- IMDb user rating: 8.8
- Season 7, episode 4
- Air date: Oct. 8, 1995

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.

- IMDb user rating: 8.8
- Season 5, episode 5
- Air date: Oct. 28, 1993

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.

- IMDb user rating: 8.8
- Season 5, episode 4
- Air date: Oct. 21, 1993

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 "Simpsons" episodes of all time, Entertainment Weekly ranked this one #4.

- IMDb user rating: 8.8
- Season 2, episode 11
- Air date: Jan. 24, 1991

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.

- IMDb user rating: 8.8
- Season 4, episode 9
- Air date: Nov. 19, 1992

Here's yet another classic episode that provides a not-so-subtle exploration of 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.

- IMDb user rating: 8.8
- Season 8, episode 15
- Air date: Feb. 16, 1997

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.

- IMDb user rating: 8.8
- Season 8, episode 18
- Air date: March 16, 1997

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."

- IMDb user rating: 8.8
- Season 3, episode 10
- Air date: Nov. 21, 1991

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.

- IMDb user rating: 8.9
- Season 4, episode 3
- Air date: Oct. 8, 1992

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 oversized presence and having five fingers on both hands.

- IMDb user rating: 8.9
- Season 6, episode 13
- Air date: Jan. 22, 1995

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.

- IMDb user rating: 8.9
- Season 5, episode 15
- Air date: Feb. 24, 1994

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.

- IMDb user rating: 9.0
- Season 7, episode 1
- Air date: Sept. 17, 1995

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.

- IMDb user rating: 9.0
- Season 9, episode 1
- Air date: Sept. 21, 1997

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.

- IMDb user rating: 9.0
- Season 7, episode 21
- Air date: April 14, 1996

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 their 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.

- IMDb user rating: 9.0
- Season 4, episode 17
- Air date: March 11, 1993

"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.

- IMDb user rating: 9.0
- Season 7, episode 7
- Air date: Nov. 5, 1995

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 by his brother in a previous episode.

- IMDb user rating: 9.0
- Season 6, episode 12
- Air date: Jan. 8, 1995

Homer overcomes decades of rejection when he's put in charge of the Stonecutters, a secret society modeled 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.

- IMDb user rating: 9.0
- Season 6, episode 9
- Air date: Nov. 27, 1994

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.

- IMDb user rating: 9.1
- Season 8, episode 10
- Air date: Jan. 12, 1997

While not the only crossover in "The Simpsons" history, this one ranks the highest among fans. When Homer spots an alien on his way home from the bar, "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.

- IMDb user rating: 9.1
- Season 4, episode 12
- Air date: Jan. 14, 1993

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, the episode 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.

- IMDb user rating: 9.2
- Season 8, episode 2
- Air date: Nov. 3, 1996

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 super spy makes a short-lived appearance. Driving the parody home is a song called "Scorpio," which plays over the closing credits.

- IMDb user rating: 9.2
- Season 6, episode 25
- Air date: May 21, 1995

Taking inspiration from TV's "Dallas" and its "Who shot J.R.?" storyline, "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?

- IMDb user rating: 9.2
- Season 6, episode 6
- Air date: Oct. 30, 1994

A short story by Ray Bradbury, "Soylent Green," and "The Shining" all get 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.

- IMDb user rating: 9.2
- Season 5, episode 2
- Air date: Oct. 7, 1993

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 storyline is lifted straight out of the source material, it also references other horror movies such as Alfred Hitchcock's "Psycho." Sideshow Bob has since appeared in at least 20 episodes overall.

- IMDb user rating: 9.3
- Season 8, episode 23
- Air date: May 4, 1997

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.