The Simpsons, as one of the longest-running TV shows in history, has brought several generations countless laughs over the decades. However, so it goes that there can’t be comedy without tragedy, andThe Simpsonshas plenty of that to offer audiences as well.
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Often the show will play the tragedy for jokes, like Homer’s stupidity, the family’s lack of money, orBart’s misbehavior, but sometimes it really goes for the emotions. WhenThe Simpsonswants to, it can strike the audience right in the heart and bring them to tears like the best dramas, coming from a real earnest place.
Updated June 02, 2025, by Tom Bowen:Though it may be a comedy at heart, The Simpsons is able to evoke a wide range of emotions in viewers. Besides making viewers laugh, the show’s writers are perhaps most adept when it comes to making them cry, with plenty of heart-wrenching moments to be found throughout the show’s 33 seasons. In fact, the saddest Simpsons episodes are arguably a lot more memorable than the funniest, and the speed and ease with which the writers are able to change an episode’s tone has played a huge role in the show’s continued success over the past three decades or so.
12Bart and Lisa’s Rivalry - Lisa on Ice
Given how often they may find themselves competing for their parents' attention, it’s only natural that some siblings will develop a bit of a rivalry. In some extreme instances, however, these rivalries can become incredibly toxic, as is the case in the eighth episode of season six, Lisa on Ice. The episode sees Lisa signing up to play in goal for Apu’s hockey team, with the spikey-haired saxophonist soon becoming the team’s star player.
Homer then stokes the rivalry between Bart and Lisa ahead of a big game between their respective teams, with things turning nasty pretty quickly. Just as it appears that the pair are ready to beat the snot out of each other though, they each remember the good moments that they’ve shared. With the game tied, the crowd begins rioting as Bart and Lisa drop their hockey sticks and skate off together into the sunset while Marge smiles proudly.
11Grandpa Gives Away Homer’s Dog - To Cur, with Love
Most people gave up onThe Simpsonslong before season 24 rolled around, but those who stuck with it were treated to an incredibly emotional episode in the form of To Cur, with Love. It’s one of the series' many flashback episodes and tells the story of Homer’s beloved dog Bongo. Despite the pair’s incredibly strong bond though, things end on a bitter note following an unfortunate incident at the nuclear power plant.
After Bongo bites Mr. Burns to protect Homer, Abe ends up giving him away to prevent Burns from having him killed. After a few months, Homer tries to rescue Bongo from his new home but finds that Bongo is not only happy, but has seemingly forgotten all about his former best friend. He later finds out that this isn’t actually the case, but the pain that he feels during that moment will likely hit pretty hard with all animal lovers.
10BartBuys Marge A Present - Marge Be Not Proud
The show as a whole is full of Bart atonement stories. These stories involve Bart doing his usual misbehavior, but taking it too far and feeling he needs to make amends. There have been various angles on it over the years, but the episode Marge Be Not Proud is by far the best.
After being caught shoplifting, ruining a family photo, Marge finally gives up on Bart, treating him with a heartbreaking sense of coldness, which makes Bart immediately regret his actions. To make things right, Bart returns to the store he shoplifted from to buy a nice picture of himself for his mother, which causes Marge to hug him in one of the show’s sweetest endings.
9Homer Awaits Death - One Fish, Two Fish, Blowfish, Blue Fish
Despite going through over 30 seasons,The Simpsonshas never really tried to convince the audience that a member of the family was about to die. They’ve been in mortal peril plenty of times, but everyone knows that something will always come along to save them at the last moment.
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When the show was only in its infancy, Season 2, the writers thought they could pull this trick. After eating some bad fugu,Homer Simpsonbelieves he has just 24 hours left to live. The moment where he accepts his fate is very sobering, as he sits looking out his window listening to the Bible in a unique moment for the show. Very few people actually believed Homer was really going to die, but the moment where he slumps over still hits the heart in a weird way looking back.
8Bart Fails - Bart Gets An F
Another Bart sympathy romp, this episode takes quite a different route to the emotional low that Marge Be Not Proud does. Where that episode is all about Bart coming to terms with what he did wrong, this episode focuses on Bart trying his hardest to make amends.
After being told he’s going to fail the 4th Grade, he has an upcoming test to save himself, however, try as he might, he just can’t focus on studying. Eventually, he makes the commitment and even gives up a joyous Snow Day to study for this test, which makes it absolutely devastating when he fails anyway. Bart properly breaks down into tears like the show very rarely shows, and even though he manages to earn an extra point to pass, the moment where he fails is still hugely impactful.
7Homer’s Speech To Lisa - Lisa’s Wedding
Most of the flash-forward episodes ofThe Simpsonsdon’t usually go for the emotion. It’s too good of an opportunity to make jokes about the future or tell fun stories about the characters to get bogged down in emotionality. Lisa’s Wedding manages to get the best of both worlds, having this lovely moment in a hilarious episode.
Just beforeLisa is about to walk down the aisle, Homer visits her and espouses a gorgeous speech talking about how much he loves his daughter. The line “you’re my greatest accomplishment, and you did it all yourself” is the perfect summation of their relationship and how Homer truly loves Lisa like no one else.
6Maggie’s First Word - Lisa’s First Word
The episode hits fans with a double-whammy of emotional moments. Telling the story of how Bart responded to Lisa’s birth and the changes it entailed, the two finally come to terms when Lisa speaks her first word, “Bart”, which Bart loves, and they instantly become friends.
One of the great running jokes in the episode is tormenting poor Homer. Homer keeps trying to get his kids to call him “daddy”, but they keep calling him “Homer” instead. This culminated beautifully at the end of the episode when Homer puts Maggie to bed, and just before she falls asleep, she takes out her pacifier and says “daddy” in the show’s most adorable moment.
5We’ll Really Miss You Mrs. K. - Four Regrettings And A Funeral
A moment that comes from real-life sadness, as the character of Edna Krabappel sadly had to be retired in 2013 after her voice actress, Marcia Wallace tragically died. The show has paid tribute to her in several ways over the years, with both Ned Flanders and Nelson Muntz stating how they’re “really gonna miss her,” but this small moment hits the hardest.
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Inthe opening title sequence, Bart’s chalkboard gag is one of the staples, where some silly one-line will be written to kick things off fast-paced and fun. However, this time there was just one short sentence written on the chalkboard that read “We’ll Really Miss You Mrs. K.” as Bart looked on mournfully. It was a small gesture, but an incredibly powerful tribute to one of the show’s greatest performers.
4Bleeding Gums Murphy Tribute - ‘Round Springfield
Lisa doesn’t often get characters to look up to in her life. While her parents love her very much, they can’t connect with her on her hobbies, and Bart is far from a constructive force in her life. So when she meets a character like Bleeding Gums Murphy, who shares her passion for Jazz, she clings to them very hard.
Sadly, that makes it all the more tragic when they inevitably have to leave. In Bleeding Gums Murphy’s case, he died in hospital before Lisa could say goodbye. She can’t find a way to pay proper tribute to him until Bart comes along in a fit of brotherly compassion and gives up his $500 legal win to buy her a record that can be played on the radio. It’s a touching scene as Lisa gets to say goodbye whilst the entire town enjoys Murphy’s record.
3You Are Lisa Simpson - Lisa’s Substitute
Where Bleeding Gums Murphy connected with Lisa over a love of Jazz, a few seasons earlier she found someone to connect with over her love of education. A substitute teacher, Mr. Bergstrom teaches more passionately than anyone before and Lisa is amazed by it.
Such is the life of a substitute, though, that eventually, her regular teacher comes back, and Mr. Bergstrom must say goodbye. Lisa doesn’t want to let him go, and Mr. Bergstrom helps her by handing her a note that he says will help her whenever she feels like she’s alone in the world. When she opens it, it simply says the words “You are Lisa Simpson”, a powerful message of self-affirmation reminding Lisa and the audience to always stay true to themselves.
