The 25 Greatest Moments from The Simpsons

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The 25 Greatest Moments from The Simpsons
intro
Almost 35 years after its debut as a short on The Tracey Ullman Show, The Simpsons has produced 700 episodes, in addition to a movie, video games, theme park attractions and more merchandise than you can fit in Springfield Gorge. If you’re reading this, it’s likely that you have your own history with the Simpson family, but out of all the characters’ many adventures (and misadventures), what would you say are the best moments? We’ve whittled the list down to 25 of what we consider to be essential moments in The Simpsons history, which reveal just why it’s so enduring. What are your favourites?

By Victoria Luxford

27/26
Culture
The 25 Greatest Moments from The Simpsons.
13-1
Honourable Mention: Homer Vs Peter (The Simpsons Guy – Family Guy, Season 13, Episode 1) – Family Guy patriarch Peter Griffin and Homer come to blows over the merits of their hometown beers in a thinly veiled debate on each other’s shows. You may notice that only one moment in this list takes place after Season 10. It’s a generally held belief by fans that the show’s best moments are all in the first ten seasons, and this crossover with Fox comedy Family Guy (broadcast during The Simpsons’ 26^th Season) affectionately jabs at the show that inspired so many.

26/26
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The 25 Greatest Moments from The Simpsons.
08-10
The Springfield Files (Season 8, Episode 10) – Two ‘90s icons collide as X-Files agents Mulder and Scully investigate Homer through a variety of tests. It’s a hilarious contrast between the very serious sci-fi show and the buffoonery of Springfield’s favourite oaf, particularly the moment where he’s asked if he understands how a lie detector test works, and breaks the machine by saying “yes”.

25/26
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The 25 Greatest Moments from The Simpsons.
07-17
“Is It About My Cube?” (Homer The Smithers – Season 7, Episode 17) – Another moment of staggering ineptitude, but also an example of how sharp The Simpsons’ jokes can be. Homer takes over as Mr. Burns’ assistant, and displays his lack of understanding by relaying a series of messages about his car being impounded and cubed. Before Burns can berate him, Homer answers the phone, and his boss brilliantly caps the scene by asking “is it about my cube?” A little moment of genius.

24/26
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The 25 Greatest Moments from The Simpsons.
05-12
“Damn You… A Box!” (Bart Gets Famous – Season 5, Episode 12) – A fine example of Homer’s ability to spectacularly misread a situation. Bart goes missing from a ‘thrilling’ trip to the box factory, and Homer demands to know how Principal Skinner could lose his son, before a misunderstanding leads him to assume Bart is now… a box. It shows how The Simpsons rarely let a scene go by without fitting in a gag that will have you doubled over.

23/26
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The 25 Greatest Moments from The Simpsons.
04-21
“I’m Not Wearing A Tie At All!” (Marge In Chains – Season 4, Episode 21) – The Simpsons is of course about a lot more than, well, the Simpsons. A cavalcade of supporting stars have wormed their way into our hearts, including inept attorney Lionel Hutz. Voiced by the late Phil Hartman, this scene is a prime example of the hapless Hutz failing upwards. When Marge is harshly prosecuted for shoplifting, the lawyer strikes gold through a clumsy and dishonest trick played on witness Apu. In Springfield, even moments of triumph have a tinge of disaster.

22/26
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The 25 Greatest Moments from The Simpsons.
07-05
“It’s Still Good!” (Lisa The Vegetarian – Season 7, Episode 5) – Rapid-fire sight gags fly at us as Bart and Homer chase a runaway hog roast, following a protest by newly vegetarian Lisa. Homer’s desperate plea of “It’s still good! It’s still good!” has become highly quoted by fans, and is a great tribute to how far Homer will go to save his favourite foods. However, everyone gets in on the fun, from Marge assuming Bart was behind the mischief, to Mr Burns observing the flying pig from his office.

21/26
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The 25 Greatest Moments from The Simpsons.
04-10
Maggie’s First Word (Lisa’s First Word – Season 4, Episode 10) – The first moment on our list that brings a tear to your eye. After trying to get Maggie to speak, the family reminisces about Lisa’s first word. In a gorgeous end scene, Homer concludes that “the sooner kids talk, the sooner they talk back. I hope you never say a word.” Except, in private, Maggie does say her first word: “Daddy”. This first word was delivered by Hollywood legend Elizabeth Taylor, and Maggie has since only had fellow Oscar winners providing her voice: Jodie Foster and James Earl Jones (both in fantasy segments).

20/26
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The 25 Greatest Moments from The Simpsons.
04-02
Marge Becomes Blanche (A Streetcar Named Marge – Season 4, Episode 2) – What’s it like to be married to someone like Homer Simpson? We see the inner rage of Marge come out as she rehearses for A Streetcar Named Desire, interrupted by numerous mishaps from her hubby. The sequence is held up by Homer’s silliness, but gives Marge a rare chance to shine as she overpowers an oddly muscular Ned Flanders, to the delight of an unhinged theatre director.

19/26
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The 25 Greatest Moments from The Simpsons.
02-19
You Are Lisa Simpson (Lisa’s Substitute – Season 2, Episode 19) – At its best, The Simpsons can deliver moments of drama that would make most live action series envious. Lisa is often the foil for her brother’s antics, while her intelligence makes her an outcast in her family and at school. In this early classic, she says goodbye to Mr Bergstrom, a substitute teacher and the only person who truly understands her passions and potential. In a train platform departure reminiscent of an old movie, Bergstrom leaves her with some advice, and an unforgettable note.

18/26
Culture
The 25 Greatest Moments from The Simpsons.
08-08
Ned’s Meltdown (Hurricane Neddy – Season 8, Episode 8) – Mild-mannered Ned Flanders gets a moment of catharsis as he lets loose on the inept residents of Springfield. After seven seasons of taking life’s knocks with a smile and a prayer, Ned delivers some harsh observations to a shocked and appalled crowd, before calling Homer the worst human being he has ever met (which Homer takes as “getting off light”). If you have ever had an issue with anyone in the series, this goodly neighbourino delivers some vicarious satisfaction over two blistering minutes.

17/26
Culture
The 25 Greatest Moments from The Simpsons.
08-02
“Nobody Ever Says Italy” (You Only Move Twice – Season 8, Episode 2) – Despite only appearing in one episode, Hank Scorpio became a cult figure for many Simpsons fans over the years. In “You Only Move Twice”, Homer is recruited by the friendly billionaire, oblivious to the fact that he is a supervillain intent on world domination. Critics have since remarked how Scorpio foreshadowed the hip tech moguls of today, but it’s Albert Brooks’ wonderful asides that make the character who he is, including this discussion about least favourite countries!

16/26
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The 25 Greatest Moments from The Simpsons.
10-19
Everything’s Coming Up Milhouse! (Mom and Pop Art – Season 10, Episode 19) – Bart’s bestie Milhouse is a tragi-comic character within The Simpsons universe. Manipulated by Bart, barely tolerated by his bickering parents, and forgotten altogether by Homer, he doesn’t get many wins in life. Therefore, this celebration of a small victory is joyous to watch, and is one of those phrases from the show that has entered the cultural lexicon. Adorning T-shirts, mugs and various other merchandise, these four little words have become our favourite loser’s greatest moment.

15/26
Culture
The 25 Greatest Moments from The Simpsons.
05-05
Homer Sells His Soul… For A Doughnut! (Treehouse of Horror IV – Season 5, Episode 5) – What’s not to love about this segment of the iconic “Treehouse of Horror” series? Flanders being The Devil is a masterstroke (“it’s always the one you least suspect!”), but nothing encapsulates the compulsive behaviour of Homer more than selling his soul for his favourite treat. Deliciously, he works out a loophole that also sees him outsmart the Prince of Darkness, but those familiar with the episode will know that the last piece of “forbidden doughnut” won’t last long.

14/26
Culture
The 25 Greatest Moments from The Simpsons.
07-19
Planet Of The Apes: The Musical (A Fish Called Selma – Season 7, Episode 19) – Described by the writers as “a magic visit from the joke fairy”, side character Troy McClure gets the spotlight in this episode where the C-list actor’s career is revived through his marriage to Marge’s sister, Selma. The peak of his success, and the episode, is a rock musical based on The Planet of the Apes which features the most memorable musical numbers in the show’s history. “I hate every ape I see. From chimpan-a to chimpan-z” Troy sings, making this show within a show an all-time classic.

13/26
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The 25 Greatest Moments from The Simpsons.
08-23
Frank Grimes (Homer’s Enemy – Season 8, Episode 23) – ‘Grimey’, as he was dubbed by Homer, earns his place in Simpsons lore by being an antagonist who might actually have a point. A man who has worked hard for everything in his life is infuriated by Homer coasting through his existence, and becomes irate when he observes the achievements he has stumbled into. Met with complete confusion by Homer, who meekly asks “you’ve never been?”, when mentioning his trip to space, Grimes sums up Homer as “everything that’s wrong with America”. In a sense, he’s correct – for three decades Homer has been a satire of the more unappealing elements of the US, summed up by President George H. W. Bush when he remarked that Americans should be “a lot more like the Waltons, and a lot less like the Simpsons”.

12/26
Culture
The 25 Greatest Moments from The Simpsons.
06-18
Boo-Urns (A Star Is Burns – Episode 6, Episode 18) – A short gag, but one that gets better every time you see it. Mr Burns seeks to polish his public image with a heavily fictionalised biopic of himself, which is met with boos from a film festival crowd. In a moment of desperate sycophancy, Mr Smithers assures him the crowd are saying “boo-urns”, which is denied by all but one crowd member seconds later. Another catchphrase that will instantly win a knowing nod from fellow Springfield lovers.

11/26
Culture
The 25 Greatest Moments from The Simpsons.
movie
Spider-Pig (The Simpsons Movie, 2007) – The only moment that comes after season 10 is from the wildly successful spin-off movie. Having become obsessed with a new pet pig, Homer leaves Marge astounded when she discovers him walking the pig on the ceiling, singing the Spider-man theme. The film is filled with cultural cues from the late 2000s, and Spider-pig is a reference to the excitement surrounding Spider-man 3, which came out the same summer. That film was a disappointment, but Spider-pig became so popular that he was brought back for future episodes of the show.

10/26
Culture
The 25 Greatest Moments from The Simpsons.
05-02
Sideshow Bob Vs The Rakes (Cape Feare – Season 5, Episode 2) – The most recognisable sight gag in the show, from one of its greatest guest stars. Cape Feare, where Sideshow Bob seeks revenge on Bart, was Kelsey Grammer’s third appearance as the demented former TV sidekick. However, this episode is surely his finest, with Bob mixing moments of menace with outright hilarity. This high point, where Bob continuously steps on rakes, wasn’t even meant to make the cut. Reportedly, the show was running short, and so instead of one rake, Bob stepped on nine. Out of necessity came one of the show’s finest moments.

9/26
Culture
The 25 Greatest Moments from The Simpsons.
03-23
Channelling Dr Jones (Bart’s Friend Falls In Love – Season 3, Episode 23) – There are movie parodies, and then there are Simpsons movie parodies. While spoofs were certainly a part of pop culture, The Simpsons always seems to balance the comedy with a faithful nod to what made the particular movie great. That’s never more evident than in this tribute to Indiana Jones and the Raiders of The Lost Ark, where Bart steals a change jar in the manner of Dr Jones: outrunning a rolling boulder, which in this case is Homer falling down the stairs.

8/26
Culture
The 25 Greatest Moments from The Simpsons.
04-12
“Monorail, Monorail” (Marge Vs The Monorail – Season 4, Episode 12) – Springfield as a community is often presented as panicky, rash and inept at deciding what is best for its future. It bungled its way out of hosting the Olympics, and became so environmentally unfriendly that the government isolated it from the rest of the country. The town’s lowest point, however, is surely being duped by a con man into paying for a faulty monorail it doesn’t need when it receives a financial windfall. Won over by cheap compliments and charm, our favourite characters are soon singing along with the shyster as Marge remains the only dissenting voice. While the cast were not fond of the episode at the time, we have all since been won over.

7/26
Culture
The 25 Greatest Moments from The Simpsons.
02-08
Homer Jumps Springfield Gorge (Bart The Daredevil – Season 2, Episode 8) – A moment that Simpsons creator Matt Groening has said defines the humour of the show: instead of traditional cartoons where a character may hover for a few seconds before falling, Homer genuinely believes he’s going to make it when he accidentally jumps the deadly Springfield Gorge. When he does fall, we see a litany of comedy injuries, followed by an inept rescue. One of the earliest favourites, it still holds up over 30 years on.

6/26
Culture
The 25 Greatest Moments from The Simpsons.
07-21
Steamed Hams (22 Short Films About Springfield – Season 7, Episode 21) – It’s likely that, before a couple of years ago, the Steamed Hams sketch may not have been thought of by many, as it was just one of 22 short skits in this Season 7 episode. However, the segment took off as an internet meme, with people putting their own twists on the exchange between Principal Skinner and Superintendent Chalmers. Its popularity has shown the writing in a new light, and while we include the original sketch for context, we encourage you to seek out the various remixes online.

5/26
Culture
The 25 Greatest Moments from The Simpsons.
07-08
Goodbye Mother Simpson (Mother Simpson – Season 7, Episode 8) – In the middle of all the slapstick and catchphrases, The Simpsons can often deliver something so beautiful it catches you off guard. Homer is reunited with his long-lost mother (voiced by Glenn Close), an eco-activist who offers him the support and affection he’s always yearned for. Unfortunately, this reunion is short-lived as her protests find her on the run from the law. After an emotional farewell, Homer simply sits on his car and looks at the stars thoughtfully. It is a great moment that highlights the writers’ ability to encapsulate the feelings we can’t quite put into words.

4/26
Culture
The 25 Greatest Moments from The Simpsons.
06-12
The Stonecutters Song (Homer The Great – Season 6, Episode 12) – “Who keeps Atlantis off the maps? Who keeps the Martians under wraps? We do, we do…” While not a musical series, the show has featured some memorable tunes over the years. This ditty, sung by the mysterious organisation Homer joins, boasts about all the conspiracies they’ve engineered. Brilliantly composed, there’s something so buoyant and cheerful – and at the same time intelligent – in this satire of popular conspiracy theories.

3/26
Culture
The 25 Greatest Moments from The Simpsons.
06-13
Do It For Her (And Maggie Makes Three – Season 6, Episode 13) – Perhaps the ultimate moment of agonising beauty from the show’s golden era. Homer recalls giving up his dream job at a bowling alley to return to Mr Burns’ power plant, all so that he can support the arrival of third child Maggie. What seems like a downbeat tale is given the sweetest of endings, when a sign that reads “Don’t Forget, You’re Here Forever” is altered with pictures of Maggie to read “Do It For Her”. A parent’s sacrifice put simply, and beautifully.

2/26
Culture
The 25 Greatest Moments from The Simpsons.
06-25
Who Shot Mr Burns (Season 6, Episode 25) – The entire two-part arc (the last episode of Season 6 and the opening of Season 7) is the show at its most intricate and hilarious, with audiences at the time being made to wait four months to solve the mystery. Mr Burns, in his most sinister guise, upsets everyone in Springfield before unveiling a plan to block the sun, making people reliant on his nuclear energy. In the glorious crescendo of the first episode, Burns is shot by a mystery assailant, with everyone in town becoming a suspect. A parody of ‘80s show Dallas, it is perfect storytelling – and for us, it’s the prime case for the argument that The Simpsons is the greatest TV show ever made.

1/26

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The 25 Greatest Moments from The Simpsons

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