Coming up with the most memorable Simpsons moments is a relatively thankless task; we’ve all got our loves and hates, and we’re never gonna agree on which is best. We’ve all got a favorite episode, quote, song, character – and during The Simpsons Week we’ve shared what what we think is the best. Here’s a selection of diverse moments we think have been most influential, most amusing and most overlooked in the building of The Simpsons into the cultural phenomenon we know and love.


Sideshow Bob Rakes

One of the most iconic jokes in The Simpsons started as a mistake. With the episode running considerably short, the writers scrambled to lengthen it, reusing a particularly long couch gag and adding an Itchy & Scratchy cartoon to fill it up. The masterstroke, though, was extending the joke from one rake to nine – the comedy staple of repeating until something stops being funny, then keeping it going until it becomes funny again.

The downtrodden Bob manages to follow the Simpsons from Springfield to Terror Lake by clinging to the bottom of their car (which Homer drives through a cactus patch), before walking into a circles of rakes and eventually being run over by the Terror Lake tribute to Hannibal’s crossing of the Alps. You would almost begin to feel sorry for him, were he not trying to kill Bart. After all, nobody who speaks German could possibly be a bad man…


Complete and Utter Dependence

Amidst the satire in The Simpsons lies a heart of pure saccharine. The relationship between Homer and Marge has been explored in some depth – from their school days and their life as newlyweds to their struggles with country music singers, French bowlers and attractive coworkers and musical theater.

The bedrock of their relationship was never better summed up than in the episode where Homer teaches an adult education class on matrimony, sharing the intimate secrets of his marriage to Marge with half of Springfield. Homer’s slow realization of how lucky he is to have Marge is heartwarming, as is his typically idiotic-yet-inspired admission of what he can offer Marge – “complete and utter dependence.”


Boys Kiss Girls Lisa

The Simpsons have never been shy on their political views. Despite the caricature of creator Matt Groening as a radical right-wing hack, the writers have always been firmly progressive, most notably when championing gay rights. Their most openly political episode on the subject remains “Homer’s Phobia,” in which Homer’s views – “I like my beer cold, my TV loud and my homosexuals fa-laming” – are challenged by a gay shop owner that befriends the family, but the small one-line jokes permeate the show, such as when Lisa complains that Gore Vidal has kissed more boys than she ever will, only to be dead-panned by a recalcitrant Marge: “Girls kiss boys Lisa, girls kiss boys…”


Lisa and Bart Ice Hockey

The sibling rivalry between Bart and Lisa is a primary motor of the show, with Bart’s charisma and attitude played off against Lisa’s brains and integrity. Their ability to pick a fight with each other is usually superseded by the familial solidarity in the end, and the knowledge that together they can save Itchy & Scratchy, reunite Krusty with his estranged father, stop Whacking Day with Barry White and, inadvertently, start a riot at a hockey game. Their rivalry, intensified by Lisa’s newfound goalkeeping abilities, has the town in a frenzy, but with a crucial penalty shot to win the game, Bart refuses to play against his sister, ending the game in a draw. As the townsfolk riot, they embrace in the center of the rink. If only they had peewee hockey when I was a lad…


Hank Scorpio Loses the Plot

Hank Scorpio is pretty widely considered the best one-episode character in the history of the show – run close by Mr. Bergstrom, perhaps – and “You Only Move Twice” is one of the most memorable episodes. The genius of it lies in the last 10 minutes, when the plot completely dissolves, replaced by surrealist rampage from Scorpio, the majority of whose lines were improvised by Albert Brooks.

Scorpio is the eccentric boss of Homer’s new employers in Cypress Creek, designed as an anti-Mr. Burns (and a thin Richard Branson parody), and the ideal person to work for. As Homer finds himself finally enjoying his job, it all unravels, as Scorpio’s true identity as an international supervillain comes to the fore, holding world leaders to ransom, torturing James Bont and wielding a flamethrower in his underground bunker. Homer is oblivious to this all, until the Denver Broncos turn up on his front lawn. The Simpsons at its very silliest.


The President Wore Pearls

It’s pretty common knowledge that The Simpsons lost it at some point in the late ’90s – some chart it to the death of Phil Hartman, voice of Lionel Hutz and Troy McClure, others to the beginning of Mike Scully as showrunner. “The President Wore Pearls” comes from the bad era – season 15 to be precise – but proves that, even if the decline has been consistent, there still is something left in the series. A parody of Evita, with Lisa in the title role, it harks back to big musical numbers of the Golden Age, as well as the guest turns (Michael Moore in this case), and crucially, the idea that there was always an emotional core to the comedy. Most people don’t bother with anything post-millenium, and they’re broadly right to do so, but “The President Wore Pearls” is a rare late gem, worth digging out.


Behind the Laughter

Rated amongst the writers as being the most recent in their top 15 episodes and the only one considered as a potential finale, “Behind the Laughter” is possibly the last great episode of The Simpsons. A radical departure from the standard format, it is a mock-history of the series, almost at times more like a sketch show than a sitcom. While it was clear that, by season 11, the rot had set in, this episode shows that the satire, self-parody and silliness was still there, and that the show wasn’t quite dead yet. Oh, and the Huckleberry Hound joke at the end still ranks amongst their best ever.


Johnny Cash, Talking Coyote

Initially rejected for being too odd, “El Viaje Misterioso de Nuestro Jomer” (“The Mysterious Voyage of Homer”) is one of the iconic episodes of the peak of the The Simpsons, when the show was at its height of its popularity and self-confidence. The standout moment is the guest performance from Johnny Cash, with the wizened country star playing a “space coyote” that acts as a spirit guide for a hallucinating Homer, induced by Chief Wiggum’s extra hot chilli peppers. Cash was an inspired piece of casting, his Southern drawl standing apart from the usual Springfield voices and suitably jarring with the psychedelic animations.


The Springfield Shopper

Less of a moment, more of a series of tiny moments – the pages of The Springfield Shopper have provided hundreds of mini-jokes over the years in The Simpsons. From the meta – “Spinning Newspaper Injures Printer” to the puns that would put a British tabloid to shame (“America’s favorite pencil #2 is #1”), the newspaper is another satirical and surrealist (“Old man yells at cloud”) insight into Springfield life. A personal favorite – “unusually large, ugly baby born,” when Homer looks up the day of his birth…


22 Short Films about Springfield

The Simpsons loves a cinematic parody – they took off Citizen Kane, Cape Fear, All the President’s Men and Rear Window, to name a few, but their eye has been by and large focused on the mainstream. Not so in this episode, a pastiche of the lesser-known arthouse flick Thirty Two Short Films About Glenn Gould. For a show that is built on the cast of supporting characters, the residents of Springfield that give the show its charm, it was a masterstroke to devote a whole episode to fragments of the lives of Springfielders, with cameos from Cletus, Herman, Dr. Nick and, in a turn I’m still quoting to this day, Principal Skinner, serving up steamed hams to Superintendent Chalmers.

See the rest of our Simpsons Week content.

Words by Mike Wood
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