The Simpsons: Top 10 episodes from the golden era everyone should rewatch

If you ask any diehard fan of The Simpsons about the so-called golden age, they’ll tell you the show peaked somewhere between seasons 3 and 9. We are taking the time from 1991 to 1997 when the show set a cultural benchmark for satire and storytelling in a sitcom format.

Back in the day, The Simpsons wasn’t just another cartoon clogging up Fox’s schedule. It started as these little shorts in 1987, grew some legs, and by 1989 had exploded into a cultural juggernaut. It was way sharper and funnier than most sitcoms. And it got away with stuff you’d never see on TGIF. The jokes were layered, the satire was on point, and the characters felt like people (well, yellow people, but you get it). Springfield turned into this funhouse mirror for America, especially during all that post-Cold War, neoliberal chaos.

The writers weren’t just throwing gags at the wall; they were roasting politics, media, family life, and everything. If you were around in the ‘90s, you couldn’t escape The Simpsons quotes or memes, even if we didn’t call them memes yet.

Pretty much everyone with taste agrees that seasons 3 through 9 are the sweet spot. The Simpsons hit a balance of jokes that landed, stories with heart, and characters who made sense. People rewatch those episodes for a reason. They’re smart, sometimes surprisingly deep, and just relentlessly funny. After that…well, let’s just say things got a little shakier.

Ask any fan about The Principal and the Pauper (season 9), and you’ll probably get an eye roll or a full-on rant. That episode gets blamed for killing the golden era, mainly because it just undid years of character work in 22 minutes.

Now, if you want to see The Simpsons at its absolute best, the following top 10 episodes are where it’s at. These episodes are the cream of the crop, the ones critics, fans, and even TV scholars agree matter. They changed TV, shaped pop culture, and they’re still funny.

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The Simpsons: Top 10 episodes from the golden era everyone should rewatch

“Marge vs. the Monorail” Season 4, episode 12 (1993)

If you haven’t seen Marge vs. the Monorail, let us tell you that it is unarguably the peak of The Simpsons. Springfield gets a pile of money, thanks to Mr. Burns, who gets caught polluting and has to pay up. Then along comes Lyle Lanley, a snake-oil salesman with jazz hands, convincing the whole town that what they need is a flashy, totally pointless monorail.

Homer, who is obviously about as qualified as a potato, ends up driving the thing. Everything spirals. Marge, being the only adult in the room (as usual), does some detective work with help from a washed-up engineer to try and save everyone from disaster.

Why is this episode legendary? For starters, Conan O’Brien wrote it. The gags don’t stop, and the jokes are sharp. The whole thing is a send-up of towns falling for big, dumb civic projects because they sound cool. Plus, Phil Hartman as Lanley just owns it. You’ll be quoting this one for years once you watch it.

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“Homer at the Bat” Season 3, episode 17 (1992)

This one is for sports fans. Mr. Burns wants to win a softball game, so his solution is to hire a bunch of real Major League Baseball stars and bench the regular guys. But then, in true The Simpsons fashion, all these pros get taken out by the most random stuff. In the end, it’s Homer, of all people, who saves the day.

This episode is wild. You’ve got actual MLB legends acting goofy, mixing with the Springfield crew. It’s a parody of every sports movie ever, but with more donuts and way more ridiculousness. Also, it’s a fan favorite for a reason: people still argue it’s one of the best The Simpsons episodes ever made.

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“Cape Feare” Season 5, episode 2 (1993)

Sideshow Bob is back, and he is out for Bart’s blood. It gives straight-up horror movie vibes, except with cartoon violence and a lot of rakes. The Simpsons get shoved into witness protection, but Bob is like a cockroach; he just keeps showing up, leading to an epic showdown on a houseboat.

The episode is suspenseful and completely bonkers at the same time. Kelsey Grammer nails it as Bob (as always), and the whole thing is a masterclass in parody. Also, you’ll never look at garden rakes the same way again.

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“Treehouse of Horror V” Season 6, episode 6 (1994)

If you only watch one Treehouse of Horror, make it this one. It’s got everything: Homer losing his mind in a parody of The Shining, some wild time-travel toaster shenanigans, and teachers eating kids in the cafeteria. The writers just let their freak flags fly, and it did work.

People love this episode for good reason: it’s bold, it’s weird, and it’s packed with references. Even horror nerds and sci-fi geeks give it props. Plus, the animation gets super creative, which just adds to the madness.

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“Homer’s Enemy” Season 8, episode 23 (1997)

Frank Grimes is a normal, hardworking guy who just can’t wrap his head around how Homer is…well, Homer. Idiots surround him; no one seems to notice, and his life spirals just trying to cope. The ending is way darker than you’d expect from The Simpsons, but it hits hard.

This one is a classic for a reason, as it’s both hilarious and a little bit uncomfortable. Grimes is the audience, watching Homer bumble through life, and it kind of breaks the sitcom rules. People still debate whether it’s genius or just plain mean. Either way, it’s unforgettable.

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"The Itchy & Scratchy & Poochie Show" Season 8, episode 14 (1997)

The Itchy & Scratchy show is losing steam, so the bigwigs panic and toss in a new character--Poochie, the try-hard, sunglasses-wearing dog nobody asked for. Bart and Lisa, being the snarky audience stand-ins, watch as the fans lose their minds and the writers scramble. Homer gets roped into voicing Poochie, but the whole thing goes awry. Poochie’s exit is so abrupt that it becomes meme legend.

This one is the gold standard for TV shows roasting themselves. It pokes fun at what happens when creators run out of juice and fans start calling the shots. There are meta jokes everywhere, and fourth-wall breaks galore. People still toss around “Poochie” whenever a series tries (and fails) to stay “fresh.”

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"Bart Sells His Soul" Season 7, episode 4 (1995)

So Bart decides souls are fake and literally sells his to Milhouse for five bucks. Suddenly, weird stuff starts happening--automatic doors don’t open for him, laughter just dies in his throat, and general existential dread sets in. Meanwhile, Lisa is busy pondering the meaning of souls. Eventually, Bart gets his soul back, and there is a heartfelt sibling moment.

It asks big questions about existence, but tells it through a kid’s eyes. Genuinely funny, but it’ll gut-punch you when you least expect it. It’s proof that The Simpsons could get deep and moving, all in one go.

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"Lisa the Iconoclast" Season 7, episode 16 (1996)

Lisa, doing her overachiever thing, discovers Springfield’s founder, Jebediah, is a total fraud. She’s torn between nuking the town’s sacred legend or keeping quiet. So, she tells the truth, but nobody wants to hear it, not even her own family. In the end, she sticks to her guns, even if it means standing alone.

The Simpsons episode tackles how we build myths, cling to comforting lies, and dodge hard truths. Lisa’s moral struggle is as real as it gets for a cartoon kid. It’s sharp, it’s sad, but it has hope. People still talk about this one when they’re arguing about history and what we choose to believe.

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"Who Shot Mr. Burns? Part One" Season 6, episode 25 (1995)

Mr. Burns is stealing oil from the school, ticking off pretty much everyone. Then he gets shot. The Simpsons season ends with a cliffhanger, launching a media frenzy. Fans everywhere lost their minds trying to guess “whodunit” all summer. Even the promo campaign went wild.

Two-parter, which was a big flex for The Simpsons, showing they could pull off real suspense (and still be hilarious). The mystery angle had everyone obsessed. Plus, it lampoons TV cliffhangers and murder mysteries, never taking itself too seriously.

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"Simpson and Delilah" Season 2, episode 2 (1990)

Homer, in a rare stroke of luck, scores a miracle hair formula. Now he has got luscious locks, a fancy new job, and a loyal assistant, Karl (voiced by Harvey Fierstein). As you’d expect, the bubble pops when his secret leaks, but Homer learns who has his back.

Early Simpsons, but already landing real emotional punches. Karl’s character is groundbreaking for TV, especially for LGBTQ+ rep back then. The episode nails what makes Homer so watchable: he is a lovable screwup, but he’s got heart. It’s funny, but it also sneaks up and makes you feel stuff.