If you’ve been watching The Simpsons for their entire 26-year run — or even if you’ve just watched the first eight seasons — you know they’ve done some serious tearjerkers over the years. But which one was the saddest of them all? Let’s look at some classic Simpsons episodes and determine which was one was most likely to leave fans crying a river of tears.
5. “Simpson and Delilah” — Original Air Date: Oct. 18, 1990
Homer was never particularly good at his job, but in the early years, it wasn’t played for laughs as much. He at least tried to be a competent employee. He gets a boost in this episode, both from the hair he grows by taking Dimoxinil and from Karl, his assistant whose powerful advice gives him the confidence he needs to succeed. Unfortunately, Bart ruins Homer’s supply of Dimoxinil while trying to grow a beard. Homer is bald yet again, and he has to deliver a big speech. Karl tells him that it was never the hair, and his ideas will win the crowd over. Of course, The Simpsons is far too cynical for that to happen. He bombs without his hair, and Burns demotes him back to where he was. It’s a brutally honest take on how shallow and vapid society can be, but the kicker comes at the end when Homer is worried that Marge won’t love him now that he’s back to being a bald member of Sector 7G. She responds by serenading him with “You Are So Beautiful,” which ranks among the sweetest moments in Simpsons history. On a personal note, I saw Joe Cocker perform that song live in 2010 when he toured with Tom Petty. I cried the entire time, almost entirely because of this episode.
4. “Bart Gets an F” — Original Air Date: Oct. 11, 1990
What makes this episode so damn sad is that for all of Bart’s efforts, he still fails the big test. The scene of him studying by candlelight in his room, and yelling at himself for not taking things more seriously over the years is brutal, but when he gets a 59 (“a high F!”) on the final exam, that’s when the waterworks start flowing. Yes, Krabappel gives him an extra point for “applied knowledge” that allows him to pass the fourth grade, but let’s be honest, that was a Deus Ex Machina device. The episode had to end on a happy note, with Bart passing. Of course, Bart spends the entire run of the series in the fourth grade, so the test that seemed important at the time actually wasn’t a big deal in terms of the show’s progression. Still an incredibly powerful episode, though.
3. “And Maggie Makes Three” — Original Air Date: Jan. 22, 1995
Okay, the ending shot above is really all you need to know here. Who didn’t cry the first time they saw this one? But if we explore the theme of the episode, we discover that Homer has ambitions; fairly modest ones, like being able to work a low-paying-but-fun job in a bowling alley while making just enough money to support a wife and two kids, but ambitions nonetheless. This gets shattered when the presence of a third child on the way means that Homer will need to make more money. Having already quit the power plant, he has to *literally* come crawling back to Mr. Burns, who gives him his job back, but with the de-motivational plaque that reads “don’t forget, you’re here forever!” Homer is miserable, and even resentful of the new baby’s presence in his life, until she is born, and it’s love at first. We get a fun bit of comic relief when Homer mistakes the umbilical cord for… something else, but this scene brilliantly depicts the instant love that Homer has for Maggie, and the tearjerker ending really drives it home.
2. “Lisa’s Substitute” — Original Air Date: April 25, 1991
This episode really explores Lisa’s status as an intellectual misfit, which is touched on lightly in other episodes, and became a source of humor later on. When Mr. Bergstrom takes over Ms. Hoover’s class, Lisa has someone she can relate to on an intellectual level. More importantly, she has a father figure who she has a lot more in common with than Homer. They key here is that while we feel sorry for Lisa, we can empathize with Homer, as well. Sure, he’s a “baboon,” but he’s not trying to be one. I think that’s what makes this episode work so well. If Homer’s insensitivity were deliberate, we’d be rooting against him, but because it’s just oblivious, we want him to figure things out and be there for Lisa after Mr. Bergstrom leaves. Sure enough, he gets his act together and gives Lisa the cheering up she needs. He also makes Bart feel better about not getting elected Class President, by reminding him that a job like that is more boring work than fun stuff. As someone who was Class Treasurer my freshman year of high school, I can report that Homer is dead on here.
1. “Mother Simpson” — Original Air Date: Nov. 19, 1995
What stands out to me about this one is that, unlike every other episode here, this one didn’t have an “everything’s back to normal!” ending. Homer’s relationship with his mother remains unresolved, and the point is driven home as Homer just stares into the desert as the credits roll. This one didn’t offer us any solace as it delivered its incredibly sad ending. In that regard, we can view this episode as the blueprint for Futurama‘s equally depressing “Jurassic Bark.” There’s something so powerful about an episode that doesn’t give you the happy ending you see coming. The conclusion of this episode is one of the saddest moments in Simpsons history, and it easily qualifies for top honors on this list.
