Top 10 DARKEST Episodes of The Simpsons That Are Really Messed Up 

Remember to subscribe and hit that notification bell!

When homer sits looking at the stars after his mom leaves makes me cry

What about the episode where Bart lose a baseball game and the whole town turns on him?

When Bart studies his hardest and still gets an F and failing That gets deep and relatable R.I.P

**about to commit suicide** Homer: “Well, live and learn” That’s pretty damn funny, actually

You know, I'm shocked that the episode where Bart gets hated by almost everyone in Springfield over a baseball game isn't on here.

Sideshow Bob's accent is *not* British. That's the transatlantic accent that was popularized by Hollywood and used by the American upper class from about the 1920s through the 50s. It's a manufactured accent (as opposed to a regional accent that evolved naturally) that was intended to make its speakers both be understood clearly and seem cultured and posh.

There’s the episode where Bart and Lisa thought they killed Martin. Everyone was miserable in Who Shot Mr. Burns? It was pretty sad when Grampas girlfriend died. Or when bleeding gums Murphy died.

There, I watched it. Are you happy now RU-vid!?

The credits at the end of "Mother Simpson" when it first came out in the mid 90's, it made me cry but Sideshow Bob always stepping on a rake always cheers me up

There's one episode I can think of and it's one of my favorites. I don't remember the title of the episode, but it's where Homer as a kid discovers the corpse of Smithers' father and becomes traumatized.

Not the darkest, but the episode that always gets me is the one where Lisa's class gets Mr. Bergstrom as a long-term substitute, and he's one of the first and few people to really get her, so when their regular teacher comes back, Lisa is heartbroken. She finds him at the train station and he writes something on a piece of paper and tells her to look at it whenever she feels alone. As the train is taking him away, he tells her to look at the note, and it says, "You are Lisa Simpson," and I'm honestly tearing up right now thinking about it, because it's so simple and yet so powerful.

We all gonna forget how suicidal moe is?

well to Lisa's creditably for my sister my sitter, when she did call 911 the operator did hang up on her after saying "Simpson? Look, we've already been out there tonight for a sisterectomy, a case of severe butt-rot, & a leprechaun bite! How dumb do you think we are?"

What about the Simpson's episode where ned loses his mind so badly he swears tells everybody off and commits himself

Mother Simpson is more tragic than dark. It shows how a childhood with an absent parent and the other parent being somewhat abusive can cause someone to grow up damaged and having trouble relating to family. Plus the ending is brutally tragic and sad. Watching Homer stare at the sky while that sad music plays is heartbreaking. The ending is even sadder now I have lost one of my parents.

the one where smithers father died was really dark to me

I would say that one tree house of horror Skit when sideshow bob actually kills bart revives him and repeats the thing over again.

Frank Grimes is a dark comedy and satire on how unreistic the Simpson's is. He's a quasi real world person in the Simpson's hence why he can't survive in it.

Sideshow Bob does not have a British accent. He just has a “cultured” American accent

I remember a VERY dark moment from the Simpsons: In the season 2 episode “The Way We Was” Marge’s then-boyfriend Artie Ziff tries to force himself on her in his car after the prom. Luckily, she slaps him out of it. Essentially an attempted date rape. It’s an especially dark moment by today’s standards with the #metoo movement.

S2 E11 One Fish, Two Fish, Blowfish, Blue Fish: Homer believes he has consumed the venom of the blowfish and has only 24 hrs (well, 22. Sorry to keep you waiting so long) to live. He creates a bucket list and attempts to do as many as he can as he and Marge prepare for what they believe to be Homer's last day on earth.

Frank Grimes was actually intended to be the show's attempt at showing on a real person from the real world would react to someone like Homer Simpson.

I pEed oN tHe SeAt, GIve mE a RAIsE

"Homer's Enemy" was a total foreshadowing of Jerkass Homer. It's just that we'd never seen Jerkass Homer before, and it was played for sick laughs in such a shameless and in-your-face fashion that we overlooked it. Next episode we were all glad to see regular Homer back, not knowing that Jerkass Homer would become regular Homer.

The narrator of this video kinda sounds like Milhouse's dad XD

Really?! No mention of the episode where Bart accidentally ruins Christmas by burning down the tree and presents, then blames it on fictitious robbers? That definitely should have been on the list. Also, these episodes aren't really dark. It's more that they are more emotionally poignant than the other stories tend to be.

"I’m peeing on the seat! Give me a raise!" Hank Hill: "You’re fired!" Mr. Burns: "Uh, actually, that is *my* employee." Hank Hill: "Well, I strongly recommend you terminate this unhygienic employee right away!"

The term “dark” gets thrown around A LOT these days...

Rest in peace Frank Grimes, or "grimey" as he liked to be called.

I think Barts Comet is way darker than Lisa listening to the recorded message of Marge singing. The whole town thinks they're going to die (pre movie) and have to kick one person out to fit which is Ned. Once Ned says goodbye to his family he starts singing and everybody feels guilty as they listen to Ned sing.

I was legitimately creeped out by "The Bob Next Door" episode. You know, the one where Sideshow Bob cuts off his and his cellmate's faces and switches them, so that he can escape jail and move next door to Bart.

Me: I'm fine "Still, Lisa practically crying herself to sleep listening to a tape of her mom singing? Pretty dark if you ask me." Me: *sobbinG*

Really surprised to see noone's mentioned The Crepes of Wrath on here (or was it grapes), when bart is tricked into working as a slave in France by a foreign exchange facade

The last thing Ned said to Maude- no footlongs!

"Kids can be so cruel" "We can? Thanks, Mom!"

WHAT ABOUT THE EPISODE WHERE HOMER HAS 24 HOURS TO LIVE AND HE SNEAKS OUT OF BED IN THE MIDDLE OF THE NIGHT, SAYS GOODBYE TO ALL HIS SLEEPING CHILDREN AND THEN SITS ON THE CHAIR IN THE LOUNGE, WAITING TO FUCKING DIE?? WHAT ABOUT THAT ONE?!??! 😭😭

The episode where Bart falls in love with a teenager, then has a daydream where she reaps his heart out of his chest. I was so little I didn't understand that was just a metaphor and was seriously scarred.

Sideshow Bob ... a British accent? What?

There's also that episode where Marge and Homer hid Bart's twin brother in the attic and where Bart discovers him. I just thought it was creepy.

I completely agree with the top two, but it's not because of the darkness of the episodes that stick in my mind. It is more how it makes two characters (one in each, Bart in one, Homer the other) even darker than normal. Yes, Bart has a reputation as a prankster, but in episodes like the one where he screws with Mrs Krabappel's love life, he realises that what he did was wrong. In my sister my sitter, Bart borders on sadistic in the lengths he goes to to make Lisa's babysitting hell. It rewrites his character, negatively in my view, don't like it. The same applies to Homer in Homer's Enemy. Most of the time, even though he may not be very good at his job at the power plant, nor enjoy it, but at least he tries his best for his family, even though he can bungle in his foolishness sometimes. But in Homer's Enemy, he is portrayed as someone who is completely negligent and not caring about anything until Frank Grimes discloses to Homer that they're enemies. The scene where Homer nearly drank a beaker of Sulfuric Acid sums up how negatively I view the episode. Grimes saved Homer from killing himself, and yet all Homer could think of doing was say "...boy would my face have been red," and bursting into an annoying laugh to which Grimes points out how close Homer came to killing himself. To cap it off, when Mr Burns asked about the subsequent damage to the wall, Homer immediately blames Grimes. Grrr! It infuriates me every time I watch that episode! Seriously, it was the only time I wished someone working with Homer would give him a sandwich of the knuckle sort, snap him out of it

I always found the Babysitter Bandit to be the creepiest growing up.

"Fader" is spelled f-a-d-er. Fadder is pronounced fahd-der; as in mudder & fadder (mother & father).

My vote is for the episode Bart gets an F

What about when sideshow bob cuts off someone's face to escape prison

I also think Kamp Krusty had its dark moments, especially when Krusty took a vacation in Wimbledon, leaving the campers to be tormented by Mr. Black and the bullies from being forced to eating pine cones to making Gucci wallets to be exported to Hong Kong. When Bart realized that Barney was acting as Krusty, he sparks an outrage among the campers, who cause destruction at the camp site.

Bart pissed me off in My Sister, My Sitter

Can’t believe that The Boys of Bummer wasn’t on the list. The town makes Bart feel humiliated, taunt him, throw beer cans at him, makes him cry, drives him insane, makes him attempt to commit suicide and even after all that, they still hate him.

The t-shirt cannon salute at Maude's funeral had me literally crying of laughter. :D :D

Sideshow Bob doesn't have a British accent. 🤭 It's Kelsey Grammer doing a theatrical dramatic voice. THAT'S THE JOKE. An auteur actor that worked as a mute sidekick on a kids show. His voice doesn't even sound British.

The best part of Cape Fear is when Lisa calls Moe's Tavern to "knock it off" and he releases a pack of panda bears...

The one where Ned literally has a mental breakdown

The one with Bart struggling and failing to pass his test in school gets me. It's not overly dark, but it's dark to me because it just felt REAL.

Bart of Darkness is a quite dark episode. Also when Bart flashes back to when he was 2 and had the clown bed.

Funny note about the Bart sells his soul episode: the scene where Bart comes to Milhouse to try and buy his soul back is taken from an episode of the horror anthology series "Tales from the Darkside". In the episode two ruthless, rich old men, begin talking about souls and one of them gets the other one to sell him his soul. Weird things start to happen and his health takes a turn so he goes to the other guy to try and get his soul back. The scene has the guy working in his garden (in the Simpsons Milhouse is playing army men in his back yard) the way the scene is presented is a clear call back to that episode.

I think the darkest episodes are whenever Lisa always sacrifices her ideals to fulfill her vanity. Normally she has the moral high ground, but there are moments and episodes when Lisa is absolutely unfair and a terrible human being: Whenever she makes Marge feel like she is nothing, because Marge is "just" a housewife; whenever Lisa is willing to lie/cheat or sabotage others to fulfill her own goals or to keep up a certain standard/idea others have of Lisa; Whenever Lisa is ashamed of her family and lies to fulfill her idea of a perfect family. I also hate the episode where Lisa finally makes a friend and as soon as the little girl shares that she likes to eat meat and only lied about being vegetarian to please Lisa, Lisa shows no empathy at all and leaves her immediately. For me personally, Lisa is the most immoral and dark character because she keeps up a lovely and kind pretence and yet she is dark and twisted on the inside that doesn't really know her limit and has no real empathy for the needs and views of others. I mean most of the episodes she punishes herself for the way she makes others feel, but still, there is something seriously wrong with that kid. (Just remember the episode when Bart and Lisa believe to have killed Martin, Lisa is the first to say: Let's forget about it, why should this ruin my life? and trying to make evidence disappear while Bart is feeling the guilt and wanting to confess.)

I'm glad you included "Marge Not Be Proud." I was very uncomfortable with Marge refusing to buy Bart the video game, then Marge getting so upset with Bart for shoplifting said game that she stops loving him. Instead of Marge recognizing why Bart did wrong and making sure he learns his lesson, she just disconnects from him. It makes it even worse by making Bart responsible for making Marge love him again. The episode is a good example of how Marge isn't much of a better parent than Homer.

It's Mr. Plow, that's my name. That name again is Mr. Plow.

I hope Frank Grimes comes back as a ghost to haunt Homer in a Tree House episode. Then again I think he'll still fail at that too.

I always thought the one where Krusty gets accused of robbing the quick e mart was a bit dark.showing the abject fear of how you know you or someone you know is innocent, yet seemingly impossible act of finding the proof of their innocence.

The episode Where the Earth is being evacuated- Lisa Chooses Marge to board the Ship with them leaving Homer and Bart. Homer and Bart manage to get on a ship but with (i think) failed actors. The Ship is heading towards the sun - Homer gets fed up with their singing and ejects him and Bart into outer space where their heads explode.

Change the channel, Marge.

use a pen sidebob

What about that episode where the school staff starts eating the students and it finishes off with the entire Simpsons family getting turned inside out with Santa's Little Helper dragging Bart away and eating him off screen?

Homer sitting on the bonnet of his car at the end of that episode about his Mother kills me every time.

Flaming Moe's deserves a mention in my opinion.

He mispronounced the 1st episode title.

#7 Had one of my favorite scenes in that episode. When they were clearing out the barracks for Lisa, the Instructor told one of the boys he is no longer the girliest one in the group. And he answers in a whispy voice, "Well, we'll see about that!"

My Sister, My Sitter; "Here's your giant sandwich, swimming in vinegar just how you like it"

British accent - are you sure?

It's not a British accent.

Funny that most of these episodes were in seasons 1 - 10. Because after that, the Simpsons went from a critical cartoon to a slapstick party with bs jokes and more and more having guest star celebrities on it. Season 3-9 are the best simpsons seasons, when they actually did not give a crap and were sometimes even bitter but still brilliant.

Truth-be-told, _Homer's Odyssey_ was actually not that dark of an episode when we look at the core of its ending. Homers personal crusade to make Springfield safe not only for his family but for everyone else as well had earned him praise, acceptance, and a new creed to live his life by, the last obstacle in his way was that of the Springfield Nuclear Power Plant where he originally worked at as a common worker. Knowing that he would never be free of his inner demons until he puts Montgomery Burns in his place for operating an unsafe worksite that was dangerous to everyone. Monty Burns tries to bribe Homer into giving him his old job back, which Homer considers since it would help give back financial stability to his family; but the catch being that Homer would have to quit his role as Mr. Safety and lie to the people of Springfield that the Nuclear Plant was always safe. Homer carefully considers the offer at the cost of his newly-formed moral code as Mr. Safety and was almost prepared to sell out his cause to regain his job, but Homer backed out of the deal and worked Monty Burns into one that will easily benefit the both of them, Homer wouldn't accept the job on the grounds that it would go against his moral code brought about by all of the freetime he now possesses as Mr. Safety, and that it would keep up unless Mr. Burns happens to offer to him a better-paying position in the Nuclear Plant that fits in-line with Homers' ideals: Chief of Security, Homer here felt that the only safe way to earn both his job and not compromise his morals were to become the very role he had aspired to become once he became Mr. Safety: to protect the people of Springfield from all forms of public dangers, and while he was indeed forced to tell his adoring public of himself stepping down as Mr. Safety, he said it in a way that would assure them all that he will still be keeping people safe as the new Chief of Security of the Nuclear Plant.

Sideshow Bob doesn't have a British accent. Have you ever even watched the show?

Very well-worded analysis. The reason The Simpsons occasionally hit something deep inside, esp. on the issue of coping with childhood trauma. BTW, the first 10 seasons are astonishingly brilliant in themes and comic timing. That group of writers was up there with the greatest, including Monty Python and Chaplin.

"Hello Gutter, Hello Fadder" was the show's true jumping-the-shark moment. When Homer contemplates suicide after bowling a perfect game - and to a Doors soundtrack, no less - it was the perfect metaphor for the writers having run out of ideas.

Im peeing on the seat give me a raise this is way to much LMAO

Some dark ones I thought of that haven't been mentioned in the comments yet. "Bart the Fink" when Bart thinks he was responsible for killing Krusty. "Bart the murderer" When he thinks he was responsible for the mobsters killing Skinner and the mobsters implicating Bart as the one responsible. I might come up with more after I think about it a while. Some of the darker ones that I feel are stronger candidates for the top ten list that have already been mentioned in some comments are "The Blunder Years" where Homer as a kid finds a dead body and "The Days of Bummer" where Bart messes up a catch in baseball and everyone hates him.

I don't remember subcribing to this channel.

I did not realise, that these episodes were this dark

The episode where Bart and Lisa have to face each other on opposite hockey teams has some dark moments, especially when the whole crowd is cheering them on to rip the other person apart.

"I'm peeing on the seat, GIVE ME A RAISE!"

You left out the most disturbing moment of "My Sister, my Sitter." After Lisa's worst fear is realized and the entire town sees her dragging her gravely injured brother to the harbor with her baby sister caged in a pet carrier they still hire her to baby-sit for them, dismissing any concerns over her being a demonstrated danger to their children saying "but it's so hard to find a sitter." Yeah, some real great parents in Springfield.

I always thought the Forget Me Shot was one of the darkest. It shows Homer's suicidal tendencies but at the very moment he changes his mind, Patty and Selma attempt to murder him. He doesn't even realise this fact and goes about his day as if nothing happened. I think that's pretty dark

sideshow Bob and the rakes. Still has me in tears today. One of the funniest things I have seen on TV

The real darkness is Homer's mother. The entire character! Just like Frank Grimes her character is so weird and disturbing. Atleast they killed Grimes quickly, but her? I always cringed at her stories, they were sad and no even funny in a twisted way.

Ya know that one when they learn about Depression and They take drugs? That one is really dark lol

Cape Feare would've been unnerving if I wasn't laughing at the untold amount of legendary gags in the episode!

There was one season where Sideshow Bob and Bart become friends, but Bob still gets arrested because of his evil brother. A season later Bob hates Bart again for no given reason.

When Flanders Failed. 'Nuff said.

Does anybody want a burger?

As a kid, I felt really uneasy about the episode where Bart steals the head of the statue of Jebediah Springfield and gradually becomes haunted by guilt. It was portrayed quite viscerally and I guess it made me feel kinda bad about my own little misdemeanors

I knew right away what #1 would be. But, I have to say, I'm glad "Homer's Odyssey" and "Mother Simpson" made the list. The former is my vote for the darkest episode of the entire series, and the latter is one of the top three most emotionally resonant episodes.

Bold of you assume my parents loved me in the first place

I remember when I just turned 8 and I was like, “one day I’ll be older that Bart. I’m 11 now and Bart is 10 (I think)

im pretty sure that everytime an actor leaves or dies, their character in the show gets killed

Surprised his mother passing wasn’t a darker one with finally seeing his mom again. It was pretty sad because she kept ditching him much like Jenny would ditch Forrest.

*DARKEST* ??? Your wayyy too soft if this stuff disturbs you

It sounds like you think anything substantive where characters have to grow is dark.

The Halloween episode where Bart has an evil twin unsettled me. Mainly the part when Homer and Marge realise they made a mistake and put the wrong twin in the attic and so switch them back. Just suddenly being banished by his parents like that scared me as a child.