1. 1. Season 7, Episode 11 “Marge Be Not Proud”
What’s Sad? Bart, televisions original “lil shit”, decides to steal a video game that his mother, Marge, refuses to get him. Marge is very disappointed to learn Bart has shoplifted when they return to the scene of the crime; a local store (Try-N-Save) where they typically get their Christmas picture taken. Needless to say, their Christmas photo is ruined. Concerned that his mom doesn’t love him anymore, Bart picks up something at the Try-N-Save and returns home. Fearing his son has shoplifted again, Marge forces the object out of Bart’s jacket, and discovers he has paid for a Christmas photo of himself as a gift to his mom.
Why The Tears? Bart’s “lil shit” badassery is put on the back burner in order to win back the affection of his mom. Who knew Bart was such a mommy’s boy after all? A heartwarming and touching episode that shows that sometimes a boy’s best friend really is his mother.
2. 2. Season 1, Episode 1 “Simpsons Roasting on an Open Fire”
What’s Sad? I’m sorry, is this supposed to be a comedy show? Where we get to laugh and stuff? So why is the PILOT EPISODE on this list? Oh, I’ll tell you. After Homer doesn’t get his usual Christmas bonus, the family scrambles to buy Christmas gifts. Homer, desperate for money, secretly takes up a mall Santa gig, and is revealed when Bart harasses him at work. Taking what little money he made at the mall, Homer bets it all on a 99-1 long shot dog, coincidentally named “Santa’s Little Helper”. The dog finishes dead last, Homer loses his money, big surprise. The dog’s owner disowns him after finishing so poorly, and Bart begs Homer to keep the dog as a family pet. In lieu of gifts, the Simpson family gets a dog for Christmas instead.
Why The Tears? This has all the classic elements of a tearjerking Simpson episode: Bart ashamed of his mistakes, Homer trying to provide for the family, and a heartwarming ending. Bonus because there’s a dog involved! This was one hell of a pilot episode!
3. 3. Season 3, Episode 1 “Stark Raving Dad”
What’s Sad? This is a very complicated episode to explain, so I’ll cut to the meat of it. After spending some time in a mental institution, Homer comes back with a man claiming to be Michael Jackson (who is actually voiced by Michael Jackson). There’s so much excitement about MJ’s arrival in Springfield, that Bart once again shafts Lisa on her birthday, which he has done every year. Bart overhears Lisa saying she’s going to disown him as a brother, and panics. He and Michael collaborate together to give Lisa her birthday gift: a song just for her.
Why The Tears? Awwww Bart is being so sweet! The lyrics to the song are easy to sing and the tune is so happy and jovial (warning: if you listen to it, it will be stuck in her head BIG TIME). Plus, given the untimely and recent passing of M.J. this episode is extra sentimental to watch.
4. 4. Season 4, Episode 15 “I Love Lisa”
What’s Sad? On the surface, this is set up to be a pretty easy to watch Valentine’s Episode. NOPE! Everyone in little Lisa’s class is passing around Valentine’s cards (as one does in elementary school), when Lisa realizes that nobody bothered to make a card for Ralph. Out of pity, Lisa gives him the now infamous “I Choo Choo Choose You” card, which sparks a romantic interested in Ralph. He invites Lisa to join him to a taping of the Krusty The Klown show, despite Lisa telling Ralph she does not like him “like that”. Mid-show, Ralph declares (on television!!) that he loves Lisa and he intends to marry her. Oops. Lisa goes nuts and reveals the truth; that she doesn’t love him and she gave him the card because she felt sorry for him. Damn Lisa!! Lisa apologizes and makes it up to him by giving him a card that says “Let’s Bee Friends”.
Why The Tears? Lisa is ice cold in this episode, dude. But Ralph needs to learn “no” means “no”! The tears are more sweet than sad at the end of the episode, and the “Choo Choo” card has now become more famous than the episode, itself! Consider it a history lesson then.
5. 5. Season 12, Episode 9 “HOMR”
What’s Sad? Classic Homer. When an X-Ray reveals that Homer has a crayon lodged in his brain (because of course Homer has a crayon lodged in his brain) surgeons remove the crayon, and Homer’s IQ jumps significantly; he’s a smart guy now! He begins to get along better than ever before with his daughter, Lisa, but at a price. His intelligence has alienated him from his life, his friends, and even his job. Homer decides to “go back to normal” much to the dismay of Lisa, and with the help of Moe, shoves the crayon back in his brain. Lisa discovers a note that Homer wrote her before he went back to “dumb Homer” that says she is “amazing”. Father/daughter hugging ensues
Why The Tears? Awww this is a sweet episode! In lieu of an explanation, here’s the text from the letter so you can get a good cry right now, too. “Lisa - I’m taking the coward’s way out. But before I do, I just wanted to say being smart made me appreciate just how amazing you really are.” Isn’t that cute??
6. 6. Season 2, Episode 1 “Bart Gets An F”
What’s Sad? Another early one for the books! Bart is at risk of flunking fourth grade, and vows to make better grades in order to be promoted to fifth grade (which I guess never happened because we’re on season 25 and I’m pretty sure he’s still in fourth grade). He studies very hard, and even sacrifices a day of fun during Springfield’s snow day in order to do his work. He tries his best, and unfortunately fails by one point: a 59. Devastated, Bart breaks down and manages to impress Mrs. Krabappel enough that she passes him with a D-. Bart proudly displays his grade on the refrigerator at home.
Why The Tears? Oh who hasn’t been in Bart’s shoes? Especially academically speaking? Bart putting forth his best effort and ultimately winning is a heartwarming reminder to never give up.
7. 7. Season 11, Episode 14 “Alone Again, Natura-Diddily”
What’s Sad? This episode is almost sadistic in terms of shear levels of emotional pain. It rivals an episode of Game of Thrones. Ned Flanders, everyone’s favorite, goofy, Christian neighbor, gets thrust into a world of grief when his wife, Maude, suddenly dies at a speedway racetrack. “The Shirt Cannon Shot Heard ‘Round the World” The whole episode is filled with teary gems including Homer treating Ned nicely and even confiding in him. However, the episode comes to a head when Ned, mid-prayer, begins to curse God for not responding to his prayers
Why The Tears? Who knew Ned Flanders had it in him to command such an emotional episode? And who knew any of us gave a shit about Maude Flanders until she died? Honorable mention goes to the episodes following this one, which occasionally showed glimpses into Ned’s grieving. I still get goosebumps whenever Maude is mentioned on the show. Arguably one of the most important deaths in The Simpsons.
8. 8. Season 4, Episode 4 “Lisa the Beauty Queen”
What’s Sad? The episode begins with Lisa is having self esteem issues (aww) and Homer winning the Duff Blimp. Lisa decides to boost her body image by entering a beauty pageant, but the entry cost is pretty steep. Homer, in an act of love for his daughter, sells the blimp and puts her in the pageant. In the long run, Homer technically spoils Lisa’s chances of winning, but she’s not mad; her confidence is back up and she loves her father anyway.
Why The Tears? Don’t you just love a good father-daughter bonding story?
9. 9. Season 7, Episode 5 “Lisa the Vegetarian”
What’s Sad? After a visit to a petting zoo, Lisa decides to become a stone-cold vegetarian, much to the ridicule and dismay to her family and friends. With some help from Apu and Paul and Linda McCartney (literally Paul and Linda McCartney), she perseveres. The episode hits it’s emotional peak at the end, where Homer (who had previously been the worst person in the anti-vegetarian movement) frantically apologizes to Lisa for all he’s said and done in regards to her decision. He offers her a “veggie back” ride as “Maybe I’m Amazed” by Paul McCartney plays in the background.
Why the Tears? Haven’t we already established how much of a softie I am for Homer and Lisa story lines? And this is one of the most important episodes in the series. Bonus tears for the use of “Maybe I’m Amazed” and EXTRA CRY POINTS for the inclusion of Linda McCartney in the episode. RIP to a truly beautiful soul (and a staunch vegetarian.)
10. 10. Season 3, Episode 3 “When Flanders Failed”
What’s Sad? Not much. Flanders opens up a store specifically for left-handed people, and Homer (being Homer) hopes the new store fails just for the shits of it. When Flanders business really does start to fledge, however, Homer rounds up a hoard of people and together they save the store.
Why the Tears? Um, it’s Homer being nice to Flanders. Like, genuinely nice. One of the sweetest endings to any Simpsons episode!
11. 11. Season 7, Episode 8 “Mother Simpsons”
What’s Sad? Homer discovers his mother, Mona (who he thought was dead for the past 27 years), is actually alive! She’s been living life on the lamb after being a badass with a heart of gold hippie protestor. She turns out to be a very kind lady, and even winds up being the only Simpson family member to intellectually connect with Lisa. Things turn sour when Mr. Burns calls in a tip to the FBI and they track down Mona. She is forced to leave her family once again and go on the road.
Why The Tears? This episode reaches sobbing levels of sad in the final moments of the episode. Mona flees into the night, and Homer sits on his car and watches the stars longingly. HUG YOUR MOTHERS TIGHT TONIGHT KIDS! Bonus tears because god, listen to this music.
12. 12. Season 6, Episode 19 “Lisa’s Wedding”
What’s Sad? Another flashfoward episode. Lisa goes to a fortune teller, and she tells her about her wedding day. Lisa is getting married to a British man named Hugh (original) who, though very charming, has made it clear that he has no intentions to continue a relationship with his father-in-law or anyone else in the Simpsons family. Outraged, Lisa calls off the wedding, claiming that (despite their shortcomings), Lisa and her family go together hand-in-hand. Lisa in her present day, eight-year-old self, reunites with her father and she enthusiastically listens about his crazy day.
Why The Tears? More than once we’ve had Homer and Lisa episodes clock in on this list, but this is the first time where Lisa is the reason you’re crying. Homer accepts and loves Lisa though she’s a vegetarian and just, in general, the opposite kind of person he is. But Lisa loving and accepting her goofy dad? Now that’s sweet. And hey! This episode won an Emmy! Bonus tear point for that!
13. 13. Season 2, Episode 11 “One Fish, Two Fish, Blowfish, Blue Fish”
What’s Sad? God this episode is equal to the scene in Toy Story 3 where all the toys are about to go into the flaming inferno, in terms of shockingly sad and horrifying all at the same time. Homer is poisoned at a sushi restaurant and has twenty-two hours to live. This is a comedy…right? For starters, Homer and Marge find out he’s going to die, and Homer doesn’t want to tell his kids, so they can just enjoy their last day together. Wow, I’m already sad, aren’t you?? So how does Homer spend his day? Having a “man” talk with Bart, listening to Lisa play her saxophone, reconciling with his father Abe, making a video message for his baby Maggie, drinking with his friends, oh and making love to his sweet, sweet wife Marge. Around midnight, Homer wishes his family goodbye and goes to the living room where he listens to the Bible on tape (as narrated by Larry King) and basically waits to die. But praise, he’s alive! And things go back to normal
Why the Tears? Okay, much like Brian Griffin this year, we knew Homer wasn’t actually going to die…right? RIGHT? This episode has us all fucked up, that’s for sure. The real emotion of the episode is in seeing Homer prioritize his life and seeing how he spends his last precious moments on earth; with his friends and family. Don’t we all want a man like Homer Simpson in our life?
14. 14. Season 4, Episode 10 “Lisa’s First Word”
What’s sad? A generally funny and run-of-the-mill Simpsons episode until the very end. The family is trying to get Maggie to speak, and Homer and Marge reminisce on Lisa’s first words. The story hits it’s first peak of emotions when the family recalls that Bart hated the new baby Lisa at first, and was all but ready to run away until he heard Lisa say her first word: “Bart!” Awww. But then the episode really tugs at the heartstrings in the conclusion. Lisa and Bart both find it funny that, despite Homer’s best intentions, his kids call him “Homer” instead of “Daddy”. As Lisa, Bart, and Marge go back to their daily routine, Homer tucks the baby Maggie into bed. When Homer leaves the room, Maggie takes out her signature pacifier and utters her very first word: “Daddy”.
Why The Tears? SO MANY TEARS! For starters, aren’t we all suckers for a good, cute sibling story? Especially one between Bart and Lisa? Then, we have that sucker punch of an ending, topped off with an enduring Homer moment (which this list is full of, by the way). Want another reason to cry about it? The voice of Maggie is voiced by the late Elizabeth Taylor. Go ahead, cry about it some more.
15. 15. Season 6, Episode 13 “And Maggie Makes Three”
What’s Sad? Yet another episode on this list which is actually told as a flashback. The family recalls when Marge became pregnant with Maggie. Homer had just quit his job at the Springfield Nuclear Power Plant and was eager to start his new dream job working at the bowling alley. Life was good for Homer, until Marge accidentally became pregnant. The first emotional roller coaster of the episode occurs when Marge tries her best to cover up her pregnancy, knowing that a third child would mean Homer would have to quit his dream job in order to financially support a family of five. Bummer. Her evil, twin sisters, however, completely blow the secret, much to the dismay of both Homer and Marge. When Homer realizes he can’t possibly raise three kids on his bowling salary, and he won’t be making any more money than he already is, he begs Mr. Burns back for his job at the Power Plant. To add insult to injury, Mr. Burns gives Homer his miserable job back, with a plaque that reads “DON’T FORGET: YOU’RE HERE FOREVER”. Homer is, once again, very unhappy, until Maggie is born. He instantly falls in love with his new daughter, and as an act of devotion to his new baby and family, he redecorates the plaque in his office. With photos of Maggie, he successfully covers up a few letters so the plaque reads “DO IT FOR HER”.
Why The Tears? This episode is famously a tear jerker in The Simpsons and online community. It’s a great demonstration of the fact that The Simpsons mirrors everyday American life, and sometimes the difficult decisions we have to make in order for our families and success. How many moms and dads could identify with this episode? And how many children learned just how much their parents sacrifice for their well being? Ugh, tears. Tears everywhere.
16. 16. Season 2, Episode 19 “Lisa’s Substitute”
What’s Sad? Another classic tear jerker from Team Groening. When Lisa gets a sub named Mr. Bergstrom (who actually teaches) she falls in love with. While Lisa and Homer are at the museum, they run into the Bergstrom and Lisa is ecstatic! Of course, her joy is cut short when Homer makes an ass out of himself in typical Homer fashion. Dads, amirite? Upset that Homer embarrassed her, Lisa calls him a baboon and storms out. When she returns to school and sees her old teacher back, she is devastated. She discovers he is leaving for another job and races to meet him before he departs the train station. After declaring she will be “lost” without him, Bergstrom tells her, “Whenever you feel that you’re alone and there’s nobody you can rely on, this is all you need to know,” and hands her a note. The note simply says “You are Lisa Simpson”.
Why The Tears? Look, Lisa’s a very smart girl, but much like many other smart girls, she struggles with confidence and maintaining friends. The reminder from a man she admires that she is exactly who she’s supposed to be is heartwarming, touching, and iconic. Many claim this is the most touching episode in the series! And shoutout to Dustin Hoffman for being Mr. Bergstrom!
17. 17. Season 6, Episode 22 “Round Springfield”
What’s Sad? Of course, a Bleeding Gums Murphy episode had to be on here, so why not make it the absolute most sad episode of all? Lisa’s longtime (well, on-again, off-again) saxophone mentor, Bleeding Gums Murphy, dies suddenly in Springfield. Lisa is the only one to attend his funeral, and vows to make Murphy a household name in Springfield. With some money very selflessly donated by Bart (which that’s a mini tearjerker right there), Lisa buys his final album and plays it on a local radio station. Sadly, not many radios actually pick up the small station, and essentially no one can hear it. Until, that is, a lightning bolt strikes the radio station, and the entire town of Springfield hears Murphy’s song. Lisa proudly says, “That was for your Bleeding Gums,” and he appears in the sky as a vision to Lisa, saying she’s made an old jazz man happy.
Why The Tears? Look, any Murphy episode is a tearjerker, okay? Actually ANY episode where Lisa gets a mentor that is taken away from her is a tearjerker. But this one is especially sad, since it marks the end of Murphy’s appearances on the show. RIP Bleeding Gums.
18. 18. Season 19, Episode 19 “Mona Leaves-a”
What’s Sad? Another episode of Homer’s mother, Mona, which are always tear jerkers for me. But I think this one, by far, takes the cake. Mona steps back into Homer’s life unexpectedly and is (this time) staying for good. Homer lashes out at his mother, saying he won’t accept her back in his life because of all the time she’d left him before. Eventually, Homer comes around and tries to apologize to his mother, but by the time he gets to her with a nice apology card, Mona has passed away. I know, right? Sob. The story continues with Homer trying to dismantle Mr. Burns one last time to fulfill her final wishes. The episode really drives the point home when they conclude with a montage of Mona and Homer in simpler times.
Why The Tears? HOW COULD YOU NOT BE CRYING?? Oh my god I can’t even write about it, I’m getting upset. This has you emotionally on a ride from the get-go, and just when you think it can’t get any more sad, the episode is dedicated to the mothers of Dan Castellaneta (the very talented voice of Homer and many other characters) and Harry Shearer. It’s worth noting now that Castellaneta gives a killer performance in this episode, so it’s really worth a re-watch if you’re in the mood. It’s also a staple of Mother’s Day, which is when people just looooove to rerun this one!
19. 19. Season 25, Episode 3 “Four Regrettings and a Funeral”
What’s Sad? Actually, the plot itself isn’t sad at all, it’s a pretty run-of-the mill Simpsons episode. But the opening chalk gag left me crying before the episode even started. Bart was writing on the board, “We’ll really miss you Mrs. K.”
Why the Tears? For Marcia Wallace, who passed away in October 2013. What diehard fan didn’t cry when we heard the news? She was a big part of my childhood, and obviously, a big part even into my adult years. She was a gifted actor and a very important part of The Simpsons. RIP Marcia Wallace.
20. 20. Season 2, Episode 12 “The Way We Was”
What’s Sad? SURPRISE! Another flashback episode! This time, it’s Homer and Marge retelling the story of how they first got together in high school, complete with a beautiful rendition of The Carpenters’ “Close To You” (which I can never hear without thinking of Marge and Homer). Long story short, Homer pisses of Marge, and as an act of vengeance, Marge winds up going to prom with the future billionaire Artie Ziff, who turns out to be a total skeez. He tries to put “the moves” on Marge and winds up tearing her prom dress. UGH! As Marge is driving herself home, she sees a lonely Homer, walking alongside the road. She picks him up, and Homer even has the heart to fix Marge’s broken dress. Then, the single greatest bit of dialogue ever uttered on The Simpsons is said:
MARGE: Why so glum?
HOMER: I’ve got a problem. As soon as you stop this car, I’m gonna hug
you, and kiss you, and then I’ll never be able to let you go…
[cut to present time Homer and Marge]
HOMER: …and I never have.
Why The Tears? Okay, not so lowkey this is my all-time favorite episode of The Simpsons. It’s just so sweet and Homer. HOMER!! What a cutie! And Marge and Homer’s marriage really does make me believe in love, y’know? Bonus points to this episode because it has one of my favorite Simpsons one liners: “English. Who needs that? I’m never going to England!” Classic.
Thanks Matt Groening and The Simpsons team for all the tears! And sometimes the laughter, too. Here’s to another 25 seasons!
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