Top 10 DARKEST Simpsons Moments

Welcome to WatchMojo, and today we’re counting down our picks for the Top 10 Darkest Simpsons Moments. For this list, we’ll be looking at the most bone-chilling, psychologically-tormenting, and visually disturbing moments from “The Simpsons,” though we’ll be excluding those from the “Treehouse of Horror” series. We’ll also only be looking at moments from the titular show, so extended material like games, comic books, or movies are out. This list also has spoilers, so consider yourself warned! Is there a dark moment that we missed? Let us know in the comments! Just don’t tease us like Nelson.

#10: Banksy’s Couchgag

“MoneyBart”
The artist known as Banksy provided a very memorable “Simpsons” moment. It came when he got to direct the couch gag for this episode. His rendition was hard to forget, complete with kittens, wood chippers, and children being forced to work with dangerous chemicals in an overcrowded factory. Those were just some of the bleak things Banksy showed that made viewers (and the bigwigs) uncomfortable. Some moments from the gag actually ended up getting censored by Fox. The couch gag could be a bit tough to watch. But Banksy’s social commentary was a clever way to shed light on some important issues.

#9: Sideshow Bob’s Revenge

“Cape Feare”
Sideshow Bob has always been an unhinged individual. Yet “Cape Feare” is arguably his most terrifying appearance! That’s because in this episode—which was directly inspired by the ‘91 Robert De Niro movie “Cape Fear”— Sideshow Bob tries to kill Bart! Terrified, the Simpsons family goes into hiding and gains new identities. That’s still not enough to evade this bloodthirsty psychopath, though. Bart and the family manage to survive Sideshow Bob’s pursuit. But his sheer dedication, pure bloodlust, and obvious insanity were enough to make us want to sleep with the nightlights on!

#8: Frank Lets Loose

“Homer’s Enemy”
Don’t try to get too comfortable, it might just kill you. Down on his luck Frank Grimes gets a job at the Springfield Power Plant. But when he meets Homer, all he can think about is how a guy like him has a nice house, family, and friends. Everything that Frank’s only ever dreamed of. This unhealthy obsession with Homer leads Frank into a downward spiral. And he meets his grim end when he tries to follow in Homer’s footsteps and loosen up. We wish Frank would have gotten the happy ending, but sadly, fate (or the writers anyway) had other plans.

#7: They Killed Martin?

“Dial ‘N’ for Nerder”
Bart and Lisa tangled with their guilt after they thought they were responsible for the death of Martin. The panic all started after Bart decided to play a prank on the unsuspecting classmate. While Lisa tried to rescue Martin from the cliff he stumbled onto, she made things worse by accidentally causing him to fall off of it! The apparent death was a dark enough moment just on its own. But the choices that Bart and Lisa weighed over were just as unsettling. Bart suggested they tell the authorities, while Lisa suggested otherwise. The drastic change in character for both of them was surprising. But thinking you’re responsible for the murder will probably do that! Luckily, it was revealed that Martin actually survived!

#6: The Babysitter Is a Criminal

“Some Enchanted Evening”
Bart and Lisa were in for the shock of a lifetime when they discovered that Ms. Botz, the woman who was babysitting them, was actually a wanted criminal. Home invasions are no joke, and seeing Botz tie the kids up and ransack the house did little to quell our nerves. Thankfully, Lisa and Bart are eventually able to break free and knock her out. What happens in the episode isn’t the only dark thing. If things had gone as planned, this disturbing episode (which was the Season 1 finale) actually would’ve been aired as the show’s pilot! We’re kind of glad that this intense episode wasn’t the show’s very first.

#5: Bart’s Clown Bed

“Lisa's First Word”
When Homer builds a bed for Bart, the heartwarming gesture is soured by the fact that the bed resembles a gigantic clown. Sure, Homer meant well, but there’s just no way Bart’s going to be able to sleep well with this! And we can’t say we blame him. Bart’s immense fear of clowns (which we’re no strangers to) makes it impossible for him to sleep, let alone breathe! As soon as Bart sees this nightmarish contraption, all he can imagine is the clown trying to eat him. And laughing in a way that sends chills down our spines. Next time just get a bed from IKEA, Homer, one that’s preferably not from the “traumatize my kids” collection!

#4: Homer’s Face Melts Off

“Brother from the Same Planet”
Bart and Homer’s relationship has always been a little rocky. That’s the only real conclusion you can make when one of the show’s longest-running gags is Homer strangling Bart. One of the lowest points was when Homer was considerably late arriving to pick Bart up from soccer. But what makes this moment so horrifying is what Bart imagines happening to Homer. Homer (completely oblivious to his son’s anger) rattles on. As he does, Bart imagines his skin melting right off of the bone! The scene was visually startling and completely out of left field since everything else in the episode up until then was normal. Well as normal as an episode of “The Simpsons” could be!

#3: Homer's Impending Death?

“One Fish, Two Fish, Blowfish, Blue Fish”
What would you do if you knew time was running out? When Homer eats a blowfish that might not have been cooked right, he’s told he only has 24 hours to live! He creates a bucket list of things to do before he dies. Like listening to Lisa play the saxophone and reconnecting with his dad. This episode is dark, but maybe not in the way you’d expect. There’s no creepy monster or disturbing ax murderer here. Just a sinking feeling of dread as Homer is forced to confront his own mortality. Despite everything, Homer actually survives! It turns out his dinner wasn’t that deadly after all.

#2: Tied To A Boulder

“Homer's Odyssey”
Apart from being one of the show’s earliest episodes, “Homer’s Odyssey” is arguably one of its most serious because of the subject matter. When Homer is fired from his job at the power plant, he decides to take his life. His attempt is an elaborate one. He ties a large boulder to himself and tries to jump from a bridge. His family notices his erratic behavior and tries to stop him. It’s only when Homer saves them from getting hit by a car on the busy road that he’s snapped out of his dishevelment.

#1: Ned Loses His Wife

“Alone Again, Natura-Diddily”
One of Ned’s darkest hours came when his wife Maude met her untimely end. It happened when she was struck in the head by multiple t-shirts fired from a cannon. The force of the strike was so strong it caused her to stumble from the bleachers and crash directly to the ground. It was such a bizarre and sudden way to go. And Maude’s death remains one of the show’s most tragic. Unsurprisingly, the death is difficult for Ned and the kids. But the saddest moment might be when Ned goes to bed by himself. He instinctively puts his hand on the pillow next to him as if Maude were still there. Unfortunately, that’s no longer the case.