The 8 Best Golden Age Simpsons Episodes

The Simpsons is, believe it or not, one of the most important TV shows in history. While it’s become a shadow of its former self, during the golden age of the Simpsons, its cultural impact was immense, and can still be felt today.

The good news is that you can easily access the entire, enormous catalog of Simpsons episodes, and if you want to see exactly why this show is so important, start by watching these top-tier examples.

8

Marge vs. the Monorail (S4E12)

There are many Simpsons episodes that have had a lasting impact on our culture and language, and Marge vs. the Monorail stands near the top of that list. Written by Conan O’Brien, and featuring a cameo by Leonard Nimoy, this episode is eerily prescient when it comes to how some government agencies like to waste money on infrastructure boondoggles.

The town of Springfield gets a major windfall, and has to decide how to spend the money. Should they fix Main street? No, a fast-talking salesman uses the power of song and dance to convince the townsfolk that what they need is a monorail.

These days, whenever some company pitches the latest Gadgetbahn, all it takes to mock them into submissions is yelling “Monorail!” and everyone knows exactly what you mean.

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7

Last Exit to Springfield (S4E17)

With some tinges of The Man Who Knew Too Little, Last Exit to Springfield sees Homer accidentally become the union president for the nuclear power plant, and then bumble his way into getting Mr. Burns to agree to their demands.

On the way to this happy resolution, Lisa has to get the most hideous braces known to man while their dental insurance is suspended, and we get one catchy protest song too.

It’s a great blend of comedy and sharp social commentary about labor, capital, and all that. What really matters, however, is that Lisa got her braces.

6

You Only Move Twice (S8E2)

This is, hands down, my personal favorite Simpsons episode of all time. In it, Homer gets a better-paying job in a much nicer town. So the Simpsons pack their bags and move to the idyllic Cypress Creek.

Homer’s new boss, Hank Scorpio, takes a liking to him and gives him a motivational job in the nuclear division. Despite being a supervillian, Hank is a really nice guy and genuinely seems to care about his employees.

One of my favorite scenes is when Homer tackles not-James-Bond as he tries to escape and Hank tells him “When you go home tonight, there’s gonna be another story on your house.” For the first time, Homer has a boss that tells him “I’m proud of you” and actually rewards him when he does good things.

Home proudly tells his family that he’s doing great in his new job, but it turns out the rest of them really hate it in Cypress Creek. Homer asks Hank what he should do, and Hank tells him to do what’s best for his family. Later, Hank even writes to Homer, and sends him a football team as a present. It turns out he’s successfully taken over the East Coast of the US.

This episode is great in so many ways, but it’s mainly how cool Hank Scorpio is, and how oblivious Homer is to the fact that he’s working for an evil organization. This is an all-time great episode.

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5

Lisa’s Substitute (S2E19)

This is an important episode in the canon of the show because it’s where we really start to understand Lisa Simpson’s character, including her flaws. A new substitute teacher (played by Dustin Hoffman) shows up to replace a sick teacher at Lisa and Bart’s school, and Lisa is quickly enamored with him, looking up to him as a role model.

Unfortunately for Lisa, her regular teacher recovers faster than expected, and in a heartbreaking turn of events the substitute must move on to a new school. The actual episode is a bit of a tearjerker, and I don’t think people really expected a cartoon comedy to hit them with “the feels” back when this aired. Of course, Matt Groening would turn this trick up to 11 with Futurama, but Lisa’s Substitute stands on its own as a boundary-pushing story for its time.

Also, this is where we get to see how Homer doesn’t measure up to his own daughter intellectually, but is in fact a loving dad and tries his best in his own way.

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4

Treehouse of Horror V (S6E6)

I had to have at least one Treehouse of Horror episode on this list, and if I can choose only one of the annual Simpsons anthology episodes, it’s going to be the fifth one.

In “The Shinning” (which is obviously a lampoon of The Shining), Bart has psychic powers which groundskeeper Willie humorously called “The shinning”. Homer is in the role of Jack Torrance and goes crazy because Mr. Burns cuts off his TV and beer supply, and poor Marge is in the role of Wendy. It doesn’t quite go like the original movie however, and in the end the entire family is frozen solid in front of the TV, like a very late-episode couch gag.

In “Time and Punishment” Homer turns his toaster into a time machine by accident, and then alters reality by swatting a prehistoric mosquito. This results in a present time when Ned Flanders rules the world, and so Homer has to go back and make things right, except he just makes them worse.

The best one is however, “Nightmare Cafeteria” which has an awesome twist ending, and features school-based cannibalism.

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3

Bart Sells His Soul (S7E4)

This is another personal favorite of mine. Bart tells Milhouse that he doesn’t believe there’s such as thing as a soul, so Milhouse buys Bart’s soul for $5. Despite thinking that he’s just cheated Milhouse out of five bucks, weird things start happening, like the automatic doors at the Kwik-E-Mart won’t open for him, and his sense of humor goes away. Bart becomes paranoid that maybe he did have a soul after all, but Milhouse now wants ten times the money to sell it back to him.

I like this episode for a couple of reasons, apart from the premise being truly hilarious. The writers carefully avoid letting on if Bart really has a soul or sold it or not, but it is actually pretty harrowing seeing how he realizes he might have made a mistake and has a crisis of faith. Also, fun fact, this is one of show creator Matt Groening’s favorites too.

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2

Homie the Clown (S6E15)

Did you ever notice that Krusty the Clown looks pretty much exactly like Homer Simpson? Well, this is a leftover from the fact that in an early concept of the show, Homer and Krusty were the same person, and the schtick was that Bart adored Krusty, but didn’t respect Homer, without knowing they were the same person.

That’s obviously part of the inspiration for this episode where Homer attends Krusty’s clown college, and then starts impersonating him. It turns out there are lots of benefits to being mistaken for Krusty, but at the same time the Springfield mob is after him for gambling debts, which leads to Homer being kidnapped.

This episode is hilarious, and I like how it’s connected to the deep lore of the show, but the best part is realizing, at the end, that Krusty only owed the mob $48.

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1

The War of the Simpsons (S2E20)

The whole point of the show is how dysfunctional the family is, and although Homer and Marge have proven to have a relationship made of titanium-strength loyalty over the years, this early episode shows their marriage on the rocks after Homer embarrasses himself by getting drunk at a party.

Marge insists they go to marriage counseling, but the venue is next to a lake, so Homer decides he wants to go fishing instead, and the rightly-miffed Marge attends the sessions alone.

In the meantime, Homer battles a legendary catfish on the lake, and finally manages to bring him home. However, to show Marge how much she means to him, Homer lets his trophy go. The best part of the whole episode is the folk legend that Homer left behind, as one store clerk put it when asked if the legendary catfish had ever been caught: “Well, one fella came close. Went by the name of Homer. Seven feet tall he was, with arms like tree trunks. His eyes were like steel: cold, hard. Had a shock of hair, red, like the fires of Hell.”

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I don’t know when, if ever, The Simpsons will finally end, or if the show will ever return to the sharp and witty heights of its golden age, but no matter what, we’ll always have these best episodes to watch over, and over, and over again.