Why 15 of the highest rated episodes of ‘The Simpsons’ were all released in the 90’s

The Simpsons isn’t just a successful animated sitcom; it’s an American institution. With over 700 episodes since its 1989 inception, The Simpsons is the longest-running animated series, American sitcom, and scripted primetime TV series but why are viewers rating the newer series as highly as the one’s from the mid-late ninety’s?

America’s favorite dysfunctional family, Homer, Marge, Bart, Lisa, and little Maggie, have more than 30 years’ worth of hijinks in the bag. While every fan has their favorite episode, most agree that these top 10 Simpsons episodes have the perfect mix of satire and irreverence that makes The Simpsons magic.

15 “Homer the Heretic”

Season 4, Episode 3 (1992)

The Simpsons established itself as an animated series for mature viewers early on, especially through episodes like “Homer the Heretic.” The episode depicts Homer’s string of good luck after deciding to stay home on a Sunday instead of going to church with the rest of his family. Instead, he enjoys dancing around in his underwear, making his special waffles, finding a penny, and more. When he decides never to go back to church again, God pays him a visit.

A fantastic example of how the series presents social commentary in humorous ways, the episode highlights the absurd obsession with religion and conformity (and the social repercussions of choosing otherwise).

14 “22 Short Films About Springfield”

Season 7, Episode 21 (1996)

A loose parody of Pulp Fiction, “22 Short Films About Springfield” is an episode with a title that reveals the entire plot. It portrays a variety of Springfield’s residents – Bart and Milhouse, Apu, Mr. Burns and Smithers, Moe, and more – experiencing their own little stories that are soon revealed to be interconnected.

The episode is a wonderful view into the lives and personalities of the characters fans know and love. Each story is creative and entertaining, from Principal Skinners’ disastrous roast and Lisa’s hair issue to Bart’s daring prank and Chief Wiggum’s conversation about McDonald’s.

13 “Homer Badman”

Season 6, Episode 9 (1994)

A misunderstanding with their new babysitter Ashley puts Homer in an awful situation in “Homer Badman.” After the babysitter, who is also a feminist graduate student, mistakes Homer’s drooling for candy as a sexual advance, the Simpsons’ lives are turned around by the ensuing media frenzy around the case.

Certainly one of the sitcom’s more daring social commentaries, the episode critiques media sensationalism and highlights its effects on once-unknown citizens (like Homer). It does so with the same humor, wit, and absurdity that the series has become known for at this point.

12 “Who Shot Mr. Burns? Part Two”

Season 7, Episode 1 (1995)

As Mr. Burns lies in the hospital with a gunshot wound, the investigation into his attempted murder gets intense. Everyone in Springfield has a motive, but when Chief Wiggum relies on an Agatha Christie novel to guide him, things don’t go well until Simpson DNA turns up on Burns’ suit.

This episode opens with Burns in Smithers’ shower, and for a moment, fans are led to believe it’s all been just a dream, reminiscent of Dallas’ infamous cliffhanger. Sideshow Mel pulls a Sherlock Holmes, Lisa speaks in Twin Peaks tongue, and Groundskeeper Willie channels Sharon Stone in Basic Instinct. To keep the ending from leaking, several alternates were animated, some of which aired during “The Simpsons 138th Episode Spectacular!,” including Apu, Barney, Smithers, and Santa’s Little Helper as the gunmen.

11 “The Springfield Files”

Season 8, Episode 10 (1997)

After scoring “Boris Yeltsin” on the breathalyzer test, Homer attempts to walk home, but crossing through a spooky forest; he encounters an alien. The glowing creature tells him, “Don’t be afraid,” which has the opposite effect on Homer. Agents Mulder and Scully (of The X-Files) visit Springfield (with Gillian Anderson and David Duchovny providing voices) to investigate Homer’s claims.

Fans remember this one fondly for Red Tick Beer which “needs more dog,” Chief Wiggum’s invisible typewriter, a turtle wearing Grampa’s teeth, and a cameo by the Cigarette Smoking Man. It’s positively bursting with sci-fi references, including Close Encounters of The Third Kind and E.T. An alien lineup includes Marvin the Martian, Gort from The Day The Earth Stood Still, Chewbacca from Star Wars, ALF, and either Kang or Kodos, which producer Mike Reiss calls the most illegal shot in the show’s history.

10 “The City of New York vs. Homer Simpson”

Season 9, Episode 1 (1997)

On Barney’s turn as designated driver, Duffman shows up with bottomless beer. This breaks poor Barney; when he drops Homer off that night, he disappears with the Simpson car, leaving it illegally parked at the World Trade Centre for two months. While the rest of the family goes sightseeing in NYC, Homer has to wait by his car from 9 to 5, though some clam juice derails his best intentions.

Fans love this episode for the pickled egg draw, Homer’s Flushing Meadows fantasy, the parking enforcement department that only hires Steves, Marge’s humble dream “of being in a Broadway audience,” and Bart’s visit to MAD Magazine. This episode was removed from syndication after 9/11 but went back into rotation in 2006 with some scenes edited out. Producers later donated a hand-drawn cel from the episode to the National September 11 Memorial & Museum.

9 “Last Exit to Springfield”

Season 4, Episode 17 (1993)

Eight-year-old Lisa needs braces. It’s bad timing since the power plant has just nixed the union’s dental plan in favor of a beer keg at all their meetings. Instead of braces, Lisa gets a headset that predates stainless steel, “so you can’t get it wet.” Homer takes over as union president and goes head-to-head with Mr. Burns, leading the plant employees on strike.

The episode’s most memorable elements include Grampa’s pointless story, Lisa’s protest song, Mr. Burns’ likeness to The Grinch, the horrifying Big Book of British Smiles, and the first of many gags involving Burns’ never remembering who Homer Simpson is. Producers tried to get a big name on board to voice the orthodontist, but Anthony Hopkins and Clint Eastwood refused. Anthony Perkins (of Psycho) agreed but passed away before he could record his lines. Hank Azaria wound up crushing the role.

8 “King-Size Homer”

Season 7, Episode 7 (1995)

When Mr. Burns enacts a required morning calisthenics program at the nuclear power plant, Homer does whatever he can to get out of it. In “King Size Homer,” fans watch as he embarks on a dangerous journey to qualify as disabled by eating enough food to increase his weight to 315 pounds. Once he does, Homer finally gets what he wants and is allowed to work from home, which soon turns into his worst nightmare.

Highlighting the show’s signature satire and wit, the episode comes from one of the best seasons of The Simpsons and prods at the prevalent obsession with weight in pop culture. It also has some gut-busting and unforgettable moments like Homer’s donning of a bright muumuu and his climactic jump.

7 “Homer the Great”

Season 6, Episode 12 (1995)

“Homer the Great” revolves around the ancient group known as the Springfield chapter of the Stonecutters, which Homer joins after feeling envious of Lenny and Carl. Things predictably go wrong when Homer destroys one of their sacred items, which leads to his exile. But, Homer’s rare birthmark soon doesn’t just get him a way back in, but brings him to the very top.

The wacky episode pokes fun at secret societies and elite groups in general in absurdly hilarious ways. A searing critique of groupthink and the strange things people will do to be part of the “it crowd,” it’s a fan-favorite episode for a reason (that’s still relevant today).

6 “Marge vs. The Monorail”

Season 4, Episode 12 (1993)

Mr. Burns is forced to pay a $3 million polluter’s fine, and Springfield gets to decide how they’ll spend this sudden influx of cash. Marge has the town enthused to finally fix up Main Street when in walks Lyle Lanley (voiced by Phil Hartman). After a very catchy song and dance number, the town impulsively buys a monorail from him. Lanley’s hasty training and random appointment of Homer as conductor leaves Marge to save Springfield from its dangerous new investment.

Written by Conan O’Brien, this episode was instantly embraced by both fans and critics. It continues to be beloved due to its Flintstones-inspired opening, a spectacular Simpsons musical number, a surprising cameo by Leonard Nimoy, iconic details such as the popsicle stick skyscraper and the escalator to nowhere, and memorable lines like “I call the big one Bitey.”

5 “You Only Move Twice”

Season 8, Episode 2 (1996)

After consulting absolutely no one, Homer moves his family to another town to take a better job. His new boss, Hank Scorpio (voiced by Albert Brooks), delivers perks and praise effusively, and Homer’s team is competent enough to make him look good at his job. It’s really the perfect situation, except Marge is miserable with no homemaking to do in their largely automated house, Bart is sent to a remedial class, and Lisa is allergic to the whole town.

In what is almost the best Simpsons episode, Brooks’ Scorpio is a legendary one-off character, and much of the episode’s humor is derived from the fact that Homer doesn’t seem to realize his boss is actually a Bond villain. Fans are fond of Bart’s slow Canadian classmate, the illustrious hammock district, Lisa’s chipmunk encounters, and the scathing Denver Broncos burn. “You Only Move Twice” is a fantastic Bond parody and an unforgettable Simpsons episode.

4 “Who Shot Mr. Burns? Part One”

Season 6, Episode 25 (1995)

While burying class pet Super Dude, Willie strikes oil, and Springfield Elementary is suddenly very, very rich. Mr. Burns burns with jealousy until he finds a way to trick the kids and steal the oil, making him greedier. Ready to take on his greatest enemy yet, the sun, he invests his profits in a sun-blocking machine which will make his power plant all the more necessary.

At yet another productive town hall meeting, most of the residents are stroking guns and plotting revenge. When Mr. Burns winds up shot at the end of the episode, nearly everyone’s a suspect. Never excluded from any discussion of The Simpsons‘ best episodes, “Who Shot Mr. Burns” is peppered with clues about who the killer will be, and savvy viewers searched diligently via freeze-frame.

3 “Treehouse of Horror V”

Season 6, Episode 6 (1994)

In the show’s first vignette, a parody of The Shining sends Homer off the deep end when “No TV and no beer make Homer go crazy.” In Time and Punishment, Homer keeps traveling back in time and accidentally making the future worse. And in Nightmare Cafeteria, the teachers feast on kids sent to detention.

Throughout all three, a running gag sees Willie rushing in to save the day, only to immediately take an ax to the back. The perfect irony is achieved in the middle vignette when Homer rejects an otherwise wonderful world for its lack of donuts, only for the audience to learn that donuts fall from the sky. In what is considered one of the best Treehouse of Horror and funniest Simpsons episodes, fans loved seeing the Simpsons freeze to death, get lobotomized, and dance a skinless Broadway number, at least until Bart’s intestines are devoured by his best friend.

2 “Cape Feare”

Season 5, Episode 2 (1993)

Bart’s been receiving death threats written in blood, and fans immediately suspect Sideshow Bob (Kelsey Grammer) even though he’s in prison. However, Blue Haired Lawyer is awfully convincing, and the parole board grants Bob clemency despite some pretty damning evidence from other people he’s tried to kill. The “Thompsons” go into witness relocation in Terror Lake, but a wily Bob is two steps ahead (or rather, hiding under their car).

This entire episode is a send-up to the 1962 film, Cape Fear; the “Thompsons” get their name from its director, J. Lee Thompson. When the episode proved a little short, Sideshow Bob’s rake gag was extended, making for an iconic Simpsons moment. Grammer is asked to sing almost every time he guest stars. In this episode, Bart saves his bacon by asking Bob to sing the score from H.M.S. Pinafore; Grammer sings this same excerpt in his sitcom, Frasier.

1 “Homer’s Enemy”

Season 8, Episode 23 (1997)

In the highest-rated Simpsons episode, Frank Grimes is featured as a character who struggled for literally everything in his life, even studying science by mail to earn his degree in nuclear physics. Working alongside Homer, Grimes is repeatedly confronted by Homer’s laziness. He attempts to expose Homer’s idiocy by tricking him into competing in a children’s contest, but when Homer wins, Grimes has a meltdown, ultimately electrocuting himself to death while imitating Homer.

What makes “Homer’s Enemy” the best episode of The Simpsons to fans and critics alike is that it introduces a realistic person to Springfield. Homer is an acknowledged dolt, yet everyone in Springfield tolerates him as if his tremendous stupidity is just another quirk to be put up with. Grimes, however, holds up a mirror to Homer by being a professional with a strong work ethic. He is understandably resentful of Homer because he’s had to work so hard for the things Homer accidentally falls into. This is the most self-reflection viewers have seen from The Simpsons, and it was a compelling view.