The Four Most Heartbreaking Moments In 'The Simpsons' History

10 August 2014 | 10:32 am | Mitch Knox

Another Springfield death is upon us - but it won't be the first time the TV toons have broken our hearts. Let us count the ways.

The twenty-sixth season of animated institution The Simpsons is almost upon us, with the first episode, Clown In The Dumps, set to air in the States next month.

The season, before it begins, has already generated significant controversy over the revelation that a long-time character would be killed off in its opening episode, with most speculation as to the terminal party falling on or around Krusty The Clown as a result of the aforementioned title.

Naturally, it would be easy to write this all off as a cheap gimmick a la Brian's death on Family Guy, but it's even easier to forget, amid all the comedy and goofishness and slapstick, that, at its core, The Simpsons is an emotional show, and there's no reason to think that its crew wouldn't be able to make Clown In The Dumps a gut-wrenchingly moving episode for seasoned fans of the show.

Don't believe me? Well, then, prepare to cry like a baby.

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Art imitates life

When veteran Simpsons cast member Marcia Wallace passed away last year, we lost the irreplaceable mastermind behind beloved yet belligerent schoolteacher Edna Krabappel, which would be sad enough in itself without the show’s creative team reflecting the real world’s cruelty by killing off Mrs K.

This is markedly different to, say, when Phil Hartman — the voice behind long-gone-but-never-forgotten characters Troy McClure and Lionel Hutz — was killed by his wife in 1998; The Simpsons was a different show back then (cram it, naysayers of modern Simpsons; it’s not the time to get cute). Although the show is hardly reliant on season-long story arcs these days, it certainly has developed a wider sense of continuity than it used to possess, and so where it was easy (well, maybe that’s the wrong word) for the writers to simply “retire” the Hutz and McClure characters upon Hartman’s death — they weren’t involved in any particular storyline at the time — they couldn’t do the same in 2013 with Krabappel, who had not-that-long-ago started a new relationship with now-two-time widower Ned Flanders.

Sorry, Ned.

And, yet, it isn’t the sweet little scene of a mourning Ned sitting in an armchair, daydreaming about dancing with her, thinking about Edna’s laugh and the short time they had together that is the most moving nod from the show to their departed family member, at least as far as I’m concerned.

To be honest, because of the untimeliness of Wallace’s death, that scene seemed to have been kind of shoehorned in to provide a final punctuation piece on the relationship, hinting at maybe an episode unfinished that would have given us a greater look at the ‘Nedna’ dynamic, and to give Ned a moment of closure for a wife the writers cared about (The death of Ned's first wife, Maude, was the result of a payment dispute with her voice actor; they may as well have tossed her off a cliff and laughed about it for all the gravity her demise was given).

No — for my money, this eclipses that:

Consider, for a moment, that in the context of the show, this is not just a chalkboard gag, as we see it. This is not only the writers and showrunners and Matt Groening and his developers paying tribute to a dearly loved, departed cast member. Yes, it’s all those things, but at its base, it is Bart — Bartholomew “underachiever and proud of it” Simpson — mourning the loss of a teacher, and not just a teacher, but one who has been so much more than a source of cheap laughs and easy pranks over the years.

Edna Krabappel was one of Bart’s first romantic encounters (via his Woodrow Wilson pen-name); she taught him the value of hard work and study (Bart Gets An F — still in my top 20 episodes of all time); they even shared an approximation of a friendship when Bart got Edna fired and helped her open a muffin store.

This is a kid that everyone – everyone – has written off as a delinquent and a ne’er-do-well, and despite Krabappel’s obvious disdain for the educational profession and those in her charge, she unfailingly kept a kernel of hope alive for Bart Simpson, and that makes this message to his deceased teacher all the more special for it.

Speaking of Bart…

Monsters and the people who love them

The relationship between Bart and his mother, Marge, has always affected me. I have a close relationship with my parents — which was bound to happen given the fact my nuclear family lives half a world away from anyone else remotely related to us — and The Simpsons, especially under the guidance of long-time on-and-off-and-on showrunner Al Jean (and to a lesser extent, boy-wonder duo Bill Oakley and Josh Weinstein, who went on to executive-produce for Futurama), has always paid special attention to the strong ties the Simpson parents share with their children.

Sure, Homer and Lisa's relationship immediately springs to mind as one more often canvassed in the show — from Daddy/Daughter Day and Homer giving up a ticket on the Duff Blimp, to taking a second job to buy her a pony, leaving her a heartfelt, literate note before he has his brain-crayon re-inserted and helping her break into a museum to see an Egyptian exhibit, The Simpsons has paid plenty of attention to the unique and special bond that exists between a father and his daughter.

However — and maybe it's because it's a pairing that I can genuinely relate to on a personal level — Marge and Bart's relationship, though generally given less airtime than the Homer/Lisa combo, is truly one of the most affecting elements on the show. But its strongest moment comes not from Marge's Son Poisoning, the episode in which Bart and Marge become friends and go on tandem bike rides together; nor does it come from Marge Be Not Proud, another eternal favourite of mine and still one of the most emotionally stirring episodes the show has produced, front to back (show me one son who hasn't fucked up and experienced the icy dread of feeling like their mother doesn't love them any more, and I'll show you one surprised writer).

No — the best crystallisation of the Bart/Marge dynamic comes in Bart The Mother, when, after ten seasons of being at some sort of odds, they finally come to understand each other, even if only fleetingly.



(GIFs via FYS)

Oh, I'm not saying it's one of the series' more subtle moments. It all but spells out the parallels between Bart and his monsters, and Marge and hers. But that in itself — that explicit admission by Marge that she knows what other people think of her son and she could not give a damn — is what carries this as one of the sweetest televised moments of the past 25 years. Because, as horrifying as it is when you think you've lost your mother's love, there is no way to compare the joy that comes from knowing that, despite everything — every misstep and bad choice and stupid decision — you've always had it, will always have it, and nothing society says will ever change that fact.

Yeah, this is gonna get much worse, really quickly.

"Do it for her"

Oh, man, this one hurts. Before Futurama perfected the trick, The Simpsons was making giant strides in the field of Blindsiding The Shit Out Of Audiences With Heartfelt Sentiment When They Thought They’d Be Laughing.

And, boy, did they come scarily close to nailing it with the closing scene of And Maggie Makes Three. You all know the episode – Bart and Lisa express puzzlement at the apparent lack of photographic evidence around the house of their baby sister, which upon first thought kind of makes sense: Homer tends to forget about Maggie. A lot. He thinks her name is “Magaggie”. When Marge told him they had three children, he told her Santa’s Little Helper didn’t count as a child. And, to be fair, Maggie did try to kill him with a hammer on at least one occasion.

All of which makes it crazy-disarming when we suddenly find out where Homer's been keeping all those Maggie photos — where he needs them most:

Bam. Right in the feelings. He does care. He more than cares. He cares so much for his little girl that he's willing to stick out an unfulfilling, dead-end job working for the most cruel man on the planet just to make sure that she's clothed and fed and looked after the way that, for all his failings as a parent, he knows she should be.

That's more than we can say for *his* parents...

O, Mother, where art thou?

I know – it seems unthinkable that there could be an instance in The Simpsons’ long and colourful history that could possibly be purer, sweeter or more heartwrenching than Homer’s workplace monument to his infant daughter, but, for my money, there is just one.

Unfortunately, it’s a moment that newer fans of the series have likely never experienced as it was meant to be seen – at least, not if they’ve only ever seen it on free-to-air television.

See, sometime around the turn of this century, TV networks started to realise that a show’s ending credits were pretty much the perfect time to squeeze up half the screen and start plugging whatever else they had scheduled in the near future, because otherwise that’s just empty space that could be making them money, right?

Well, generally – but not so in the case of The Simpsons, and especially early The Simpsons (seasons 1-10), which was produced before credit-squeezing was the norm. The show was once renowned for its various cinematic interpretations of its closing theme (the Dragnet homage at the end of Who Shot Mr Burns? remains incredible to this day, as does the Hill Street Blues-influenced theme after The Springfield Connection), and occasionally would include some kind of accompanying shot for added effect.

In Mother Simpson, it was this:

Although that’s just a freeze frame under the track, the combination of that sad little ditty laid over the actual, animated sequence of Homer waving his long-lost mother off on a bus and then sitting, waiting, silently, thoughtfully, as the sun goes down and the stars come out, is hands-down the most beautiful, soul-destroying moment in The Simpsons’ 26-year history (I seriously cannot even write about it without tearing up slightly).

It’s a gorgeous scene just by itself, and that’s before you even take into account that this may very well be the most poignant minute-and-a-bit of Homer’s life to date.

Sure, we’ve seen him be a good father to Bart, Lisa and Maggie, and we know he loves Marge more than life itself, so we’re not completely left thinking that he’s incapable of expressing any emotion other than unfocused rage – but it’s important to remember that this is a man, a man so often chalked up as little more than a big, dumb brute who lives hard and thinks softly, at his most painfully, affectingly vulnerable, reduced to nothing more but the scared, confused and worried little boy who woke up one morning to find his life-giver suddenly gone, without explanation, leading him on a mental path that everyone who's ever had someone leave them has gone down: Why didn't they want me? And The Simpsons sells all of that by having him wait sadly on the hood of his car for a mother that isn't coming back.

It's an especially revealing contrast to his relationship with his father — itself a minefield of tear-worthy sentimentality if you pay close-enough attention amid all the geriatric rambling and easy gags — and I dare say we’ll never see Homer in another moment quite like it, which is why it tops my list.