10 Saddest Simpsons Episodes That Make Fans Cry Every Time (2024)

The Simpsons is still regarded as one of America's best sitcoms, mainly because it manages to blend a wealth of elusive animation skills with a typical sitcom format. Thus, this working-class family is able to explore the ends of the earth before being transported straight back to Evergreen Terrace to start their next adventure. As such, for 36 seasons, fans have been avidly following the tribe to see what crazy antics they get up to each week.

Though the sitcom is often labeled childish and perhaps immature, true fans of The Simpsons know that the show can make fans laugh and cry within the same scene. Since this show follows the arduous ups and downs of family life, it comes as no surprise that the sitcom occasionally takes a darker turn and forces fans to realize that not everything is perfect in Springfield. In turn, fans often appreciate the show's sadder episodes because they help the audience appreciate the long-running lore that surrounds this quirky sitcom.

Bart Finally Warms to His Sister

Season 4, Episode 10, "Lisa's First Word"

As the family struggles to encourage Maggie to say her first word, they think back to a time before they lived in their iconic house. In a flashback sequence, the couple is struggling to raise Bart in their run-down apartment. But, when Abe gives them the money to move into a bigger place, Homer and Marge are excited about raising their two young children in a new home. Unsurprisingly, Bart doesn't enjoy his baby sister's company and tries everything to get rid of her. Yet, he takes the role of big brother very seriously when Lisa's first word is "Bart." In the final scene, the audience is transported back to the present, where Maggie says her first word in private; "Daddy."

This episode is one of the sweetest, but the audience can't help but feel sorry for Homer. Bart and Lisa bond over the fact that they both refer to their father as Homer, which could also be seen as a sign of disrespect. But, when one of his children finally does say his name, he isn't around to hear it. So, even though this episode is remarkably adorable, it's still sad that Homer doesn't get to share this special moment with Maggie.

Lisa Is Forced to Make a Heartbreaking Decision

Season 6, Episode 19, "Lisa's Wedding"

During a trip to the local Renaissance fair, Lisa visits a fortune-teller who gives the audience a glimpse into her future. At age 23, Lisa is set to marry Hugh Parkfield, a clear parody of Hugh Grant. Homer asks his future son-in-law if he can wear his signature comedy cufflinks at their wedding, which Parkfield does not appreciate. So, he asks her to abandon her family as soon as they get married so that he won't have to put up with them anymore. In typical Lisa Simpson fashion, she decides to call off the wedding in favor of her dysfunctional yet loving family.

Though Homer Simpson is hardly Father of the Year, he truly loves his daughter and wants nothing more than for her to be happy. Another interesting aspect of this episode is how the animators portrayed the future. For example, they made the sky redder because they were convinced that pollution would be more prominent in the year 2010. Overall, this episode deepens the relationship between Lisa and Homer and proves that the little girl doesn't think her father is an idiot after all.

Bart Struggles With His Overwhelming Guilt

Season 7, Episode 11, "Marge Be Not Proud"

See Also

Watch Revolutionary Love Episode 11 at NewasiantvThe Return of the Condor Heroes (1983) Série TV 1983 - - Casting, bandes annonces et résumé

After Marge refuses to buy Bart a new video game, he decides to shoplift a copy from the local discount store. Though the audience assumes that it's just one of Bart's usual antics, it's evident that Marge has had enough. So, Bart has to work twice as hard to regain her love and trust.

There's no denying that Bart's rebellious nature is a key part of his character, and, for the most part, audiences just see it as a source of comic relief. Yet, this episode places audiences in Marge's shoes and forces them to realize that Bart often makes motherhood a chore. However, the boy makes up for it by purchasing a framed photograph of the pair of them smiling together as Marge's Christmas gift.

Ned Questions His Relationship With God

Season 11, Episode 14, "Alone Again, Natura-Diddily"

Ned Flanders is best known for his unshakable positive attitude and relentless faith in God. But when his wife, Muade, falls to her death, his entire life is turned upside down. After a string of unsuccessful dates, Ned prays for some kind of relief but receives no response, prompting him to disregard his immense faith.

Not only does this episode explore Ned's loss of faith, something he takes great comfort in, but also the loss of his beloved wife. Though Flanders can be a bit grating at times, his charm and honesty make him an effective contrast against the Simpson family. As such, many fans were upset that Flanders was dealt a pretty terrible hand throughout this episode.

Bart Tries to Impress His Latest Crush

Season 20, Episode 17, "The Good, the Sad, and the Drugly"

During a reluctant visit to the Springfield Retirement Center, Bart meets a young lady named Jenny. She's smart, charitable, and adorable, causing Bart to fall head over heels in love with her. But Milhouse frequently attempts to sabotage their relationship by threatening to tell Jenny how rebellious and naughty Bart can be. After too many threats, Bart tells Jenny about his troubled past, forcing her to break up with him.

Though Milhouse is usually quite harmless and meek, this episode paints him in a completely new light. Here, the audience discovers that he can get quite jealous and can also become quite manipulative when Bart tries to expand his horizons. Though a lot of audiences appreciated Jenny's character and were sad to see her go, a lot of fans agreed that it was probably for the best.

Bart Relies on God to Save His Grades

Season 2, Episode 1, "Bart Gets an F"

Many avid fans of The Simpsons will know that Bart isn't keen on being an academic prodigy like his sister. But, when the school psychiatrist suggests that he retake the Fourth Grade, he vows to get his grades up. As time slips through his fingers, he prays for a miracle so that he will have more time to study. Even when God mysteriously provides Springfield with a snow day, he struggles to focus on the material.

Back at school, Bart fails his test by one point, exclaiming, "No, you don't understand. I really tried this time. I really tried!" Though Mrs. Krabappel eventually raised his grade to a D-, there's no denying that this was a very relatable moment for fans. This episode offers fans the opportunity to see Bart's inner turmoil, proving that he's not a careless rebel but actually a smart little boy who just wants the world to give him a chance. As such, "Bart Gets an F" sits at the halfway point on this list because it provides fans with a poignant look at Bart's struggles as a student.

Bart and Lisa Take Their Feud to the Next Level

Season 6, Episode 8, "Lisa on Ice"

As Lisa attempts to improve her grades in gym class, she quickly discovers that sport is not her strong suit. But, after seeing her quick reflexes at Bart's hockey team, Apu appoints her as the goalie of the Kwik-E-Mart Gougers. Surprisingly, she leads the team to their best-ever season and goes head-to-head with Bart's team, The Mighty Pigs. But, the competition gets too heated, and the siblings reflect on the good times they had together. So, they put down their sticks and hug it out.

Though a lot of fans were disappointed that Lisa gave up hockey to help her brother, the vast majority of the audience appreciated seeing the duo come together. Seeing the kids share ice creams or help each other up after they've fallen down is a genuinely charming addition to this episode. So, even though Lisa could've been Springfield's hottest hockey star, she shines best when she's just being a sister.

A Touching Tribute to an Iconic Character

Season 25, Episode 3, "Four Regrettings and a Funeral"

When Springfield resident Chip Davis sadly passes away, the community ponders on their biggest regrets. Homer expresses his disappointment about selling his Apple stock too soon, and Marge worries that listening to Kiss while pregnant made Bart the way he is. Of course, the joke here is that Chip Davis is an unknown character who is made look significant by superimposing him into notable moments throughout the show's history.

But the saddest moment of this episode starts before the episode even begins. This episode is dedicated to Marcia Wallace, who was best known for voicing Bart's teacher, Edna Krabapple. As such, the signature chalkboard gag simply reads, "We'll really miss you, Mrs. K," as Bart looks solemn.

Lisa's Substitute Teacher Gives Her a Chance

Season 2, Episode 19, "Lisa's Substitute"

After Mrs. Hoover takes a leave of absence from Springfield Elementary, the students are introduced to their latest substitute, Mr. Bergstrom. Since he's charming, smart, and teeming with dashing good looks, it's no wonder that Lisa quickly became attached to him. Throughout his time at the school, Mr. Bergstrom nurtured Lisa's love of learning and even tried to convince Homer to be a better role model. But, before he exits her life forever, he leaves her a note that reads, "You are Lisa Simpson."

Mr. Bergstrom is arguably one of the best minor characters in Simpsons history because he works to place Lisa in the spotlight for a change. He promises her that things will get better and encourages her to believe that the world will see her for what she's truly worth. But fans can't help but tear up when this inspirational man is snatched away from her without a moment's notice.

Homer Gets a New Source of Motivation

Season 6, Episode 13, "And Maggie Makes Three"

"And Maggie Makes Three" sits at the top spot on this list because it's a prime example of Homer as a doting father. While looking through the family photo album, Bart and Lisa question why there aren't any pictures of Maggie. Then, the audience is transported back to when Homer was working at the bowling alley. When he discovers that Marge is pregnant again, he quits his dream job to go and work at the power plant. Later, Homer reveals that he keeps a collection of Maggie's baby photos in his cubicle. Though the plaque used to read "Don't forget: You're here forever," Homer organized the photos so it read "Do it for her."

Many fans regard this as one of The Simpsons' saddest episodes because it highlights that Homer is willing to sacrifice things for his kids, even if they don't believe him. Though the man spends most of his working day asleep in an office chair, it's clear that Homer works purely to support his family. So, even though he had to give up his dreams, it's clear that he has everything he's ever wanted in the form of his loving family.

The Simpsons

TV-14

Animation

Comedy

The satiric adventures of a working-class family in the misfit city of Springfield.

Release Date

December 17, 1989

Cast

Dan Castellaneta , Nancy Cartwright , Harry Shearer , Yeardley Smith , Julie Kavner , Hank Azaria , Pamela Hayden , Tress MacNeille

Main Genre

Animation

Seasons

36

Creator

James L. Brooks, Matt Groening, Sam Simon

Production Company

Gracie Films, 20th Television Animation, Fox Television Animation, The Curiosity Company

Number of Episodes

761

Streaming Service(s)

Hulu