Top 10 Most Disturbing 'The Simpsons' Moments.

Posted on March 11, 2014 - 12:50pm by The Stickman






Y'know, if you want to...



Heeeeey guys! Welcome back to Non-LEGO Rest of Year! I very much hope you enjoyed last months assortment of LEGO related content, but now we're back to normal random crap, and we're kicking things off with something quite special.

A couple years ago I made a Top 10 pertaining to the worldwide phenomenon that is 'The Simpsons', sure it may not be anywhere near as good as it once was, but you can't deny that it's longevity is hugely impressive, and it has a global brand recognition very few shows can also claim to have. If you haven't already checked the blog out, you can do here, and when you do, you'll notice that it's done rather fact it's done so well it actually managed to break 1 million views late last year just crazy, and a huge honour for me. Naturally, with a viewership like that, there's clearly an interest in Simpsons blogs, and after just under two years, I've finally decided to do a follow-up blog, in this, The Simpsons' 25th year on the air, and this time, we're looking at disturbing moments across the series' run, and given there's been almost 550 episodes? Yeah, there was plenty to choose from.


So, before we kick off, there are a few things I should lay out. Firstly, by "disturbing" moments we're talking scenes which crossed the line in terms of violence, tone, theme or character behavior. I'm excluding the Treehouse of Horror episodes due to their intentional hyperviolent/"scary" nature, and just in case you hadn't worked it out already, this is about Simpsons episodes, not games/films/comics and the such. Still, there's a lot of episodes with disturbing moments in them, so if you feel a big one has been missed out, just accept that with other 500 episodes to paw through, some are bound to be left off, but others may have been considered and omitted intentionally as well.

Finally, something that people seemed to miss with the first one around, this isn't an entirely serious list, although more so than 'Sad Truths', if you feel like I'm missing the point, I'm not. A lot of the placements on this list are both funny and disturbing, but that doesn't relegate the disturbing factor, so maybe this time don't assume I don't understand the show, okay? OKAY! HERE WE GOOoooooooooo...


10. Homer and Marge end up on Death Row.

From : 'The Frying Game', Season 13, Episode 21.

Lets kick things off with a bit of murder/execution, shall we? The series of events that cause this disturbing moment to take place are rather convoluted, in true 'Simpsons episode that starts out in a completely direction to how it ends' fashion. So, Homer buys Marge a koi pond, that happens to have a rare, endangered insect called the 'Screamapillar' residing within it, which the family is then ordered to take care of it, and naturally, Homer ends up crushing it with a book by accident, and is made to partake in Community Service as a Meals on Wheels driver, where he meets Mrs Bellamy, an old widowed lady who takes advantage of Homer as a 'strong man', ending up with both Homer and Marge as her maids before *GASP* being murdered by a mysterious 'man with braces', who vanishes into the night, leaving Marge and Homer as the sole suspects over her death due to their placement in her will. *DEEP BREATH*
Yeah, that's quite a bizarre series of events, but it brings us to the first disturbing moment of the list where Homer and Marge Simpson are sentenced to death by electric chair and after an emotional final night behind bars on Death Row, Homer confesses to being the guilty member, letting Marge free to live her life and watch the children grow up whilst resigning himself to a brutal execution for a crime he didn't even commit. So...yeah...that's pretty disturbing! We have to go through Homer being walked down Death Row, into the execution chamber, where Marge is waiting in the viewing room  to watch him die. There's sad music, there's tears (Wiggum's tear itself is pretty heartwrenching)...Homer is strapped in and the switch is pulled...and then it turns out its all an elaborate FOX reality show starring Carmen Electra ("I KNEW IT" says Homer). So it turns out this was all a hoax and the murder was completely fake, so it's fine...but before that there's no hint that this is all staged, Homer and Marge, hell, not even the Police knew that they weren't actually about to fry Homer in the chair for murder, and neither do the audience. For the entirety of the third act you have no idea it's all fake...I mean, you obviously know Homer won't die, but the rug is only pulled at the last second and before all that? Emotional and very much disturbing stuff, when you think about it.
9. Maude is Killed.

From : 'Alone Again, Natura-Diddily', Season 11, Episode 14.

Moving on from Homer being wrongfully accused of murder to Homer being indirectly responsible for a death, we come to one of the shows few points of continuity, the death of Maude Flanders. As you'll probably know (And plenty of people pointed out on the last blog...), the show is very loose with its continuity, a lot of things happen that have no lasting impact on the show regardless of their scale, and the characters never age, or even change their clothes beyond the occasional winter/summer outfit. Which is why these sort of episodes stand out a lot, Lisa's change of faith and vegaterianism, Apu getting married/having children, Selma adopting...that sorta thing. This episode was the first, and currently only to feature a regular character dying permanently on screen, with two recurring guest star characters' deaths being the only other two of note. Naturally, a character dying on the show is disturbing in its own right, but the cause of death, and the various details that surround it only add to the disturb-o-factor. Maude's death took place at a speedway track, where she was unexpectedly struck by a barrage of t-shirts, which sent her plummeting from the top of the stand to the ground below, in what can only be presumed as a messy, gruesome death.
The rest of the episode deals with the impact of her death on the remaining family members, which whilst often rather funny, is one of the few emotional episodes of the show, but it's the specifics of her death that strike me particularly disturbing. Basically, her death was caused by Homers goading of the speedway t-shirt canon...girls (I'm not sure if this is a thing) into firing six of them at him, which he ducked away from at the last minute, leaving an unsuspecting, happy Maude to suddenly be struck and sent to her death in front of her loved ones, who never got a chance to say goodbye, or say they loved her. Later on its stated that because Homer parked in the Ambulance lane of the circuit, any chance of resuscitation was nixed, meaning Homer is responsible for her death on potentially two counts, something which doesn't seem to bother him nearly as much as it should. Homer has to live with the knowledge that he was the cause of her death, and Ned has to live with the fact that the killer of his wife is essentially living next door without any repercussions for himself. Ned later remarried to Edna Krabapple in another rare continuity moment for the show, but due to the tragic passing of the actress behind the character, Marcia Wallace, some explanation will be needed for her permanent departure...and one can only assume that'll result in further heartbreak for Springfield's goodiest two shoes.
NOTE : After the writing of this placement but before posting, an episode was aired which briefly dealt with the death of Edna in a mid-credits sequence.
8. Bart gets Flashed.

From : 'Beware my Cheating Bart', Season 23, Episode 18.

Taking a break from murder and general death....I present to you, boobies! Now Bart Simpson is no stranger to odd relationships, having previously fled to Utah in an attempt to get married to a pregnant 15 year old girl in order to appease her parents wishes of only having a child in wedlock. That is a weird premise indeed, but due to the innocent, good intentioned reasoning behind it all, doesn't really come across as disturbing so much as just odd. Now this particular underage relationship? This is where things get rather disturbing. Basically, Bart meets Shauna, the 14 year old girlfriend of Jimbo Jones, one of the local bullies, after being forced to escort her around a few places by Jimbo, Shauna thanks Bart by, what else? Flashing her god damn underage tits at him!, who's a 10 year boy gets flashed a pair of tits by a 14 year old girl....who's already in a relationship with another boy....this...that...WHAT!? Shauna is underaged anyway, and Bart is 10...why is flashing tits even a thing to her!? WHY WOULD SHE FLASH THEM TO HIM!? WHAAT!? ARRGGHHH!!!! It gets even worse after that, as both Bart and Shauna end up in a relationship behind Jimbo's Shauna is now cheating on Jimbo....with a 10 year old....who she showed her tits....HRRHGH...Now, although weird, a 14 year old is somewhat likely to have some basic sexual interests these days...MAYBE....but Bart is one of the few people with actual Cootie Insurance, he clearly has no real interest in women why she would flash her tits to him and think that's an okay thing to do I just don't fucking know...and why would the writers think that, for that matter? Nobody seems to bat much of an eyelid at this relationship in the episode beyond the basic 'Ohhnooo, Jimbo found out now he's going to kiilll me!''s just weird and hugely unsettling, and definitely the sign of a show at its lowest. Whilst other disturbing moments on this list make for good episodes or funny moments...this one is just...ergh...
7. Frank Grimes goes insane and kills himself.

From : 'Homer's Enemy', Season 8, Episode 23.

Probably the best 'disturbing' moment of the list, from one of my favourite Simpsons episodes, I simply couldn't leave this one off even if it makes me's just so god damn dark and  gets more and more disturbing the more you think about it. In this episode, Homer meets his first self-titled enemy in the form of one Frank 'Grimey' Grimes, a hard lucked individual who's struggled in pain all his life in order to succeed in life, and he finally thinks he has when he gets hired at the Springfield Nuclear Power Pant due to Mr Burns' fleeting respect, but from the moment he meets his fellow 7G colleague, Homer Simpson, you just know things will only end badly for this guy, which is rather sad because...for all intensive purposes, he's not actually a bad guy, just someone who's been pushed and provoked his entire life and refuses to let someone spoil this big break for him. After first attempting to tolerate Homer's buffoonery, he quickly decides to instead pit himself against him, and attempt to prove to the entire Plant, who all seem to just accept or applaud Homer's behavior, that he's an idiot. Inevitably, Frank's attempts fail, and things come to a head at...where else? A childrens model Nuclear Plant contest, which Grimes tricks Homer into entering, who then ends up winning despite not being a child...causing Grimey to finally snap and after a manic rush across the Plant, ends up taking his own life by grabbing exposed electric cables without safety gloves ("BECAUSE I'M HOMER SIMP-*Sizzle*"). Basically, Homer has once again caused the death of another Springfieldien resident due to his own stupidity, and what a awfully dark death at that! Whilst Maudes death was a tragic accident, Frank Grimes, for all intensive purposes commit suicide in front of everyone after having a mental breakdown because of Homer Simpson. A man who struggled to survive his entire life against cruel odds ends up taking his own life because of one mans incompetency. To make matters even worse, at his funeral, his loathed nickname 'Grimey' is engraved on his tombstone, and Homer ends up disrupting the memorial by falling asleep, causing everyone to laugh. This man, who tragically died at (literally) his own hands meant nothing to these people despite trying so hard to impress them, and that's rather depressing...and very disturbing, in one of the shows blackest comedy moments.
6. Moe hangs himself.

From : 'Whiskey Business', Season 24, Episode 19.

The most recent entry on this list, airing for the first time last May, no less, is also one of the few entries not actually meant to be funny on some level. Moe Szyslak's penchant for suicide is a long running 'gag' for the show, his attempts never really shown on screen but instead the aftermath being played for laughs, for instance suing a rope company for his noose breaking ("They gave me a new rope!"), or his attempts at plummeting to the earth being scuppered by hot air balloons, for instance. But last year things finally came to a head and for the first time we see Moe actually attempt to kill himself, tying a noose to a roof beam, slipping it around his neck and (although technically by accident, though the intention was still there) kicking the chair away. The only reason he doesn't die is because the roof beam breaks under his weight, but watching a beloved main character from the show visibly attempting to end his own life is hugely disturbing, and the rest of the episode deals with his friends trying to show him that life is worth living, and give him some hope/self confidence. The majority of the episode, bar the ending is pretty standard 'new Simpsons' fair, but the opening is particularly heartbreaking and disturbing both because of the general theme of suicide/despression (A theme which got this episode pushed past the watershed here in the UK), and also the specifics of his attempt. Basically, when Moe goes into his backroom to end it all, before doing it he turns back to the bar, where Homer and the other barflies are acting their usual selves...and he actually cries out to them for help, screaming out for one last chance at life, but they completely ignore him, and he ends up trying to go ahead with it, and the only reason they ever even notice is because the beam breaks and makes a loud noise. During this sequence it's clear that this isn't the first time Moe has ended up in the backroom with a noose hanging before that begs the question of how many times has he actually done it....and worse than that, how many times has he screamed out for help from his supposed friends, only to be ignored? That's...kinda devastating, to be honest...sorry! Also, this is yet another near-death caused in some way by Homer, in case you're not counting at home, that's 3 possible deaths caused in some way by Homer it too late to change my 'Sad Truths' list?
5. Homer frames Marge for a DUI.

From : 'Co-Dependents' Day', Season 15, Episode 15.

This is probably the most oddball inclusion of this list, but I do think it deserves its placement, even if the show kinda brushes over the implications of what happens in this particular moment. This episode is known more for its lead in plot than the 'main story', the lead in being Bart and Lisa basically tracking down George Lucas in California to complain about how much the Star Wars prequel's sucked, which means it includes a lot of nerdy satire which people always lap up when it comes from the show. What I'm looking at is instead the main thread which involves Homer and Marge becoming drinking buddies, which allows them to have the most fun they've had in their marriage for a long time. Of course, things don't end up well for them, after they both get drunk at Oktoberfest and Homer crashes the car and puts a passed out drunk Marge in the drivers seat to frame her for the DUI incident in order to save his Drivers License...WHAT!? Due to her inebriated state, even Marge believes she drove under the influence and gets herself sent to rehab, dealing with the guilt and shame of something she didn't even do, as well as all the legal ramifications being found guilty of DUI brings. Let me sum that up for you, Homer frames Marge for a crime she didn't commit, and has even her believe she did it. That's awful! That goes beyond the simple, good natured idiocy of Homer actions past and delves straight into dark, manipulative behavior that makes it hard to look at the character the same way again. It's disturbing to think that not only would Homer do such a thing in an attempt to save his own skin, but also that Marge would simply forgive him for it! How could you trust someone after they did something like that? It's leaves her in what's now a borderline abusive relationship! I chalk all of this down to weak writing, but in the 'canon' of the show this is a really dark, disturbing moment that brings into question just how good natured Homer actually is, for all his stupidity, and just why Marge continues to stick with him.
4. Sideshow Bob's first murder attempt on Bart.

From : 'Cape Feare', Season 5, Episode 2.

Another classic, surprisingly dark Simpsons episode makes the list for the very simple notion of a psychopath being on the loose with nothing but murderous revenge on his mind for one of the Simpsons family. Although very much played for laughs throughout the episode, that doesn't change the fact that, when you really think about it, this is one messed up, disturbing episode seemingly more suited for a Treehouse of Horror segment than a proper 'canon' storyline, especially given its actually a 20 minute send-up of an actual horror movie, again something usually left for the series' legendary Halloween specials. Sideshow Bob was a recurring character for many years before turning his eye to murdering Bart, the child who'd foiled his previous schemes which included framing Krusty the Clown and staging the death of Selma Bouvier. Now, clearly he'd had enough and only one scheme was on his mind, the brutal murder of a 10 year old boy....if you don't think that's disturbing...WELL...OKAY THEN. The Simpson family even have to go into witness protection to escape Bob after he's released from prison early due to good behavior and poor treatment, and goes on to haunt Bart with letters written in blood and grim messages on the radio, none of which can be tracked back to him (Despite his blood being used? Hmm...) and therefore leaves them with no choice but to flee Springfield. Y'know, nothing says comedy gold quite like a insane murderer chasing a defenseless family out of their home with violent, graphic threats, MM MMM. He then ties up the rest of the family, sets their new boathome out into the middle of nowhere and comes for Bart in his sleep with a I even need to say anything about this? The whole episode is gold, and full of laughs, but when you strip those away and look at the basic premise? That's some dark, disturbing shit for a comedy series! Sideshow Bob has gone on to become a regular villain who's mission is generally to put Barts life in jeopardy, and whilst those turned out both good and bad, none of them match the initial shock factor of the first Sideshow Bob vs Bart encounter.
3. Bart and Lisa cover up the murder of Martin Prince.

From : 'Dial 'N' for Nerder', Season 19, Episode 14.

Probably the least known episode on the list due to not being all that new, but at the same time not being all that old, 'Dial N for Nerder' is definitely one of the strangest, darkest episodes of recent Simpson memory, and deals with two children attempting to cover up the supposed death of a friend and all the psychological implications of doing so. The sequences that kicks the main thread of this episode into motion involves Martin Prince, everyone's favourite dorky punching bag seemingly plummeting to his death off the edge of a cliff due to a prank by Bart going horribly wrong. Given Martin is really nothing more than a side character these days (Having played more of a role in the first couple of seasons), it doesn't really take that much to believe he could be killed off in an episode with little continuity impact, and the show doesn't really reveal he's alive until the last minute, although....I don't think many people would think the show would actually have Bart and Lisa be responsible for the actual death of a friend and then cover it up, still, the episode plays it very much that way, having everything from a memorial service at the school, to a puma being found with shreds of Martin's clothes in his mouth where the body would have landed. So, Bart and Lisa pretty much know they were responsible, but don't want to go to jail (Or juvie, or whatever) so fake ignorance over the whole thing, which in itself is pretty messed 8 year girl and a 10 year old boy kill someone and cover it up...hmm. Things get tricky when Nelson Muntz goes full on Columbo and begins to slowly unravel their cover-up, which leads to a dramatic showdown in...WHERE ELSE? A butterfly tent. Lisa is the disturbing factor of this cover up, she seems to be willing to go to such extreme lengths to fake her innocence and manipulates her less intelligent brother into going along with her wishes....this is an 8 year old girl tricking her older brother into covering up a murder so she doesn't become an accessory and lose her future...EXCUSE ME!? And then when Nelson finds out, she attempts to flirt him into looking the other way....AGH...AGHHHH...but of course, in the end it turns out Martin is alive and well, no harm done, and life goes back to normal for the four children...but...really? This is a messed up episode which reveals a chillingly dark streak behind what many consider the most normal of the Simpson family, Lisa. And I didn't even mention that at one point its briefly suggested that Bart is about to commit suicide....y'know, ending his life due to the crippling guilt of taking another? MMM, COMEDY.
2. Homer gets raped by a Panda.

From : 'Homer vs. Dignity', Season 12, Episode 5.

As we get to the penultimate entry on this list, we reach an infamously disturbing moment for the show, one which many consider the tipping point for the show in terms of quality, you've heard of 'Nuking the Fridge' and 'Jumping the Shark', now meet 'Raping the Panda'. Although I was still very much consistently enjoying The Simpsons well up to around Season 18, and I do actually like this episode, I must admit this scene was a bit too much for a show considered (Wrongly) by many to be for family,  or even just kids. Basically, this episode is all about Homer trying to earn more money to pay for the families numerous steep bills and cash flow problems by becoming Mr Burns' "Executive in Charge of Recreation" or 'Prank Monkey', which leads him to do all sorts of anti-social, humiliating things in order to get a boost in revenue, including dressing up as a baby, throwing pudding cups at Lenny and, yes, dressing up as a Panda...which is where we get to the controversial scene in question. Mr Burns makes Homer dress up as a female Panda and then tells the Zoo he's donating her to them, which is a big draw for tourists and the reveal gets a big crowd of Springfieldiens all excited to see the new arrival, who's actually Homer in a realistic (in a cartoony way) Panda costume. That's when they introduce the other Panda already at the Zoo, who's a male, and very much interested in attempting species repopulation, if you catch my drift....what? You don't? He wants to fuck Homer because he thinks he's a female Panda. And then Homer ends up with his ass presented to 'Ping-Ping', who then drags him off kicking and screaming to mate with as the curtains go down and people start to cheer. The next shot is Homer being spooned by a sleeping male Panda, post-sexy times. WHAT. THE. FUCK. Homer Simpson, dressed as a girl Panda, is violently dragged off and raped by a male Panda as an audience of young families cheer them on.......why am I not surprised people see this as the downfall of the show? It's played off as a joke, and, at least for me, being such a sick and twisted individual, I did find it funny...but that's a messed up scenario for a cartoon which isn't technically an adult show to deal with....and it's never brought up again, that's that, there's no real point to this scene beyond the "LOL HOMER GOT RAPED BY A PANDA" gag...which is rather disturbing, really.
1. Homer dreams about murdering Grandpa.

From : 'Papa Don't Leach', Season 19, Episode 16.

And here we are, at the number 1 Most Disturbing moment from The Simpsons, in an otherwise uninteresting, mediocre and forgettable episode lies the most unpleasant, darkest moment in the shows 25 year history. In the opening sequence to 'Papa Don't Leach', Homer murders an already wounded Grandpa by smothering him to death...except he doesn't...because it was all a dream...Homer has a graphic dream about brutally murdering his father, in probably the shows most pointless, uncomfortable sequence and what I consider to be the true point of no return for the series. So, for more detail/context, the episode opens up with this sequence, not explaining it to be a dream until the bit finishes, it starts with Homer and Grandpa in a car together at night arguing over the radio and various other things, y'know...nothing too big, and then they end up swerving off the edge of the cliff-side road they were driving on, crashing and spinning down to the bottom, both of them physically in pain and naturally tattered up by the ordeal...okay...a little strange, but I guess this is the set up for the episode? Homer gets up and starts to dial 911 to call an ambulance for his father, but when Grandpa starts to tell him about how he'll have to visit him in the hospital and care for him afterwards (Implying he's suffered a severe injury...y'know, comedy gold yet again), he instead puts his phone away, turns around, places his hands over Grandpa's nose and mouth and chokes him to death........I'm not fucking kidding! He actually murders his own father in graphic detail, we watch him struggle, and then fall silent and still....and then it turns out this was all a dream of Homers (Who is smiling during it) and the episode continues on without any further reference to it. Why? What led the makers of this show to include the sequence? Not only does it have absolutely zero bearing on the episode, or the show whatsoever, it's not even funny, it's just...disgusting, and unsettling to open the episode like this, without any hint that this is a dream sequence, and then to imply that Homer has happy dreams which involve murdering his father in brutal fashion? Apparently, it's a homage to one sequence from one episode of The many people are going to get that? And even then, it's not even a joke, it's just a straight up send off of the scene! For people who get it, it'll just be a pointless homage to a show that'd been over for a year by the time this episode aired, and for those who don't get it, it's just a disturbing, pointless sequence that leaves a bitter aftertaste for the rest of the episode, which has no relevance to the sequence whatsoever. The Simpsons have a proud history of legendary movie/TV parodies, but this is a dark stain on that tradition, an obscure reference, and a genuinely unpleasant moment for the series, and easily the most disturbing 'The Simpsons' moment of all time.
And there you have it! My Top 10 Most Disturbing Moments from 'The Simpsons'! What did you think? Got a moment you feel should have been on the list? Let me know in the comments below! And until next time, Later Gators!

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