Saddest Moments in the Simpsons

The Top Ten

1 This Time I'm Awake for Your Goodbye - Mother Simpson

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! - ShaunFan04

I knew well this would be number 1! This is the saddest part in Simpsons ever in my opinion...


2 Daddy - Lisa's First Word

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.6 - ShaunFan04

3 Do It for Her - And Maggie Makes Three

Do it for her! Awww so sad...

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. - ShaunFan04

4 You are Lisa Simpson. - Lisa's Substitute

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! - ShaunFan04

5 You Don't Understand, I Really Tried This Time! - Bart Gets an F

Bart fails his test again but this time he says that he tried his hardest and he still failed. This moment hits me so hard as I myself was struggling to pass my subjects at school. I feel real sympathy for Bart in this tough time and when Ms Krabappel let's him pass after spouting some random history fact I feel so joyous. Bart gets so happy that he passed and tells everyone he got a D- and he passed! - ShaunFan04

6 Great Game Bart! - Lisa on Ice

Bart and Lisa play on opposing hockey teams. When it comes down to the final penalty shot to be taken by Bart with Lisa in the net. Bart was about to take a shot but then remembers how Lisa helped him through some times such as helping him steal from the cookie jar. Lisa also has memories of Bart cheering her up as when her ice cream fell off the cone, Bart gave her some of his. In the end, Bart and lisa realise that they needed each other and allow the draw. - ShaunFan04

7 I Did the Best I Could Bleeding Gums... - 'Round Springfield

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. - ShaunFan04

8 I Just Want It Back... Please? - Bart Sells His Soul

Bart doesn't believe in the soul so he sells his for 5 bucks to Milhouse. When realising how much he needed his soul Bart gets reduced to praying for it where it falls in front of him. - ShaunFan04

9 The Good Book, on Tape? - One Fish Two Fish Blowfish Blue Fish

God this episode, This episode is where Homer almost dies, it's very sad that he only had 24 hours to live, thankfully in the end he was alive so he got to live! - ShaunFan04

10 Hurry Neddy Hurry! My Golly It's a Miracle! - When Flanders Failed

Um, it’s Homer being nice to Flanders. Like, genuinely nice. One of the sweetest endings to any Simpsons episode! - ShaunFan04

The Contenders

11 Maude Flanders Dies - Alone Again, Natura-Diddily
12 Mona Simpson Dies - Mona Leaves-A

She died in a very sad way

13 Barney's video - A Star is Burns
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