10 Heartbreaking Simpsons Moments

– By Andreas


“Don’t cry for me; I’m already dead.” – Barney

Back in June, I composed a list of “10 Scary Simpsons Moments.” This is a companion piece of sorts, demonstrating the show’s emotional breadth with ten of the sweetest, tenderest, and most touching moments of the show’s run. Although renowned for its cynicism and satire, The Simpsons always had powerful, James L. Brooks-influenced emotion at its core. It was never just about hollow laughs; instead, each episode was invested in relationships, families, and the oft-painful quirks of human behavior.

But it also never took the typical sitcom shortcut of cheap schmaltz: its emotional arcs were steeped in character development and real-life resonances. The Simpsons, at its best, was about well-rounded human beings with foibles, feelings, and heartbreaks. Here are ten tear-jerking, heartstring-tugging examples…

10) “Dog of Death”

This episode has a twofer: its first act confronts the agonizing facts of pet mortality (and middle-class penny-pinching), while the rest is devoted to Bart searching for the lost, brainwashed Santa’s Little Helper. It climaxes with a montage celebrating pet/child rapports and the merciful restoration of the status quo, reaffirming the lesson of Old Yeller and all those Lassie movies: few emotional forces are more potent than the relationship between a boy and his dog.

9) “Lisa on Ice”

Bart and Lisa’s sibling rivalry was a staple of the show’s B-plots, but no other episode exploited their love/hate relationship as skillfully as “Lisa on Ice.” Most of the episode teeters toward the “hate” end of that dynamic, but as with “Dog of Death,” all that conflict leads to a hug-it-out climax and an adorable montage of Bart and Lisa’s shared childhood. This being The Simpsons, though, their heartfelt reconciliation plays out with a hockey riot raging in the background.

8) “I Married Marge”

The flashback episodes are gold mines of masterfully orchestrated sentiment. “And Maggie Makes Three,” with its “DO IT FOR HER” ending, nearly made this list, as did “The Way We Was” for Homer’s closing monologue. But “I Married Marge” has Homer and Marge’s tragic separation as newlyweds when Homer goes off to become a man, and their reunion in the Gulp ‘n’ Blow drive-thru with the words “Pour vous.” It’s a note-perfect, bittersweet back story for Our Favorite Family.

7) ” ‘Round Springfield”

Poor Lisa, condemned to lose every positive male role model (see #2). The loss of Bleeding Gums Murphy really hurts; he’s such a gently paternal presence, and he’s Lisa’s only mentor as a jazz saxophonist. (Mr. Largo, his passion dulled by years in the public school system, could never come close.) Unlike a certain gimmicky, ratings-grabbing death from Season 11, Murphy’s passing is handled with tact and humor, making it all the more painful.

6) “Bart Sells His Soul”

This episode topped my “scary” list, and the same spiritual fears that feed its horror also make it an emotionally heavy experience. Bart’s prayer at the end is a tour de force for Nancy Cartwright; she cuts right through his “underachiever and proud of it” schtick, revealing the lost little boy underneath. “Bart Sells His Soul” delves into the anxiety and loneliness that constitute dark side of childhood, and the redemption that lies just beyond.

5) “Home Sweet Homediddly-Dum-Doodily”

After a diabolically brilliant first act that degenerates into a nightmare, “Home Sweet Homediddly-Dum-Doodily” tests the Simpson family’s mettle like no episode before or since. But the intensity of their trial by social services fire makes the resolution that much more gratifying (and emotionally overwhelming), and Marge’s climactic line can still bring tears to my eyes: “Oh, Maggie, you’re a Simpson again!”

4) “One Fish, Two Fish, Blowfish, Blue Fish”

When Homer ingests some potentially deadly sushi, he gets put through the existential wringer: as Dr. Hibbert informs him, he only has 22 hours to wrap up his life on earth. His attempts to do so are tragicomic, as he earnestly carries out some tasks while botching others; however, the episode goes all-out emotionally for Homer’s last night. Sitting awake in the living room, he’s no longer a wacky TV dad. He’s just a working stiff, staring into the abyss. Powerful stuff.

3) “Like Father, Like Clown”

You’d think that estranged parents and Jewish culture, thorny topics for any show, would prove impossible for an animated sitcom. But leave it to The Simpsons to entangle the two in its hilarious, heartfelt riff on The Jazz Singer. The ending is utterly moving, as Krusty and his father join in singing “O Mein Papa”—just the kind of big, emotional finale you’d expect from a larger-than-life showbiz figure like Krusty.

2) “Lisa’s Substitute”

“You are Lisa Simpson.” Such a simple sentence, but it rings so true. Coupled with Dustin Hoffman’s understated performance as Mr. Bergstrom, it’s enough to put a lump in my throat every time I watch the phenomenal “Lisa’s Substitute.” A touchstone for brainy kids everywhere, the episode makes the tragic acknowledgment that loss is part of personal growth, but no easier for it. We’ll miss you, Mr. Bergstrom.

1) “Mother Simpson”

The other episodes on this list tell some pretty heartrending stories about loss and reconciliation, but nothing can match the emotional scope, gravity, and finesse of “Mother Simpson.” Homer’s long-lost mother may disappear again, but he learns that she loves him, and that’s enough. The ending, with Homer pensively stargazing, is both a model of restraint and a signal to start crying. It’s a sobering reminder of how powerful silence can be.

28 Responses to “10 Heartbreaking Simpsons Moments”

  1. 1 Derp
    15 September 2011 at 2:07 pm

    I swear, just seeing the screen capture of Homer staring into the sky makes me feel emotional. It’s a perfect pick for first place and something even zombie simpsons couldn’t full undermine.

  2. 15 September 2011 at 2:37 pm

    Great list. So many choices to choose from, it’s hard to narrow it down to 10. For me, a few scenes in particular stand out above the rest. The scene in “Barts Dog gets an F” where Bart has to say goodbye to Santas Little Helper always got to me when I was a kid, as I too had a dog I had to give up. Fortunately for Bart, things turned out okay. My favorite Homer and Marge scene is from “Duffless” where they ride off into the sunset singing Raindrops keep falling on my head. Then there’s Homer’s “Do It For Her” scene with all the photos of maggie carefully placed over Burns’ plaque. And finally, there’s the scene where Maggie calls Homer “daddy” which in my opinon would have made for a great series finale. To have Maggies first word be the last word ever spoken on the show. If it were up to me, I would have saved that episode for around season 7 and ended the show on that note. Better than sticking around for another 100 years.

  3. 4 lennyburnham
    15 September 2011 at 4:28 pm

    “‘Round Springfield” and “Lisa’s Substitute” get to me every time! But where’s “Moaning Lisa”? That episode is my absolute favorite emotional episode. “Lisa refuses to play dodgeball because she is sad” is so perfect.

    Also, Selma is just a heartbreaking character. “Principal Charming”, “Selma’s Choice” and “A Fish Called Selma” all have moments where you just feel terrible about how lonely this person is. And you see that her and Patty are so close, but that ultimately Patty can’t totally understand her because Patty is so content being alone– and has to live with being partially responsible for Selma’s loneliness.

    Great post!

  4. 5 Gil
    15 September 2011 at 4:40 pm

    So, you’re not gonna put Ol’ Gil’s life in that particular list, even a single moment?
    Awwww geez ya gotta get me some sympathy, I’ve been eating cat food out of a bag, the dry cheap kind.

  5. 15 September 2011 at 5:17 pm

    The episode of The Simpsons that made me feel the most emotional is the end of ‘Bart Gets an F,’ at which point you’ve felt Bart’s pressure and fear of failure throughout the entire episode, and yet he still doesn’t succeed, and gives in to tears.

  6. 7 Homibart
    15 September 2011 at 6:03 pm

    How about “Most spiritual” moments list ?

  7. 8 P. Piggly Hogswine
    15 September 2011 at 6:13 pm

    Great list. All worthy moments. The one from “Lisa on Ice” always gets me, though the one that makes me emotional is when Lisa and Marge hugged it out in “Lisa the Beauty Queen” after she realised that Homer had sacricifed his ride on the Duff Blimp for her, followed by Homer tearing up in the kitchen.

    Though no Simpsons moment will ever make me feel as sad as the ending of the Futurama episode where Seymour the dog was waiting for Fry, who would never rejoin him. Heartbreaking stuff.

  8. 11 Disco stud
    15 September 2011 at 6:16 pm

    Homer’s speech towards the end of Lisa’s Wedding always does me in. It’s emotional and honest without being too sentimental or manipulative. Just perfect.

  9. 15 September 2011 at 6:34 pm

    Having just watched it, Homer praying at the hospital in “Homer’s Triple Bypass” really got to me. I forgot all about it; it felt so honest and real. I also second Homer’s speech in “Lisa’s Wedding,” followed by Lisa and Hugh’s break-up; an emotional one-two punch.

  10. 13 Zac
    15 September 2011 at 7:30 pm

    “Do it for her” gets me every time. Tops my list, for sure.

  11. 14 Patrick
    15 September 2011 at 8:07 pm

    number 1 gave me tears a few times and fuck ZS to the ground

  12. 15 A.BRA C.ADAVER
    15 September 2011 at 8:35 pm

    great list, totally agree with number one. The fact that the staring up at the stars lingers on even during the end credits suggests that this scene meant a lot to the creators too, imo….

    Like others have mentioned, “Homer’s Triple Bypass” (pretty much the whole last act of the episode makes me tear up, but especially at the end when an extremely medicated Homer sees his family waiting for him) and the end of “Duffless” (“Raindrops keep falling on my head”) have always made me weep.

    This may be unpopular (since it’s season 12, though I think it’s about the last really good episode of the series…), but I always thought the end of “HOMR” was pretty great, too — very sad, like Lisa finally had a father to be happy about and look up to, and though it’s hilarious when he crashes through the window to prove he’s an idiot again, the little note he wrote to Lisa before his operation always got me.

    There’s just too many to name — really, that’s what makes the early Simpsons so good to me (especially season 2, for some reason… many episodes seemed very emotional to me): it had heart. I mean, Springfield is just about the most depressing town ever — everyone in it is an angry, depressed person, who is terrible at their jobs, and even those who are good at their jobs (Principle Skinner) are constantly ridiculed. The only character who doesn’t seem to have many dark, depressing moments is Dr. Hibbert, though he does have two long lost brothers… but yeah, even Mr. Burns is unhappy. Once you have everything, there’s nothing left to strive for, I guess. Just about everyone suffers from unrequited love or some kind of heartbreaks or emotional trauma. Of course, now the characters are cheap cutouts, punchline pullstring dolls… utilized only for absurdity and cheap meta- or pop culture-jokes. There’s a reason why the early episodes are so timeless — many reasons, in fact — and that timeless quality doesn’t really date the older episodes and makes them endlessly rewatchable (unlike the newer ones, which may make you chuckle once or twice, but probably won’t make you FEEL, let alone REALLY laugh, let alone ever want to watch again… let alone want to FINISH THE EPISODE, in most cases).

    Simpsons forever.

    • 16 Shane
      15 September 2011 at 11:57 pm

      Nice post! Between all the jokes I feel Season 2 got some very good ‘serious’ dialogue in. One of my favourites is from Lisa’s Substitute, and in its way its just as emotive as the ‘you are Lisa Simpson’ climax. I always liked Bergstrom’s “That’s the problem with being middle-class. Anybody who really cares will abandon you for those who need it more.”

  13. 17 Anonymous
    15 September 2011 at 8:50 pm

    How about Rod and Todd’s sadness after Maude dies?

  14. 16 September 2011 at 2:43 am

    Thanks for all the feedback!

    These comments have some great additions, many of which (“Bart Gets an F,” “Moaning Lisa,” “Lisa the Beauty Queen,” “Lisa’s Wedding”) made my shortlist and were just barely booted off the list. I also like “Duffless,” which didn’t occur to me but is so poignant and a fantastic example of how The Simpsons could take a movie parody and make it something real and powerful. Also, “Homer’s Triple Bypass” would’ve easily made the list, if only for Homer’s heart-to-heart with his kids (“you’ve got a big brother who loves you…”), but I decided it was too similar to “One Fish, Two Fish”—you can only have one “Homer might die” episode per list, right?

    And I haven’t seen it in a while, but as I recall, “Jurassic Bark” is basically the “Mother Simpson” of Futurama, a guaranteed tear-jerker but also one hell of a well-written episode. (And one which somehow made the song “I Will Wait for You” even more overwhelming, even though it’s already from The Umbrellas of Cherbourg, a movie that makes me cry every time… but I digress.)

    Oh, and @A.BRA C.ADAVER: I think you might slightly overstate just how miserable a place Springfield; sure, it has incompetent officials and stupidity reigns over all, but it also has moments of great tenderness and happiness. Everyone’s flawed and compromised, but they take their pleasure where they can. In fact (for better or worse), I’d say it’s disturbingly like the real world. That said, you’re dead-on about season 2, The Simpsons having a heart, and why Zombie Simpsons can’t compare.

    And @Shane: Rewatching “Lisa’s Substitute,” I was startled by that line. It’s so incredibly incisive and true-to-life that, frankly, I’m shocked it made it to TV. But surprises like that, after all, are why we watch The Simpsons.

  15. 19 Thrillho
    16 September 2011 at 10:47 am

    No complaints about the number 1 choice. One thing I love about that scene is how it finds the right balance between humorous and heartwarming right before its memorable finish (i.e., Homer’s mother saying “You’ll always be a part of me” before hitting her head on the top of the car and saying “D’oh!”)

    The entirety of Lisa’s Sax also qualifies in my book.

  16. 20 Charlie Sweatpants
    16 September 2011 at 3:10 pm

    I’ll just generally second everyone who said this was a great list. As was noted in the post (This being The Simpsons, though, their heartfelt reconciliation plays out with a hockey riot raging in the background.) and a couple of times in comments (Homer’s mother saying “You’ll always be a part of me” before hitting her head on the top of the car and saying “D’oh!”), what’s so amazing about many of these is that they are genuinely touching and yet they’re never far from a joke nor are they handled in a way that makes you feel like the episode has come to a stop and said “We’re Being Emotional Now, Pay Attention!”. There are a ton of examples of this, so I’ll just go with with a couple that have already been mentioned.

    When Patty dumps Skinner in “Principal Charming”, Selma asks her if she’s throwing away her last chance at happiness for her. That’s a crushing line, and yet instantly they’re back to their old selves as Patty deadpans “Yes” and Selma just says “Thanks” and they head off to get some pancakes. It’s funny because it’s so perfectly them.

    When Homer tells Lisa how much he loves her at the end of “Lisa’s Wedding”, his speech is heartfelt, but it’s also so incoherent as to border on free association. It’s exactly the kind of thing Homer would say because, let’s face it, he’s clueless when it comes to that sort of thing. That we learn Lisa used to pin her own diapers is just a bonus. This show gave classes in the deft handling of easy to fumble things.

    • 21 Shane
      17 September 2011 at 1:45 am

      Bart’s speech at the end of Separate Vocations is yet another example, with his line about how he’ll be right there to borrow money from Lisa.

  17. 22 Sandypants
    26 September 2011 at 3:54 pm

    Bart vs Thanksgiving has the great rooftop scene. Lisa asks Bart “why did you burn my centerpiece? Is it because you hate me… or is it because you’re bad?”

    Yeardly Smith knows how to deliver a gut-punchingly sad line.

  18. 23 Charles Southern
    12 April 2012 at 8:20 am

    In “Old Money”, when Grampa uses Bea’s money to spruce up the retirement home, after presenting his companions with a new dining room he simply says…”Dignity is on me friends.”

    Superbly done and totally heartbreaking, especially if you have elderly relatives.

  19. 24 Charles Southern
    12 April 2012 at 8:22 am

    Everyone singing “Put on a happy face” after The Leftorium comes back always gets me too, in a much happier way though.

  20. 25 r
    10 July 2012 at 11:28 am

    This episode made Neddy so human…

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