Saddest Moments in the Simpsons

The Top Ten
This Time I'm Awake for Your Goodbye - Mother Simpson

I knew this would be number one! This is the saddest moment in The Simpsons ever, in my opinion.

Daddy - Lisa's First Word

SO MANY TEARS! Aren't we all suckers for a good, cute sibling story, especially one between Bart and Lisa? Then, that sucker punch of an ending is topped off with an enduring Homer moment (which this list is full of, by the way).

Want another reason to cry? The voice of Maggie is by the late Elizabeth Taylor. Go ahead, cry about it some more.

Do It for Her - And Maggie Makes Three

This episode is famously a tearjerker in The Simpsons and online community. It demonstrates how The Simpsons mirrors everyday American life and the difficult decisions we must sometimes make for our families' well-being and success.

How many parents could identify with this episode, and how many children learned just how much their parents sacrifice for their well-being? Ugh, tears. Tears everywhere.

You are Lisa Simpson. - Lisa's Substitute

Look, Lisa is a very smart girl, but 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! Shoutout to Dustin Hoffman for being Mr. Bergstrom!

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

Bart fails his test again, but this time he says he tried his hardest and still failed. This moment hits me hard, as I also struggled to pass my school subjects.

I feel genuine sympathy for Bart, and when Ms. Krabappel lets him pass after recalling a random history fact, I feel so joyous. Bart is so happy that he tells everyone he got a D- and passed!

Great Game Bart! - Lisa on Ice

Bart and Lisa play on opposing hockey teams. When it comes down to the final penalty shot, with Bart taking the shot and Lisa in goal, Bart is about to shoot but then remembers how Lisa has helped him, such as when she helped him steal from the cookie jar.

Lisa also recalls Bart cheering her up by sharing his ice cream after hers fell. In the end, Bart and Lisa realize they need each other and allow the game to end in a draw.

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

Look, any Murphy episode is a tearjerker. Actually, any episode where Lisa has a mentor taken away from her is a tearjerker.

But this one is especially sad, as it marks the end of Murphy's appearances on the show. RIP, Bleeding Gums.

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

Bart doesn't believe in the soul, so he sells his for five bucks to Milhouse. Realizing how much he needed his soul, Bart is reduced to praying for its return, and it falls in front of him.

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

God, this episode is where Homer almost dies. It's very sad that he only had 24 hours to live, but thankfully, in the end, he was alive and got to live on!

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

It's Homer being nice to Flanders. Like, genuinely nice. One of the sweetest endings to any Simpsons episode!

The Newcomers

? Edna Krabappel's Death - The Man Who Grew too Much
? Nelson Father - Sleeping with the Enemy
The Contenders
Maude Flanders Dies - Alone Again, Natura-Diddily
Lenny's reaction to Carl's betrayal - The Saga of Carl

I cried harder than anyone ever cried. Lenny is my favorite character, and it broke my heart to see him go through this much pain because I knew how intensely he loved Carl. The fight scene surprised me, but I think I can explain it.

Up until that point, most of Lenny's character revolved around his friendship with Carl, so it was very out of character for him. This led me to believe he was angrier at himself than at Carl. As I mentioned, this friendship was his main character trait at the time, and he would never harm Carl. Therefore, he must have had another motive. I might be biased because Lenny is my favorite character, but he thought he had...

Mona Simpson Dies - Mona Leaves-A
Barney's video - A Star is Burns
Papa, Can You Hear Me? - Sleeping with the Enemy
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