25 All-Time Iconic Episodes Of 'The Simpsons'

“The Simpsons” is one of the longest-running shows currently on television and continues to be a popular success. It first aired on Fox in late 1989 and has since found its way into people’s hearts worldwide. From its zany cast of characters, clever writing, and satirical nature, there’s no sign that this show can be canceled anytime soon. With hundreds of episodes airing over 30 years, “The Simpsons” have solidified themselves as an irreplaceable part of American culture and created backstory lore that won’t soon be forgotten. The show remains as fresh today as it was when it first premiered, proving timeless for viewers of all ages.

I am going to share the most iconic episodes of The Simpsons sorted by their average IMDB ratings.

25 Most Iconic Episodes of ‘The Simpsons’

With 34 seasons and over 700 episodes, it’s no surprise that The Simpsons has seen some great episodes throughout its three decades. This show has earned its reputation from cult stories featuring classic one-off characters to heartwarming tales about family tensions. With such an expansive catalog of great classic TV, narrowing things down takes time and effort. Still, the 12 most iconic episodes offer something for everyone.

Homer’s Enemy

Season: 8, Episode: 23

IMDB Rating: 9.3 by 6.3k Votes

Aired on: May 4, 1997

The episode “Homer’s Enemy” from The Simpsons is one of the most well-loved episodes by both fans and critics. It stands out for introducing Frank Grimes, a realistic individual who takes his job seriously and puts in the hard work that Homer often overlooks. This juxtaposition creates dynamic tension and forces viewers to take a closer look at Homer’s awful character flaws, which makes it one of the most thought-provoking episodes in the series. Despite Grimes eventually exiting Springfield after being driven insane, his entrance made a lasting impression on the show, forcing viewers to consider what was sometimes an uncomfortable self-reflection about the characters’ lives.
You Only Move Twice

Season: 8, Episode: 2

IMDB Rating: 9.2 with 6k Votes

Aired on: November 3, 1996

You Only Move Twice, part of The Simpson’s eighth season and episode two, is still beloved by longtime fans for its clever writing. The story follows the Simpson family as they move to Cypress Creek for a better life. Things appear to be going well at their new home thanks to the service of a kindly yet mysterious employer, who we later learn is an evil genius named Hank Scorpio. He forces Homer into an unlikely mission, including taking over the East Coast nuclear missile silos. He allows him access to incredible amenities, such as a giant volcano and a bowling alley. The hilarious plot becomes more outrageous when Secret Agent Number Three refuses to report Scorpio’s nefarious plans. It’s a comic gem that proves you can find laughter even in potentially dark circumstances!
Cape Feare

Season: 5, Episode: 2

IMDB Rating: 9.2 by 5.3k Votes

Aired on: October 7, 1993

Season 5 of The Simpsons was packed with comedic gold, but many fans remember the episode with Sideshow Bob particularly fondly. The family is placed in witness protection mode when it looks like there’s no way to keep Bart safe from Bob’s schemes.

This episode brought many twists and turns, with its underlying theme centered around the classic gangster movie “Cape Fear” starring Robert de Niro. It begins when Sideshow Bob receives parole and returns to kill Bart in retribution for all the times he foiled his plans. To protect Bart and the rest of their family, Homer relocates them to an isolated cabin in Cypress Creek.

Of course, as luck would have it, Sideshow Bob follows them there, and hilarity ensues from that point on as he attempts one plan after another to carry out his mission. This episode involves lots of comedy, dramatic moments and even a few musical interludes scattered throughout. It has been said this episode is among their best and has been critically acclaimed by critics and fans, making it well worth watching.
Marge vs. the Monorail

Season: 4, Episode: 12

IMDB Rating: 9.1 with 5.3k Votes

Aired on: January 14, 1993

The episode “Marge vs. the Monorail,” from season 4 of The Simpsons, is a comedic classic. In this delightfully absurd 22 minutes, Springfield’s government is persuaded by a shady salesman, Lyle Lanley (voiced brilliantly by Leonard Nimoy), to build a monorail to nowhere. In what can only be dubbed a moment of inspired lunacy, the townspeople embark on this wasteful venture. Marge Simpson is the only one with enough wit and grit to stop them. Of course, it all ends with hilarity and destruction as the monorail careens off its rails and through Springfield’s town hall – but that’s just another day in Wiggyland! Overall, “Marge vs. The Monorail” is an iconic Simpsons episode and will long remain a testament to the infallible creativity of its writers.
The City of New York vs. Homer Simpson

Season: 9, Episode: 1

IMDB Rating: 9.0 with 4.7k Votes

Aired on: September 21, 1997

The City of New York vs. Homer Simpson from The Simpsons Season 9, episode 1, is an epic battle between the Big Apple and everybody’s favorite, Homer. After his car breaks down in Manhattan, Homer finds himself hauled into court for driving without a license. His day turns into chaos and comedy as maniacal lawyer Lionel Hutz attempts to get him off the hook by citing numerous fictitious laws and precedents. Homer gets help from no less than Mayor Quimby himself along the way! When under pressure and in need of sage advice, Homer is reminded that there’s no “Moe” opinion than his own – which ultimately saves him from jail time, much to the immense pleasure of both himself and everyone watching this hilarious episode.
Who Shot Mr. Burns? Part Two

Season: 7, Episode: 1

IMDB Rating: 9.0 with 4k Votes

Aired on: September 17, 1995

With a pair of binoculars in hand, the mystery of who shot Mr. Burns begins to unravel in The Simpsons Season 7 Episode 1. After hitting him with a clue-by-four allegedly by Maggie Simpson, the search for a shooter leads investigators to Skinner’s Office, where Superintendent Chalmers found what appeared to be a rifle belonging to Bart. Of course, Bart eagerly denies his involvement and claims he played around with plastic toys on the roof when Mr. Burns passed by. While Bart may seem innocent enough, Homer manages to spoil any chance at an acquittal when he reveals that the gun belonged to him and used it previously to shoot rabbit pelt out of desperation. With no other suspects present in the area at the time of the attempted murder, only one conclusion can be reached Homer Simpson is indeed the culprit responsible for attempted murder against Springfield’s most notorious billionaire, Mr. Burns!
Homer The Smithers

Season: 7, Episode: 17

IMDB Rating: 8.8 with 3.9k Votes

Aired on: February 25, 1996

The beloved animated comedy The Simpsons Season 7, episode 17 brings viewers an iconic pairing in the form of Mr. Burns and Smithers but with a surprising new addition to the mix: Homer Simpson! When Smithers is sent on vacation, Mr. Burns looks to replace him with “the last man on earth capable of surpassing his talents” and chooses his reliable reactor core cleaner; much to Smithers’ dismay, Homer is the only candidate for the position. This episode hilariously examines their unique relationship and showcases how Homer’s incompetence serves as a foil to show just how competent Mr. Burns truly is and why he needs someone like Smithers by his side throughout each misadventure.
Homer at the Bat

Season: 3, Episode: 17

IMDB Rating: 8.7 with 4.4k Votes

Aired on: February 20, 1992

One of the most beloved episodes of the classic cartoon The Simpsons is the iconic story of Homer at the Bat in season 3, episode 17. During this episode, Mr. Burns signs nine Major League Baseball superstars to try and win a softball game against a rival business. We watch as these superstars fumble, dropping pop flies and more, before giving way to faithful employee Homer Simpson. As sharp viewers predicted, Homer somehow saves the day with a miraculous hit that sends Mr. Burn’s team soaring to victory. Despite the fictitious baseball stars pulling from the likes of Wade Boggs and Don Mattingly, it’s Homer and his simple ‘roll-in-dust’ technique that proves successful time and time again for Springfield Nuclear Power Plant!
Lisa’s Substitute

Season: 2, Episode: 19

IMDB Rating: 8.6 with 4.6k Votes

Aired on: April 25, 1991

Lisa’s Substitute from The Simpsons Season 2, episode 19, is a powerful story that tells the tale of a substitute teacher (Mr. Bergstrom) who imparts an essential lesson to Lisa. Having grown tired of her school’s lessons, Lisa finds joy and challenge in Mr. Bergstrom’s approach to teaching by giving her more responsibilities and, thus, more confidence. As the episode progresses, it is revealed that Mr. Bergstrom will only be around for a limited period before his departure. This saddens Lisa as she finds out he must leave as soon as possible due to personal reasons. However, Mr. Bergstrom promises that while physically he may not be there anymore, his lessons remain with her forever, which allows Lisa to confront what she cares about most – her relationship with her father, Homer. This heartfelt reminder shows Lisa how powerful she is. It ultimately provides her with the strength to reach out to Homer again.
Barthold

Season: 27, Episode: 9

IMDB Rating: 8.4 with 2.2k Votes

Aired on: December 13, 2015

The ninth episode of The Simpsons Season 27, titled ‘Barthood,’ provides a creative and thoughtful look at the life of a young Bart Simpson. Through poignant flashbacks, viewers are taken on an emotional journey where they see Bart growing up, making mistakes, and ultimately learning essential life lessons. The show cleverly frames this story within its usual style of tongue-in-cheek humor and allusions to pop culture. Viewers are left reflecting on how the events of this episode not only reflect what it is like for young Bart but also the broader themes of growing up that resonate with all of us.
Burns Verkaufen der Kraftwerk

Season: 3, Episode: 11

IMDB Rating: 8.2 with 3.4k Votes

Aired on: December 5, 1991

In the third season of The Simpsons, the episode “Burns Verkaufen der Kraftwerk” saw Mr. Burns trying to sell off his nuclear power plant. After unsuccessfully trying to create a peaceful transaction with rival power plant entrepreneur Lindsey Naegle, Burns decides that he has had enough and instead opts to take full advantage of his position to deliver a curveball that throws Naegle for a loop. In response, Smithers conjures up what is likely one of the most excellent savvy sales tactics ever seen on the small screen: coercing Naegle into purchasing the plant by citing her love for puppies and pestering her with puppy-related chants until she agrees. Ultimately, the ploy works as Naegle signs off on it. Mr. Burns can finish his transaction before preparing for a prime-time power barge excursion.
Skinner’s Sense of Snow

Season: 12, Episode: 8

IMDB Rating: 7.9 with 2.5k Votes

Aired on: December 17, 2000

The story of Skinner’s Sense of Snow is a hilarious episode from The Simpsons Season 12. Principal Skinner sends the school on an unexpected three-day Christmas vacation after incorrectly predicting the snow won’t fall for Springfield. Still, the opposite occurs, resulting in chaos. The misadventure brings forth plenty of comedic moments and touching, heartfelt scenes that make this episode one of the most memorable from The Simpsons. Every time this episode airs, it brings smiles and laughter while simultaneously tugging at our heartstrings with its charming character relationships.
Treehouse of Horror V

Season: 6, Episode: 6

IMDb Rating: 9.2 by 4.8k Votes

Aired on: Feb 5, 1996

This episode is divided into three parts, the first short story is a parody of the Movie “The Shinning” where Mr. Burns employs the Simpsons to take care of his mansion during the winters. Mr.Burns confiscates his beer and television which makes him crazy. Homer loves his beer and TV and he would do anything, run any lengths for it. Moe then informs him that killing his family will get his beer and television, to which he readily agrees. Going on a hunt for his family, he is knocked down by Marge with a baseball bat. The second short story, “Time and Punishment,” deals with Homer trying to fix his Toaster and by mistake, converting it into a time machine. He travels back to prehistoric times and turns the present into a city where Ned Flanders is the ultimate ruler. In the third short story, “Nightmare Cafeteria” of the episode, Principal Skinner tries to deal with a meat problem in an unorthodox way and decides to kill children for meat sources. There is one ‘Treehouse of Horror episode in every season of the series, and the one from season six is considered the best one. The three parts are made very well and there contains loads of dark turns and gore in all of the parts.

Iconic Scene/Dialogue

Marge: Hello once again. As usual, I must warn you that this year’s Halloween special is very, very scary, and those of you with young children may want to send them off to bed-(Someone hands her a piece of paper)Oh my! The show seems so scary that Congress won’t even let us show it. Instead, they suggested the 1947 classic Glenn Ford movie 200 Miles to Oregon. Mr. Burns: (after an elevator empties a huge amount of blood) Hmmm… that’s odd. Usually, the blood gets off on the second floor.
Who Shot Mr. Burns? Part 1

Season: 6, Episode: 25

IMDb Rating: 9.2 by 4.4k Votes

Aired on: Jul 2, 1995

While burying the dead, Groundskeeper Wille discovers an oilfield under the elementary school. Principal Seymour consults the children to decide how to spend their newfound wealth. When Burns is unsuccessful in tricking Skinner, he sets up a slant oil rig which causes huge problems for the citizens like Moe, Barney, and even Abe, and enrages the whole school for stealing their resources. Homer is angry that Burns does not remember his name at the plant. When Homer sends Burns a box of sweets, the whole Simpson family receives a thank you card, except for Homer. This sends Homer into a rage fit and security has to carry him out. Enraged by Burns’s actions, Homer and the rest of the city swears vengeance. After attending a town meeting, Mr, Burns gets into an altercation with someone in the dark, is shot, and passes out near a sundial.

Iconic Scene/Dialogue

Homer: [out of breath] Here’s your package, Mr. Burns.Mr. Burns: [sputters] My name is the return address, you senseless dunderpate. Smithers, who is this nincompoop? Grampa: The lamp is getting away!Bart: That’s my dog, man.Grampa: So long, lamp.
Last Exit To Springfield

Season: 4, Episode: 17

IMDb Rating: 9.0 by 4.9k Votes

Aired on: Mar 11, 1993

At a regular dental checkup, it is discovered that Lisa would require braces. Marge calls Homer to use the dental insurance that he receives from his job. Later that day, during a union meeting Carl announces that their Dental insurance is being revoked in favor of a Beer keg. Paniked Homer reminds everyone how important the dental plan is, and is made the leader of a revolt against the rule change.

Iconic Scene/Dialogue

Homer: (answering the door) Who is it?Voice: Goons.Homer: Who?Voice: Hired goons.Homer: Hired goons? (opens the door; goons take Homer away) Dr. Wolfe: I’m also afraid little Lisa is going to need braces.Lisa: Oh, no! I’ll be socially unpopular! More so!
The Springfeild Files

Season: 8, Episode: 10

IMDb Rating: 9.0 by 4.4k Votes

Aired on: Mar 30, 1997

While returning home after having 10 beers at Moe’s, a drunken Homer is forced to walk home after a Breathalyzer test. While navigating his way back home, Homer takes a wrong turn and ends up stranded in the woods, looking around, Homer notices a gaunt glowing Alien and runs away scared. When no one believes his story, he contacts agents Fox Mulder and Dana Scully from the FBI to investigate his case. A crossover episode between two of the most loved Fox IPs, The Simpsons and X-files turned out to be one of the series’ best episodes. The chemistry between the crossover characters is really fun to watch, and the mystery element keeps you gripped.

Iconic Scene/Dialogue

Marge: Have you been drinking?Homer: No! Well, ten beers. Bart: (telling a scary story) …and that’s how much money college will cost for Maggie.Homer: No… no… NOOOOOOOOOOO!
22 Short Films about Springfield

Season: 7, Episode: 21

IMDb Rating: 8.9 by 4.8k Votes

Aired on: Aug 18, 1996

As the name of the episode suggests, it contains 22 short stories about the mundane life of all the identifiable characters when Bart ponders over the daily lives of Springfield citizens and if they did anything interesting in their lives. With a total of 22 stories told in a single episode, it would be hard to pick one but the standout short in the short would be the Principal’s disastrous steamed hams lunch with Superintendent Chalmers. Another fan-favorite is Milhouse’s Pulp-fiction-inspired adventure.

Iconic Scene/Dialogue

[Skinner enters and leaves the kitchen swiftly upon seeing it is now on fire]Skinner: [yawn] Well, that was wonderful. A good time was had by all. I’m pooped.Chalmers: Yes, I should be–good lord, what is happening in there?!Skinner: Aurora Borealis? Bart: Milhouse, do you ever think about the people in those cars?Milhouse: I try not to. It makes it harder to spit on ’em.
Homer The Heretic

Season: 4, Episode: 3

IMDb Rating: 8.9 by 4k Votes

Aired on: Oct 8, 1992

After noticing the stinging cold outside and ripping his pants when trying to wear them, Homer decides to skip going to the church. While home, Homer goofs around the house and treats himself to all the fatty food he likes. When the family returns, Homer announces that he will never go the church again, a decision he’d later regret. This very relaxed and laid-back episode would make even the watcher want to relax a little. Watching Homer goof around in his house is loved by the audience and all love the twist at the end.

Iconic Scene/Dialogue

Homer cooking the now famous “Moon Waffles”. Homer: Boy, everyone is stupid, except me.(A few moments later he falls asleep and the cigar sets the house aflame).
Rosebud

Season: 5, Episode: 4

IMDb Rating: 8.8 by 4.1k Votes

Aired on: Nov 13, 1993

When moving out of his old house in the Arctic, Mr. Burns dropped his favorite toy Bear in the snow. In the present, Mr. Burns is so distraught about losing his bear that he breaks up his birthday party by beating the guests. Bart brings an ice pack for Homer’s injury, when the ice melts away Bart finds Bobo, Mr. Burns’s bear. With season 5 heavily diving into Movie Parodies, this episode takes a spin at Orson Well’s Citizen Kane. Filled with clever humor, subtle hints and references, and even The Ramones as celebrity guests, Rosebud counts as one of the best Simpsons episodes.

Iconic Scene/Dialogue

Mr. Burns: How much do you want?Homer: A million dollars and three Hawaiian islands. Good ones, not the leper ones. Marge: I’m sure he’ll offer a fair reward. And then we’ll make him double it.Family: Huh?Marge: Well, why can’t I be greedy once in a while?
Homer The Great

Season: 6, Episode: 12

IMDb Rating: 9.0 by 4.1k Votes

Aired on: Jan 29, 1995

When Homer notices that some of his coworkers have been receiving special treatment, he investigates and finds out that they have joined a secret society “stonecutters”. Feeling left out, Homer finds a way into the secret society and is made “The One” that they were looking for. Filled with references to the brim, jokes that land well, and an interesting story, this episode shows why ‘The Simpsons’ was as popular as it was in its golden age. The episode does a really good job of depicting the feeling of being left out.

Iconic Scene/Dialogue

Homer: Why won’t those stupid idiots let me in their crappy club for jerks? Marge: Kids can be so cruel.Bart: We can? Thanks, Mom!(Bart runs into Lisa’s room and smacks her)Lisa: Oww! Cut it out, Bart!(Bart laughs)
King Size Homer

Season: 7, Episode: 7

IMDb Rating: 9.0 by 4.3k Votes

Aired on: Jan 7, 1996

As Mr. Burns implements a calisthenics program for all employees but Homer decides to take a different route than exercising, Homer decides to gain weight till he is above 300 lbs, unbothered about his health, and thinks this would deem him disabled and allow him to work from home. After reaching the weight goal, Homer’s life takes a turn for the worse. This episode encircles around how Homer finds different ways to enjoy his work from his job but is asked to leave every time he tries to do so due to his increased weight, fed up with this he eventually decides on getting liposuction fully funded by Burns.

Iconic Scene/Dialogue

Lisa: Dad, what are you doing down there?Homer: Washing my fat guy hat, honey. Homer: All my life I’ve been an obese man trapped inside a fat man’s body.
Homer Badman

Season: 6, Episode: 9

IMDb Rating: 8.9 by 4.4k Votes

Aired on: Nov 27, 1994

After successfully stealing a bucket load of gummy Venus de Milo from a candy convention, Homer loses track of a super rare Venus de Milo gummy. When dropping her babysitter home, Homer finds the gummy stuck to her pants, when he grabs the candy the babysitter mistakes this for a sexual advance, and the media completely villanizes him while attracting a load of bad reps for the Simpson family. Homer’s actions are mistaken, where all he tried was to get his hands on the rare candy. However, when groundskeeper Willie saw the tape and informs the Simpsons about what had actually happened following which Ashley and the media apologize to Home for showing him in bad light and deeming him a pervert.

Iconic Scene/Dialogue

Marge: Homer, that’s your solution to everything. To move under the sea. It’s not going to happen!Homer: Not with that attitude. Ashley: Hmm. Homer, I thought you were an animal, but your daughter said you were a decent man. I guess she was right.Homer: You’re both right.
Mr. Plow

Season: 4, Episode: 9

IMDb Rating: 8.8 by 4.2k Votes

Aired on: Nov 19, 1992

After being convinced about buying a pickup truck with a snowplow, Homer decides to start a business of plowing snow for customers. When the business doesn’t take off, Lisa suggests that he should put an advertisement with a catchy jingle on late-night TV, and that advertisement worked wonders for Homer’s business. With business booming, Barney sets up a rival company and badmouths homers company. The episode provides a gripping narrative and makes you laugh out loud from start to end. The flashbacks, self-deprecating jokes from celebrity cameos, and a positive message at the end of the video make for a compelling Simpsons episode.

Iconic Scene/Dialogue

Homer: My prices are so low, you’ll think I’ve suffered brain damage! Bart: Dad, who’s watching TV at 3:17 a.m.?Homer: Alcoholics, the unemployable, angry loners.
And Maggie Makes Three

Season: 6, Episode: 13

IMDb Rating: 8.8 by 3.6k Votes

Aired on: Jan 22, 1995

While going through a photo album, Marge notices that they do not have any photos of Maggie and Homer starts recounting why. After receiving a paycheck that would clear all of his debts, Homer leaves his job at the power plant and starts his dream job at a Bowling alley. After realizing Marge is Pregnant, Homer is put between a rock and a hard place as his current job doesn’t pay as well but he would hate going back to his old one. One of the best emotional episodes of the series, this episode keeps the humor on the back burner and focuses on Homer as a character and how far he is willing to go for his family’s sake. A highlight of the episode is Homer turning “Don’t forget: you’re here forever” to “Do it for her”.

Iconic Scene/Dialogue

Lisa: Anyway Dad, to get back to our first question, where are the pictures of Maggie?Homer: Where they are most needed.Several images of Maggie have been used to adorn Homer’s vacant desk, turning Burns’ “demotivational plaque” into a new plaque for the character.Plaque: DO IT FOR HER Lisa: Why aren’t there any pictures of Maggie?Homer: Well I’m glad you asked. It’s actually a very interesting story.(Bart and Lisa groan)
Bart Sells His Soul

Season: 7, Episode: 4

IMDb Rating: 8.8 by 3.8k Votes

Aired on: Dec 3, 1995

After being snitched on by Milhouse for changing a church hymn, Bart is punished by the Reverand to clean the organ pipes. When Milhouse exclaims that he doesn’t want his soul to go to hell, Bart refuses the existence of ‘souls’ and decides to sell his soul to Milhouse for 5 dollars on a piece of paper that read “Bart Simpson’s soul”, even after Lisa’s warning not to fall into Mihouse’s trap. With quite a witty setup to the episode, the humor used is very sharp and lands perfectly, but the more interesting part of the episode is when it makes crucial observations on the recent changes in religionism and commercialism.

Iconic Scene/Dialogue

Reverend Lovejoy: [discovering Bart’s hymn prank] Wait a minute! This sounds like rock and/or roll! [a beach ball bounces off his head] Homer: With the change in my piggy bank.Bart: There’s no change in your piggy bank.Lisa: Not any of the ones you know of.

25 All-Time Iconic Episodes Of ‘The Simpsons’

25 Most Iconic Episodes of ‘The Simpsons’

Homer’s Enemy

You Only Move Twice

Cape Feare

Marge vs. the Monorail

The City of New York vs. Homer Simpson

Who Shot Mr. Burns? Part Two

Homer The Smithers

Homer at the Bat

Lisa’s Substitute

Barthold

Burns Verkaufen der Kraftwerk

Skinner’s Sense of Snow

Treehouse of Horror V

Who Shot Mr. Burns? Part 1

Last Exit To Springfield

The Springfeild Files

22 Short Films about Springfield

Homer The Heretic

Rosebud

Homer The Great

King Size Homer

Homer Badman

Mr. Plow

And Maggie Makes Three

Bart Sells His Soul

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