Top 10 The Simpsons Episodes of the 90s

First up on our list is “Homer Goes to College,” the third episode of The Simpsons‘ fifth season. As a college student myself, I found this episode to be really funny.

After causing a chaotic nuclear plant meltdown, Homer is forced to enroll at Springfield University to keep his job. But being classic Homer, he thinks college is all about slacking off, drinking, and pranks rather than studying and academics.

One of the episode’s most memorable scenes involves Homer persuading three nerds to help him pull a major prank: stealing the mascot pig from their rival school. Homer’s irresponsible nature and idiotic influence take over when hanging out with these straight-laced college students. Their prank leads to all of their expulsions. As a result, the nerds move in with the Simpsons, causing even more chaos as they’re the worst possible roommates.

This episode hilariously nails the traditional and crazy college experience through the show’s trademark satirical humor.

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Next up on our list is “The Itchy & Scratchy & Poochie Show.” This is the fourteenth episode of The Simpsons eighth season. As someone who enjoys pop culture, I found this episode particularly entertaining, as it pokes fun at the entertainment industry’s tendency to revamp shows by adding new characters in a desperate bid to boost ratings.

In the episode, the producers of the Itchy & Scratchy Show decide to introduce a new character, Poochie, to help revive the interest of viewers of the series. Homer auditions and lands the role of Poochie’s voice, bringing his unique goofiness and cluelessness to the job. Despite his best efforts, the addition of Poochie fails to resonate with fans, leading to Poochie’s removal from the show.

When curating this list, this episode stuck out to me as one of the top The Simpsons episodes of the 90s because of its satirical take on the entertainment industry.

Next up on our list is “Homie the Clown,” the fifteenth episode of season six of The Simpsons.

To begin, the story kicks off with Krusty the Clown in debt to the Springfield Mafia due to his gambling addiction. To make extra money, Krusty opens a clown college, which Homer joins after seeing a billboard. After graduating from college, Homer starts impersonating Krusty at various events in town. He enjoys the perks of being mistaken for Krusty and gets special treatment. However, this comes back to bite him when the Mafia kidnaps Homer, thinking he is the real Krusty.

The episode, filled with similar mafia themes, includes clever references to iconic movies like The Godfather. Its humor and commentary on the similarities between Homer and Krusty make it a standout episode that is definitely worth making our list of the top 10 The Simpsons episodes.

Next on our list is “Treehouse of Horror V,” the sixth episode of season six of The Simpsons. “Treehouse of Horror” episodes from The Simpsons are annual Halloween specials known for their unique and often spooky storytelling. Each episode typically contains three separate segments, each parodying horror, science fiction, or supernatural themes. This episode parodies classic horror and sci-fi themes across its three segments: “The Shinning,” “Time and Punishment,” and “Nightmare Cafeteria.”

In “The Shinning,” a spoof of The Shining, the Simpsons become caretakers at Mr. Burns’ mountain lodge. The lack of TV and beer drives Homer insane. The next segment, “Time and Punishment”, features Homer accidentally turning a toaster into a time machine. This leads to various chaotic alternate realities. The final segment, “Nightmare Cafeteria”, shows Principal Skinner and Lunch Lady Doris turning students into cafeteria food … truly spooky.

This episode is memorable for its dark humor and clever references to films like The Shining and Soylent Green. As the screen fades back to the Simpson household, Marge tells the family that they need to go to bed. Instead, they break into a rendition of “One” from the musical A Chorus Line. This unexpected musical finale is in great contrast to the horror-themed stories that came before it. It provides a light-hearted end to the episode, earning it a place on our top 10 The Simpsons episodes list.

Another iconic episode that made our top 10 The Simpsons episodes list is “You Only Move Twice,” the second episode of season eight of The Simpsons. Originally aired on November 3, 1996, this episode is a fan favorite for its memorable guest star, Albert Brooks. The story revolves around the Simpsons moving to a new town where Homer unknowingly works for a supervillain.

In the episode, Homer gets a job at the Globex Corporation, requiring the family to move to Cypress Creek. Homer’s new boss, Hank Scorpio, appears friendly and supportive, but what Homer doesn’t know is that he is a supervillain. While Homer excels at his job, the rest of the family struggles with their new environment. As Homer thrives at work, Scorpio continues his villainous activities, including threats to the United Nations and attempts to kill his arch-nemesis. Homer, notorious for his aloofness and stupidity, does not notice these activities.

Later, despite his success and after pleas from his family, Homer and The Simpsons decide to move back to Springfield. In a parting gesture, Scorpio gives Homer a gift of the Denver Broncos. Although Homer is annoyed that he didn’t get the Dallas Cowboys like he wanted.

The seventeenth episode of season four of The Simpsons, “Last Exit to Springfield,” originally aired on March 11, 1993, and many regard it as one of the series’ best. This episode’s plot revolves around Homer becoming president of the Springfield Nuclear Power Plant’s union and leading a strike.

Frustrated by the loss of their dental plan in exchange for a keg of beer, Homer rallies the workers to become their new leader. Mr. Burns challenges the union by revoking their dental benefits. After a city-wide blackout fails to break the strike, Mr. Burns gives in. He reinstates the dental plan in exchange for Homer resigning as president.

Ultimately, scenes of Lisa’s successful protest song and Homer’s heroic negotiation tactics make “Last Exit to Springfield” such an iconic episode. It made sure to snag a spot on our top 10 The Simpsons episodes list for its satirical take on labor and corporate greed.

Up next on our list is “Marge vs. the Monorail,” the twelfth episode of the fourth season of The Simpsons. After speaking to multiple die-hard The Simpsons fans, this episode is consistently a favorite. The story begins when Springfield comes into a large sum of money from a fine on Mr. Burns’ nuclear power plant.

At a town meeting to decide how to spend the money, conman Lyle Lanley convinces the residents to build a monorail instead of fixing the town’s infrastructure. Marge is one of the first to become suspicious of Lanley’s motives. Later, Marge’s concerns grow, especially when Lanley disappears with the money.

However, Homer is chosen to be the monorail conductor by random drawing, and he eagerly embraces his role. During the maiden voyage, the monorail malfunctions and speeds out of control. Marge teams up with Leonard Nimoy, who happens to be aboard, to save the passengers.

This episode makes our top 10 list because “Marge vs. the Monorail” cleverly satirizes government spending and the persuasive power of charismatic salesmen.

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“Lisa the Vegetarian” is episode five from season seven of The Simpsons, which first aired on October 15, 1995. The episode follows Lisa Simpson’s decision to become a vegetarian after bonding with a lamb at a petting zoo.

During this episode, Lisa is mocked by both family and peers for her new lifestyle choice. At school, Principal Skinner labels her an “agitator” after she objects to dissecting a worm in class. During a barbecue, Homer ridicules Lisa’s attempt to serve vegetarian dishes like gazpacho.

An important part of this episode is when Lisa briefly gives in to peer pressure and eats what she thinks is a hot dog. Later, thanks to Apu, she discovers it’s tofu. He introduces her to Paul and Linda McCartney, reinforcing her commitment to vegetarianism and teaching her to tolerate differing opinions.

“Lisa the Vegetarian” made our list for its cultural references and handling of sensitive themes, like the exploration of ethical eating. In fact, it has received awards, such as the 1996 Environmental Media Award for Best Television Episodic Comedy, for its portrayal of environmental and animal rights issues.

Another standout episode on our list is “Mr. Plow,” the ninth episode of season four of The Simpsons. Dan Castellaneta, who voices various characters on The Simpsons, won an Emmy for his voice work in this episode, solidifying it as one of the series’ best.

In the episode, Homer buys a snowplow and starts a business plowing driveways after crashing his car. Thanks to Lisa’s idea of making a commercial, his business, “Mr. Plow,” becomes a huge success. However, Barney, envious of Homer’s success, starts a rival company, Plow King, and quickly puts Homer out of business.

In an attempt to regain his customers, Homer tricks Barney into plowing a dangerous mountain, which leads to Barney getting trapped in an avalanche. Feeling guilty, Homer rescues him, and they decide to become business partners. Unfortunately, a sudden warm spell melts all the snow, putting both out of business.

Another iconic episode in our top 10 The Simpsons episodes is “Cape Feare.” This is the second episode of season five. This episode features Kelsey Grammer in his third appearance as Sideshow Bob, who tries to kill Bart after getting out of jail. The episode parodies the film Cape Fear and alludes to other horror classics like Psycho.

In the episode, Sideshow Bob sends threatening letters to Bart from prison, seeking revenge and plotting to kill him. The episode follows Bob, after his release, confronting Bart at a movie theater. Realizing Bob sent the letters, the Simpsons join the Witness Protection Program. They move to a houseboat in Terror Lake and change their last name to “Thompson” to protect their identity. Bob follows them here, continuing his attempt to kill Bart.

This episode made my list because it makes many iconic references and blends suspense and humor. Sideshow Bob’s relentless pursuit of Bart offers a thrilling plot, while the rake scene and musical performance at the end of the episode add a layer of unforgettable comedy.