12 All-Time Iconic Episodes Of ‘The Simpsons’

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.

12 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.

  1. Homer’s Enemy

    Season: 8, Episode: 23
    IMDB Rating: 9.3
    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.

  2. You Only Move Twice S8.E2

    Season: 8, Episode: 2
    IMDB Rating: 9.2
    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!

  3. Cape Feare

    Season: 5, Episode: 2
    IMDB Rating: 9.1
    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.

  4. Marge vs. the Monorail

    Season: 4, Episode: 12
    IMDB Rating: 9.1
    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.

  5. The City of New York vs. Homer Simpson

    Season: 9, Episode: 1
    IMDB Rating: 9.0
    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.

  6. Who Shot Mr. Burns? Part Two

    Season: 7, Episode: 1
    IMDB Rating: 9.0
    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!

  7. Homer The Smithers

    Season: 7, Episode: 17
    IMDB Rating: 8.8
    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.

  8. Homer at the Bat

    Season: 3, Episode: 17
    IMDB Rating: 8.7
    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!

  9. Lisa’s Substitute

    Season: 2, Episode: 19
    IMDB Rating: 8.5
    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.

  10. Barthold

    Season: 27, Episode: 9
    IMDB Rating: 8.4
    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.

  11. Burns Verkaufen der Kraftwerk

    Season: 3, Episode: 11
    IMDB Rating: 8.2
    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.

  12. Skinner’s Sense of Snow

    Season: 12, Episode: 8
    IMDB Rating: 7.9
    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.

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