15 Saddest Episodes Of The Simpsons, Ranked

Since premiering in 1989, “The Simpsons” has been hailed as the best animated sitcom of all time. Despite its creative ups-and-downs, the show has stood above other cartoon comedies not just for its humor, but for its heart. The best episodes of “The Simpsons” prove that animated characters can engender just as much empathy as live-action ones, and the show’s willingness to explore realistic stories of middle-class life opened the door for other animated programs to move beyond the boundaries of kids entertainment.

One can credit the show’s mixture of laughter and pathos to executive producer James L. Brooks, who created some of the best sitcoms ever made (“The Mary Tyler Moore Show” and “Taxi”) and won Oscars for writing, directing, and producing “Terms of Endearment.” In his best films and TV shows, Brooks mined humor from pain (and vice versa), which proved to be a good counterbalance for creator Matt Groening’s satirical bent.

Throughout 37 seasons and counting, “The Simpsons” has been whimsical, sardonic, and, ultimately, touching. While some episodes make us laugh with their caustic wit, others make us cry with their insight. Here are the 15 saddest episodes of “The Simpsons,” ranked.

Bart might be a little stinker, but that doesn’t mean he won’t drop that facade from time to time, as he does in “Bart Gets an ‘F’.” In the Season 2 premiere, Bart is faced with repeating the fourth grade after failing his last four history exams. Desperate to escape his dreaded teacher, Mrs. Krabapple, Bart hunkers down to study, seeking guidance from class nerd Martin Prince and even missing a snow day to read up on the Declaration of Independence.

When Bart fails yet again despite his best efforts, he cries in front of Mrs. Krabapple, who drops her own disdain for the class cut-up to comfort him. It’s a rare moment of vulnerability for Bart, who ultimately gets a passing grade for demonstrating applied knowledge. Bart becomes so overjoyed he actually kisses Mrs. Krapabble, which he quickly regrets. It isn’t often that we get to see Bart behave in such an emotional way, and whenever he does, it brings a tear to our eyes.

Christmas episodes are always emotional, as the holiday season touches upon the importance of family and community. That’s certainly the case with the seventh season “Simpsons” installment “Marge Be Not Proud,” which begins with Marge refusing to buy Bart a new video game for fear it’s too violent. Unable to rent a copy, Bart tries to steal one, only to be banned from the store by the intimidating Detective Brodka. When Marge takes the family to that same store to get their family Christmas photo taken, Bart’s crime is revealed, and he loses his mother’s love.

What makes this episode so touching is Bart’s attempt to win back his mother’s affections, which he took for granted for so long. His guilt is punctuated by being excluded from holiday traditions like decorating the tree and building family snowmen, which underscores how important those activities are. By the end, Bart manages to win his mother back by buying her an early Christmas gift: A photo of him, complete with a proof-of-purchase receipt.

Bart’s animosity toward Mrs. Krabapple has provided “The Simpsons” with lots of comedy gold, as well as a lot of heart. Take, for instance, the Season 3 episode “Bart the Lover,” in which Bart decides to get revenge on his teacher for placing him in detention. When he discovers she has placed an ad in the personals column, Bart responds under the pen name Woodrow, writing romantic letters and using a photo of hockey star Gordie Howe. He goes so far as to set up a date, and feels remorse when he sees Mrs. Krabapple alone at the restaurant, crying after being stood up.

For all of the complaints parents had about Bart being a bad influence, he did show a capacity to learn and grow from his mistakes. In “Bart the Lover,” he recognizes that his prank was more hurtful than intended, and it’s genuinely heartwarming to watch him make up for that with some help from his family. The farewell letter “Woodrow” composes has the dual effect of healing Mrs. Krabapple’s heart and bringing her closer to Bart.

From the beginning, “The Simpsons” showed a willingness to explores stories that were considered too mature for animated programs. The Season 1 episode “Moaning Lisa” is the earliest example of that, and it’s fitting that it’s the first to center on sensitive middle child Lisa. When Lisa wakes up one morning with overwhelming depression, the family has no idea how to deal with it. She finds an outlet for her existentialism when she meets saxophone player Bleeding Gums Murphy, who teaches her to channel her feelings into the blues.

What makes “Moaning Lisa” so moving isn’t simply its exploration of depression, but the lesson about how to deal with it. That comes through in the final moments, when Marge encourages Lisa to simply put a smile on her face no matter what she feels inside, only to reverse course when she sees her daughter suppressing her true self. Marge’s advice for Lisa to act however she feels helps cheer her up, as does a trip to the jazz club to watch Bleeding Gums perform a song she wrote.

Although they’re like oil and water, Bart and Lisa love each other as only a brother and sister can. Their unique bond is explored in the fourth season installment “Lisa’s First Word,” one of many “Simpons” flashback episodes. As the family encourages Maggie to finally speak, Marge reminisces about Lisa’s first word, which takes them all the way back to 1984. Bart is upset when the arrival of a new baby sister takes the spotlight away from him. He decides to leave home, only to stop when he hears Lisa speak her first word: “Bart.”

“Lisa’s First Word” proves that at the end of the day, there’s no stronger bond than that between siblings, as there’s no one else on Earth who will know you better than someone who’s known you for your entire life. Bart and Lisa may fight constantly, but their bond is as strong as glue. As if that ending weren’t touching enough, the episode really makes us sob when Maggie says “Daddy” after Homer puts her to sleep and shuts the door (voiced by Elizabeth Taylor).

Grampa is among the most ridiculous characters on “The Simpsons,” as his rambling stories and general confusion serve as a constant source of humor. Yet the Season 2 episode “Old Money” grants him a degree of dignity that’s surprisingly refreshing. Grampa falls in love with Bea, a new resident at the retirement home. Although they make plans to spend her birthday together, Homer insists he join him and the family on safari, believing Bea is just a figment of his imagination. When Bea dies, Grampa disowns his son for depriving him of one last day with her.

Suffice it to say, it’s sad to see Grampa suffer from a broken heart, and the episode is as sentimental as they come. What’s really moving is the Capraesque second act, in which Grampa inherits $106,000 from Bea’s estate and decides to spend the money fixing some of Springfield’s many problems. Desperate to raise enough money to help everyone, Grampa tries to win big at a casino, and Homer stops him from losing the entire inheritance on a bad bet. This brings father and son back together, which is ultimately what Bea would’ve wanted.

Homer’s gluttonous appetite has provided “The Simpsons” with a lot of laughs, but his junk food diet proves nearly fatal in “Homer’s Triple Bypass.” In this Season 4 installment, Homer has a heart attack, necessitating a triple bypass surgery. The news is so shocking that it gives him another heart attack, raising the cost from $30,000 to $40,000. Attempts to secure an insurance policy prove futile when Homer suffers a third heart attack before signing the policy, leading him to accept the less-expensive services of Dr. Nick Riviera.

Before Homer goes under the knife, he brings Bart and Lisa to his hospital bedside for what might be a goodbye. Unable to come up with the right words, he relies on his children to tell him what to say, with Lisa whispering words of love for Bart before Bart does the same for Lisa (albeit with one of his trademark digs thrown in). It’s one of the most emotionally impactful scenes in the history of “The Simpsons,” as it shows how the family expresses their love for each other in their own unique ways.

Ned Flanders is one of the best characters on “The Simpsons,” as his relentless cheerfulness and Bible-worshiping constantly grate on Homer’s nerves. Yet his faith and friendliness are put to the test in the Season 11 episode “Alone Again, Natura-Diddly.” While attending an auto race, Homer taunts a cheerleading squad to fire a T-shirt air cannon at him. When the entire squad turns their cannons upon him, they inadvertently hit Ned’s wife, Maude, causing her to fall to her death. Homer’s guilt is compounded by having parked in the ambulance zone, so he tries to help Ned find a new girlfriend.

Although Homer feels seething contempt for his next-door neighbor, he has shown a capacity to empathize with him from time to time, as he does in the aftermath of Maude’s death. The episode’s real power derives from Ned’s conflict with his faith, as he questions why God would punish someone who has been so loyal to him. In the end, his faith is restored through the power of a Christian rock band headlined by Rachel Jordan, who agrees to go out on a date with him.

There are few things more emotional than a good wedding episode, even if the bride and groom don’t end up tying the knot. That’s certainly true of “Lisa’s Wedding,” one of many “Simpsons” installments that looks into the theoretical future. In this Season 6 episode, Lisa visits a fortune teller’s booth while at the Renaissance fair. She gets a glimpse of her 23-year-old self, studying abroad in London and falling in love with her university classmate, Hugh Parkfield, who she wants to marry.

Much to Lisa’s dismay, the posh and proper Hugh doesn’t take to the Simpson clan, and he’s especially appalled when Homer gifts him a pair of pig cufflinks to wear at the wedding. Hugh relents, but only if Lisa agrees never to see her family again. Like many of the best “Simpsons” episodes, “Lisa’s Wedding” shows that despite his shortcomings, Homer is a loving husband and father who wants nothing but the best for his family. Even though she often feels out of place, Lisa recognizes that and, at the end of the day, will always be a Simpson, which makes her final decision so heartwarming.

There’s nothing like a near-death experience to make you reevaluate your entire life, which happens to Homer in the Season 2 episode “One Fish, Two Fish, Blowfish, Blue Fish.” Desperate to try something new, Lisa convinces the family to go to a new sushi restaurant. Although initially reluctant, Homer takes a liking to sushi and even eats a potentially poisonous pufferfish. After being informed he might have less than 22 hours left to live, Homer makes a list of everything he wants to accomplish during his last day on Earth.

This “Simpsons” episode came up with the concept of a bucket list long before the 2007 Rob Reiner movie did, and it’s just as effective in its depiction of it. As Homer goes through his to-do list, from teaching Bart how to shave to listening to Lisa play the saxophone to recording a tape for Maggie, you understand just how much his family means to him. By the end, you’re thankful that Homer has another chance at life, even if he does spend it in front of the television.

Many of the most emotional episodes of “The Simpsons” revolve around Marge, the show’s moral center. In the Season 4 installment “A Streetcar Named Marge,” the put-upon housewife lands the role of Blanche DuBois in a musical production of “A Streetcar Named Desire,” retitled “O, Streetcar!” As Homer repeatedly interrupts the rehearsals, Marge finds herself channeling some of her rage into the role, even going so far as to attack her co-star — Ned Flanders as Stanley Kowalski — with a broken bottle. By the time the curtain raises on opening night, Homer sees Marge for the talented performer that she is.

“The Simpsons” has had many great musical episodes, and “A Streetcar Named Marge” features its fair share of catchy numbers. But what makes this episode so special is how it strengthens Homer and Marge’s marriage. Seeing his wife play the role of a neglected woman makes him realize he’s been doing just that to her, and he finally shows her the compassion she’s so desperately in need of.

Although he only made two significant appearances, Bleeding Gums Murphy is a major part of two of the best “Simpsons” episodes. In “‘Round Springfield,” Bart is given an emergency appendectomy after eating a jagged metal Krusty-O cereal prize. While visiting her brother in the hospital, Lisa finds Bleeding Gums in another room, and the jazzman lends her his saxophone for a school recital. She returns to the hospital after the performance, only to learn that her mentor has died.

“The Simpsons” has never shied away from dramatizing death, and “‘Round Springfield” deals with the harsh realities of dying alone. Lisa is so incensed that no one knows who Bleeding Gums Murphy was that she vows to share his music with the world, and is dismayed to learn that the only copy of his jazz album she can find costs $500. Thankfully, that’s exactly how much money Bart got from his settlement against Krusty the Clown, and he gifts his sister the record. It’s an act of love that shows the importance of forming attachments throughout your life, as those are what will survive you.

Of all the great final shots in “The Simpsons” history, few are as impactful as the one from the Season 6 episode “And Maggie Makes Three.” When the family asks why there are no photos of Maggie in the family album, Homer takes them back to 1993, when he quit his job at the power plant to fulfill his lifelong dream of working at the bowling alley. Things are going well until Marge gets pregnant again, forcing him to return to the power plant and beg for his old job back. To further punish Homer, Mr. Burns puts a plaque in front of his desk that reads: “Don’t forget: you’re here forever.”

As Bart points out, that doesn’t explain why there are no photos of Maggie in the album, and that’s when the episode pulls its real gut punch. Homer assures Bart that the photos are where he needs them the most: Taped on his office wall, covering the plaque so that it now reads “Do it for her.” It’s a moment that shows that even though life doesn’t go exactly the way you planned it, you can still find joy in it.

Everyone remembers their favorite teacher, the one who taught them to believe in themselves when it mattered the most. That’s why “Lisa’s Substitute” hits us so hard. In this Season 2 episode, Lisa’s teacher, Mrs. Hoover, takes a leave of absence due to a Lyme disease diagnosis. Her class is taken over by Mr. Bergstrom (voiced by Dustin Hoffman), who takes an instant liking to Lisa, recognizing her intelligence and sensing how embarrassed she feels about her father’s ignorance.

When Mrs. Hoover’s disease proves to be psychosomatic, Mr. Bergstrom leaves Springfield, and a tearful Lisa catches him at the train station. He gives her a handwritten note that tells her exactly what she needs to know in that moment: “You are Lisa Simpson.” As if that weren’t gut-wrenching enough, the episode really makes us cry when Lisa calls Homer a baboon, and he apologizes for not understanding her pain at having lost someone special to her. As Homer tells his daughter, everyone who’s special to him is at home, and his reconciliation with Lisa is among the most beautiful moments in the show’s entire run.

There’s perhaps no sadder episode of “The Simpsons” than “Mother Simpson,” which leaves a lump in our throat that’s hard to get rid of. In this Season 7 installment, Homer fakes his own death to get out of work, which leads him to discover that his long-deceased mother is actually alive. When his mom appears at what she believes to be her son’s grave, Homer learns the truth about why she disappeared. A ’60s radical, Mona Simpson (voiced by Glenn Close) plants an antibiotic bomb inside a germ warfare laboratory owned by Mr. Burns, forcing her to go into hiding.

It isn’t long before Mr. Burns learns that Mona has resurfaced, and she’s forced to go underground once again. After helping her evade Chief Wiggum, Homer shares a tearful goodbye with his mother, and he sits on the hood of his car watching the stars after she leaves. Although “The Simpsons” is first and foremost a comedy, its emotional core is always what’s made it special. You’d have to have a heart made of stone to not cry at the end of “Mother Simpson,” which touches upon universal feelings of loss and grief as few TV shows ever have.