The Simpsons: 10 Saddest Episodes of All Time, Ranked  

The Simpsons is broadly considered one of the most successful and influential animated TV shows of all time, with its lasting impact on pop culture and the genre plain for all to see. The show has tackled various issues over its multiple decades on the small screen, with episodes examining or lampooning current events and other relevant features of modern society for many years. While The Simpsons keeps its focus predominantly on comedy, it hasn’t been afraid to branch over the course of its run so far, delivering stories that are heartfelt, interesting, and, on more than one occasion, surprisingly emotional.

In fact, there have been several episodes of The Simpsons that have been downright sad. While the wacky adventures of the titular family typically gives way to comedic antics, there are times when the subject matter is a little more serious, and that can often prove to be unexpectedly emotional. While they may be somewhat rare, especially in the show’s more recent seasons, the saddest episodes of The Simpsons are more than capable of making its audience well up with tears.

10) Moaning Lisa (S1, E6)

In one of the best episodes of The Simpsons season one, the focus was on Lisa as she faced something of an existential crisis. As well as a subplot involving Homer attempting to beat Bart at a video game, the episode’s main story followed an incredibly disillusioned Lisa as she tried to find some meaning or purpose to her life. “Moaning Lisa” ultimately saw Lisa identify her passion for music, particularly jazz, with the help of musician Bleeding Gums Murphy.

What makes “Moaning Lisa” such a sad episode is not necessarily the thrust of its narrative, but the actual subject matter. Seeing Lisa despair over various elements of her life is something that many viewers can likely identify with, compounded by her young age and the reactions of those around her. While its ending ultimately sees Lisa gain a creative outlet, seeing her so upset throughout the episode is something that makes it an especially sad early chapter in The Simpsons‘ history.

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

One of The Simpsons‘ best running gags throughout its run has been its chalkboard gag, in which the opening of each episode features a different—and usually hilarious—written message in front of Bart on a chalkboard. However, season 25’s “Four Regrettings and a Funeral” featured a different sort of message: an emotional farewell to Mrs. Krabappel after her voice actor, Marcia Wallace, passed away. The sad tribute is capped off by Bart’s troubled expression, making it an especially upsetting moment.

The episode itself is also decidedly sad in tone. It features multiple characters reflecting on their biggest regrets at the funeral of a local man, making it a morbid commentary on life, death, and seizing the moment. While “Four Regrettings and a Funeral” is a relatively sad episode from beginning to end, it’s really the opening chalkboard gag, and the real-world context behind it, that makes it such an emotional watch.

8) Bart Gets an F (S2, E1)

Since the very earliest episodes of The Simpsons, Bart has been the show’s prankster. Introduced as a lovable rogue, Bart’s childhood troublemaking became a core part of the character and his stories, though other aspects of his personality have also been explored. Season 2’s “Bart Gets an F” establishes Bart’s academic difficulties, as its story follows the young student as he attempts to pass a difficult test in order to earn a passing grade for the entire year.

What makes the episode such a sad one is simply that its story is relatable to so many, and it shows a much more vulnerable side of Bart as a character. Seeing Bart struggle to study and apply himself no matter how hard he tries is something that the majority of people have experienced in their life, and the emotional roller coaster of the episode’s story makes it one of the most unforgettable entries to The Simpsons‘ early years. Though it’s relatively mundane in its subject matter, “Bart Gets an F” is one of the most emotional episodes from across The Simpsons‘ entire run.

7) Lisa’s Substitute  (S2, E19)

Over the course of The Simpsons, Lisa has changed considerably since the show’s beginnings. Season 2 in particular saw her develop massively as a character, with one of its most heartfelt episodes standing out as an important moment for Lisa. “Lisa’s Substitute” saw the introduction of Dustin Hoffman’s Mr. Bergstrom, a substitute teacher who swiftly became something of a hero to Lisa, with his immersive lessons and sensitive nature striking a chord with the young Simpson.

The episode inevitably ends with Berstrom’s departure, though not before he’s able to share one final piece of moving advice with Lisa. Its ending also sees an inattentive Homer realize his error and attempt to make things right with Lisa, prompting one of the most tear-inducing endings to any episode across the show’s run. “Lisa’s Substitute” is an episode that stands out as especially sad, even several decades after it initially aired.

6) Old Money (S2, E17)

While it may not be the most memorable of Simpsons episodes, season 2’s “Old Money” is an incredibly sad chapter in the lives of the Simpson family, particularly that of Homer’s father, Abe. It sees Grampa Simpson fall in love with Bea, another resident at the Retirement Castle, with the pair flirting and enjoying one another’s company. However, after Homer patronizes his father and drags him away from a date with Bea, Grampa later learns that she died, leaving him a considerable sum of money.

Seeing Grampa briefly find love in his old age only to have it taken away so abruptly is upsetting enough, but the episode’s exploration of his dismissal of the money is especially heartbreaking. Everything about the episode’s story is deeply upsetting, from Grampa and Bea’s short-lived relationship to his abject misery following her death and everything in between. It’s an episode that tugs at the heartstrings from beginning to end, making it an incredibly sad moment in the show’s history.

5) ‘Round Springfield  (S6, E22)

Airing squarely within the golden era of The Simpsons, Season 6’s “‘Round Springfield” serves as an example of the emotionally complex storytelling the show is capable of. After learning that her hero, Bleeding Gums Murphy, is in the hospital, Lisa reconnects with him. However, the subsequent death of the classic Simpsons character then hits her incredibly hard, and the episode then goes on to follow Lisa trying to honor Bleeding Gums’ memory even as she mourns his loss.

It’s an episode that delves into grief, particularly the ways in which children process death and loss. It’s an episode that brings yet more sadness to Lisa Simpson’s life, but all the while shows that she can lean on her family and her own emotional maturity to navigate through the difficulties of grief. Bleeding Gums’ final farewell to Lisa is a moment that stands out as one of the most emotional in the history of the entire show, making “‘Round Springfield” an especially poignant episode.

4) Mother Simpson  (S7, E8)

Season 7 saw the introduction of Homer’s mother, Mona, to The Simpsons, filling in a blank in the character’s backstory. His enigmatic mother appeared after believing her son had died, prompting the pair to reconnect. The episode, “Mother Simpson”, explains the reasons for Mona’s absence while also exploring Homer’s past and his feelings toward the mother who he believes abandoned him.

“Mother Simpson” is an episode that is packed with laughs, but still manages to be incredibly sad. The story of how Mona was forced to leave her son behind is tragic, while the brief connection she shares with her family is made all the more upsetting when it’s ripped away again. “Mother Simpson” is an episode that manages to blend comedy with truly emotional drama, and its final scene of Homer silently watching the sky is one of the most poetically sad endings in the show’s history.

3) Dog of Death (S3, E19)

There are many Simpsons characters who deserve more attention, and Santa’s Little Helper is often considered one of them. Despite being a part of the titular family, the Simpson’s dog is rarely the focus of whole episodes. Interestingly, when he is, it often makes for incredibly memorable and emotional scenes, with the bond between human and canine facilitating decidedly powerful narratives. Season 3’s “Dog of Death” was among the first Simpsons episodes to focus specifically on Santa’s Little Helper, and it’s consistently sad right up to its final moments.

The episode sees Santa’s Little Helper get sick and require expensive veterinary treatment. The resulting financial strain this puts on the family causes the upset dog to run away, ending with him being reconditioned as a brutal attack dog by Mr. Burns. The culmination of this is a scene in which Santa’s Little Helper remembers all the happy memories he has shared with the Simpson family, breaking through his conditioning in a moment capable of bringing a tear to the eye of even the most hardened viewer, and establishing “Dog of Death” as a uniquely emotional episode of the show.

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

Although it aired just after the end of what is widely considered The Simpsons’ golden era, season 11’s “Alone Again, Natura-Diddily” is an episode that still stands out. It marked one of the most shocking and unexpected developments in The Simpsons‘ history, as it saw Maude Flanders be abruptly killed off. The death of the Simpsons’ neighbor caused her husband Ned to spiral into a pit of grief, with the episode going on to chronicle his short-lived relationship with a Christian rock musician shortly after Maude’s death.

There are several moments of comedy in the episode, but it’s still unbelievably sad. For the show to kill off one of the Simpsons’ closest neighbors was shocking, and seeing Ned’s difficulty in processing the sudden loss of his wife is deeply tragic and incredibly upsetting. Ned’s grief is the focal point of the entire episode, making it a rare Simpsons story that is based purely on a deeply sad emotional premise.

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

Season 2 of The Simpsons featured a number of episodes that were distinctly emotional, but none stand out quite as much as “One Fish, Two Fish, Blowfish, Blue Fish.” The episode sees the Simpson family dining at a sushi restaurant, only for Homer to eat a rare and exotic fish that is deemed highly poisonous. Told he likely only has 22 hours to live, the episode takes the viewer on an emotional journey of a father and husband attempting to make the most of his final day on Earth.

Seeing Homer bravely face the prospect of death and trying to work through a list of final tasks is pretty powerful in its own right. However, the melancholic thrust of the episode stems largely from Homer’s inability to please everyone, forcing him to constantly revise his list as the time ticks away. The episode’s final scene sees Homer prepare himself for death by tuning into to an audiobook of the Bible, only to awake in the morning to find that the danger has passed. The ending makes it one of the most heartwarming Simpsons episodes, although its story is deeply unsettling right up to the final moments.