The Simpsons’ 10 Darkest Episodes, Ranked

While The Simpsons is a lot lighter and more family-friendly than its animated cousins Family Guy and South Park, the show has been known to veer into dark territory, either for a one-off joke in the middle of an episode or for an entire storyline that explores heavier themes than fans are used to.

Throughout the show’s three-decade run, the writers have tried out just about every storyline under the sun. From the titular family joining a cult to a hard-working man being driven insane by Homer’s ineptness, there are a handful of dark episodes of The Simpsons to enjoy.

10 Cape Feare

Although it’s a parody of the Scorsese/De Niro thriller and to a lesser extent, the earlier Robert Mitchum thriller it was based on, season 5’s “Cape Feare” is still a pretty dark Simpsons episode. The plot sees Sideshow Bob getting released from prison and cooking up an elaborate plan to murder Bart.

The Simpsons are put into federal protection and relocated with new identities, but Bob follows them to their new houseboat, ties up the family, and actually does try to kill Bart.

9 Dial N For Nerder

After a prank gone wrong in “Dial ‘N’ for Nerder,” Bart and Lisa think they’ve accidentally killed Martin and spend the rest of the episode trying to deal with the guilt.

Nelson investigates Martin’s apparent death and eventually finds him alive and well — after deducing what Bart and Lisa did and driving them to a confession.

8 The Blunder Years

Homer gets hypnotized in season 13’s “The Blunder Years” and it awakens a repressed trauma. When he was a kid, Homer and his friends went down to the quarry to swim in the water, but found the water pipe blocked.

When he unblocked it, a rotting corpse washed out into his lap. The corpse turns out to be that of Smithers’ father, who died a hero sacrificing himself to prevent a meltdown.

7 El Viaje Misterioso De Nuestro Jomer (The Mysterious Voyage Of Homer)

After trying keep Homer from finding out about a local chili festival, Marge makes him promise not to drink while he’s there. But he eats a pepper that’s so spicy that he desperately grabs a bunch of beers and pours them down his throat. Slurring his words, he tells Marge, “I need it!!”

Then, he runs off into the desert and the pepper makes him hallucinate a “Space Coyote” (played by Johnny Cash). Through delightfully surreal animation, “The Mysterious Voyage of Homer” explores some heavy themes.

6 The Joy Of Sect

The Simpson family joins a cult called the Movementarians in “The Joy of Sect.” The writers were influenced by all kinds of organizations — including Heaven’s Gate, Peoples Temple, the Unification Church, the Rajneesh movement, and the Church of Scientology — in devising the ominous belief system of the Movementarians.

The episode has been analyzed by religious scholars and is frequently ranked among the most culturally significant Simpsons episodes ever made.

5 Bart Sells His Soul

The season 7 episode “Bart Sells His Soul” explores the notion taught by all religions that everyone has a soul separate from their body. Bart sells his soul to Milhouse for $5 to prove souls don’t exist, then begins to experience strange occurrences like the Kwik-E-Mart’s automatic doors not opening for him.

The episode’s darkest element is Bart’s recurring nightmares, in which he sees all his friends canoeing to a paradise with their souls, while he struggles to row his boat alone.

4 Alone Again, Natura-Diddly

Maude Flanders was permanently killed off in “Alone Again, Natura-Diddly” when Homer asked for a t-shirt cannon to be shot at him and then ducked, allowing the t-shirt to hit Maude, sending her over the back of the bleachers and onto the ground below.

It was tough to maintain The Simpsons’ usually zany comic sensibility in the face of a grieving Ned Flanders, while Homer’s direct involvement in Maude’s death (albeit unintentionally) is pretty uncomfortable.

3 One Fish, Two Fish, Blowfish, Blue Fish

Homer is told that he has only one day to live after eating improperly prepared blowfish in a sushi restaurant in season 2’s “One Fish, Two Fish, Blowfish, Blue Fish.” For a lot of fans who grew up with The Simpsons, this episode was the first time they accepted the reality of death.

He makes a list of all the things he wants to do on his last day, but he doesn’t have enough time to complete. By the time he gets home, Marge and the kids are asleep and, fully expecting to die, Homer falls asleep listening to the Bible on tape, read by Larry King.

2 Some Enchanted Evening

Although it aired as the final episode of the first season, “Some Enchanted Evening” was actually produced first and was intended to be the pilot episode of the half-hour adaptation of The Simpsons’ early shorts on The Tracey Ullman Show.

The outcome might’ve been very different if “Some Enchanted Evening” aired first because it’s a pretty disturbing episode. The Simpson kids are left with a babysitter who turns out to be a dangerous psychopath.

1 Homer’s Enemy

A common pick for The Simpsons’ darkest episode is “Homer’s Enemy,” in which Frank Grimes — a man who has struggled his whole life to scrape the bare minimum — is hired to work at the power plant and finds Homer’s incompetence astounding.

He can’t understand why Homer is popular among his co-workers, lives in a nice house, and has a loving family. It eventually drives him insane and he accidentally kills himself trying to let loose and act like Homer.

About The Author

Ben Sherlock
(3461 Articles Published)

Ben Sherlock is a writer, comedian, independent filmmaker, and Burt Reynolds enthusiast. He writes lists for Screen Rant and features and reviews for Game Rant. He’s currently in pre-production on his first feature (and has been for a while, because filmmaking is expensive). You can catch him performing standup at odd pubs around the UK that will give him stage time. Previously, he wrote for Taste of Cinema, Comic Book Resources, and BabbleTop.

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