unintentionally contribute to this change. When the dog falls sick and requires expensive surgery, the family must make financial adjustments to cover the costs. Struggling with the sacrifices made, they begin treating him harshly, eventually leading to his departure. After wandering for a few hours as a stray, he is taken in by Mr. Burns, who turns him into a brutal attack dog through training.

A Monster Bred at Home

Surrounded by a chilling atmosphere, “The Hound of Doom” delves into the desolate effects of solitude and inhumane treatment inflicted upon pets. The story’s dreamlike sequence is occasionally interrupted by eerie allusions to popular culture (for instance, employing the Ludovico technique from Stanley Kubrick’s “A Clockwork Orange” to reprogram Santa’s Little Helper).


In a chilling sequence of events, the haunting melody adds to the growing sense of danger as Bart finds himself in a relentless ordeal with the dog. Fortunately, Santa’s Little Helper returns to its normal dog behavior towards the end, saving Bart from further harm.

5 “The Way We Was”

Season 2, Episode 12

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“The Way We Were” is another heart-wrenching episode that takes us back to 1974. In this time, teenage Homer finds himself smitten with Marge. To be near her, he cleverly hires her as his French tutor. As they spend more time together, she too begins to harbor feelings for him. However, when she realizes he’s not a student but pretending to be one, she becomes upset and turns down his prom invitation, instead choosing Artie Ziff to accompany her on that special night.

The Most Miserable Homer Has Ever Been

Relationships based on deceit are bound to fall apart, and unfortunately for Homer, it seems he reaps what he sows. It’s painful to witness his despair as he laments a lost opportunity to find a girlfriend. Alone at prom, an experience that is undoubtedly the worst possible scenario for a teenager, he endures. To make matters worse, Marge appears unsympathetic when she encounters him weeping in the corridor.

4 “‘Round Springfield”

Season 6, Episode 22

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In the episode titled “‘Round Springfield'”, Bart falls ill. During his hospital stay, Lisa encounters her idol, “Bleeding Gums” Murphy, in a different ward. She pays him a visit and they share stories, strengthening their bond. Murphy eventually lends Lisa his saxophone for a school concert. Lisa’s improvisation talents shine during the performance, making her the center of attention. Upon returning to the hospital to share her success with Murphy, she learns that he has sadly passed away.

The Painful Loss of a Musical Mentor

Music has always played a significant role in Lisa’s existence, thus witnessing one of her idols pass away leaves a profound wound. Murphy was instrumental in helping her weave feelings into her music, enhancing her as an artist. After his demise, she finds herself devoid of inspiration and emptiness within. The show underscores the harsh reality that some people can be heartless through Murphy’s death. Although he touched countless lives with his saxophone melodies, only Lisa attends his funeral.

3 “Grampa vs. Sexual Inadequacy”

Season 6, Episode 10

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On the outside, Homer and Grampa appear as a harmonious father-son pair, but beneath that facade, their relationship is simmering with tension. In the episode titled “Grampa vs. Sexual Inadequacy“, it’s revealed that Homer and Marge’s intimacy diminishes due to routine bedroom activities. However, Grampa steps in by creating a rejuvenating potion for them. The duo then contemplates marketing the tonic across America, but their partnership crumbles when Grampa admits he never wanted Homer as his successor.

A Tonic Cannot Erase the Scars of Estrangement.

As a cinema enthusiast, I must say that just like Simpson & Son’s Revitalizing Tonic might have mended Homer and Marge’s marriage, it seems to have done little in cooling down the explosive father-son relationship. It’s a pity because for a brief moment, it appeared as if they had both left their past behind and were on the verge of making a fortune from their new bond. Grandpa really needs to watch what he says! However, there’s a silver lining: Homer’s harsh remark has made him promise to be more attentive towards his children.

2 “Donnie Fatso”

Season 22, Episode 9

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“Donnie Fatso”, modeled after one of the iconic ’90s gangster films, Donnie Brasco, portrays a character who, much like the original, is notorious for his self-preservation strategies. In this instance, Homer takes on the role of an informant and strikes a deal to infiltrate Fat Tony’s criminal organization as a means of lessening the penalty for his bribery conviction. However, when Fat Tony discovers Homer’s treachery, the revelation proves so crushing that he suffers a fatal heart attack.

Homer the Rat

Homer is known for his numerous mistakes, yet few anticipated he’d betray a friend to such a degree. Throughout the series, Homer and Fat Tony built a rich history together, making it hard to believe that Homer would reject the FBI’s proposal. Given Fat Tony’s portrayal as a more likable Don Corleone-like mobster rather than a heartless one, his demise is particularly poignant.

I’m glad the episode concluded on a side-splittingly funny note! You see, Fat Tony’s relative, the fit and trim Fit Tony, steps into the boss’s shoes, only to discover that the pressures of the position lead him down a path of overeating. In no time, he transforms from Fit Tony into a spitting image of his predecessor – the new Fat Tony!

1 “Lisa’s Substitute”

Season 2, Episode 19

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In the story titled “‘Lisa’s Temporary Teacher,’” Lisa’s usual educator, Miss Hoover, temporarily steps away due to suspicions of Lume disease (later discovered that her symptoms were psychosomatic). A fresh substitute teacher, Mr. Bergstrom, takes her place, and Lisa admires his teaching style, making school days something she eagerly anticipates. However, when Miss Hoover resumes her duties, Lisa is deeply saddened. Over time, Lisa learns to seek inspiration in various individuals around her, including Homer, as new role models.

Lisa is Forced to Let Go

As a devoted Simpsons fan, I consider “Lisa’s Substitute” one of the most heartfelt episodes. A particularly poignant moment occurs when Lisa rushes to the train station, pleading with Mr. Bergstrom not to depart, confessing that she’d be adrift without him. But what truly tugs at the heartstrings is the note he leaves her – a message that lingers long after the credits roll.

“You are Lisa Simpson.”

“This thought serves as a gentle reminder to Lisa that her strength lies within her – it empowers her to create her own happiness, rather than relying on others.

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2024-09-08 00:02