10 Saddest ‘The Simpsons’ Episodes of All Time, Ranked

The Simpsons is one of the best animated shows of all time, but not just because it’s funny. While it can be pure joy and silliness, it’s also among the best animated sitcoms at getting its audience to tear up. Melding humor in with pathos is exceptionally hard, but this show at its prime made it look effortless. Great writing, splendid animation, top-notch directing, brilliant voice acting—they all combine into something that can really move its viewers. Of course, not every Simpsons episode shoots for that effect, and some of the series’ best entries just try and make us laugh. Season eight’s “You Only Move Twice” is probably the prime example of that.

But there’s no denying the power of the show’s more plaintive stories. Sometimes you can immediately tell an episode is going to be in a sadder mode, like in “Barthood,” and sometimes it comes out of left field. The plot twist in “One Fish, Two Fish, Blow Fish, Blue Fish,” for instance, shifts the story from being a funny family visit to a sushi bar with some lighthearted karaoke and endless seafood to being a contemplative and mournful reflection on all the things we wish we’d done in our lives. There are also many episodes that try to be sad but aren’t written well enough to pull off as much emotion as they want, such as “Alone Again, Natura Diddly.” The following ten episodes not only have the premise but also the execution to tug at fans’ heartstrings better than the rest. (Warning: proceed with a handkerchief.)

10

“Bart the Lover”

Season 3, Episode 16 (1992)

One of Bart’s most touching and hilarious episodes, “Bart the Lover” is also arguably Mrs. Krabappel’s (Marcia Wallace) best episode. She’s so lonely that she offers to do the children’s homework for them if they’ll just stick around after class—giving the story a sad tone while the opening credits are still rolling. She buys a soup called “Chef Lonelyhearts” and puts a rather desperate personal ad in the paper. So Bart (Nancy Cartwright) writes to her, pretending to be the perfect man, and it works. The viewer cannot help but feel awful for poor Edna, who will inevitably be devastated by this farce.

After having his alter-ego stand up to his teacher, Bart sees Mrs. Krabappel crying alone in a restaurant where the date was set. It’s such a sad moment that even Bart realizes that he screwed up. He needs to break things off, but doesn’t know how, so he humbly asks the rest of his family to help him. The letter they collectively write is both funny and tender. Though the episode ends on a surprisingly warm note, the viewer can’t help but see that Edna’s still single in the end.

9

“Round Springfield”

Season 6, Episode 22 (1995)

Season six’s “Round Springfield” is set off by a jagged metal Krusty-O in Bart’s cereal box, which wins the boy a trip to the hospital and $500 in damages. It’s pretty funny to watch his teacher take her sweet time before sending him to the nurse, but once Bart’s recovering in the hospital, Lisa (Yeardley Smith) hears Bleeding Gums Murphy in another room. She’s the first visitor he’s had, and he gives her his saxophone, which she proudly plays at her recital.

Afterward, she tries to tell him how well she did, but Bleeding Gums has already passed away. Lisa spends the second half of the episode mourning him, and it’s hard not to pity the man whose funeral goes so unattended. “Sex on the Beach” was his only recorded album, so Lisa plays it on the radio to get him some posthumous attention. A cloud in the shape of his face thanks her and bids her farewell, a sweet ending to an episode that can help fans get over a period of loss.

8

“Barthood”

Season 27, Episode 9 (2015)

A great Simpsons parody episode of the film Boyhood, “Barthood” takes us through what we’re led to believe are some of the most influential parts of Bart’s childhood. It’s tough to see Homer (Dan Castellaneta) disapprove of Bart’s drawings at such an impressionable age. The boy is also disappointed by the “camping trip” that Homer takes him on, and the bumper sticker that he asks his father to put on his car doesn’t get any respect.

We see Bart from a somewhat different perspective here. He feels dumb in comparison to his sister, harboring jealousy for her and a need to act out for attention. Interestingly, we never see Bart at his normal age of 10—only when he’s younger and older. It’s both telling and hilarious when Homer isn’t willing to go after him because “he’s walking kinda fast.” The man even manages to hurt Bart’s feelings when he’s high. Other scenes, like Bart visiting Grampa’s grave or failing spectacularly, make for an episode with more affecting melancholy than most.

7

“A Streetcar Named Marge”

Season 4, Episode 2 (1992)

Marge (Julie Kavner) is auditioning for a musical version of A Streetcar Named Desire, but nobody—not even Lisa—seems to notice. Marge tries to talk about it a bit more, saying she hasn’t been in a play since high school and would like to make some adult friends. Spending all day alone with Maggie makes her sometimes feel like she doesn’t exist, and Homer’s total indifference to all this is both comical and crushing. It’s a struggle for Marge to simply practice before her audition, and getting gaslighted at home puts the audience completely on her side.

The audition doesn’t go as she hoped. Dejected by getting turned down, Marge calls Homer in one of the saddest moments in Simpsons history. Her luck quickly turns around, yet even after she gets the part of Blanche, the obvious connection she has with that tragic character imbues the rest of her storyline with a melancholic tone. Homer is so frustrating here, but even he’s able to eventually draw a parallel between himself and Stanley. Overall, this is one of the most moving episodes about the Simpson matriarch.

6

“One Fish, Two Fish, Blow Fish, Blue Fish”

Season 2, Episode 11 (1991)

Don’t like it till you try it: a lesson that Homer takes to heart a little too hastily in season two’s “One Fish, Two Fish, Blow Fish, Blue Fish.” The Simpsons decide to go out for sushi, and Homer winds up ordering literally every single thing on the menu. That is such an expensive meal, but it also winds up being a dangerous one. Since the assistant chef cut the pufferfish, Homer’s told he’s probably been poisoned.

So it looks like Homer’s got 22 hours to live, and he tries to spend them doing all the things on his checklist. We all know Homer somehow won’t be dying at the end, but the darker tone still works anyway, focusing more on his rushed attempt to make the most of what is presumably his final day on Earth. There is one particular scene in which we see Homer listening to an audiobook of the Bible as he sits in a chair awaiting his death. This is an especially moving shot in a beautifully sad episode.

5

“Old Money”

Season 2, Episode 17 (1991)

In “Old Money,” the usually incoherent Grampa Simpson falls in love with a woman named Bea when they both get the wrong pills. You’ve got to love how they ingest their medication flirtatiously. After a brief montage, their connection is palpable. Homer’s response to Grampa saying he has a girlfriend is so patronizing, and it’s sad to see Abraham get dragged away from a date he cares so much about.

When he finds out that Bea died of a burst ventricle, he says she died of a broken heart. Blaming Homer for losing her, Abe tells Homer he has no son. She leaves him about $100,000, but the old man doesn’t find much happiness with his new fortune. Meanwhile, we get a moving shot of Homer pitifully moping on the sofa in a shadowy living room. That close-up on two wrinkled hands, a shot of the elderly walking onto a bus, the name of a new dining hall—these moments all stir up emotions in a way that most Simpsons entries don’t.

4

“Moaning Lisa”

Season 1, Episode 6 (1990)

This story is literally about depression. Lisa’s got the blues, and she’s got them bad. All the suffering in the world has made her wonder what the point of life really is, and everyone around her has either been completely insensitive to her or totally unable to help (despite good intentions). The kids at school pelt her with dodgeballs, while her father and brother are too busy playing a boxing video game to fully engage with (or even understand) Lisa’s problem.

One of the greatest episodes about Lisa culminates in the introduction of a new character. Lisa hears a saxophone blaring in the distance, so she follows the music until she finds Bleeding Gums Murphy. Their little chat is part of Simpsons legend, and the ending cements this as one of the first season’s strongest episodes. It’s also a happy resolution to a story that seamlessly blends humor into its rather somber topic.

3

“Principal Charming”

Season 2, Episode 14 (1991)

At a co-worker’s wedding, Selma thinks back to when the groom flirted with her first. Her twin ruined it, and the rest is history. She was pressured into celibacy, but now she’s so desperate to find a man that she begs Marge for help. Marge enlists Homer, who eventually finds Principal Skinner (Harry Shearer). Selma’s so nervous when she meets him that she has her twin serve him food instead. Skinner is immediately smitten, even as Selma tries and fails to gain his attention from her sister (who initially doesn’t even want it).

Intriguingly, Selma winds up having Patty accept his request for a date, and Patty even falls for him. There’s a moment when she tries to reject Seymour but feels too bad. Meanwhile, poor Selma is jealous and obviously not finding any luck. As an episode that ends sadly for every main character involved, “Principal Charming” is an oft-forgotten but exceptionally sad Simpsons tale.

2

“Mother Simpson”

Season 7, Episode 8 (1995)

Though season seven’s “Mother Simpson” contains funny moments to be sure, this is largely a sad episode. Here we meet Homer’s mother (voiced by Glenn Close), who’s been absent from his life since he was a kid. Thinking he died, she goes to his grave and finds him very much alive—and they reconnect as she tries to hide her past. Some of the small jokes have heartbreaking implications, like when Homer finds out he could have stayed in contact with his mother all these years if he only tipped his letter carrier for Christmas.

Part of what makes this entry so melancholic is that Homer’s mom is so kind and fits in so well with the rest of the family. She was apparently just as precocious as Lisa; she made Homer happy, and she was an enemy of Mr. Burns. The flashback scenes with Homer as a child are a bit difficult to watch, especially when she kisses him goodbye without telling the young Simpson why she has to go. The ending involves a man sitting alone in his car and staring off into the night sky, a scene that makes this arguably one of Homer’s most moving episodes.

1

“Lisa’s Substitute”

Season 2, Episode 19 (1991)

You never know who or what you’re going to get when your regular teacher is out. In “Lisa’s Substitute,” Lisa gets the best substitute teacher ever. Voiced by Dustin Hoffman, Mr. Bergstrom’s immersive lessons really strike a chord with Lisa. She develops a crush on him, but, more importantly, she sees him as a paternal influence that her own father cannot live up to. Meanwhile, Homer is even more insensitive than usual in this episode; the contrast between them has never been sharper.

With Mr. Bergstrom, Lisa finally feels understood, which will inevitably lead to profound disappointment. Every substitute has to leave sometime, after all, and it’s devastating to watch Lisa rush to say goodbye to Mr. Bergstrom one last time. The note he leaves her is so moving, containing a message that anyone who’s feeling low can use when they need it. Along with the ending, in which Homer tries to redeem himself, this may be the most tear-inducing episode of the series. Which also makes it one of the greatest Simpsons episodes of all time.

NEXT: The Best Maggie Episodes in ‘The Simpsons,’ Ranked