The 10 Darkest Episodes of The Simpsons

Blogging about my top 15 Simpsons episodes the other day got me in the mood to formulate another list about everyone's favourite yellow family. This time, I'll be looking at the episodes that troubled me, psychologically. Don't get me wrong. I enjoy all of the episodes in this list, but damn, they all contain some "I can't believe they went there" moments. Some of the moments are just plain scary. I've decided not to include any Treehouse of Horror episodes in this list. Two of the episodes on this list featured in my previous blog, so I apologise if I repeat myself. Now, let's begin the countdown!

10. El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer) (season 8)

Plot: At a chilli cook-off, Homer eats several ultra-hot Guatemlan peppers, sending him into a hallucinatory state. When he regains his consciousness, he re-evaluates his relationship with Marge, questioning whether or not she is his soulmate.  

What makes it dark?: This episode isn't especially dark, which is probably why it comes in at number 10 on this list. Nevertheless, the existential crisis that Homer goes through is unsettling at times, and a large chunk of this episode has a melancholic vibe to it. The scene depicted above, wherein Homer thinks he has 'found' Marge in his hallucination, only to discover it's a mound of coloured sand that looks like her, is a beautifully-animated sequence, but also very distressing from Homer's perspective...which is essentially ours, too. And there's a haunting, moody scene where Homer walks by himself around town, trying to find his soulmate. Everywhere he looks, he is met with rejection. Even the community outreach centre doesn't want him. This is underscored very nicely by the sound of Janis Ian's At Seventeen. P.S. I would love to see David Lynch interpret some of the hallucination scenes in a live-action adaptation of this episode. 

9. Alone Again, Natura-Diddily (season 11)

Plot: After Maude Flanders is tragically killed at a speedway, Homer tries to find a new partner for Ned.

What makes it dark?: First of all, I'll explain WHY the character of Maude Flanders was killed off. Maggie Roswell, who voiced the character, left the show in 1999 following a pay dispute. Rather than find a new voice actor for Maude, the producers decided to kill off the character to pave the way for new storylines. They also thought this would lead to a ratings boost. Already, we can see that the episode sprung from cynical motives. There's a considerably small portion of this episode that's related to the Flanders family in mourning, and you would think that makes the episode more lively and jovial. Well, it does...but it also undermines what Maude meant to Ned, Rod and Todd. Homer makes a dating tape to 'sell' Ned to women, and these scenes are rather funny, but you'd think that Ned would need some more breathing space and alone time if he were a real person. Some other dark lines: 

* Moe tells Ned, "...if it was you that died, I would have been on her (Maude) so fast."

* Rachel, lead singer in a Christian band, tries to empathise with Ned, "We just lost our drummer...to a Pentecostal ska band. Uh, I know it's not the same but..."

* A song from Rachel's band plays over the end credits, with the lyrics: "It's a show about Ned / About him losin' his sweet wife / She landed on her head / But now it's time to get on with his life."

8. The Joy of Sect (season 9)

Plot: A cult called the Movementarians takes over Springfield and brainwashes its citizens.

What makes it dark?: Admittedly, I haven't seen this episode that many times, and cannot remember too many specific scenes. Generally speaking, cults are pretty freaky, and it's worrying how easily the members of Springfield are won over by The Leader. One line that sticks out is when Bart monotonously says "I love The Leader," after encountering a Movementarian recruiter behind a closed door. But the scene that I always remember when this episode is mentioned is Marge's escape from the compound. During the night, she approaches the exit, where the Squeaky-Voiced Teen is on security. Surprisingly, he tells Marge, "Lady, people are free to go whenever they wish," but there's a catch. To escape the compound, Marge must cross terrain that's littered with landmines, attack dogs, alligators in water, and barbed wire. She's even 'chased' by a mysterious balloon. Luckily, she escapes unscathed. 

7. Das Bus (season 9)

Plot: Bart, Lisa and other children from Springfield Elementary School are stranded on an island and are forced to work together. Meanwhile, Homer founds his own Internet company.

What makes it dark?: This parody of Lord of the Flies doesn't always make for cheerful viewing. We slowly witness the students lose their sanity as they turn on one another, but no one cops more punishment than Milhouse. He is wrongly accused of eating all the snacks, and the other students TRY TO KILL HIM once he is acquitted by Bart. Things escalate into a 'Savages vs Dorks' scenario, whereby the savages are led by Nelson, and all don war paint. This is about as intense as The Simpsons gets, and it's genuinely uncomfortable to see everyone angry at each other. Oh, and what happened to bus driver Otto? He was picked up by some Chinese fishermen who plan to use him for slave labour. 

6. Cape Feare (season 5)

Plot: When Sideshow Bob is released from prison, he tracks down the Simpson family and attempts to murder Bart.

What makes it dark?: So many things make this episode dark. Sideshow Bob's 'Die Bart, Die' tattoo, Homer racing into Bart's room to show off his new chainsaw and hockey mask...I could go on forever. But what scares me the most about this episode is how intent Sideshow Bob is on finding Bart in the first place. Here's a man who literally wants to murder a ten year-old boy. It's especially creepy how Bart initially receives threats from Sideshow Bob, the most memorable coming over the radio, "All right, this is dedicated to Bart Simpson, with the message, 'I am coming to kill you slowly and painfully.'" A forgotten scary moment from this episode is when Ned Flanders brandishes a glove with knives on the fingers (à la Freddy Kruger) and tells Bart to "say his prayers," before lightening up and inverting the sentence to something innocent. P.S. This is also the best Sideshow Bob episode ever. I usually hesitate to label something as the 'best', but I can confidently use it here. 

5. My Sister, My Sitter (season 8)

Plot: Marge and Homer go to a party and leave Lisa to babysit Bart. Bart does his best to annoy Lisa at home, and eventually injures himself. Lisa must find a way to get medical attention for him without losing her reputation as a good babysitter. 

What makes it dark?: First of all, this is one of the most underrated episodes of the series. People often cite this as the episode where Bart is on his all-time worst behaviour. That's a big call, but it's valid. You can't help but feel sorry for Lisa, who must shoulder the burden of an injured brother, while simultaneously fearing the repercussions this will have on her reputation. It's rather repulsive that Bart slams his head against the wall to make the lump he has sustained even bigger. The darkest part of this episode is the ending. Lisa puts Bart into a wheelbarrow, along with Maggie, who is in a pet cage. She can't get an appointment at the emergency clinic, so she takes Bart to the hospital by foot. Bart falls out of the wheelbarrow and tumbles down a muddy hill. Lisa, Maggie and the wheelbarrow come falling after him. Now, they are on full show to their parents and other Springfield residents, who assume that Bart is dead, Lisa is on drugs, and Maggie is about to be drowned. Now if that's not dark, I don't know what is. 

4. The Secret War of Lisa Simpson (season 8)

Plot: Bart gets sent to a military academy as punishment for bad behaviour. While visiting the academy, Lisa sees that the school is far more challenging than hers and she decides that she wants to attend as well.

What makes it dark?: This episode makes for extremely uncomfortable viewing. The colours are very drab and depressing, and even as a viewer, you feel as though you're in unfamiliar territory, and are just as unsafe as Bart and Lisa. This was the season 8 finale...what a depressing note to end on. Anyway, why is it so damn grim? An air of hopelessness hangs over the whole episode. No one at the military school is sympathetic towards the Simpson kids. They are put through rigorous tests of endurance. It's just horrible. The element of common struggle unites Bart and Lisa, and it's hard to think of another episode where they're as close with each other. Oh well, at least there's a happy ending (and even that can only loosely be described as happy)

3. Homer's Enemy (season 8)

Plot: The Springfield Nuclear Power Plant hires Frank Grimes as a new employee. Homer is friendly towards Grimes, but Grimes grows frustrated with the fact that Homer is lazy and nonchalant, yet lives a more comfortable life than he does. In the subplot, Bart buys a dilapidated factory for a dollar at an auction.

What makes it dark?: Frank Grimes was abandoned by his family, and copped the full brunt of a silo explosion. Despite this, he went on to complete a degree in nuclear physics. This man deserves a life of success and happiness, but when he must work alongside Homer at the power plant, he loses his grip on reality. It is a natural trait of the intellectual to marvel in bewilderment at the antics of the stupid. Grimes cannot believe that a man as lazy and as stupid as Homer has had a more successful life than he has. Grimes lives between two bowling alleys, while Homer has "Everything! A dream house! Two cars! A beautiful wife! A son who owns a factory! Fancy clothes and...lobsters for dinner." Grimes is not inherently spiteful (he saves Homer's life when he's about to drink sulfuric acid); he's merely envious, and he has the right to be. And the exclamation point on this sad episode (yes, it IS sad, despite the laughs) is Grimes' death. He becomes a man possessed, mimicking Homer Simpson, and virtually becoming him. Even sadder is Grimes' funeral. Reverend Lovejoy says a few words, while Homer talks during his sleep, "Change the channel, Marge." Lenny chimes in with "That's our Homer!" It seems this episode was one huge celebration of Homer's stupidity, which, personally, I think is sometimes overdone on the show.

2. Marge Be Not Proud (season 7)

Plot: Marge refuses to buy Bart the new video game Bonestorm, so he steals it from a local discount store. Bart ends up being estranged from his mother when he gets caught, and fearing that he has lost her love, he decides he must regain it.

What makes it dark?: Although this comes in at #2 on the list, if I were ranking these episodes based on levels of realism, this would top the list. I couldn't believe how mean-spirited the writers made Marge in this episode. OK, Bart stole a video game. He didn't burn a puppy to death or drive the family car off a cliff. The level of passive-aggression that Marge displays here is chilling just to think about. This episode seriously disturbs me, because it makes me wonder how I'd feel if my mother practically disowned me. When Bart comes home to see the rest of his family making snowmen, and asks why they didn't wait for him, Marge replies "I figured you were getting a little too old for this. But you can still make one: there's some snow left under the car." We see the snow she's talking about. There's not much of it, and it's rather dirty. How can Bart be "too old" for making snowmen when Homer and Marge each made one? What Marge wants to tell her son is "Hey Bart, I fucking despise you now." Bart goes to Milhouse's place, and even wants to hang out with Milhouse's mother because Marge won't show him any love or attention. Poor kid. Huge props to the late Lawrence Tierney, who voiced Don Brodka. Tierney's gravelly, remorseless voice plays well here, and makes things even scarier for Bart. Overall, this episode is hard to watch because it feels so damn real. This is the sort of thing that could happen in real life. It's not scary due to supernatural elements, and it doesn't rely on any extravagant circumstances. Bart steals a game. He gets caught. Marge hates him for it. It's as simple as that. 

1. Bart Sells His Soul (season 7)

Plot: Bart declares that there is no such thing as a soul, and to prove it, he sells it to Milhouse for $5, in the form of a piece of paper that has 'Bart Simpson's soul' written on it. After this transaction, strange things begin happening to Bart. In the subplot, Moe renovates his tavern, turning it into a family restaurant called 'Uncle Moe's Family Feedbag'.

What makes it dark?: We're used to seeing Bart so confident and cocky, so to see him genuinely afraid is kinda unnerving. As I mentioned in my previous blog entry, there are two scenes that make this episode especially disturbing. 

1. The rowboat nightmare sequence (pictured above). Bart dreams that all the kids of Springfield are rowing with their souls, while he is left out. He tries rowing out to sea, but his boat only goes in circles. Sherri and Terri (and their souls) chant "Bart, it's time to end this dream / And don't forget the standard scream," right before Bart wakes up.

2. Bart begging a helpless Ralph Wiggum for his soul. It's night time, and Chief Wiggum has left Ralph by himself in a squad car while he talks some sense into a derelict. Bart propositions Ralph after a friendly introduction, telling him "I need a soul, Ralph. Any soul! Yours!" Ralph bawls his eyes out in fear, and when Chief Wiggum returns to the car, Bart hisses and vanishes into the misty night. 

And there are some other dark moments, like when Lisa says grace at Uncle Moe's, praying for everyone's soul except Bart's, of course. I think this episode works so well at unsettling us because it's not as though any of us know if the soul exists. We can speculate all we like, but it can't be proven. I don't believe in the soul, but this episode of The Simpsons is scarily convincing at times. I always have to remind myself that it is fiction.