The Very Best of The Simpsons’ Golden Age

Distilling such quality television as the Golden Age of The Simpsons into a list of the best episodes seems like it would be an impossible task. Having attempted it here, I can say with certainty that, among such gems, the best cannot be easily distinguished — diamonds are diamonds, whether there’s 5 or 500 of them. The influence and popularity that The Simpsons had at its height cannot be understated, and now, 33 years down the line from where it all began, the shine of its best years has not been dulled.

The exact duration of the Golden Age for the show remains a hotly debated topic among fans. Speaking generously, it’s considered to be between season 1 or 2 and season 9 or 10, with some great exceptions in later seasons, like “Simpson Safari” from season 12. Where the exact cream of the crop lies is more a matter of opinion than anything objective, although the highest rated seasons are indisputably from 3 to 8. For me, the Golden Age lies happily between season 1, and season 8, the seasons which I’ll be focusing on in this piece.

Season 1: “Simpsons Roasting on an Open Fire”

This episode is perhaps famous for being the very first episode of the very first season. While the show was still finding its feet here, with the animation and comedy a little slower than later seasons, season 1 had plenty of powerful moments, some of which can be found in this very episode.

Here, we’re first introduced to the Simpson family as we know them. We see them struggling with finances running up to Christmas after they have to spend their savings on Bart’s tattoo removal. It’s the kind of real-life conflict that always made the family feel so relatable and set the show apart from anything else, the almost surreal comedy of 10-year-old Bart’s tattoo offset against such a widespread and inescapable problem as money. There are little moments in this very first episode that define the Simpson family in our minds, as easily as if we’d been watching them for several years — Bart’s impulsive choice to get an illegal tattoo, Homer spending his last 13 dollars on a bad bet, even Maggie in her iconic star-shaped snow suit.

And of course, the addition of Santa’s Little Helper, a staple member of the family from this first episode, brings it all together. It ends with a display of heart very typical of the show in its best years — the family, together at Christmas, happy despite everything.

Season 1’s honourable mention would have to be “Moaning Lisa”, for the brilliant exploration of Lisa’s character, the introduction of Bleeding Gums Murphy, and of course, some of the most stellar parenting Marge Simpson ever delivers.

Season 2: “One Fish, Two Fish, Blowfish, Blue Fish”

This particular episode would be a difficult one for anybody to forget given its particularly hard-hitting subject matter. When Homer is given just 24 hours to live after eating — surprise, surprise — a poisoned blowfish, he sets about ticking off each item on his bucket list. The list itself is a heart-breaking read, with items like ‘make videotape for Maggie’ and ‘be intamit with Marge’, because it shows unequivocally, despite all of Homer’s shortcomings, that he loves his family above all else. It’s clear to us here, if it wasn’t before, that Homer himself is the heart of the show, the glue without which the show wouldn’t quite stick.

Naturally this bitter thread is contrasted with the show’s comedy, by now coming into its own. The absurdity of Bart and Lisa singing “Theme from Shaft” on the karaoke always makes me laugh, just as much as what we think to be Homer’s last moments in that armchair bring me sadness. The episode still tugs at my heartstrings despite the fact that I know Homer isn’t going to die, and that is a testament to the show’s writing. There’s emotion from both ends of the spectrum in spades here, and any show that can balance comedy and tragedy so perfectly is nothing short of genius.

Two honourable mentions here because, while not every episode of this season was a hit, the good ones landed well. The first is “Lisa’s Substitute”, another iconic Lisa-centric episode, and the second is “Oh Brother, Where Art Thou?” for some of the funniest moments in the entire season, and of course, for Danny DeVito.

Season 3: “Homer at the Bat”

My love for this episode is less about heart, and more about the brilliant comedic beats it boasts. It’s not exactly one for powerful moments — in fact, it appears to be more of a showcase of special guest stars all starring as themselves, but therein lies a gold mine for comedy. Putting nine famous and well-respected Major League Baseball players in an episode of The Simpsons, where absurdity and slapstick comedy reign, makes for some brilliant moments — Roger Clemens being hypnotised to act like a chicken (which he continues to do throughout the entire episode), and Steve Sax’s ridiculous brush with the law are just two of those moments.

Naturally, once again Homer is at the centre of the episode as the lovable underdog hoping to stand out amongst such hard-hitting talent. Which, of course, given the unfortunate situations the rest of his team have found themselves in, he does — and although it’s not the most heroic win, we still want to celebrate because, well…it’s Homer.

The honourable mentions for this season include the wonderful “When Flanders Failed”, for one of the most poignant moments shared between Homer and Ned as well as that ending song — and “Bart the Murderer”, for a plotline that just keeps on giving.

Season 4: “Lisa’s First Word”

I have a lot of nostalgia surrounding this episode, which probably played a major part in me picking it over the highly rated and well loved “Marge vs. the Monorail”. While the latter is not a bad episode, there’s so much more substance and soul in “Lisa’s First Word”, from the great flashbacks of Bart’s infancy, to the image of the family sat together, doing something as simple and heartfelt as sharing their memories.

This episode treats us to a peek at an otherwise inaccessible part of the Simpson family’s life, and every single character becomes even richer for it. By season 4 they’re already fleshed out — we know them well. But here, we’re shown depth and context that only adds to that. We see all the little details that make the Simpson family feel even more real than they already did — their first, modest home, a younger Marge and Homer and their highs and lows as new parents. We see Bart’s jealousy of the new baby — typical of many older children when a younger sibling is born — until he’s won over by Lisa’s love for him. We see Homer sincerely struggling as a new father to provide for his family, and the huge sacrifice that Grampa Simpson makes for him. We see them buy and move into 742 Evergreen Terrace, just as much a part of the family as Homer himself. And the ending is one characteristic of The Simpsons’ Golden Age — Maggie finally removing her pacifier to speak her first word.

While the fourth season isn’t as jam-packed with gems as some of the other seasons, I still had to mention two of the brilliant episodes it does boast. “Marge in Chains” is a fantastic episode because it centres on the underappreciated character that is Marge Simpson, and “New Kid on the Block” introduces Laura Powers, one of the more interesting one-off characters of the show.

Season 5: “Sweet Seymour Skinner’s Baadasssss Song”

Again, this is far from the highest rated episode of season 5 but, for me at least, it’s the season’s most powerful, and that’s what has always stuck with me since first seeing it. It perhaps isn’t the most thrilling watch if you’re not a fan of Principal Skinner, and I empathise with that — when it comes to favourite characters, Skinner doesn’t even make my top 10. But this episode shows a side of him, and a complexity to his and Bart’s relationship, that I can’t help but love.

Writing their characters as multi-faceted beings is something the writers of the Golden Age seasons were incredibly skilled at. Even secondary characters received this treatment for the most part, like Skinner himself. Here, his character is explored, and we’re shown the genuine love he has for his job, his school and the children in it. There’s real grief there when he loses his job, and a real friendship between him and Bart once his authority is lost. Even when we see him as a sergeant in the military, he’s no longer just the stereotypical slavedriver because we’ve seen him from a different angle, buying his detergent from a laundromat vending machine, and actually enjoying the company of Bart. The two come to appreciate each other outside of their roles as enemies, and it makes for a beautiful episode.

Picking the honourable mentions for this season was difficult because it’s full of great episodes, but I eventually settled on “The Last Temptation of Homer” for its incredible comedy and unique conflict, and “$pringfield (Or, How I Learned to Stop Worrying and Love Legalised Gambling)”. The latter is full of great subplots for so many characters — like Marge, Lisa, Homer, and Mr. Burns — and has some real heart.

Season 6: “Lisa on Ice”

One thing I’ve always loved about The Simpsons is that, while Bart and Lisa do bicker in standard sibling fashion, it isn’t afraid to show the moments when they not only get along but show genuine love for one another. It’s just another example of the great character development and writing that the Golden Age is well-known for. One of the finest episodes to showcase this is “Lisa on Ice”.

The sibling rivalry is clear when Bart and Lisa end up competing on opposing ice hockey teams, making for some classic comedy when Homer begins encouraging it. This bitter feuding means that the ending, where Lisa and Bart come together as brother and sister rather than enemies, is made all the more sweeter — precipitated, of course, by flashbacks of their younger years together. It carries the age-old message that the need or desire to win, to be the best, should never come above familial love, and despite all their flaws, the one thing the Simpson family has in spades is love. Here, quite simply, the Simpson children are at their very best.

“And Maggie Makes Three” is the first honourable mention for this season. It’s not the highest rated episode of season 6, but it absolutely earns its place here with the sincerest show of love in perhaps any episode. The second is “’Round Springfield”, for bringing back (and rounding off) the brilliant character of Bleeding Gums Murphy, with Lisa at her best.

Season 7: “Marge Be Not Proud”

I love this particular episode for the simple fact that it’s one of Bart Simpson’s finest moments. I sometimes find it difficult to fully enjoy Bart’s character because of his often-polarising behaviour. Out of the entire Simpson family, he’s probably my least favourite. But — as with “Lisa on Ice” — there are some episodes where Bart’s own unique brilliance shines through, and “Marge Be Not Proud” is probably the brightest of Bart’s highlights.

Here, we see the Simpson family in real crisis over Bart when he’s caught stealing. We see Bart himself in crisis over Marge’s disappointment, and over the resulting distance she puts between them. His quick wit and boundless devilry can make it easy to forget that Bart is only a young boy, one who makes mistakes like any other child. We might judge him for stealing, but this episode’s writing does well to remind us that this is not a choice that defines Bart. It could, if he let it. But there is always good that prevails in Bart, and his gift to Marge — a framed photo of himself — is testament to that. It’s an episode that showcases perhaps the best and worst of Bart as a character, and explores the real intricacies of growing up, parenting and the choices that come with both.

Honourable mentions include another Lisa classic, “Summer of 4 Ft. 2”, as well as “Raging Abe Simpson and His Grumbling Grandson in ‘The Curse of the Flying Hellfish’” for some of the season’s most hilarious comedic moments. It’s also an absolute delight to see Grampa Simpson in a major role.

Season 8: “The Springfield Files”

Being a horror lover, this one was an obvious pick for me. I’ve unfortunately never been a major fan of the highly acclaimed “Homer’s Enemy”, whereas the unique blending of The X-Files with an episode of The Simpsons always felt special. Not only could the writers balance comedy with heartfelt moments, they could also balance it with horror — writing one or the other is hard enough, but balancing both is an art.

This episode is nothing short of a testament to that skill. It’s perhaps the first real instance where horror plays any part of The Simpsons, which is a refreshing concept for the show. The part where Homer is stumbling home, lost in the woods, still makes the hair on the back of my neck stand on end with the eerie score and fantastic atmosphere. Even with the comedic beats peppered here and there, the suspense is not broken — and similarly, the suspense doesn’t keep me from enjoying those comedic beats. The reveal that the alien is actually Mr. Burns is a brilliantly bizarre manoeuvre typical of The Simpsons, as is the gentle mockery of such serious characters as Mulder and Scully. In short, the episode is yet another example of the gold-standard writing that made The Simpsons the world’s favourite television show.

The most obvious honourable mention in this entire list would perhaps be “You Only Move Twice”, for a stellar plot partly held up by the lovable villainy of Hank Scorpio. The second, “Hurricane Neddy”, is perhaps less obvious with a lower rating, but still a great episode for its exploration of Ned Flanders as a character.