Episodes That Defined The Simpsons

Episodes That Defined The Simpsons

January 28, 2015 0 By EVA

A television dynasty built one episode at a time; The Simpsons has been a cultural touchstone for nearly three decades. Let’s find some of the keystones in its construction.

Having grown up with the yellow-skinned family it’s hard to think of how they could not exist in my world. But it is still a TV show, and there was never any guarantee it would go anywhere. Hard to believe in todays’ gross-out, explicit, adult comedy animation, that many once called it disgrace and degrading to family values. Yet the show survived and thrived through its good heart, world of great characters and some of the best writing on any sit-com for years.

Those first few years are tough, they define if you survive and, if you do, what kind of show you will be. So let’s look at the episodes from the first five years that helped express the Simpsons and cement its long running place in telly-vision land.

The Telltale Head
(Season 1 – February 25, 1990)


The Simpsons had the comforting and traditional feel of a sitcom in their first season. The family would adventure but by resolved by the end of the episode everything would be resolved in time for next week. Usually it was pretty small scale.

Bart cutting the head off the statue of beloved town founder, Jebediah Springfield, exploded the scale of the show. The entire town, in full mob mode, chases Bart and Homer in the opening moments before we flashback to see how things arrived at this point.

From Bart’s moral conundrum, trying to impress the local bullies, Homer’s useless advice, and a talking bronze head, the episode was both a good family story that also took advantage of the limitless scale of animation. Throw in a few first appearances from characters like Krusty the Clown and Sideshow Bob, (and Space Aliens!), and you have an exploding roster.

This episode turned Springfield into a more rounded place, introduced some brilliantly original characters, and all while dealing with the issues of identity, social acceptance and adolescences. And you can’t go wrong with a title from literary pedigree.

Krusty Gets Busted
(Season 1 – April 29, 1990)


Directed by someone named Brad Bird, who was never heard from again, we are given the Simpsons take on Scooby Doo. A bumbling Homer is caught in a robbery at the Kwik-E-Mart. A middling crime that becomes a scandal when the prime suspect is Krusty the Clown; beloved children’s TV entertainer and Bart’s hero.

Bart and Lisa, like any good meddling kids, chase down the clues and eventually reveal a set-up pulled off by none other than Krusty’s most trusted friend, Sideshow Bob.

Hearing the warm, direct tones of Kent Brockman is enough to make this episode a winner. What really sells it as a classic is putting the focus on the siblings, the incompetent adults having no faith (or intelligence) and the cinematic pace it sets.

The episode is great for its tone and attitude. It both lampoons and pays homage to classic tales, like many an episode to follow would do, in this case the detective story. It also established more connections between the family unit and the wider world, through the media, police and entertainment industry.

Bart the Daredevil
(Season 2 – December 6, 1990)


Of all the images in Simpsons history there are few more well-known that the endless, crushing, bloody tumble Homer takes down Springfield gorge. Twice.

The second season of The Simpsons is filled with key moments melding to the collective consciousness as the show began to grow in popularity (and infamy). Bart’s dedicated attempts to follow the thrilling daredevil stunts of Lance Murdock with ever-riskier leaps, end with facing a jump over Springfield Gorge.

On his skateboard. Of course.

Homer’s desperate attempt to stop his son leads to him perched on the skateboard and hurtling over the abyss. His joy at nearly making it giving the inevitable Wile.E Coyote plummet all the more brilliance. Unlike the classic cartoon smoke plume, however, Homer is bashed and banged all the way down.

It is a stunt that could never be done in a live action show, not that well, and not that glorious, and yet it still decided to show the blood, breaks and ‘D’oh’s’ all the way down. Twice. (Specially added to the clip show)

The episode was a highlight for the show and is credited as one of its best. Again it fused outlandish plot with family heart. So fondly is it known that it is referenced in later seasons and even the feature film.

Homer at the Bat
(Season 3 – February 20, 1992)


Hitting its stride, The Simpsons Season three created ever more cinematic episodes, greater penetration to the culture with celebrity guests and the first hints of a long-term continuity. From Mr. Burns selling the power plant, Krusty reuniting with his estranged father, Moe’s newfound success (Flaming Moe’s!), or Ned Flanders and his new Left Handed store, this season shifted the focus to other Springfield residents. It expanded the cast and showed there was a whole world of stories surrounding the main family.

Dustin Hoffman and Michael Jackson had already appeared but Mr. Burn’s attempt to introduce ringers to the Power Plant softball team took special guest appearances up a notch. A host of superstar baseball players take on mundane roles beside Lenny, Carl and Homer. Like all good Simpsons cameo’s they’re given real characterization and unique moments. From learning what to do when you spill radioactive waste to the unsolved crimes of Springfield each member of the team has a great scene.

Yet the episode is best because it is still, as with most of the best, all about Homer and his journey. Combined with film references, as always, and one of the best songs ever written the episode is just pure enjoyment from start to finish. It was the Simpsons full of confidence and reveling in its own silliness and beloved characters.

You felt safe with this writing, sure it might be silly but there was no flippancy to it. The care and love for the characters radiates from the script and is, thankfully, full of hilarious ideas.

Marge vs. the Monorail
(Season 4 – January 14, 1993)


Almost universally loved ‘the one with the Monorail’ is a high water mark for the show. It built on all that had gone before, with each family member’s reaction perfectly realized, as well as the cutaways to the residents of the town. It had special guests, Homer at the core, a musical number and bizarre moments that only work in animation.

Season four had flash-forwards to the future, homages to classic films, a plow war between best friends and a storytelling of Lisa’s first word. It had dental plans, Duff gardens and, as befits any long running TV show, a clip episode. Amid all this the original and near-flawless Monorail is home to some of the show’s best moments of all time.

When the episode is written by Conan O’Brien, has arguably the best haircut joke in TV history, and climaxes with donuts saving us all it has to be great. It signaled a more off-beat and surreal style to the show, fully embracing its potential to go anywhere and do anything, and knowing the audience is grounded enough in the world to go along with it.

Many episodes in future owed their freedom and license to go weird to the inventiveness of this episode.

Cape Feare
(Season 5 – October 7, 1993)


Way back in Season 3 Sideshow Bob reappeared with a scheme in ‘Black Widower’, only to be foiled by a spiky haired brat. After these defeats he returns and the dynamic takes a very sinister twist. With strong references to the classic film(s) ‘Cape Fear’, Bob is out to kill Bart for the time he’s put him away leading to the family going undercover.

Bart defeats him the only way that makes sense: musical numbers! With the great restart mid-way through the episode, ‘The Thompsons’ final battle on their houseboat is the weird-but-normal standard the show had perfected at this point.

The episode also established that the world of the Simpsons, although it resets each week, still maintained continuity. Bob and Bart’s relationship is not just forgotten; it clearly exists, and continues forever after. Not only that but the episode is full of wonderful jokes, visual and dialogue driven, and even does it with touchy subject matter. After all, Bob is trying to murder children, it’s hardly ‘light’ fare, but in the hands of the Simpsons it’s a master class in comedy.

Season five had more wonderful episodes, perhaps the most to date, from Bart in the boy scouts, a new casino in town, cat burglar’s, NASA adventures and a small teddy bear, it set a new bar. By now it was the mid-nineties and the show had overcome any shock or annoyance people might have had with the dysfunctional family. It was one of the most popular shows on TV, animated or live-action, and was being broadcast all around the world.

Soon South Park and King of The Hill would be leading a new wave of ‘adult’ comedy shows, that both parodied and paid tribute to the original cartoon family.

But Homer, Marge, Lisa, Bart and Maggie are still the undisputed foundation of modern animation. They have more episodes than those other two shows combined, more than Law and Order, more than CSI, more than any other.

The Simpsons is the longest running prime time sit-com in American television history. It’s not perfect, no show can have 100% gold, but it has furnished us with hours and hours of free entertainment. What could they possibly owe us?

Nothing. We owe them thanks for a long a list of great memories.


Treehouse of Horror: Halloween Special
(Season 2 – October 25 – 1990)


‘Bad Dream House/Hungry are the damned/The Raven’

Now a seasonal fixture and home of some of the best moments in Simpson’s history, though not quite ‘real’ Simpsons, they die far too often for one thing, the Halloween Special is a seasonal highlight year after year. The first Treehouse of Horror set up the three short story style that would stick thereafter, though here it was introduced as Bart and Lisa swapping stories.

For the standard sitcom it was a brave departure that was exciting to see and purely done for the enjoyment of both the creators and the audience. Strongly referencing several famous horror films and shows, like “Poltergeist’ and the ‘Twilight Zone’, the show spun its own take on classic works, which has continued to this day.

The segment that truly stood out, and is the pinnacle of the episode, is the most incongruous, the animated take on ‘The Raven’. It was completely bizarre and yet perfectly hilarious with Homer being harassed by a winged-Bart-bird. It introduced many to the poetry of Edgar Allan Poe and still managed to keep it from being pompous or self-important.

If nothing else, the Treehouse of Horror episode in each subsequent season is one of the features of the year. It’s hard to think what other show could have had the skill, finesse or willingness to completely change it’s format on prime time national TV. I doubt we’ll ever have that again in the modern multimedia landscape. Nevermore.
This article was written for publication on The GCE by Paul Neary