Late to the Party: The Simpsons of the 20th Century (1989-1999)

When I entered this world in 1995, my father, a public school English teacher, was waging the sixth year of war against his mortal enemy. He never encountered his foe directly, except on bootleg t-shirts and bumper stickers, but he believed he saw its malign influence in class after class of belligerent, homework-shirking, back-talking ninth graders who at various times flushed his gradebook down a toilet, left chicken heads on his desk, and fumigated the classroom with the scent of pig urine. What he thought to be the wellspring of this stain upon the youth of America, he swore, would never enter his home to tarnish the soul of his newborn son.

The depth of his conviction in this matter is the only possible explanation for how it took someone like me until the year 2022 to become truly acquainted with one Bart Simpson. Despite over a decade spent commenting on the AV Club and associated communities where Simpsons quotes are the lingua franca of a dozen types of nerd, despite watching every episode of Futurama and even Disenchantment, despite being aware that every comedy writer I have ever enjoyed venerates the show’s first decade or so as a pillar of the art form, despite my father’s ire for Bart waning alongside the show’s cachet with the under-18 set, despite even riding The Simpsons Ride and drinking Duff and Dufftoberfest at Universal Studios, some part of me clung to that taboo instilled in infancy that The Simpsons was a Bad Influence to be avoided at all costs.

This year, I decided to change that.


I initially bounced off of Season 1 of The Simpsons. The Klasky-Csupo animation is crude and misshapen, and the early scripts seldom stray too far afield from the conventions of the earlier family sitcoms they were intended to exaggerate. The pacing, compared to later seasons, is languid, 80s-ish. The inciting incidents are plausible, interpersonal. There are certainly some plots that you wouldn’t expect to see on contemporary shows like Married… With Children or Roseanne, but all in all it has not yet realized that in animation truly anything can happen. It’s working with one arm tied behind its back.


How vertiginous that initial rise must have been. A media consumer of the 2010s, I’m used to shows offering meta-commentaries on how small and unloved and at risk of cancellation they are; it’s jarring to see a sitcom almost embarrassed about its own meteoric rise, as The Simpsons season 2 is.

It’s somewhat shocking that the show became such a cultural flashpoint based solely on that weak first season. This is the Bart that bedeviled my father? He now reads as only slightly more advanced at juvenile delinquency than Dennis the Menace. More than anything you want to give him credit for just getting out there and doing stuff, no matter how many times the show chides him for being a TV-addicted waste case. Real children were and are even lazier.

The rest of the show is starting to come into focus around its original breakout star in season 2 as well. Homer starts to sound like Homer, the broader cast of Springfield irregulars starts to shine, and the standard for big-name guest stars is set by the likes of Dustin Hoffman and Danny DeVito. Both of their characters represent paragons of virtues not found in the Springfield of this era: Mr. Bergstrom embodies the wit, intellectual curiosity, and bohemianism that Lisa feels incapable of finding in her backwater town, while Herb turns his honest industriousness into straightforward wealth and success in a manner that would be unimaginable in the shadow of Mr. Burns. This is a potent story engine that begins to degrade as the next few seasons go by; there are no more stories left to tell about the contrast to the world outside Springfield once everything in the world has come to Springfield.


Season three’s premiere, “Stark Raving Dad”, is an excellent example of the relative restraint the show had about Springfield’s world in the early going. It is the only episode I had to track down external to Disney+, since it was scrubbed from all official sources in 2019 after new revelations about the crimes of its guest star. Michael Jackson was not much of an actor (Captain EO aside), so he had to be playing some version of himself, but Springfield had not yet been cracked so wide open that the actual King of Pop could simply arrive there. In order to accommodate Jackson’s star power the writers felt the need to concoct the intermediary of Leon Kompowsky, a man who merely thinks he is Michael Jackson; even so, the entire town bends around the promise of his presence. This conceit makes the episode so much stronger and more poignant than it otherwise would be; it is all too easy to imagine the lazy mess of references and fawning that “The Michael Jackson episode” would have been if it were produced with the creative ethos of modern Simpsons instead.

As the show’s ability to pull celebs grew stronger, Springfield rapidly grew less provincial. Notably, “Stark Raving Dad” was the final episode produced as part of Season 2’s production run, and it seems to have broken the dam on celebrity guest stars for season 3 – only nine episodes later, the actual Aerosmith shows up to enjoy some Flaming Moes. The long slow slide to the prototypical shitty guest star introduction (something like everyone saying “Wow, [first name] [last name]!”, Homer asking “Who’s that?” and Lisa explaining their real life credentials to the audience – Stephen Jay Gould in “Lisa the Skeptic” may be the first example) had begun.

That’s a long way off though. For the most part Season 3 is the show really finding its legs and striking the alchemical balance between family sitcom plots, cartoon absurdity, and razor-sharp jokes. A standout for me was “Separate Vocations”, not an episode I see referenced often as one of the greats but one that I think embodies the show’s strengths at this phase of its existence. It is simultaneously scathingly skeptical towards all institutions (the satire of both educational aptitude tests and the delinquent-to-cop pipeline is still trenchant) but sympathetic to the people enmeshed in them (it takes Lisa’s devastation at the test seriously even while presenting the test itself as totally bogus). Most of all, it is in total command of its characters. The role reversal that makes up the bulk of the plot only works because the Lisa and Bart archetypes have been totally solidified, and their subversion is written expertly.


The level of the writing becomes increasingly virtuosic as the show rolls on into Season 4. I’ve always been drawn to dense, gag-a-second comedy, ever since my dad showed me Airplane! at probably too young an age. Arrested Development, 30 Rock, Community, The Emperor’s New Groove. It’s an ethos that for a long time was only sustainable for a 90-minute feature film, and sometimes not even then – there’s a lineage of Hellzapoppin’, Mel Brooks, Zucker-Abrams-Zucker, among others, but it does not extend to early television. Famously, when ZAZ tried to apply their approach to TV in Police Squad!, it burned out after six episodes that all put together are merely feature length. Golden-age Simpsons, once it’s spun up, takes that frantic ZAZ pace and runs with it, using the freedom of animation to whip through visual gags and comedic asides that would have required days of setup in live action. (My sense is that the reason this style exploded so hard in live action sitcoms of the 2000s is that the ease of digital photography and editing finally freed them to be as elastic in shot sequencing as animation).

That density is a key strength to the viewer in my position because, increasingly, I found myself already familiar with almost every major punchline. As the old joke goes, “What’s the big deal about Hamlet? It’s just one famous quote after another.” Same with Golden Age Simpsons to those raised online, where hundreds of quotes and gifs and memes are part of the basic semantic texture of existence. But even if I already knew all the big punchlines of iconic episodes like “Marge vs. the Monorail” or “Mr. Plow” out of context, they still hit differently when integrated into the rich tapestry of smaller gags that don’t often get Frinkiacs made of them. I do wish I could have experienced the peaks truly fresh, without peering through the dulling gauze of familiarity, but they’re still cromulent.


By Season 5, the show seems to feel it has exhausted the internal narrative possibilities of the Simpson family itself. There is no episode logline that doesn’t involve an external character interacting with a member of the family, whether it’s Michelle Pfeiffer’s excellent turn as Homer’s seeming soulmate or Bart getting an elephant in “Bart Gets an Elephant”. Fortunately this is where the deep, deep bench of supporting characters comes in handy; even the thinnest-sketched bit player has a good episode or two to be written about them, and through sheer combinatorics you can get to premises like Mr. Burns and Grampa in a love triangle, or Lisa and Smithers tracking down the creator of an ersatz Barbie, or Homer and Apu saving James Woods’ life, that work surprisingly well. At the time, it might even have seemed inexhaustible.


I don’t have many particular thoughts unique to season 6 that don’t also apply to 5 so I’m going to take this opportunity to share some lines I wrote down during my viewing that I was familiar with as phrases but did not actually know to attribute to The Simpsons until encountering them in the show:

  • It’s like a party in my mouth and everyone’s invited
  • He’s history’s greatest monster!
  • A single plum floating in perfume served in a man’s hat
  • Woozle-wuzzle?
  • Sacrelicious
  • Aw, he thinks he’s people
  • I see you’ve played Knifey Spoony before
  • And with good cause
  • Stupid babies need the most attention
  • Urge to kill… rising

There are, of course, dozens or hundreds more phrases that I encountered and then eventually did know to attribute to the Simpsons before finally watching. It’s had an indelible effect on the language. 

In our fractured age it’s hard to get into the mindset of the 90s monoculture that made these quotes and references so widespread. But I think the fact that Season 6/7’s tongue-in-cheek cliffhanger “Who Shot Mr. Burns” has arguably eclipsed Dallas’s cliffhanger, the subject of its parody and itself an era-defining cultural phenomenon, in prominence bespeaks the hegemonic power of Simpsons at its peak. 

I’m told people were mad when it was revealed to be Maggie, that they felt it was a cheap joke. To which I say: what did they possibly expect? One of the most refreshing things about the Simpsons nowadays is that it has no interest whatsoever in lore and continuity – in fact, it’s actively hostile to such notions in episodes like “Homer Loves Flanders”, which hangs a lampshade on the perpetual reset button. It was never in danger of disappearing up its own ass with self-reference and fan-service. It turned not ever-inward, but ever-outward.


By season 7, the show begins to become self-conscious about its own longevity in the same way it was about its overnight success back in Season 2. Many classic sitcoms ended at or around the seventh season; it’s when actor contracts tend to expire and premises tend to get tired. The Simpsons fights back against this tendency with increasingly avant-garde comedic experimentation – the absurd anti-celebration of “The 138th Episode Simpsons Spectacular” or the confounding  non-ending of “The Day the Violence Died” or the daring formal experimentation of “22 Short Films About Springfield”. 

This is a studio-album phase for the show. You can feel the truly niche sensibilities of the weird nerds in the writers’ room finding their full expression. But at the same time, it’s still cashing in fundamental emotional payoffs it’s thus far withheld, exploring the last nooks and crannies of the central characters even as it makes a roadmap for abandoning them. The first episode to air after I was born is in Season 7 – “Mother Simpson”. It’s a great one. Funny, poignant, guest-starring Glenn Close. It’s hard to imagine that this sweet, nerdy, slightly esoteric era of the series is the same one my father inveighed against as a base corrupting influence. But El Barto must have cast a long shadow.


All that is even more true of Season 8, which feels like the show throwing itself against the bars of its very existence – of the sitcom format, of the Fox network, of the nature of its characters. Episodes like “Homer’s Enemy” seek to grab the fundamental unquestioned assumptions of the show and break them in half. It feels like there’s a fire sale on great jokes – “A Milhouse Divided” had no less than six separate references I knew in advance without knowing what episode originated them, a record for any individual episode.

The show also achieves its greatest height as visual art this season, in “El Viaje Misterioso de Nuestro Jomer”. In general, the animation of these early seasons is interesting to consider – once they move away from the crude roughness of Klasky-Csupo to Roman Films, the animation is actually quite good, with lots of jokes sold solely on the squash-and-stretch exaggerations afforded by the medium. While the original designs of the characters were intentionally ugly and off-putting, they have become amenable through familiarity and now are positively sightly compared to much of adult animation today. What has happened to them in the 21st century though is a maddening sclerosis, all of the characters becoming pathologically and unceasingly too on-model, until they just feel like paper dolls being moved through a plastic world. “El Viaje Misterioso de Nuestro Jomer” is the opposite of this; its hallucination sequence was animated almost entirely by a single man, David Silverman, so that the creators could exercise complete artistic control over it and use the medium of animation to its fullest advantage; the result is a beautiful sequence that’s almost as big a guest star as the episode’s actual guest star, Johnny Cash.

“El Viaje” also demonstrates the Season 8 ethos in another way – it was originally pitched for the third season, but was considered “too weird” and put on a shelf for years. Season 8 is when the show felt confident enough to do the things that were “too weird”, and when the original creative crew wanted to do their last crazy ideas because they felt an era coming to an end.


Part of being aware of The Simpsons is being aware that at a certain point it Got Bad. And many pinpoint the point it Got Bad as season 9’s “The Principal and the Pauper”. Much like any consternation over the resolution of “Who Shot Mr. Burns”, though, I think the hatred for this episode is overblown by people who are overly invested in the character of Principal Skinner. I don’t care that it ‘betrays’ the reality of this absurd man, and it doesn’t either – there’s another ostentatious, meta hit of the reset button at the end. The most important thing is it’s still reasonably funny.

What is true though is that the premise feels desperate and unnatural in a way that even the craziest premises of seasons past seldom did – it’s doing shit just to have something to do, not because it’s an idea anyone was particularly enthused about. The wild, experimental energy of seasons 7 and 8 is gone, replaced by a workmanlike competence. There are still a lot of great episodes and great gags in season 9, but they feel residual, like the last meal the kitchen turned out before closing down for the night. Meanwhile, the flattening and broadening of the characters and the tendency to bring in gratuitous guest stars that will define the show’s later decades continues apace. I certainly wouldn’t call Season 9 Bad; most of it is legitimately good! But I do think it’s when the show stops being capital-G Great.


The highs of season 10 are notably lower. With Mike Scully fully in charge, the cast chafing at their contracts, and the final appearances of Phil Hartman’s iconic characters, it’s possible to feel the spiky, brilliant, unpredictable golden age getting sanded down into the aerodynamic, joyless corporate husk that will continue to glide along unceasingly on Fox’s Sunday nights for the next quarter century. It’s not that there aren’t still glimmers of goodness in Season 10 – “Bart the Mother” is a highlight, and there are still good gags here and there – but overall the show feels like it has collapsed to a lower energy state. Whatever barrier there was between Springfield and the entire rest of the world is collapsing; whatever sparks of connection existed between disparate side characters are being extinguished; whatever mysteries remained within our core family are being resolved. The world of the Simpsons is on its way to achieving maximum entropy, a heat death of sorts, where all jokes have been made and all beats have been beaten.

This total exhaustion of human interest is perhaps best exemplified by two of the final three episodes of the season, which end on a Loch Ness Monster working at a casino and Godzilla taking down a passenger plane. These are not dream sequences or Treehouse of Horror stories; they are literal in the world of the show, despite it once being too implausible to have a pop star who was actually a real living person show up in a town. The old Simpsons is dying; the new Simpsons struggles to be born. Now is the time of monsters.


I decided to stop watching at Season 10, with the exception of Season 11’s finale “Behind the Laughter”, which I had heard functions well as a series finale. It itself seems to think this – it ends on another self-deprecating joke about how tired the show has become. It’s funny enough (I’ve never seen an episode of Behind the Music, but I’ve seen enough parodies to get the idea), but it still lacks some sort of spark that the golden age possessed. Still, it is the Simpsons’ ultimate self-reflexive statement on its own creative rise and fall – perhaps it couldn’t have been made from within that acme. It had to wait until the fall in order to cover it.


But of course it wasn’t the last season














Post-script: I actually watched one episode of The Simpsons in broadcast before this year, despite continuing to observe my father’s prohibition otherwise; Season 25’s “Brick Like Me”, the gimmicky Lego episode released to coincide with the production of Simpsons Lego sets in 2014 (my love of Lego outweighing my inherited distaste for The Simpsons). It was decent enough, I recall – transposing the entirety of Springfield into brick form allowed for enough novel jokes to fill out 21 minutes. But clearly it did not compel me enough to turn me into a regular viewer.