15 Most Heartbreaking Moments From The Simpsons

In the late 80s, a dysfunctional but loving family exploded onto our TV screens and the world has never been the same. The Simpsons is an animated sitcom that airs on the Fox Network. Matt Groening created the series, which is now going into its 28th season and will air its 600th episode in the fall. Originally, The Simpsons appeared as short sketches on The Tracey Ullman Show in 1987, but was soon given its own series. The Simpsons' first official episode, “Simpsons Roasting On An Open Fire”, debuted on December 17, 1989. The series revolves around the many adventures and misadventures of The Simpsons Family, their friends and other residents of Springfield. The voices of the characters are provided by an outstanding voice cast, including Dan Castellaneta, Julie Kavner, Nancy Cartwright, Yeardley Smith, Hank Azaria and Harry Shearer.

The Simpsons has been critically acclaimed and at times criticized. The series has been praised for its writing, humor and characters while also creating controversy. The Simpsons has won 31 Primetime Emmy Awards and was awarded a Star on the Hollywood Walk of Fame in 2000. The Simpsons is the longest running American animated show, the longest running American scripted Primetime television series and the longest running American sitcom. The Simpsons has made millions around the world laugh with a wide range of humor, from the outlandish and silly to political and deeply intelligent. However, The Simpsons has also broken our hearts with some of the sweetest and saddest moments. They’ve been able to make grown adults break down and cry. The series has had many touching and heartwarming moments and also the most heartbreaking moments. Here is a look at 15 of the Most Heartbreaking Moments on The Simpsons.


15 The Death Of Rabbi Hyman Krustofski

Rabbi Hyman Krustofski (Jackie Mason) was the father of famous comedian Krusty The Clown (Dan Castellaneta). The Rabbi first appeared in the season 3 episode, “Like Father, Like Clown”, which aired on October 24, 1991. Krusty and his father were estranged for several years because the Rabbi didn’t approve of his son’s career choice. With the help of Bart and Lisa, they were able to mend fences. However, everything changed with the season 26 episode “Clown in the Dumps”, that aired on September 28, 2014. Krusty is the special guest of a roast. He gets roasted pretty badly by Sarah Silverman and Jeff Ross. A distraught Krusty goes to his father and asks if he is funny and the Rabbi dies, saying only “Eh.” Krusty struggles with his father’s death and is convinced his father didn’t think he was funny. However, with the help of Bart he soon realizes his father was a bigger fan than he realized.

14 The Love Story Of Homer And Marge

All love stories have their ups and downs. Homer (Dan Castellaneta) and Marge (Julie Kavner) have been through a lot together. There have been many moments of heartbreak and happiness throughout their relationship. They always managed to work things out, but one particular incident really tested their marriage. The Simpsons Movie was released to a wide audience on July 21, 2007. The movie was a critical and commercial success with the cast, writing and plot all being praised. Talk of a movie had started all the way back when the series began back in 1989. The plot revolved around Homer polluting the lake, which resulted in the government placing Springfield under a large dome. The family ends up being exiled from the town and Homer convinces the family to move to Alaska. The rest of the family wants to return when they realize the government is going to destroy the whole town. However, Homer is against the idea and fights with Marge and the kids. Homer goes out for a while but when he returns he finds a video from Marge. She tells him that she’s leaving him and going to help Springfield. To show how serious she is, Marge taped over their wedding. Audience members' hearts all broke at the moment. Homer is devastated but realizes his mistakes and saves his family and the town of Springfield.

13 “The Death” Of Homer J. Simpson

The five stages of grief are denial, anger, bargaining, depression and "d’oh!". The season two episode “One Fish, Two Fish, Blowfish, Blue Fish”, is a critically acclaimed episode of the series. The episode aired on January 24, 1991 to very positive reviews. The plot revolved around Homer eating a poisonous fish and finds out he has little time left to live. He tries to bond with everyone he loves before he dies. He listens to Lisa play her sax, he bonds with his father and makes passionate love to Marge one last time. In an early heartbreaking moment, Homer wakes up in the middle of the night and listens to Larry King read the bible on tape. The tape ends. Marge wakes the next morning to find Homer dead in his chair. She then realizes that his drool is warm and he's still alive. It’s a heartbreaking moment when Marge finds Homer, but has a happy ending.

12 Goodbye Smart Homer

Homer Simpson has never been the sharpest crayon in the box. He’s not the brightest resident of Springfield, but he does live with the smartest. Homer has always loved his first daughter, Lisa (Yeardley Smith). They don’t have very much in common; she likes school, art and deep conversations. On the other hand, Homer doesn’t know where the school is, and he likes farts and deeply covered glazed donuts. However, things soon changed for this father and daughter duo. In the season 12 episode, “HomR” that aired January 7, 2001, Homer finds out an interesting thing from his past. Turns out that when he was six years old, Homer lodged a crayon up his nose and it was the cause for his low IQ. Once the crayon is removed, Homer becomes intelligent, thought-provoking and he has a high IQ. This brings Lisa and Homer closer, which make Lisa so happy. She finally has someone on her level and the best part of it is it’s her dad. More than anything she just wants to have a strong connection to Homer. However, soon Homer realizes the difficulties and responsibilities that go with being smart. He has Moe shove a crayon back up his nose. The heartbreak occurs when Lisa realizes what Homer has done. She is saddened until reading a note Homer wrote for her before shoving the crayon up his nose. He admits to having a great appreciation for how smart Lisa is. The episode won an Emmy Award for Outstanding Animated Program.

11 Lisa’s Future

“Lisa’s Wedding” aired on March 19, 1995, in the sixth season and received critical acclaim. It won an Emmy Award for Outstanding episode. Mandy Patinkin and Phil Hartman guest starred in the episode. After being annoyed by her father, Lisa visits a psychic at the fair. She tells Lisa her future of falling in love with a British man named Hugh Parkfield (Mandy Patinkin). They get engaged but Lisa dreads the day Hugh will meet her family. Little has changed in the Simpson Family; Homer is still a lovable ape, Marge is the greatest mother, Bart destroys buildings and Maggie doesn’t speak. Homer puts in an effort to get close to Hugh, but Lisa learns the Hugh plans on cutting Lisa’s family out after the wedding. However, before the wedding can take place Lisa calls off the wedding. If Hugh can’t accept Homer, he can’t accept her. Back in present day, Lisa realizes how important her father is to her.

10 The Death Of Bleeding Gums Murphy

Bleeding Gums Murphy (Ron Taylor) is a saxophone player and Lisa Simpson’s idol. He first appeared in the season one episode “Moaning Lisa”. Bleeding Gums returns in the sixth season episode "Round Springfield", that aired on April 30, 1995. Bart ends up in the hospital after accidentally eating a metal jagged Krusty-O he finds in his Krusty-O's cereal. While visiting Bart, Lisa finds Murphy in the hospital. They play some music together to help Lisa get ready for her concert where she has a great performance. She returns to the hospital to find out that Bleeding Gums died. She is devastated and is even more distraught when she is the only person to attend the funeral. She attempts to buy his only album and get it played on the local radio station but can’t afford it. Meanwhile, Bart sued Krusty and won $500 in the court case. He uses the money to buy Lisa the album.

9 The Death Of Beatrice Simmons

“Old Money” aired on March 28, 1991, in the second season. The plot revolved around Abraham “Grandpa” Simpson (Dan Castellaneta) meeting Beatrice Simmons (Audrey Meadows), a new resident at the Retirement Castle. Abe is instantly in love with Bea and they go on a date. They plan a second date for her birthday but Homer kidnaps Grandpa to take him on a family trip to the Discount Lion Safari. When Grandpa returns he finds out that Bea died of a broken heart… literally, her left ventricle burst. Grandpa blamed Homer for missing their last date. Bea was wealthy and upon her death she gives everything to Abe. Abe is heartbroken and all the money in the world can’t fill the hole in his heart. Grandpa wants to give the money to the poor but realizes he doesn’t have enough. He tries to double his money at the casino but Homer is able to stop him. Grandpa and Homer reconcile and make up. After, Grandpa realizes that it’s The Retirement Castle and the residents are the ones that need the money. The Retirement Castle is renovated and includes the Beatrice Simmons Memorial Dining Hall.


8 You Are Lisa Simpson

Lisa Simpson is the middle child and is the black sheep in the Simpsons family. She is the smartest person in the family and very possibly in all of Springfield. Lisa met her substitute teacher, Mr. Bergstrom, and it changed her life. He was the most inspiring teacher and role model she ever had. Her regular teacher, Miss Hoover, became ill with what she believes is Lyme disease. Most kids would give the substitute teacher a hard time but not Lisa. She was excited to learn again. The season two episode “Lisa’s Substitute”, aired on April 25, 1991 to positive reviews from TV critics. In the end of the episode, Miss Hoover returns and Mr. Bergstrom leaves. This breaks Lisa’s heart and she meets Mr. Bergstrom one last time. He gives her a note that reads, “You Are Lisa Simpson” and he leaves. Dustin Hoffman guest starred in the episode as Mr. Bergstrom but used the alias Sam Etic.

7 Do It For Her

One day while looking through the photo album, Bart and Lisa realize there are no pictures of Maggie. Homer tells a story to help explain why. Homer Simpson had a dream; his dream was to someday work at a bowling alley. He finally got the chance to do that and he quit his job at the power plant. The pay was just enough for him to raise two kids and take care of his wife with some drinking money left over. He was so happy. Homer tells the story of Maggie’s birth in the season 6 episode, “And Maggie Makes Three”, which aired on January 22, 1995. Homer was working at the bowling alley and wasn’t very thrilled when Marge told him she was pregnant. That meant he had to quit his dream job at the bowling alley and literally crawl back to Mr. Burns in order to get his job back at the nuclear plant. Homer is miserable and sees this new baby as a curse. That is until he meets her. He immediately loves Maggie and realizes he’ll do anything for her. When he returns to work, Mr. Burns puts up a plaque that reads, “Don’t forget, You’re Here Forever.” Still, that doesn’t really explain what happened to the pictures of Maggie. It’s revealed that they’re all at Homer’s work. He uses the pictures to cover up the plaque, which now reads, “Do It For Her.”

6 Bart’s Broken Heart

Bart Simpson (Nancy Cartwright) is the controversial bad boy of Springfield. He’s rebellious, loves to pull pranks and thinks girls have cooties. However, Bart fell in love for the first time with 15-year-old Laura Powers (Sara Gilbert). Laura Powers appeared in the season 4 episode “New Kid on the Block”, which aired on November 12, 1992, and was written by Conan O’Brien. It was Bart’s first crush and he was on a cloud since meeting her. He tried to woo her by showing a more mature side but she had feelings for someone else. She reveals to Bart later that she has a boyfriend and it's Jimbo, a local bully who picks on Bart. In the famous scene, Bart is so heartbroken he feels like she ripped his heart out and threw it in the garbage. Bart was so upset that he vowed revenge. He prank called Moe and claimed to be Jimbo. Moe made Jimbo cry and Laura was kind of turned off. Laura Power was the first girl that Bart fell in love with but she certainly wouldn’t be the last.

5 The Death Of Maude Flanders

Ned Flanders has dealt with a lot of tragedy and hard times. First, the love of his life dies and he’s left to raise his two sons. He puts his life back together, falls in love again and she too, dies. On top of all that, his best friend is Homer Simpson. That can’t make life easy. Ned was originally married to Maude Flanders and together had two sons, Rod and Todd. Maude was a loving and caring wife. Maude was killed off in the season 11 episode “Alone Again, Natura-Diddily”, which aired on February 13, 2000. Maude dies in an accident at the speedway that is indirectly caused by Homer. Ned is distraught but Homer tries to match him up with other women. This leads to Ned actually losing faith in God. That’s until he meets the singer of a Christian rock band. It’s a long time before Ned meets someone who can fill that hole in his heart. Ned eventually enters into a relationship with Edna Karbappel.

4 Mona Simpson Returns And Leaves

Homer J. Simpson (Dan Castellaneta) is the dimwitted, slow, yet lovable father of The Simpsons Family. He’s married to Marge Simpson and together they have three kids; Bart, Lisa and Maggie. He has a very tense relationship with his father, Abe “Grandpa” Simpson. For the first few seasons, very little was known about his mother, Mona Simpson (Glenn Close), and Homer was under the impression that she had died. However, after Homer faked his death his mother returned to Springfield. Mona first appeared in the episode “Mother Simpson”, which aired on November 19, 1995. It’s revealed that she hadn’t died but was on the run from the police for sabotaging Mr. Burns’ lab. Homer was both elated and upset of his reunion with his mother. Unfortunately, Mona is forced back into hiding. The heartbreak begins when Homer and Mona say goodbye to each other but the tears start to flow after she leaves. The episode ends with the heartbreaking scene of Homer sitting on the hood of his car. He stares endlessly into the night and stars.

3 Lisa Breaks Ralph's Heart

A wise child once said, “My cat’s breath smells like cat food” – Ralph Wiggum. Ralph is the only child of Police Chief Clancy and Sarah Wiggum. Ralph is in the 2nd grade and the same class as Lisa Simpson. Ralph is an outsider and sometimes says the oddest things, like “Me fail English? That’s unpossilbe”. Despite being an outsider he forms a friendship with Bart. However, he falls madly in love with Lisa in the season 4 episode, “I Love Lisa”, which aired on February 18, 1993. On Valentine’s Day, Ralph is the only one not to receive a single Valentine. He was humiliated and Lisa saw this. She gave him a Valentine that read “I Choo-Choo-Choose You”, and it had a picture of a train on it. Ralph was head over heels for Lisa but she didn’t return the feeling. He was able to convince her to go to the Krusty Special were Ralph blurted out the words, “Yes, I love Lisa and when I grow up I’m going to marry her”. Lisa was outraged and broke his heart on TV. Later, Bart carefully pinpoints the exact moment that Ralph’s heart broke. However, Lisa and Ralph are able to mend fences when Lisa gives Ralph a card that reads: “Let’s Bee Friends” and it has a picture of a bee on it.

2 The Death Of Mona Simpson

Mona Simpson was married to Abe Simpson and mother to Homer Simpson. She was a devoted wife and loving mother but she saw what was happening around the world. She felt that need to get involved but ended up on the run from the police. She was forced to leave her little Homer. She returned later to reunite with her son and meet her grandchildren. She returned a few times but was always forced back on the run. Glenn Close voiced Mona Simpson to rave reviews. Mona returned once again in the season 19 episode “Mona Leaves-a”, that aired May 11, 2008. Mona promises to stay this time but Homer doesn’t believe her. She tries one last time but he’s just so stubborn. He realizes his mistake and decides to apologize to her. He finds her downstairs slumped in her seat and Homer realizes that she died. Homer is wrecked with guilt and tries to spread her ashes at Springfield Monument Park per her wishes. However, Mona had one last protest left in her. Her ashes get caught up by the wind and cause a malfunction to one of Mr. Burns' missiles, which is carrying waste to the Amazon.

1 We Really Miss You Mrs. K.

Edna Krabappel (Marcia Wallace) was the tough, no-nonsense 4th grade teacher at Springfield Elementary. Her greatest challenge in her education career was teaching the rebellious Bart Simpson. She struggled to find her true love until she finally ended up with Ned Flanders. Ned himself had suffered a loss when his wife tragically died. They were both finally so happy together. Marcia Wallace provided the voice of Edna. She had a long career in Hollywood and prior to The Simpsons, was best known for her role on the hit 70’s sitcom, The Bob Newhart Show. Sadly, Marcia Wallace passed away on October 25, 2013, due to poor health. The Simpsons decided it was best to retire one of the series' most enduring characters. The first heartbreaking moment came just days after her death. During the opening Chalkboard gag of the season 25 episode “Four Regrettings and a Funeral”, Bart writes “We really miss you Mrs. K.”. That was enough to bring tears to the eyes. At the conclusion of the episode "The Man Who Grew Too Much”, Ned fondly remembers Edna as he sits next to pictures of Edna and Maude. Local bully Nelson, shows up and gives his classic mocking laugh, “Ha Ha”, but he quickly becomes sad as well and mentions that he misses her, too.


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