The Simpsons Moments That Make You Feel Like Your Heart Copped A Football To The Groin

The Simpsons sad moments

While most people spend an average of a 1/3 of their lives sleeping, I spend it watching The Simpsons reruns.

That stat may have even skyrocketed to a strong 50% of my life given the entire 30 seasons are now on Disney+, but, for my self-esteem’s sake, let’s just cram that little tidbit into the deep crevices of my brain.

Not a single iota of my being regrets it though, as I wholeheartedly believe that The Simpsons has taught me more life lessons than anything I’ve experienced in real life.

For example, The Simpsons taught me that you can’t skateboard over a gorge. My brother falling out of a tree, on the other hand, taught me nothing – if anything, I climbed more trees after witnessing my brother crack his head open on the rocks below. True story, Mum had to sew his noggin shut in the bathroom.

The Simpsons is also the first fictional television show responsible for making me feel. Not just feel, but weep an ocean’s worth of tears. So, for every other ’90s baby out there, here’s a nice reminder of the first time you realised you could be broken by TV.

1. Marge’s D&M With Lisa – Season 2, Episode 6

“Always be yourself. If you want to be sad, honey, be sad. We’ll ride it out with you. And when you get finished feeling sad, we’ll still be there. From now on, let me do the smiling for both of us.”

As a kid, Marge‘s monologue didn’t have much of an impact on me, presumably because I was yet to appreciate a good ol’ parental pep talk. Now, on the other hand, simply reading Marge’s heartfelt conversation with her struggling daughter is enough to make me well up.

I kind of wish I was exaggerating. I’m currently having a teary right now and this is not what I had in mind for a sunny Melbourne arvo.

2. Hugh Rejecting Homer’s Gift – Season 6, Episode 19

Time to dial it back a touch so I can compose myself.

This particular moment isn’t as meltdown-inducing as the previous one but it still hurts my soul all the same.

For those who don’t recall, Lisa (somewhat reluctantly) hits up a fortune teller when the Simpsons clan attend a renaissance fair and is subsequently shown a vision of her future husband-to-be.

Turns out that the husband-to-be is a snooty-patooty who openly mocks a sentimental gift from Homer – two little piggy cufflinks that had been handed down the family.

I know it was a fleeting moment of an already emotional episode, but hearing Homer’s dejected admission that his gift mustn’t have been “Hugh‘s cup of tea” was particularly upsetting.

Just wear the damn pig cufflinks, Hugh.

3. Ralph Fails To Receive A Card For Valentine’s Day – Season 4, Episode 15

Yes, we’re all familiar with the iconic scene where you can pinpoint the exact moment Ralph‘s heart rips in half, however, that’s not the part of the episode that makes me drip from my eye holes.

The moment I’m referring to happens right at the beginning of the episode when the students are giving each other homemade Valentine’s Day cards. Poor, sweet baby Ralph eagerly checks his box – even shakes it at one point in case a pesky card got stuck to the bottom – only to discover that not one of his classmates had thought of him.

Now, chalk this down to my own experience in primary school, but no child deserves to feel unloved. Granted, the experience I’m referring to wasn’t as traumatising (unless rocking up to a party you later found out you weren’t invited to qualifies) but regardless, that uniquely horrendous feeling is universal.

Thank Jebus Lisa was an observant little trooper.

4. Marge Loses Faith In Bart – Season 7, Episode 11

Oh, Marge.

I’m not a parent so I can only imagine the heartbreak when you discover your special little guy is a special little shoplifter.

This entire episode ruins me every single time. I don’t think you need to be a parent to understand the gravity of Bart‘s faux pas. All of us have disappointed our parents at some point in time – I aim to do it twice a month for consistency reasons.

Whether you relate to Marge or Bart more, you’re still going to feel a pang of guilt regardless.

Guilt-ridden tears are the saddest of tears.

5. Ned Loses Another Love – Season 25, Episode 23

Ned Flanders deserves an award for being able to remain so optimistic in spite of so much heartbreak.

Although Ned and Mrs Krabappel didn’t also make the most sense, her death in Season 25 reflected the harsh reality of life – we’ll all lose loved ones – and for those lucky enough to have found a partner, those too – in the end.

Sorry to bum you out further, but this scene was even harder to swallow when you realise that the voice actress, Marcia Wallace, had died in real life, too.

6. Marge Serenades A Lonely Lisa – Season 8, Episode 25

Similar to relating to Ralph during his Valentine’s Day from Hell, Lisa struggling to fit in at Cadet School also hit far too close to home.

It’s difficult to explain, but you know when you’re feeling blue and a thoughtful message from a loved one makes you want to cry harder? This scene is that feeling in a nutshell.

Look, I don’t necessarily blame Bart for the way Lisa was treated. However, I will say that it took him far too long to break away from the lads and actually support his sister when she sorely needed her brother’s love.

7. Homer’s Mum Leaves Him (Again) – Season 7, Episode 8

I’ll leave you with the saddest scene from the entire franchise and a gutwrenching description by coworker and fellow Simpsons lover, Eamon:

Imagine your mother – who you remember as loving and devoted – had to go away when you were five and you had no idea why and she never, ever contacted you (to your knowledge).

She returns when you’re 36 years old. You’ve graduated, you’ve been married, you’ve had two children and you’ve been unable to share any of these experiences with her. All of these moments are squeezed into a mere few days as you, personally, regress to the attention requirements of a five-year-old.
You then have to aid her as she has to leave you, your family and children – again – without contact and with no return in sight.

RIP Mona Simpson (ah yeah, she dies in Season 19 – sorry if I spoiled anything).

All 30 seasons of The Simpsons are streaming right now on Disney+.

More Stuff From PEDESTRIAN.TV