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Best 'Simpsons' episodes of all time

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20th Century Fox Television

Best 'Simpsons' episodes of all time

When “The Simpsons” aired its 636th episode on April 29, 2018, it surpassed “Gunsmoke” to become the longest-running primetime scripted series in TV history. That’s but one among a legion of accomplishments for this animated smash hit, which began in 1987 as a series of short sketches on “The Tracey Ullman Show.” Bringing each character to life was cartoonist Matt Groening, whose previous work included a satirical comic strip called “Life in Hell.” Two years later, Groening—along with producers James L. Brooks and Sam Simon—developed “The Simpsons” as a half-hour sitcom. Television and popular culture alike have never been quite the same since.

To call the series epoch-making in the 1990s would be an understatement, as it was more like a megaton bomb of pop-culture iconography and enduring influence. Striking a deft balance between satire and endearment, the show’s best episodes hold up a mirror to American society that’s too prescient and hilarious to deny. The town of Springfield becomes a stand-in for Everytown, USA, with each of its citizens representing a familiar archetype. At the heart of every story is the Simpson family itself, comprising Bart, Lisa, Maggie, Homer, and Marge, whose unique personalities are delivered with exacting precision.

There’s so much to “The Simpsons'” lore that one could dedicate an entire college course just to the show’s timeless characters and philosophical themes. Oh wait, they did. That’s not to mention the multi-layered jokes, omnidirectional story lines, or unforgettable catchphrases like “d’oh!,” which became so integral to the Western lexicon that it ended up in the dictionary. It’s then no surprise that the series has spawned merchandise, best-selling albums and books, video games, theme park rides, memes, a blockbuster movie, and billions of dollars in profits. Winner of 31 Primetime Emmy Awards, it was also named the Best TV Show of the 20th Century by Time magazine in 1999. Meanwhile, staff members like Conan O’Brien, Greg Daniels, and Brad Bird became high-profile creators in their own right. The list of achievements goes on and on.

Despite the show’s seemingly endless production run and a slew of accomplishments, most fans would agree that its first nine seasons are far and away the best. To prove as much, Stacker surveyed all “The Simpsons” episodes’ IMDb user ratings as of August 2019 and ranked them accordingly. In the case of a tie, the episode with more user votes was ranked higher. As one will soon discover, there’s only a single episode on the list that wasn’t from the first nine seasons. But what a nine seasons they were, better known as the show’s “Golden Age.” Here are the best of the best.

You may also like: 50 best space movies of all time

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20th Century Fox Television

#50. Homer's Barbershop Quartet (1993)

- IMDb user rating: 8.5
- Votes: 2,170
- Season: 5
- Episode: 1

Homer harkens back to his time in the Be Sharps, a barbershop quartet that rocketed to success and then split up for archetypal reasons. The episode is riddled with Beatles references, including a few Yoko Ono jabs. George Harrison and David Crosby make voice cameos as themselves.

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20th Century Fox Television

#49. Trilogy of Error (2001)

- IMDb user rating: 8.6
- Votes: 1,650
- Season: 12
- Episode: 18

A high point for the show in the wake of its “Golden Age,” this season-12 episode tackles the same series of events from three different perspectives. Inspired by films like “Go” and “Run Lola Run,” the episode was originally titled “Go, Simpson Go.” Frankie Muniz of “Malcolm in the Middle” appears in a guest speaking role.

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20th Century Fox Television

#48. Bart on the Road (1996)

- IMDb user rating: 8.6
- Votes: 1,731
- Season: 7
- Episode: 20

After scoring a fake driver’s license, Bart and three friends rent themselves a car and embark on a wild road trip. When the car gets destroyed, the boys must figure out how to get back home without revealing their misdeeds. Loaded with classic one-liners, the episode references “Naked Lunch” and “The Texas Chainsaw Massacre.”

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20th Century Fox Television

#47. Mountain of Madness (1997)

- IMDb user rating: 8.6
- Votes: 1,745
- Season: 8
- Episode: 12

Set during a company-wide competition, this eighth season episode finds Homer and Mr. Burns getting stranded together inside a log cabin. As the isolation and desperation mount, so too do their respective states of dementia. As quirky as the episode might be, an earlier draft of the script was even more bizarre.

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20th Century Fox Television

#46. Homer Loves Flanders (1994)

- IMDb user rating: 8.6
- Votes: 1,816
- Season: 5
- Episode: 16

The show departs from one of its most recurring themes in this season five episode, which finds Homer taking on an obsessive affection for Ned Flanders. It was reportedly the last episode pitched by famous funnyman Conan O’Brien, who departed to headline his own late-night TV show. Homer’s iconic rendition of “Nacho Man” lives on in TV history.

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20th Century Fox Television

#45. Mother Simpson (1995)

- IMDb user rating: 8.6
- Votes: 1,836
- Season: 7
- Episode: 8

Homer reunites with the mother he never had in this classic episode, with actress Glenn Close providing the voice of Mona Simpson. Episode writer Richard Appel was married to author Mona Simpson at the time, though the character was moreover based on real-life radical Bernardine Dohrn. Because the final scene between Homer and his mom is so emotional, producers requested that the network leave it up during the closing credits.

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20th Century Fox Television

#44. Two Bad Neighbors (1996)

- IMDb user rating: 8.6
- Votes: 1,874
- Season: 7
- Episode: 13

It’s Homer Simpson versus former U.S. President George Bush, voiced by series regular Harry Shearer. Both the real-life George and Barbara Bush had previously made disparaging public remarks about the series, making the episode a joke-fueled rebuttal of sorts. Long before it aired, the writing staff and Barbara Bush engaged in a comical letter exchange.

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20th Century Fox Television

#43. Homie the Clown (1995)

- IMDb user rating: 8.6
- Votes: 1,899
- Season: 6
- Episode: 15

After becoming Springfield’s foremost Krusty the Clown impersonator, Homer finds himself in hot water with the local mob. The action culminates with both Homer and Krusty performing tricks for a purposefully stereotypical mafia don (voiced by Hank Azaria). Dick Cavett and Johnny Unitas both appear as themselves in guest speaking roles.

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20th Century Fox Television

#42. $pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling) (1993)

- IMDb user rating: 8.6
- Votes: 1,946
- Season: 5
- Episode: 10

Abandoning her role as the voice of reason, Marge takes on a massive gambling habit at Mr. Burns’ new casino. After getting kicked out of the very same casino, Bart starts his own and even books singer Robert Goulet (voiced by his real-life counterpart). The episode comes loaded with cultural references to real-life figures such as Howard Hughes and movies like “Rain Man” and “2001: A Space Odyssey.”

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20th Century Fox Television

#41. Treehouse of Horror VI (1995)

- IMDb user rating: 8.6
- Votes: 1,950
- Season: 7
- Episode: 6

The “Treehouse of Horror” episodes are nearly always laden with big laughs and classic cultural references, and this one is no exception. Its three segments respectively parody “Attack of the 50 Foot Woman,” “A Nightmare on Elm Street,” and “The Twilight Zone” episode “Little Girl Lost.” The final segment famously renders Homer in computer-animated 3-D before sending him into an even stranger dimension.

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20th Century Fox Television

#40. Itchy & Scratchy Land (1994)

- IMDb user rating: 8.6
- Votes: 1,962
- Season: 6
- Episode: 4

Making overt nods toward Disney—and movies like “Jurassic Park” and “Westworld”—this season six episode follows the Simpson family to Itchy & Scratchy Land. In the “Scratchtasia” segment, Disney-style animation goes in a brutally violent direction. Piling on the parody, the episode ends with some blatant jabs at then-failing Euro Disney.

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20th Century Fox Television

#39. Lisa's First Word (1992)

- IMDb user rating: 8.6
- Votes: 2,055
- Season: 4
- Episode: 10

As they try to get Maggie to speak, the Simpson family flashes back to the story of Lisa’s birth and early upbringing. Not only does the episode portray each child’s respective first words, but it shows the family moving into their home on Evergreen Terrace and meeting Ned Flanders for the first time. Legendary actress Elizabeth Taylor provides the voice of Maggie, who utters “Daddy” right before the closing credits.

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20th Century Fox Television

#38. El Viaje Misterioso De Nuestro Jomer (1997)

- IMDb user rating: 8.6
- Votes: 2,075
- Season: 8
- Episode: 9

Even by the show’s own standards, this season eight episode strikes a bizarre and unconventional accord. After swallowing a psychedelic hot pepper, Homer embarks on a hallucinatory journey of self-discovery. Appearing as his spirit guide is an insightful space coyote, voiced by singer Johnny Cash.

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20th Century Fox Television

#37. Homer Goes to College (1993)

- IMDb user rating: 8.6
- Votes: 2,197
- Season: 5
- Episode: 3

Conan O’Brien penned this season five episode, which sends Homer to Springfield University in pursuit of a degree. Inspired by juvenile college-themed films and shows, Homer engages in various pranks as he squares off against an affable dean. The episode itself takes direct cues from 1978’s “Animal House” and also incorporates a Monty Python reference.

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20th Century Fox Television

#36. Lisa's Substitute (1991)

- IMDb user rating: 8.6
- Votes: 2,479
- Season: 2
- Episode: 19

Actor Dustin Hoffman (credited under a pseudonym) lends his voice to this season two episode, tackling the role of the substitute teacher Mr. Bergstrom. Enraptured by Mr. Bergstrom’s unorthodox teaching methods and poignant insights, Lisa develops an early crush. Discounting a few previous background cameos, this episode marked the first appearance of Ralph Wiggum as a fleshed-out character.

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20th Century Fox Television

#35. Stark Raving Dad (1991)

- IMDb user rating: 8.6
- Votes: 2,702
- Season: 3
- Episode: 1

Season three opened with this iconic (for its time) episode, which finds Homer locked inside a mental institution. It’s there that he meets a delusional inmate by the name of Michael Jackson (voiced by Jackson himself under the name of John Jay Smith), who swears he’s the famous singer. Because of controversies surrounding the real-life Michael Jackson, the episode was recently pulled from circulation.

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20th Century Fox Television

#34. Bart's Comet (1995)

- IMDb user rating: 8.7
- Votes: 1,853
- Season: 6
- Episode: 14

A comet with Bart’s name on it is heading toward Springfield and threatening to doom all its inhabitants. So goes this hilarious episode, which eventually finds the townspeople shacking up in Ned Flanders’s bomb shelter. Look closely during the first group shot inside the bomb shelter and one can spot Waldo (from “Where’s Waldo?”) packed into the frame.

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20th Century Fox Television

#33. Boy Scoutz 'n the Hood (1993)

- IMDb user rating: 8.7
- Votes: 1,956
- Season: 5
- Episode: 8

A reference to “Boyz in the Hood” in name only, this episode opens with Bart and Millhouse taking a squishee-fueled bender through Springfield. They wake from their haze to discover they’ve signed up for the Boy Scouts, paving the way for the episode’s main story line. Actor Ernest Borgnine appears as himself in a speaking role.

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20th Century Fox Television

#32. Lemon of Troy (1995)

- IMDb user rating: 8.7
- Votes: 1,975
- Season: 6
- Episode: 24

Ripping a page out of Greek mythology, this episode centers on the perennial rivalry between Springfield and the neighboring town of Shelbyville. When the kids of Shelbyville steal Springfield’s beloved lemon tree, it sends Bart and his peers into enemy territory. One scene pokes fun at the endless number of “Rocky” films, and yet that number has now been exceeded with the latest “Creed” sequels.

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20th Century Fox Television

#31. And Maggie Makes Three (1995)

- IMDb user rating: 8.7
- Votes: 2,029
- Season: 6
- Episode: 13

It’s another flashback episode for the Simpson family, who recount the story of Maggie’s birth. The year was 1993 and Homer had just left the nuclear power plant, finally scoring his dream job of working at a bowling alley. This episode’s final shot ranks among the show’s most endearing moments.

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20th Century Fox Television

#30. Bart of Darkness (1994)

- IMDb user rating: 8.7
- Votes: 2,061
- Season: 6
- Episode: 1

Stuck in his room with a broken leg, Bart spies on his neighbors and ultimately suspects Ned Flanders of murder. The nods to “Rear Window” are so blatant that James Stewart’s character even makes a cameo. Along with the “Treehouse of Horror” installments and episodes like “Cape Feare,” “Bart of Darkness” is more or less a joke-laden remake of its source material.

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20th Century Fox Television

#29. Homer's Triple Bypass (1992)

- IMDb user rating: 8.7
- Votes: 2,120
- Season: 4
- Episode: 11

Homer’s outrageously unhealthy and stress-filled lifestyle finally catches up to him in this wrenching episode. In need of expensive heart surgery, he cuts costs by visiting the infamously incompetent Dr. Nick Riviera. The episode opens with clips from “COPS: In Springfield,” referring to Fox’s hit reality series.

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20th Century Fox Television

#28. Bart the Murderer (1991)

- IMDb user rating: 8.7
- Votes: 2,209
- Season: 3
- Episode: 4

Local crime boss Fat Tony (voiced by Joe Mantegna) makes his small-screen debut in this season three episode, which finds Bart working as a bartender for the mob. References to movies like “The Godfather” and “Goodfellas” are present, but surprisingly restrained. At the end of the episode, actor Neil Patrick Harris plays a dramatized TV movie version of Bart.

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20th Century Fox Television

#27. Homer at the Bat (1992)

- IMDb user rating: 8.7
- Votes: 2,373
- Season: 3
- Episode: 17

Awash with cameos from a number of Major League stars, this 1992 episode follows the Springfield Nuclear Power Plant softball team on its path to league victory. A ratings smash, it was later cited by showrunner Al Jean as one of the show’s most essential outings. In 2017, director Morgan Spurlock helmed a mockumentary built exclusively around this episode.

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20th Century Fox Television

#26. Hurricane Neddy (1996)

- IMDb user rating: 8.8
- Votes: 1,942
- Season: 8
- Episode: 8

With his house and life in shambles, perennial good Samaritan Ned Flanders lets out decades of suppressed rage that sends him to a mental institution, where he confronts his past through some unconventional therapy sessions. Briefly spotted at the same facility is the movie critic Jay Sherman (voiced by Jon Lovitz), who’s stuck in an endless cycle of saying his iconic catchphrase: “It stinks!”

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20th Century Fox Television

#25. Homer vs. the 18th Amendment (1997)

- IMDb user rating: 8.8
- Votes: 1,998
- Season: 8
- Episode: 18

Prohibition is back and Springfield is craving alcohol in the eighth season’s 18th episode, which is about the 18th amendment. When Homer becomes the town’s foremost bootlegger, it puts him in the crosshairs of an old-school government agent named Rex Banner (voiced by comedian Dave Thomas). Banner’s character is rooted in real-life lawman Eliot Ness, whose exploits provided the basis for the TV show (and later film) “The Untouchables.”

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20th Century Fox Television

#24. Bart Sells His Soul (1995)

- IMDb user rating: 8.8
- Votes: 2,078
- Season: 7
- Episode: 4

After selling his soul to Milhouse, Bart finds out the hard way that he gave up far more than he bargained for. The 1995 episode grapples with some deeply spiritual themes, though never loses its comedic edge. It’s likely no coincidence that all seven deadly sins have been accounted for by the time the closing credits roll.

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20th Century Fox Television

#23. Treehouse of Horror IV (1993)

- IMDb user rating: 8.8
- Votes: 2,191
- Season: 5
- Episode: 5

Another season means another “Treehouse of Horror” installment, and this one finds Homer selling his soul for a donut. The other respective segments serve up clever takes on “Bram Stoker’s Dracula” and “The Twilight Zone” episode “Nightmare at 20,000 Feet.” Conan O’Brien is credited as one of the co-writers.

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20th Century Fox Television

#22. Deep Space Homer (1994)

- IMDb user rating: 8.8
- Votes: 2,268
- Season: 5
- Episode: 15

Homer’s convinced he has the right stuff when he gets recruited by NASA, in their effort to boost public interest in space exploration. As virtually anyone can guess, total disaster ensues mid-flight. Real-life astronaut Buzz Aldrin appears as himself in a guest speaking role, as does musician James Taylor.

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20th Century Fox Television

#21. Flaming Moe's (1991)

- IMDb user rating: 8.8
- Votes: 2,404
- Season: 3
- Episode: 10

When Moe steals the recipe to Homer’s cocktail creation, his bar becomes the hottest locale in all of Springfield and beyond. Hovering just beneath the surface are some pointed observations on capitalism and intellectual property theft. In 2016, a Montreal bar once again robbed Homer of his due by serving Flaming Moe’s (i.e. not Flaming Homer’s) alongside pints of Duff beer.

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20th Century Fox Television

#20. Mr. Plow (1992)

- IMDb user rating: 8.8
- Votes: 2,423
- Season: 4
- Episode: 9

Here’s yet another classic episode that provides a not-so-subtle exploration on capitalism, as “The Simpsons” often does so well. After launching a lucrative snow plow business, Homer finds an unlikely adversary in Barney Gumble. The episode reveals Barney’s origins as a Harvard-bound prodigy who was pushed toward alcoholism with a little help from Homer.

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20th Century Fox Television

#19. One Fish, Two Fish, Blowfish, Blue Fish (1991)

- IMDb user rating: 8.8
- Votes: 2,533
- Season: 2
- Episode: 11

In one of the show’s more heartfelt episodes, Homer eats poisonous fish and gets confronted with his impending death. When it turns out he’s going to make it, he promises to live life to the fullest before heading to the couch with a bag of pork rinds. Larry King appears as himself and actor George Takei provides the voice of a character named Akira.

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20th Century Fox Television

#18. 22 Short Films About Springfield (1996)

- IMDb user rating: 8.9
- Votes: 2,183
- Season: 7
- Episode: 21

True to its name, this iconic episode comprises various short films about Springfield and its wacky residents. Everyone from Apu to principal Skinner to Bumblebee Man gets a story of his or her own, with some plotlines feeding into or overlapping with others (à la “Pulp Fiction”). This was one among a mere handful of episodes to feature credited writing from creator Matt Groening.

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20th Century Fox Television

#17. Rosebud (1993)

- IMDb user rating: 8.9
- Votes: 2,218
- Season: 5
- Episode: 4

The nods to “Citizen Kane” go beyond the title and start as early as the opening scene, with Mr. Burns recalling his childhood stuffed bear in cinematic style. That soon puts him in pursuit of his beloved Bobo, who passed through the hands of Adolf Hitler and Charles Lindbergh before ending up in Maggie Simpson’s possession. On its list of the best “The Simpsons” episodes of all time, Entertainment Weekly ranked this one at #4.

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20th Century Fox Television

#16. Homer the Smithers (1996)

- IMDb user rating: 8.9
- Votes: 2,229
- Season: 7
- Episode: 17

To ensure he won’t lose his job while on vacation, Mr. Smithers seeks the nuclear plant’s worst employee as his temporary replacement. That employee is none other than Homer Simpson, who bungles the job so spectacularly that Mr. Burns is forced to become self-sufficient. This episode represents one of the precious few occasions where Mr. Burns actually remembers Homer’s name.

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20th Century Fox Television

#15. Who Shot Mr. Burns? Part Two (1995)

- IMDb user rating: 8.9
- Votes: 2,281
- Season: 7
- Episode: 1

Picking up where the season six finale left off, season seven’s opener uncovers the mystery behind who shot Mr. Burns. Suspects include pretty much everyone in town, though it’s Smithers who emerges as the likely culprit. “That would’ve made a lot more sense,” Lisa says in a later episode.

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20th Century Fox Television

#14. Homer's Phobia (1997)

- IMDb user rating: 8.9
- Votes: 2,370
- Season: 8
- Episode: 15

John Waters guest stars as the voice of John, a new friend and lovable store owner of the LGBTQ+ persuasion. That’s bad news for Homer, who has obtuse and uneducated views on sexual identity. Fox network president John Matoian was initially reluctant to air the episode which was only approved for broadcast after he stepped down.

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20th Century Fox Television

#13. Homer the Great (1995)

- IMDb user rating: 9
- Votes: 2,253
- Season: 6
- Episode: 12

Homer overcomes decades of rejection when he’s put in charge of the Stonecutters, a secret society modelled after the Freemasons. The episode features the catchy song “We Do,” which earned an Emmy nomination for Outstanding Music and Lyrics. Actor Patrick Stewart provides the voice of Number One, former leader of the underground cult.

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20th Century Fox Television

#12. King Size Homer (1995)

- IMDb user rating: 9
- Votes: 2,388
- Season: 7
- Episode: 7

To work from home on disability, Homer takes his unhealthy diet to extremes. While the story line is arguably offensive by today’s standards, it takes a more empathetic approach than one might expect. A drinking bird desk toy that Homer uses was gifted to him from his brother in a previous episode.

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20th Century Fox Television

#11. Homer Badman (1994)

- IMDb user rating: 9
- Votes: 2,448
- Season: 6
- Episode: 9

Few classic episodes continue to resonate like this one from season six, in which Homer gets accused of sexual harassment. The story puts everything from exploitative media practices to voyeuristic video culture to unchecked mob outrage in its crosshairs, and all before smartphones were even a thing. Homer is eventually cleared of the charges, but that does little to assuage the episode’s unsettling ramifications.

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20th Century Fox Television

#10. Homer the Heretic (1992)

- IMDb user rating: 9
- Votes: 2,596
- Season: 4
- Episode: 3

Underlying several iconic episodes are some surprisingly spiritual themes, which reinforce rather than negate the importance of faith in a higher power. Homer discovers as much after skipping out on church and then suffering the near-fatal consequences. This is the first episode to feature God as a character, who’s distinguished from lowly mortals by his oversize presence and his five fingers on each hand.

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20th Century Fox Television

#9. Marge vs. the Monorail (1993)

- IMDb user rating: 9
- Votes: 2,985
- Season: 4
- Episode: 12

Vulture’s Adam Frucci once described “Marge vs. the Monorail” as the “best sitcom episode ever” and he might very well be right. Written by Conan O’Brien, it dispenses with pop-culture references and rapid-fire gags before leaving the town of Springfield with a massive cash surplus. Enter a monorail salesman named Lyle Lanley (voiced by Phil Hartman), whose crafty scheme comes straight out of capitalism’s worst nightmares.

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20th Century Fox Television

#8. Who Shot Mr. Burns? Part One (1995)

- IMDb user rating: 9.1
- Votes: 2,525
- Season: 6
- Episode: 25

Taking inspiration from TV’s “Dallas” and its “who shot JR” story line, “The Simpsons” veers into serialized territory with this sixth season closer. After blocking out the sun and tightening his control over Springfield, Mr. Burns gets shot by one of the town’s inhabitants. Did Homer finally snap over the fact that his boss never remembers his name, or is musician Tito Puente (voiced by himself) to blame?

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20th Century Fox Television

#7. Treehouse of Horror V (1994)

- IMDb user rating: 9.1
- Votes: 2,657
- Season: 6
- Episode: 6

A short story by Ray Bradbury, “Soylent Green,” and “The Shining” get respectively parodied in this acclaimed “Treehouse of Horror” installment. As if that weren’t referential enough, the episode’s introduction pays homage to the 1960s TV series “The Outer Limits.” Add to that Moe’s “gang of ghouls,” which appears in the first segment and includes a host of classic horror movie characters.

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20th Century Fox Television

#6. The Springfield Files (1997)

- IMDb user rating: 9.1
- Votes: 2,666
- Season: 8
- Episode: 10

While not the only crossover in “The Simpsons” history, this one ranks the highest amongst fans. When Homer spots an alien on his way home from the bar, “The X-Files” Agents Mulder (voiced by David Duchovny) and Scully (voiced by Gillian Anderson) take on their worst assignment yet. “Star Trek” alum Leonard Nimoy guest stars as himself, marking the second of two appearances on the show.

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20th Century Fox Television

#5. Last Exit to Springfield (1993)

- IMDb user rating: 9.1
- Votes: 2,730
- Season: 4
- Episode: 17

“Dental plan! Lisa needs braces. Dental plan! Lisa needs braces...” That’s the sound of Homer’s brain as it struggles to link his company’s lapsing insurance policy with his daughter’s last trip to the dentist. So begins his role as de facto union leader, putting him up against the likes of Monty Burns in this prescient episode.

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20th Century Fox Television

#4. The City of New York vs. Homer Simpson (1997)

- IMDb user rating: 9.1
- Votes: 2,787
- Season: 9
- Episode: 1

Season nine opened with a trip to the Big Apple, Simpsons style. As Homer tries to take back his car from the city, each family member undergoes many misadventures. From the Harlem Globetrotters couch gag to the various urban landmarks, this episode is replete with New York’s timeless iconography.

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20th Century Fox Television

#3. Cape Feare (1993)

- IMDb user rating: 9.1
- Votes: 3,104
- Season: 5
- Episode: 2

Spoofing both 1962’s “Cape Fear” and the 1991 remake, this classic episode sees the return of Bart’s arch nemesis, Sideshow Bob (voiced by Kelsey Grammer). While the story line is lifted straight out of the source material, it also references other horror movies such as Alfred Hitchcock’s “Psycho.” As of this article, Sideshow Bob has appeared in at least 20 episodes overall.

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20th Century Fox Television

#2. You Only Move Twice (1996)

- IMDb user rating: 9.2
- Votes: 3,564
- Season: 8
- Episode: 2

Homer’s cushy new job sends the Simpson family to the idyllic town of Cypress Creek and puts him under the wing of charming supervillain Hank Scorpio (voiced by Albert Brooks). Not only does the episode parody the James Bond franchise—hence the title—but a Bond-like superspy makes a short-lived appearance. Driving the parody home is a song called “Scorpio,” which plays over the closing credits.

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20th Century Fox Television

#1. Homer's Enemy (1997)

- IMDb user rating: 9.3
- Votes: 3,532
- Season: 8
- Episode: 23

His name is Frank Grimes but everyone knows him best as “Grimey,” and he rues the day he met Homer Simpson. That lays the groundwork for this truly iconic outing, which takes on an uncommonly dark tone by its final scene. It’s one of Matt Groening’s favorite episodes and an ultimate fan favorite as well, with the 9.3 IMDb rating to show for it.

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