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The Simpsons' 10 Saddest Moments, Ranked

The Simpsons always managed to make us laugh and cry in almost equal measure. The saddest moments on the show were what made it so great.

Despite the fact that The Simpsons is one of the funniest TV shows of all time, with countless quotable one-liners and unforgettable sight gags, it has also given us some really hard-hitting dramatic moments. The moments that make you laugh far outweigh the moments that make you cry – this is a comedy, after all – but the moments that make you cry are there, especially in the show’s earlier seasons.

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In fact, the show’s infamous decline in quality came about when it lost sight of its delicate balance between the absurd and the sincere. So, here are The Simpsons’ 10 Saddest Moments, Ranked.

10 Homer and Bart watch Itchy and Scratchy: The Movie

In the episode “Itchy and Scratchy: The Movie,” the titular film adaptation of Bart and Lisa’s favorite cartoon sweeps the nation. Homer and Marge have promised not to let Bart see the movie as punishment for his bad grades after Mrs. Krabappel convinced them he could be a Supreme Court Justice with better discipline.

While Lisa and everyone else at school are raving about how it’s the greatest movie ever made, Homer still won’t relent. It’s a situation that everyone can relate to, because both Bart and his parents have valid points. The episode ends with a heartwarming flash-forward to a future in which Bart is a Supreme Court Justice and Homer finally takes him to see Itchy and Scratchy: The Movie.

9 Bart buys Lisa a Bleeding Gums Murphy album with his Krusty-O’s settlement

In the episode “‘Round Springfield,” Lisa’s hero, jazz legend Bleeding Gums Murphy, dies suddenly. She decides that the best way to honor him would be to play his album on the radio, but it costs $500. Meanwhile, Bart has had to undergo surgery, due to a jagged piece of metal in his box of Krusty-O’s.

Following a $100,000 settlement and Lionel Hutz’s “legal fees,” Bart is left with $500, which he intends to use to buy a Steve Allen pog. But seeing how heartbroken Lisa is over Bleeding Gums Murphy’s death, he decides to buy her the album instead. As much as they bicker, Bart really cares about Lisa.

8 Lisa gets a note from smart Homer

“HOMR” is a classic episode of The Simpsons, because it reveals something about the mythology of the show – why Homer is so stupid – in a satisfying way. Turns out, he has a crayon lodged in his brain. After it’s removed, he’s a genius. But he alienates all of his friends until, tragically, he decides to have the crayon reinserted.

Lisa is sad, because smart Homer had developed a really close relationship with her, and she couldn’t relate to stupid Homer as much. But then she found a note left for her by smart Homer before the surgery: “Lisa, I’m taking the coward’s way out. But before I do, I just want you to know being smart made me appreciate how amazing you really are.”

7 “Happy Birthday Lisa”

All throughout “Stark Raving Dad,” Lisa keeps reminding Bart that, every single year, he forgets about her birthday. This year, he’s determined to actually put some thought into her gift. But then Homer gets institutionalized, meets a man with the voice (but not appearance) of Michael Jackson, and then promises to bring Jackson home.

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So, Bart gets distracted as he tells everyone in Springfield that the King of Pop is coming to his house. As he overhears Lisa expressing her disappointment that he forgot about her birthday again, Bart acts fast and writes a really heartfelt birthday song for Lisa.

6 Homer’s speech at Lisa’s wedding

Season 6’s “Lisa’s Wedding” was the first flash-forward episode, and so far, the only one to effectively use the flash-forward format. It’s impossible not to choke up during Homer’s speech:

“Little Lisa, Lisa Simpson. You know, I always felt you were the best thing my name ever got attached to. Ever since the time you learned to pin your own diapers, you’ve been smarter than me. I just want you to know I’ve always been proud of you. You’re my greatest accomplishment, and you did it all yourself. You taught me to understand my own life better, and made me a better person, but you’re still my daughter, and I don’t think anyone has ever had a better daughter than...” Lisa cuts in to say, “Dad, you’re babbling,” and Homer adds, “See? You’re still helping me.”

5 Bart fails his test again

In the season 2 premiere “Bart Gets an F,” Bart fails his history test and he’s given one more chance to take it before flunking the year. He puts off studying for a while and gets a miracle in the form of a snow day, but he eventually buckles down, despite the temptations of the snow.

And then he takes the test, fails it, and breaks down crying. Mrs. Krabappel is shocked. This was one of the early moments establishing their relationship as more complex and emotional that just a student/teacher rivalry. The clincher is when Bart says, “You don’t understand! I really tried this time!”

4 “You are Lisa Simpson”

Mr Bergstrom in The Simpsons

As the most intelligent student at her school, Lisa struggles to keep hold of friends and, as a result, also struggles with confidence. Dustin Hoffman was instantly memorable in the role of her substitute teacher, Mr. Bergstrom, an intellectual match who actually took the time to listen to her.

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But like any substitute, he had to leave, and Lisa worried that she wouldn’t be happy without him. Then he gave her a note and said, “Whenever you feel alone, like there’s no one you can rely on, this is all you need to know.” After he leaves, she reads the note: “You are Lisa Simpson.”

3 Homer listens to the Bible on tape

In season 2’s “One Fish, Two Fish, Blowfish, Blue Fish,” Homer eats a poisonous fish at a sushi restaurant and is told by Dr. Hibbert that he has 24 hours to live. So, he lists all the things he wants to do on his final day: have a drink at Moe’s, spend some time with his father, tell Mr. Burns how he really feels etc. The itinerary ends with a family dinner and some time with Marge, but he ends up spending too long with his dad and then getting thrown in jail.

It’s heartbreaking as Homer struggles to get home, only to arrive home and find Marge and the kids asleep. So, he falls asleep in the living room, listening to the Bible on tape. We all knew he’d survive, because this is a TV show, but what makes it effective is that Homer thinks he’s going to die.

2 “Do it for her”

In the episode “And Maggie Makes Three,” Bart and Lisa ask why there are no pictures of Maggie in the family photo albums. So, Homer and Marge tell the story of how a third pregnancy was unexpected. Homer had quit his job at the nuclear plant and he had to go crawling back to Mr. Burns’ office, begging for his job back.

Mr. Burns gave him his job back on the condition that he was locked into it for the rest of his life, so he put up a sign in Homer’s office: “Don’t forget: you’re here forever.” Homer took all the pictures of Maggie to cover it up to instead say: “Do it for her.”

1 Homer looks up at the stars after his mom leaves

Simpsons fans have long considered “Mother Simpson” to be one of the most emotional episodes of the series, ending with what is easily the most affecting moment in the show’s history. Homer’s long-lost mother Mona reappears and becomes a part of his life.

He grows to trust her, then the cops catch on and she realizes she has to move on, so she bids the family farewell and Homer drives her out into the desert where some friends pick her up. After she’s gone, he just sits on the hood of his car and looks up at the stars. It’s really heartwarming, and makes Homer feel like a real person.

NEXT: The Ultimate Simpsons Gift Guide

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