The World's Strangest and Most Unsettling Simpsons Endings

You know, I have to apologise. I realise there were two separate occasions where I promised something for 2017 which I subsequently never delivered - that is, a retrospective looking at Al Jean and Mike Reiss's short-lived attempt at their own primetime animated sitcom, The Critic. All I can say is that after going through all eleven episodes of Family Dog with a fine-tooth comb, I haven't quite been able to steel myself up for another full-blown, in-depth, episode-by-episode analysis of that same nature, particularly for a series with about twice as many episodes. While I still intend to deliver the promised retrospective *eventually*, I can sum up my overall opinion on The Critic right now in a nutshell - an underrated series with plenty of sharply-written gags that's hampered by one fatal shortcoming (and no, it's not that Jay Sherman himself is "too flawed to be likeable", in the words of Warren Martyn and Adrian Wood, authors of I Can't Believe It's An Unofficial Simpsons Guide. I'll be gunning for you later, Martyn and Wood, so sit tight). Namely, that its sense of story construction is really deficient. The Critic is a funny series, but also one with a penchant for spinning a lot of absurdist humour while essentially going nowhere. Episodes don't so much end as fizzle; whatever problems are established tend to be resolved abruptly or glibly, or not at all. (I believe that Season 2 did attempt to address these issues, to a point, but I should save that for my analysis proper.) Jean and Reiss had a huge deal of comic flair but narrative was blatantly not their strong point - it hasn't escaped my attention that it was during their tenure as showrunners for The Simpsons (Seasons 3-4) that the series transitioned from being a more grounded, drama-orientated animated sitcom into a wilder and wackier cartoon (whether you like the change or loathe it).

I've no doubt that a big reason why The Simpsons succeeded where The Critic fell is because it was simply a warmer show. The Simpsons may be a dysfunctional family but they are capable of weathering their difficulties as a family unit; no matter how ugly things get, those familial bonds will always endure. Jay does have a handful of positive relationships, enough to keep his life from seeming ridiculously forlorn, but one of the series' major running gags has to do with how much people actively scorn him. It doesn't exactly make for feel-good television. But what really gives The Simpsons (classic era, anyway) the edge over The Critic is that, even once the show had crossed over into more overtly cartoonish territory, it retained the sense that it was fundamentally in it to tell its audience a story. Episodes genuinely seemed to have been conceived with an interest in exploring how characters would cope with and work through certain problems, as opposed to just what scenarios could be used as a springboard for a barrage of gags. Obviously this too is something that would whittle away with time, although it was not an entirely linear process. I believe that Season 7, when Bill Oakley and Josh Weinstein came on as showrunners, did attempt to return The Simpsons to being a more drama-orientated series than it had been post-Jean and Reiss.

That's not to say that every classic era Simpsons ending, even those without Jean and Reiss's fingerprints, came about as a result of tight, lucid or meticulous plotting. There are a handful of episodes that bow out on real head-scratchers, either because the writers had written themselves into a corner and needed to bail out or, for whatever reason, they decided to throw a weird, last minute curve at the viewer. When The Simpsons gets strange, it's bound to get downright unsettling. And when things get unsettling, naturally that's going to inspire a weird kind of affection in yours truly. Here's where we celebrate that smattering of episodes that chose to close up shop by leaving the viewer in a lingering, uneasy statement of bewilderment, feebly questioning just what the hell they had seen. First, though, a disclaimer: the reason why this list is mainly concerned with the classic era episodes (ie: most of the 1990s stuff), because that's mostly what I'm familiar with personally. I ceased to watch the show religiously at around Season 14 (possibly sooner) and nowadays I usually only catch newer episodes by chance or if something about an episode happens to have piqued my interest. I acknowledge that there are some pretty significant gaps in my knowledge of the later seasons and that as a result this may not be the most comprehensive list on the subject. If there's any other particularly strange or confusing closer that you believe conforms to any of the patterns discussed on here, then by all means feel free to let me know.

The Front (Season 4)

This example is slightly different from the rest of the list, in that it has nothing to do with how the story ends per se. The episode, which sees Bart and Lisa writing for Itchy & Scratchy under a familiar pen name and Homer attending an adult education course, concludes in a fairly conventional fashion (with Homer getting a plunger stuck on his head). Then the episode fades out and we get a random thirty-second short starring Ned Flanders (much of which is taken up by a catchy title sequence). What was THAT all about?

As is often the case with the series' more curious ventures, the actual explanation turns out to be entirely banal. "The Adventures of Ned Flanders" came about purely because "The Front" was running short and the production team desperately needed a way to extend it. Hence, they threw together this bizarre bit of anti-humour with Ned and his two sons, nothing of which has any relation to the episode proper. My immediate thoughts on viewing "The Front" were, "Are there going to be more of these things?" After all, giving the short its own title sequence, and its own title ("Love That God") does convey the impression that this is all part of a series. But no, that in itself is part of the joke. It's an awful lot of hoopla over something we'll never see again. As per the DVD commentary, it was conceived as a sort of tribute to Archie Comics, who would intermittently pad out spare pages with similarly arbitrary material.

"The Adventures of Ned Flanders" was a one-off event, although it did go on to inspire the Season 7 episode "22 Short Films About Springfield" (an episode comprised of nothing but this kind of thing) so it has a legacy of sorts. As it is, it's a triumph of the non-sequitur, and also an intriguing glimpse into The Land of What Might Have Been. Let's be honest, if Ned Flanders really was given his own ongoing series of thirty-second shorts, it's hard to imagine it consisting of little more than a variation on this exact same gag - namely, that the Flanders clan are just too innocent and wholesome to be capable of delivering a punchline with any actual punch to it. But having just spent twenty-odd minutes inside the malfunctional Simpsons household there is something downright endearing about emerging through the sunny innocuousness of the Flanders' world. Perhaps an occasional return to "The Adventures of Ned Flanders" wouldn't have been at all out of order; it seems a shame that we'll never get to find out.

Treehouse of Horror IV/Treehouse of Horror V (Season 5/6)

Initially I wanted to avoid putting any Treehouse of Horror endings on here because, by definition, those things are supposed to be weird and unsettling. It's Halloween and, as per annual tradition, the Simpsons writers are given the opportunity to let down their hair, indulge in some seriously far-out plotting, and, if they're lucky, experience the thrill of slaughtering a bunch of characters who'd be otherwise untouchable in a regular episode (no continuity, no problem). I can only imagine what an enormously cathartic experience it must be. "Treehouse of Horror IV" and "V" go a step further than their brethren, in that they're strange episodes even by ToH standards. Whereas most ToH episodes tend to be a bit dark, spooky and fantastical, IV and V take twists into the genuinely nightmarish (personally, I was disturbed by the moment in "Terror at 5 1/2 Feet" where Bart and the gremlin first make eye contact and the latter smiles, as if he wants to be friends with Bart, then casually rips into the side of the bus). It's only fitting that they each should bow out with some of the most hair-raisingly non-sequitur endings in Simpsons history.  IV ends with a vampire-fied Simpson clan all poised to devour Lisa, only to hang back and wish the viewer a happy Halloween, before humming "Hark The Herald Angels Sing" a la A Charlie Brown Christmas. V ends with Bart waking up and discovering that the entire "Nightmare Cafeteria" segment was really a bad dream, only for he and his family to be turned inside out by a mysterious green fog...whereupon they start singing a corrupted version of "One" from The Chorus Line. Oh, and Santa's Little Helper goes all Jeffrey Dahmer on Bart. It's one hell of a gruesome closer.

I'm toying between which of the two endings I find more unsettling, and find myself, oddly, leaning more toward IV. It's not that I'm immune to the graphic nastiness of that V ending, or the freaky incongruousness of seeing the family perform an upbeat number whilst kicking blood all over the place (although the Chorus Line parody itself isn't quite so random - if you're an attentive viewer, then you might have recognised it as a callback to the ending of "The Shinning", when the family were forced to endure a rendition of "One"from the Tony Awards whilst freezing to death in the snow). But that Charlie Brown homage is just weird, and has no business being in a Halloween-themed cartoon. That's precisely what makes it so disturbing. That, and Santa's Little Helper's attempt to replicate Snoopy's signature dancing style, which has the effect of making it look as if he's demonically possessed. Too creepy for words, you sordid mutt.

Sideshow Bob's Last Gleaming - The Sky 1 Edit (Season 7)

This one's an esoteric choice, as it was only confusing if the sole version of this episode you had access to was the heavily truncated one aired in the UK by Sky 1 in the late 1990s. I include it here because it was the source of great personal perturbation to myself back in the day, and also because I couldn't resist the opportunity to plug the extensive coverage I wrote of this edit back in 2016. Check it out - you won't find a more loving or dedicated analysis of the subject if you tried. To sum it up, Sky 1 removed an all-important moment in which Bob is distressed by the sounds of a lowbrow sitcom featuring Vanessa Redgrave because the term "haul ass" could be heard. Unfortunately, the episode's closing gag is a direct call-back to that very moment, meaning that, in the Sky 1 edit, what we got was an entirely a random ending where Abe Simpson shows up on a bike for no reason (oh, and his own "haul ass" remark was also cut). Chattering cyclops indeed.

The Day The Violence Died (Season 7)

And here we reach the ending that pretty much inspired this whole entry. "The Day The Violence Died" is easily one of the strangest episodes of The Simpsons, period. I know that a lot of fans don't like this episode purely because of a scene where Homer gives Bart 750 dollars with no questions asked (we're told in the DVD commentary that Matt Groening took tremendous issue with this moment too), but then the episode as a whole seems to hinge on a number of bizarre twists and implausibilities. It's also an episode which shifts dramatically in its focus midway through, starting out as a bog-standard Simpsons adventure before becoming something altogether more meta and self-critical. Initially, it's about Bart's chance encounter with Chester J. Lampwick (voice of Kirk Douglas), a destitute ex-cartoonist who transpires to be the uncredited creator of Itchy the mouse, and his subsequent attempts to bring Lampwick his rightful recognition. This is resolved halfway through the episode, but from its very solution springs a brand new problem - the Itchy & Scratchy studios are left bankrupt after being ordered to pay a substantial cash settlement to Lampwick, spurring Bart and Lisa off on a new mission to save Itchy & Scratchy. They spend much of the third act spinning their wheels and running into total dead ends (Homer isn't coughing up any more dough, and Lampwick, who we would expect to play a major role in the episode's resolution, withdraws completely, flat-out stating that he doesn't care how things turn out from here). Finally, Bart and Lisa come up with a solution, only to discover that two other young Springfieldians, Lester and Eliza, have already cracked the problem and put Itchy & Scratchy back in business. Naturally, Lester and Eliza are doppelgangers of Bart and Lisa, to the extent that they have the characters' original designs from The Tracey Ullman Show interstitials. The actual Bart and Lisa wind up feeling a little dejected; Marge suggests that they should just be happy that their favourite cartoon is back in production, but neither of them can shake the feeling that there is something not quite right in their universe. The episode ends with Lester skateboarding past the Simpsons' house and glaring at Bart, while ominous music plays and Bart follows his gaze uneasily through the window. Dear god, does that ending give me the creeps. Was anyone else reminded of that Twilight Zone episode about the woman at the bus station?

This is another ending that I overthought way too much as a chlid. I noted that Lester and Eliza were really the Tracey Ullman versions of Bart and Lisa and wondered if it had something to do with Roger Meyers Jr's line about everything in animation being plagiarised from something else. Hence, the significance of Bart and Lisa getting upstaged by rip-offs of themselves...or is it the other way around? Lester and Eliza have the characters' original designs, after all, so perhaps, much like Chester J. Lampwick, they're simply looking to hone in on what's rightfully theirs. Perhaps they're even the primitive Bart and Lisa who, through some kind of freaky interference with the space-time continuum, have come for revenge on their future selves for abandoning everything they formerly stood for; that is, raw and offbeat slices of life from a contemporary suburban family?

On the DVD commentary, Bill Oakley admits that a lot of viewers were baffled by the ending and explains that it was born from the frustration of not knowing how to finish the episode. This led to the line of thinking that, "Well, why should it be up to Bart and Lisa to solve all of Springfield's problems anyway? What if some other kids elsewhere in town just happened to beat them to it this time?" Hence, we got Lester and Eliza. The ending is foreshadowed in a scene where Marge reminds Bart and Lisa of all the amazing feats they've accomplished as a team (incidentally, Marge is wrong when she tells them they've foiled Sideshow Bob on five separate occasions, as on at least two of those occasions Bart defeated Bob single-handedly). Ostensibly, Marge is giving her kids the extra confidence boost they need to pull through and save the day, but what she's actually doing, unbeknownst to herself, is underlining the sheer improbability that it should ever have fallen to a couple of children to redress so many issues of this magnitude. I've spoken previously about Season 8 being the point where the series became very self-aware and even a little uneasy about its juggernaut status, but in many respects this episode acts as a precursor to all of that, in that it's really about the show taking a good hard look at itself and shaking its head, if a little facetiously. Regardless, our sympathies remain with Bart and Lisa - we recognise that their final discontent doesn't stem from petty jealousy of Lester and Eliza so much as the chilling realisation that they were little more than irrelevant extras in someone else's narrative. It's a disturbance far more offsetting than the plight of a one-shot character like Lampwick or a tertiary character like Roger Meyers Jr.

What Oakley doesn't explain in the commentary is if there's any particular significance to Lester and Eliza having Bart and Lisa's old character designs from The Tracey Ullman Show...so far as I can tell, this is simply an in-joke for the long-term fans. However, I'm inclined to think that my old analysis about Lester and Eliza being the avenging Ghosts of Simpsons Past was on the money all along. When Bart and Lester lock eyes at the end of the episode, the true horror comes in being confronted by the self, in all its glaring, accusatory ugliness. Their uneasy stand-off signifies the gulf between the series past and present, the latter having to sheepishly admit that it's become a shadow of everything it once set out to be. The Simpson family that Lester and Eliza appear on behalf of may be long gone, but "The Day The Violence Died" suggests that the series continues to be haunted by memories of its humbler origins, a malaise underscored by an ending in which Lester roams openly around Bart's territory while Bart is confined eerily to the sidelines.

Speaking of Ms Ullman, the scariest thing The Simpsons have ever done is certainly NOT a segment from a Treehouse of Horror, but the very first of the Tracey Ullman Show shorts, "Good Night". Let's earmark that one, and the ways in which it continues to haunt my deepest, darkest nightmares, for a full discussion in itself.

Bart Star (Season 9)

Jump ahead to Season 9, the point in which the series was visibly starting to transition from the "classic era" into the pale shadow of its former self that Lester clearly saw coming. Beyond "The Principal and the Pauper" (which was a holdover from Season 8), this season found the series in a less self-depreciating mood, having moved past its anxieties and silenced those inner voices of unsolicited criticism - Frank Grimes was in his grave, Sergeant Skinner and Roy had been banished into oblivion and Lester and Eliza hadn't been seen for quite some time. While we didn't get the magic powers or long lost triplets promised by Troy McClure, there was a definite sense of the show screaming "To heck with it!" and just doing whatever it wanted, and stranger, less conclusive endings were an occasional consequence. Like this one in which Bart is last seen being dragged away in handcuffs for a crime he didn't commit, while guest star Joe Namath casually attempts to impart that the real purpose of the episode was to provide an extended PSA on the dangers of vapor lock. Whut?

(Actually, it's made all the more sinister by that startled facial expression Namath pulls at the very last second, as if it's just dawned on him that there's something very wrong with this particular closer.)

Das Bus (Season 9)

"...and eventually they were rescued by...oh, let's say Moe."

Do I really need to elaborate on this one?

We're on the Road to D'oh-where (Season 17)

I mentioned that I ceased to be a regular Simpsons viewer at around Season 14, but I have seen a smattering of later episodes here and there, among them this oddity from Season 17 (actually, I've got the whole of Season 17 on disc; it was Sideshow Bob themed, so I couldn't possibly say no). The clue here is in the title, which does more than just wink at Talking Heads - it's an episode that drives itself to a total narrative dead-end and then just...stops, with no attempt to pull out any of the wily tactics observed elsewhere in this list. The result is not only unsettling, but also a little melancholic.

For the most part, I think that this episode is watchable. The main story, which involves Bart and Homer taking a road trip so that the former can go to reform school and the latter to Las Vegas, is fairly entertaining, although the subplot, which has Marge becoming a low-level drug dealer, is pretty lame (there's also a rather tasteless suicidal Moe joke, and I'm not sure, but I think that Homer may have killed a horse). Both storylines drag out to the point where it gets a little too late to establish a reasonable means of taking the family out of their respective jams, and it becomes apparent that the only option would be a hasty deus ex machina. But nope, that doesn't happen either. Instead, Lisa arrives home from school to find Maggie unattended. She checks the answering machine and finds two messages, one from Marge, who's been busted for her backyard pharmacy and urgently needs Homer to bring the bail money, and the other from Homer, stating that he lost Bart in Las Vegas and is being held in a prison in Nevada after picking a fight with a pit-boss. Lisa turns to Maggie and admits that she always knew it would come down to just the two of them eventually. She promises to look for work in the morning and we cut to the end-credits.

It's a grim scenario. Homer and Marge are both left incarcerated, each unaware that help from the other will not be coming, and Bart appears to have fallen off the face of the planet, while Lisa and Maggie are left to fend for themselves back at Evergreen Terrace. What's disturbing, yet also strangely poetic about this turn of events is the manner in which the episode plays it off as little more than the logical conclusion to the entire Simpsons narrative. Lisa reacts not with horror, but with heavy resignation, apparently all-too aware that her family crossed the point of no return ages ago and all she can do now is embrace self-sufficiency and find her own way forward. By now, viewers should be canny enough to know that the family will be rescued from their predicament by virtue of the great reset button that will be activated in time for the next episode - but honestly, they could have made this the series finale and I would have bought it. Admittedly, that last lingering image of Maggie sitting alone in her highchair would made for one heck of a downbeat and low-key means of finishing a series this ground-breaking and influential, but perhaps that's entirely befitting for a show that always opted to walk a little on the wild side.

Bonus Round: All of Season 5

I noted at the start of this entry that it was during Jean and Reiss's tenure as showrunners that The Simpsons transitioned from being a more down-to-earth animated sitcom to something altogether fruitier. And yet, much to my surprise, when I was scanning through the series' extensive catalogue in preparation for this list, I realised that the highest number of endings consisting of surreal sight gags and meta observations actually came from Season 5, when David Mirkin took over as showrunner. I am somewhat exaggerating when I say this applies to all of Season 5, but nevertheless, this was definitely the season of the bizarro final punchline. Admittedly, a good chunk of these are just very intricate movie parodies which may be lost on you if you haven't seen the films in question (Boy-Scoutz 'n The Hood, Homer The Vigilante, Deep Space Homer and Lady Bouvier's Lover all spring to mind), but there are also a fair number demonstrating just how confident yet also amusedly fixated with its own limitations the series had become by this stage. Here are the examples that especially stick out:

• Rosebud - This ending's based on Planet of The Apes (coming off of an episode which serves as an extensive spoof of Citizen Kane - hence the title), although I don't think you need to be familiar with the source to appreciate the joke it's going for (that Burns is destined to keep on repeating this pattern with Bobo for centuries to come). It closes the episode on an awfully sinister note, one which has the viewer pondering whether the notion of Burns still being around in the distant future (albeit sans the better part of his original body) and spreading his trademark villainy across the remains of a post-apocalyptic Earth should be taken as more of a comfort or a bone-chiller. At least there's reassurance in the confirmation that Smithers is still at his side, albeit in a heavily modified form as his robotic running dog.
• The Last Temptation of Homer - Maybe it's just me, but as a kid I was always freaked out by that final gag in which Homer is hounded by the leering bellhop and then punches his lights out. It's not the most left-of-field closer, but there is something oddly disconcerting about it.
• $pringfield - This one's a bit troubling for the two story threads it just kind of leaves hanging (actually three if you recall that Smithers is last seen being held at gunpoint by a deranged, Howard Hughes-channeling Mr Burns). Lisa never gets the halfway presentable Florida costume she was promised by Marge for her school pageant and is last seen enduring a dubious award presentation at said pageant. More problematic is the handling of Marge's gambling addiction, which is glib and by god the episode knows it. After finally admitting that she has a problem, Marge ponders if she should get some professional help, to which Homer responds, "No, that's too expensive, just don't do it any more." This ending lampoons the writer's quandary of having to establish a problem and resolve it within the space of 22 minutes, the risk being that you wind up with a rather facile representation of how the world works - which is an issue when you're dealing with something as complex and potentially life-destroying as addiction. Homer and Marge kiss at the end, so we get some superficial signal that all is right in the world again, but...it's not. As Homer keeps rubbing in Marge's face, "YOU have a gambling problem!" (Incidentally, this may well be the Simpsons episode to most closely resemble an episode of The Critic, in that it's more about gags and random sketches than a particularly strong plot. They are great gags, sure, but this is such a weird episode tonally.)
• Bart Gets Famous - A highly meta episode about the hollowness of Bart's initial status as a 1990s icon. It's only fitting that it should end on a meta joke in which an assortment of Simpsons characters spout their respective catchphrases for no other reason, it seems, than to remind Lisa how painfully out of her element she is within this town. ("If anyone wants me I'll be in my room" is actually a pretty apt summarisation of her eternal predicament.)
• Homer and Apu - "There's still time; let's hug him again." The Simpson family are apparently now aware that everything must happen in 22 minutes, nothing more and nothing less. Otherwise you wind up with a non-sequitur Flanders skit in the tail.
• Homer Loves Flanders - In some respects, this episode feels like to a precursor to "The Day The Violence Died", in that it deals with the younger Simpsons being all-too aware of how their universe functions and recognising that even the tiniest scratch in its fabric has the potential to make it all unravel. Bart is unnerved by the fact that Homer and Ned are now friends despite years of (one-sided) enmity, but Lisa reassures him that if they ride it out then eventually the status quo will reset by itself. Yet toward the end of the episode, Homer and Ned have only become closer than ever; they reaffirm their friendship in a heartwarming scene that's purposely undercut by Bart and Lisa's concern that this alteration to the show's dynamic, however minor, could spell the end to their weekly adventures. At the very end, Lisa's initial forecast turns out to be entirely accurate. In the final scene, we see that Homer has reverted back to scorning Flanders, with no explanation given, other than that his attentions have simply shifted onto the next big thing - which, in a further parody of television convention, happens to be one of the hoariest-sounding plots around. Homer has been left a country house by some random relative we've never heard of (or will again) and proposes that the family stick out the weekend there to debunk local legend that it's haunted. A contrivance so nice, they skewered it twice (see also "Bart The Fink" of Season 7).