The Simpsons: 10 Saddest Episodes of All Time, Ranked

Over the years, “The Simpsons” has earned a reputation as one of the most impactful and influential animated TV series ever produced, leaving an indelible mark on popular culture and the animation genre as a whole. Throughout its long run, this show has taken on numerous topics, often satirizing current events or significant aspects of contemporary society. Despite primarily focusing on humor, “The Simpsons” has ventured into other territories during its tenure, presenting stories that are touching, engaging, and even stirringly emotional at times.

As a devoted fan of “The Simpsons,” I must confess that there have been instances when this comedic staple left me teary-eyed. Contrary to the usual quirky escapades of the Simpson clan, which are filled with laughter and mirth, there are moments when the series delves into more serious territory. These somber episodes can catch viewers off guard, striking a profound emotional chord that’s quite unexpected in such a lighthearted show. Granted, they may be few and far between, especially in the later seasons, but when they do arrive, they pack a powerful punch that could bring even the hardiest viewer to tears.

10) Moaning Lisa (S1, E6)

In one outstanding episode from the first season of The Simpsons, attention centered around Lisa, grappling with a deep personal struggle that felt like an existential crisis. Meanwhile, there was also a side plot featuring Homer trying to outdo Bart at a video game. The main narrative followed a disenchanted Lisa on her quest to discover significance or direction in her life. In the end, “Moaning Lisa” revealed Lisa’s hidden love for music, especially jazz, when she encountered musician Bleeding Gums Murphy and found solace in his tutelage.

The reason “Moaning Lisa” stands out as a melancholic episode isn’t solely due to its plotline, but rather the somber topic it explores. Watching Lisa struggle with different aspects of her life resonates with many viewers, given her youth and the responses from those around her. Although the finale offers Lisa a means of creative expression, the emotional turmoil she experiences throughout the episode makes “Moaning Lisa” a particularly poignant early installment in The Simpsons‘ storied history.

9) Four Regrettings and a Funeral (S25, E3)

One of the ongoing humor elements in “The Simpsons” series is the chalkboard gag, where each episode starts with a unique and often humorous message written on a chalkboard in front of Bart. However, in season 25’s “Four Regrettings and a Funeral,” this tradition took a different turn: instead of a joke, it served as a heartfelt farewell to Mrs. Krabappel, following the death of Marcia Wallace, the voice actress who played the character. The poignant tribute was accentuated by Bart’s concerned expression, making it an especially moving scene.

The episode carries a somber mood throughout, as various characters express their deepest regrets at the funeral of a town resident. This creates a bleak depiction of life, mortality, and the importance of living in the present. However, it’s not just the depressing nature of “Four Regrettings and a Funeral” that makes it poignant; it’s the opening joke written on a chalkboard and the underlying real-life significance behind it that truly make it an emotionally powerful viewing experience.

8) Bart Gets an F (S2, E1)

From its initial episodes onward, Bart Simpson has always been known for his mischievous pranks on “The Simpsons.” Initially depicted as a charming troublemaker, Bart’s childhood antics formed a significant aspect of his character and the show’s plotlines. One notable instance is Season 2’s episode titled “Bart Gets an F,” where Bart’s academic struggles are highlighted, as he strives to pass a difficult test to maintain a passing grade for the entire year. Other dimensions of his personality have also been delved into over time.

The episode stands out as particularly poignant due to its relatable storyline and the deep vulnerability it reveals about Bart’s character. Many viewers can resonate with his struggle to study and find success, a challenge that is universal. The emotional journey of the plot makes it one of the most memorable episodes from The Simpsons‘ early seasons. Despite its seemingly ordinary subject matter, “Bart Gets an F” stands as one of the most emotionally charged episodes throughout the entire series.

7) Lisa’s Substitute (S2, E19)

Throughout the duration of “The Simpsons”, Lisa’s character has undergone significant transformation from its early days. The second season, in particular, marked a considerable growth spurt for Lisa, with one particularly poignant episode serving as a pivotal moment in her character development. Known as “Lisa’s Substitute”, this episode introduced Dustin Hoffman’s character, Mr. Bergstrom, a substitute teacher who resonated strongly with young Lisa due to his engaging teaching methods and compassionate demeanor.

The episode concludes with Berstrom leaving, but not before imparting some poignant last words to Lisa. The episode’s finale also features Homer, who was previously distracted, recognizing his mistake and trying to mend things with Lisa. This leads to one of the most emotionally stirring endings in any episode throughout the series’ history. “Lisa’s Substitute” is a particularly heart-wrenching episode, even years after it first aired on television.

6) Old Money (S2, E17)

Although “Old Money” from Season 2 isn’t as iconic as other Simpsons episodes, it stands out as a poignant tale in the lives of the Simpson family, particularly focusing on Homer’s father, Abe. In this episode, Grampa Simpson develops an affection for Bea, another resident at the Retirement Castle, and they share pleasant moments together. However, Homer disrespectfully interrupts their relationship by taking Abe away from a date with Bea. Unfortunately, Grampa later discovers that Bea has passed away, leaving him a substantial inheritance.

Experiencing Grandpa discovering love late in life, only for it to be taken away suddenly, is already painful, but what makes this episode particularly poignant is its portrayal of his disregard for money. The entire narrative of the episode is profoundly moving, encompassing Grandpa’s fleeting romance with Bea, his profound sorrow following her demise, and every moment in between. This episode pulls at your heartstrings from start to finish, making it a remarkably sad milestone in the show’s chronicle.

5) ‘Round Springfield (S6, E22)

During the peak time of “The Simpsons” golden age, Season 6’s “‘Round Springfield” showcases the series’ ability to craft emotionally nuanced stories. When Lisa discovers that her idol, Bleeding Gums Murphy, is hospitalized, she rekindles their relationship. Unfortunately, the demise of this iconic Simpsons character deeply affects Lisa, and the episode proceeds to depict Lisa as she struggles to remember Bleeding Gums while grieving his passing.

This episode explores the complexities of grief, focusing on how children cope with death and parting. In this episode, Lisa Simpson experiences even more sorrow but is shown to rely on her family and personal emotional maturity to manage through the challenges of grieving. The goodbye scene between Bleeding Gums and Lisa stands as one of the most moving moments in the series, making “‘Round Springfield” an episode filled with deep emotions.

4) Mother Simpson (S7, E8)

As a devoted cinephile, let me share my excitement over Season 7 of “The Simpsons”, where we were introduced to none other than Homer’s mother, Mona. This was a significant gap in Homer’s backstory that finally got filled!

Mona, the elusive figure I had always wondered about, made her appearance under the belief that her son had perished. This emotional revelation sparked an unexpected reunion between them. The intriguing episode titled “Mother Simpson” delved into the reasons behind Mona’s mysterious disappearance while simultaneously shedding light on Homer’s past and his complex feelings towards the mother he believes abandoned him.

In this episode, I found myself laughing heartily, but the storyline hit a profoundly emotional chord. The heart-wrenching tale of Mona being torn away from her son left me feeling sorrowful. Yet, for a brief moment, her reunion with her family offered a glimmer of hope – until it was cruelly snatched away once more. This episode masterfully blends humor with deep emotional resonance, and the poignant closing scene of Homer gazing silently at the sky is undoubtedly one of the saddest endings I’ve ever witnessed in the show’s history.

3) Dog of Death (S3, E19)

It’s quite common for people to feel that certain characters from The Simpsons, like Santa’s Little Helper, deserve more spotlight. Despite being a family pet, the show’s dog is seldom the main focus of entire episodes. However, when he does take center stage, it usually leads to poignant and heartfelt scenes that reveal a strong connection between humans and animals. For instance, “Dog of Death” from Season 3 was one of the earliest Simpsons episodes to focus on Santa’s Little Helper, and it remains a tear-jerking watch till its conclusion.

In this episode, Santa’s Little Helper falls ill and needs costly veterinary care, causing financial stress for the family. This strain leads Santa’s Little Helper to run away, eventually landing in the hands of Mr. Burns who transforms him into a ruthless attack dog. The emotional climax occurs when the reconditioned dog recalls all the joyful moments he spent with the Simpson family, breaking free from his training and stirring tears even from the most stone-hearted viewers. This episode is particularly poignant, earning it the title “Dog of Death” in the series.

2) Alone Again, Natura-Diddily (S11, E14)

Despite airing during what some consider the end of “The Simpsons”‘ golden age in its 11th season, the episode titled “Alone Again, Natura-Diddily” remains memorable. This episode is significant because it featured one of the most stunning and unanticipated plot twists in “The Simpsons”‘ history: the sudden death of Maude Flanders. The demise of the neighboring character left her husband Ned in a state of profound sorrow, which was depicted throughout the episode as he entered a brief romance with a Christian rock musician shortly after Maude’s passing.

In the episode, there are numerous funny parts, yet it remains surprisingly melancholic. The show’s decision to eliminate one of the Simpsons’ dearest neighbors was startling, and watching Ned struggle with the unexpected death of his wife is heart-wrenching and profoundly moving. Ned’s mourning takes center stage throughout the episode, making it a unique instance in The Simpsons where the story revolves around a deeply sorrowful emotional theme.

1) One Fish, Two Fish, Blowfish, Blue Fish (S2, E11)

In the second season of “The Simpsons,” an exceptional episode titled “One Fish, Two Fish, Blowfish, Blue Fish” stands out for its emotional depth. This installment follows the Simpson family as they visit a sushi restaurant. Unfortunately, Homer consumes a toxic, exotic fish and is informed he has approximately 22 hours left to live. The narrative then unfolds into a heartfelt tale of a dying father and husband who struggles to make the best use of his remaining time on Earth.

Witnessing Homer’s valiant struggle against the looming prospect of death and his efforts to complete a series of last wishes is undeniably powerful. Yet, the somber tone of the episode primarily arises from Homer’s struggle to please everyone, which leads him to repeatedly modify his list as time runs out. The climax unfolds with Homer getting ready for death by listening to an audio Bible, but waking up the next day to find that the danger has subsided. Despite the unsettling narrative throughout, the heartwarming ending elevates this _Simpsons_ episode to one of its most touching, though its story remains deeply emotional until the very end.

2025-08-17 22:56