Simpsons

The 30 Best Episodes Of 'The Simpsons' ~

Words by Junkee

By Junkee, 14/6/2019

As of this year, 662 episodes of The Simpsons have gone to air. But the question is: which one is best? Is it the Monorail episode? Hank Scorpio? The Halloween specials? Steamed hams? The one with Mulder and Scully? The one with an uncredited Dustin Hoffman? Anything with Sideshow Bob?

We here at Junkee have been arguing about this. A lot. And so, to avoid bloodshed, we decided to go to work on our own conclusive list of the best ever Simpsons episodes. First, we came up with a shortlist of our favourite episodes. We eventually trimmed that down to 30 indispensable Simpsons offerings and from there, recruited a cast of Australia’s funniest writers to help us rank them. Every episode was scored against six different criteria, which we added up for a total score to reveal our ultimate winner. Is this scientifically rigorous methodology? Nope. Is it good enough? We reckon.

The six key areas we scored on are what make up a classic Simpsons episode. There’s how funny, how memorable and how quotable each episode is, as well as its cultural relevance (don’t expect any episodes focusing on Apu) and its emotional resonance (who didn’t cheer at the end of ‘The Last Temptation Of Homer’ when Homer ended up in bed with Marge, not Mindy?). Finally, we considered each episode’s musical contributions, because many of the show’s most iconic moments have arrived in song.

Looking back, it’s not hard to pinpoint the show’s golden era. None of the episodes we’ve selected aired before season 2, or after season 8. Season 6 proved to be the real sweet spot, with no fewer than seven entries on this list.

Without further ado, here are the 30 best episodes The Simpsons ever produced. According to us, anyway.


#30. ‘Homer’s Enemy’

Season 8, Episode 23

One of the darkest and arguably most mean-spirited episodes of The Simpsons is also one of the best. The writers really dig the screws into poor Frank Grimes, and I’ll be damned if it isn’t hilarious.

This episode really drives home what an insensitive moron Homer is, and yet as he’s snoring loudly through poor Grimey’s funeral, we end up sympathising more with him than the man he drove to an early grave. Troubling ethical questions aside, this episode is packed with great lines (“I’d say he eats more like a duck”, “Don’t ask me how the economy works”, “I’m peeing on the seat! Give me a raise!”) while the B-plot involving Milhouse as the night watchman at Bart’s factory is a weird, delightful gem.

Cultural relevance: 2/5
Quotability: 4/5
Musical numbers: 0/5
Iconic moments: 3/5
Emotional resonance: 1.5/5
Laughs: 4/5

Total score: 14.5/30

Words by: Tom Clift

#29. ‘Lemon Of Troy’

Season 6, Episode 24

Marvel vs. DC. Coke vs. Pepsi. Springfield vs. Shelbyville. The rivalry between the two towns is an iconic part of The Simpsons, and gets the full treatment in ‘Lemon of Troy’.

I love the idea of Shelbyville as a kind of bizarro Springfield, complete with Fudd Beer, Joe’s Tavern and even their own version of Milhouse (“But I thought I was the only one”, “A pain I know all too well”). This is also one of the best kid-centric episodes, with the writers nailing the dynamic of a group of boys desperate “to step out of childhood and become men”, while at the same time poking fun at the fathers who it turns out are just as immature as their sons.

Oh, and the scenes featuring Martin and Nelson are absolutely brilliant (“No one manhandles the bosom chum of Nelson Muntz. Spring forth burly protector and save me!”). Now let’s all celebrate with a cool glass of turnip juice.

Cultural relevance: 3/5
Quotability: 3/5
Musical numbers: 0/5
Iconic moments: 2/5
Emotional resonance: 3/5
Laughs: 4/5

Total score: 15/30

Words by: Tom Clift

#28. ‘Treehouse of Horror V’

Season 6, Episode 6

Everything is better when it’s a scary special edition. This was true of The Baby Sitters Club, it was true of Sweet Valley High, and it’s sure as hell true of The Simpsons. The Treehouse of Horror episodes were always Simpsons standouts, and ‘Treehouse of Horror VI’ (that’s roman numerals for 6, you’re welcome) is the undisputed king of the bunch.

The episode is a three act affair: in one, Homer travels back in time and accidentally changes the future; in another a combination of overcrowding in the school’s detention and the cafeteria being down to using Grade F meat (“mostly circus animals, some filler”) leads Principal Skinner to start cooking the kids.

But the real star of this episode is “The Shinning” (not The Shining, do you want to get sued?), in which The Simpsons take up the role of winter caretakers at Mr Burns’ lodge and Homer quickly descends into madness and tries to murder his family. It’s the segment that gave us “No TV and no beer make Homer go something something,” which alone propels this to the league of Simpsons greats.

Cultural relevance: 1/5
Quotability: 5/5
Musical numbers: 0/5
Iconic moments: 4/5
Emotional resonance: 1/5
Laughs: 5/5

Total: 16/30

Words by: Katie Cunningham

#27. ‘Mr. Plow’

Season 4, Episode 9

I thought I knew what I was getting into with this episode, but there are actually A LOT of moments in Mr Plow that made me chuckle with surprise.

Apart from the iconic jingle (‘that name again is Mr Plow’), this episode gives us some great unexpected gems that I’d forgotten about. Long before Family Guy did it, we’re served a hilarious Adam West cameo, including his classic dance, the Batusi. We also learn more about Barney Gumble’s origin story (it was Homer who gave him his first beer in college). There’s also a truly pointless but quite rewarding Linda Ronstadt appearance.

There are some great gags in the episode as well, like the model at the car show who has the same coquettish giggle for every man who asks if she comes with the car. Another other classic is Homer desperately searching for an explanation for his car crash that doesn’t involve Moe’s tavern, before landing on “Pornography. I was buying pornography”. The other nice little detail in this episode is the way Marge is turned on by Homer in his Mr Plow jacket. It’s always good to know that after all these years, Marge is still attracted to Homer, and vice versa. Good for them.

Where this episode lets itself down slightly is the lack of moral tale underpinning it. Unlike so many other classic episodes in this list, Mr Plow seems to exist solely for its own sake, but that doesn’t mean it doesn’t give us some killer gags along the way.

Cultural relevance: 3/5
Quotability: 3.5/5
Musical numbers: 1/5 (for the jingle)
Iconic moments: 3.5/5
Emotional resonance: 2/5
Laughs: 3.5/5

Total: 16.5/30

Words by: Rob Stott

#26. ‘Homer At The Bat’

Season 3, Episode 17

The Simpsons has featured countless celebrity guests over the years, often shoehorning them in awkward, ham-fisted ways. But this season three episode sets a gold standard for how to incorporate a whole heap of famous faces (or rather, voices) without having them overshadow the main characters.

It helps that the writers spend a great deal of the episode taking the piss out of Mr. Burns’ ringers, culminating in a surreal, hilarious sequence in which they each fall victim to a different, bizarre misfortune (which are then immortalised in the genius parody of Terry Cashman’s song ‘Talkin Baseball’ that plays over the end credits). Ultimately though, this episode is less about the likes of Wade Boggs, Jose Conseco and Daryl “Daaarrryyylll” Strawbery, and more about Homer. There’s something genuinely touching about the way he ends up winning the game for his team — even if it’s sort of an accident.

Cultural relevance: 1/5
Quotability: 3/5
Musical numbers: 3/5
Iconic moments: 3/5
Emotional resonance: 3/5
Laughs: 4/5

Total: 17/30

Words by: Tom Clift

#25. ‘Scenes From The Class Struggle In Springfield’

Season 7, Episode 14

‘Scenes From the Class Struggle in Springfield’ paints a line down the centre of town with the country club on one side and Evergreen Terrace on the other.

It all starts when Marge has nowhere to wear her new pink suit. She wants to wear the Chanel two-piece — that mimics the one Jackie O wore on that car ride through Dallas — somewhere it belongs, like the theatre, but Homer protests. “What’s the point of going out? We’re just gonna wind up back here anyway!”

So she puts it on to clean the house and pump her gas at the Kwik-E-Mart. That’s where Evelyn, who knew Marge Bouvier in high school, notices her and invites the family to the country club. The suit — that Marge got for $90, reduced from $2800 — gets her things her green dress or last name never could.

All of a sudden, with access to a place Lisa calls “a hotbed of exclusionist snobs and status-seeking social-climbers”, Marge cares about Bart’s hair and the length of Homer’s sleeves. She literally tells Lisa that the rich are better than they are — “Socially better. And if we fit in we can be better too!” It’s packed with observations about class and status you didn’t pick up in 1996 — like tiny liberal Lisa who wants to confront everyone at the country club (especially the women who “order [their] steaks through The New Yorker”) “if they know their servants’ last names or, in the case of butlers, their first!”

It takes a tuxedo-wearing Homer telling the kids, “You kids should thank your mother; now that she’s a better person we can see how awful we really are,” for her to drop the frown, the act and the hem of the new Chanel gown she just spent their life savings on, and eat dinner with her family at Krusty Burger.

Cultural relevance: 4.5/5
Quotability: 2/5
Musical numbers: 0/5
Iconic moments: 4/5
Emotional resonance: 4/5
Laughs: 3/5

Total: 17.5/30

Words by: Brodie Lancaster

#24. ‘Homer The Heretic’

Season 4, Episode 3

Religion and spirituality is a recurring theme on The Simpsons, but it gets probably its most complete and relatable treatment in ‘Homer The Heretic’. The episode sees Homer make a compelling case for abandoning religion (“What if we picked the wrong religion? Every week we’re just making God madder and madder”), so much so that even seemingly manages to convince God himself (“sometimes even I’d rather be watching football”).

But ultimately the writers come down on the side of faith — or at least, faith in people — after Homer is saved from a fire by his neighbours (“be they Christian, Jew or… miscellaneous”). They also manage to cram in a truly staggering number of great gags, from Homer’s fantasy about “another day in the womb” to the high-speed chase with the Flanders clan (“Dad, the heathen’s getting away!”).

If nothing else, it gave us the recipe to Homer’s Patented Out-Of-This-World Space Age Moon Waffles, which look bloody delicious wrapped around a stick of butter, don’t @ me.

Cultural relevance: 3/5
Quotability: 4/5
Musical numbers: 0/5
Iconic moments: 2/5
Emotional resonance: 4/5
Laughs: 5/5

Total: 18/30

Words by: Tom Clift

#23. ‘Lisa The Vegetarian’

Season 7, Episode 5

You don’t win friends with salad, but you can learn some valuable lessons along the way. My memories of ‘Lisa The Vegetarian’ weren’t super fresh (unlike Lisa’s sadly neglected gespacho), so I wasn’t sure what to expect going in, but this episode is actually really sweet

It’s a Lisa-centric episode, which I love, because she’s truly under-appreciated. The episode revolves around her newfound vegetarianism, which she discovers after falling in love with an adorable lamb at a kids amusement park. When Homer decides to host the biggest BBBQ ever (The extra B is for BYOBB, and the second extra B is a typo), Lisa fights back by hijacking Homer’s suckling pig and taking it for a joyride.

The episode if full of iconic moments, including the oft-quoted “You Don’t Win Friends With Salad” conga line, the flying pig, and Bart and Homer fighting over a lamb chop like two rabid dogs. It also features one of my favourite jokes when Marge brags about her dinner: “You might say the extra ingredient is… salt!”

But more than anything, this episode stands out for the way Lisa discovers something that matters to her and refuses to back down. At her lowest point, when she feels alone in the world, Lisa finds some kindred spirits in Apu and Paul and Linda McCartney, and realises that if you stay true to yourself, you’ll eventually find your place in the world. The McCartneys also teach Lisa that what unites us is more important than what divides us, prompting Lisa to reconcile with Homer in one of those touching moments that’s quite unique to those two characters.

Cultural relevance: 3.5/5
Quotability: 4/5
Musical numbers: 0/5
Iconic moments: 3.5/5
Emotional resonance: 3.5/5
Laughs: 4/5

Total: 18.5/30

Words by: Rob Stott

(tied) #21. ‘Radio Bart’

Season 3, Episode 13

Radio Bart is the sorry tale of poor, orphaned Timmy O’Toole trapped at the bottom of Springfield’s old well. Except it’s not actually Timmy O’Toole: it’s Bart playing a prank with a radio microphone that then goes horribly wrong when he actually does fall down the well.

Radio Bart may just one of the most classic Simpsons set-ups in the canon: a stupidly simple plotline that encourages touching character growth and allows them to skewer large sections of society.

On the skewer this episode is humanity’s ability to cash in on a tragedy: hawkers sell t-shirts emblazoned with ‘I Survived Timmy O’Toole Getting Trapped In A Well’, others peddle fake Timmy baby teeth, and finally the entire well site is turned into a carnival — complete with a Ferris wheel.

They also take a knife to the entertainment industry and its long history of money-grubbing charity singles, savagely parodied by the Sting-written and Krusty-promoted Timmy O’Toole ode ‘We’re Sending Our Love Down The Well’ — intended as a pisstake of Michael Jackson and Lionel Richie’s 1985 track ‘We Are The World’.

When asked by Kent Brockman what the song’s proceeds would actually go towards, Krusty replies: “Well we gotta pay for promotion, shipping, distribution…you know those limos out back aren’t free! Whatever is left we’ll throw down the well.”

But what makes Radio Bart memorable is Bart’s genuinely heart-warming journey from unrepentant prankster to remorseful son. It wouldn’t be The Simpsons without a moral teaching, after all.

Cultural relevance: 4/5
Quotability: 3/5
Musical numbers: 4/5
Iconic moments: 2/5
Emotional resonance: 3/5
Laughs: 3/5

Total: 19/30

Words by: Jules LeFevre

(tied) #21. ‘The PTA Disbands’

Season 6, Episode 21

Like most of The Simpsons’ best episodes, ‘The PTA Disbands’ has a simple premise — frustrated Springfield Elementary teachers go on strike — which lets the social satire shine through the character’s splintering reactions.

Take the kids: Bart runs wild in vignettes that soon descend from Dazed and Confused to deranged as he flies a kite at night; Milhouse exceeds when the Van Houtens hire a tutor; and Lisa goes mad without structure and a steady stream of grades and appraisal.

The show makes it clear that the problem is bigger than Springfield Elementary, as bureaucracy and a lack of funding is failing a myriad of students. When the only way to keep the school financially afloat is to rent out cupboard space to the overcrowded prison, it’s a salient comment on how educators are forced to think finance first — equally true today. But it’s never didactic, thanks to an avalanche of iconic jokes.

There’s a billion oft-quoted classics here, from the cafeteria serving gym-mat mince meat to “that’s a paddlin’”, the student stuck on the high-rings and, of course, “is that gum? Is that gum? Is that gum?”.

Jokes are fast flung, and it’s a testament to how much the show’s writers used to pack into 22 tight minutes — no room here for musical number or tear-jerking moments, though.

Cultural Relevance: 4/5
Quoteability: 5/5
Musical Numbers: 0/5
Iconic Moments: 5/5
Emotional Resonance: 0/5
Laughs: 5/5

Total: 19/30

Words: Jared Richards

#20. ‘Bart vs Australia’

Season 6, Episode 16

I SEE YOU’VE PLAYED KNIFEY-SPOONY BEFORE. This classic episode from season 6 is chock full of quotes we all still hear today (including one that inspired a Change dot org campaign).

The episode begins with Bart not believing Lisa’s assertion that water only flushes clockwise in the Southern Hemisphere, so he calls several countries and ends up on the blower to Aussie lad Tobias Dundridge and his father Bruno, costing them 900 dollarydoos in collect charges. The Simpsons fly to Australia to apologise, but challenge the additional punishment of a booting from the Prime Minister (as is the law here, of course).

This episode is iconic and hilarious because of the absurdity, highlighting just how bloody good it feels to laugh at ourselves. It’s pure, joyful silliness that pokes fun at both the US and Australia; not in a traditional satirical style seen in other Simpsons episodes but in an inane “wouldn’t it be funny if this country kicked people in the bum, called toads ‘chazzwazzas’ and only drank beer’ way. Well… maybe the latter part is true.

Cultural relevance: 5/5, due to longevity of quotes and for being embraced by Australian pop culture.
Quotability: 5/5
Musical numbers: 0/5
Iconic moments: 5/5
Emotional resonance: 0/5. All killer, no filler.
Laughs: 5/5

Total: 20/30. No music or mushy feelings but it’s 10/10 in my heart.

Words: Diedre Fidge

#19. ‘Marge Be Not Proud’

Season 7, Episode 11

It’s Christmas time and Bart wants the coolest new video game, Bonestorm, but Marge won’t buy it for him — so he shoplifts, is caught, and for a time, his entire world shatters as he deals with the consequences of his actions.

This episode packs a weighty emotional punch as we are given a look at the turbulent inner workings of both mother and son at a pivotal point in their lives: Bart navigating the murky, terribly familiar waters of growing up and fearing the loss of maternal love, and Marge trying to come to terms with a boy whose moral compass she realises she can no longer control.

Perfectly balancing the Kleenex moments with some classic Simpsons jokes (“WELCOME THRILLHO”, Camp Grenada), this one’s a keeper.

Cultural relevance: 4/5
Quotability: 4/5
Musical moments: 1/5
Iconic moments: 2.5/5
Emotional resonance: 5/5
Laughs: 4/5

Total: 20.5/30

Words: Giselle A. Nguyen

(tied) #17. ‘Cape Feare’

Season 5, Episode 2

Sideshow Bob episodes are jewels in the crown of The Simpsons’ golden era, and ‘Cape Feare’ is the best of them all. Kelsey Grammer clearly had the time of his life voicing Bob, who comes off like Frasier Crane finally went berserk after one too many snits with Niles. He’s The Simpsons’ greatest villain, and ‘Cape Feare’ finally lets him off the leash.

The plot is so bare-bones it’s barely there: Bob gets out of jail and tries to kill Bart. That’s it. No mysteries to solve like in previous Bob episodes; no subplots; just Grammer turning the murderous-fop dial to 11 and snapping it off. We never see Bob more malevolent, more single-minded in his desire to murder, more wondrously dandyish, than we do in ‘Cape Feare’.

This is one of those episodes that delivers brilliant one-liners and setpieces so fast you barely have time to appreciate one before three more have flown by. Moe dispersing his panda-smuggling ring by screaming “ándale, ándale!”; the fact that McBain’s talk-show MC is a Nazi Obergruppenführer; “Springfield Penitentiary: America’s Fastest Growing Prison”; Homer’s ‘Wide Load’ butt tattoo; Grandpa turning into a woman without his pills and being hunted by wolves; Sideshow Bob using his own blood to write a to-do list; Bob’s immortal quote: “What about that tattoo on your chest? Doesn’t it say ‘Die, Bart, Die’?”, “No! That’s German for, ‘The Bart, The’!”. They don’t make ‘em like they used to.

Oh, and three words: the rake scene.

Cultural relevance: 2/5
Quotability: 4/5
Musical numbers: 4/5
Iconic moments: 5/5
Emotional resonance: 1/5
Laughs: 5/5

Total: 21/30

Words by: Alex McKinnon

(tied) #17. ‘Bart After Dark’

Season 8, Episode 5

‘Bart After Dark’ is one of those classic Simpsons episodes where something fairly dramatic is set up — namely that most of the town frequents what is definitely a racy burlesque bar, if not actually a brothel — and then we never talk of it again. Is it canon that most of Springfield’s men go to Maison Derriere on a Friday night?

Following the story of Bart getting a job in a brothel after Lisa and Marge go to rescue animals from an oil spill, it turns into a morality crusade against the local burlesque house. Of course, Marge somehow ends up being the bad guy at the end. She has her heart in the right place.

It’s an interesting take on small town morality. We know that Springfield is run by a pious collection of religious busybodies, so it makes sense that there is a sensual underbelly. It’s a very American story.

Plus, it all leads to an excellent musical number. ‘The Spring in Springfield’ is definitely one of the catchier numbers in the show, and it’s cool that it’s sex positive I guess.

Cultural relevance: 4/5
Quotability: 2/5
Musical numbers: 5/5
Iconic moments: 5/5
Emotional resonance: 1/5
Laughs: 4/5

Total: 21/30

Words by: Patrick Lenton

#16. ‘The Last Temptation Of Homer’

Season 5, Episode 9

Some of the best episodes of The Simpsons are the ones that focus on exceptionally mundane problems within the family, such as the prospect of infidelity within Marge and Homer’s marriage. While not a new topic for sitcoms, it’s a fairly adult episode for the show.

Thankfully it has a feel-good ending, with Homer remaining committed to his marriage and not cheating on Marge (“All I’m going to use this bed for is eating, sleeping and maybe building a little fort”). Yay!

The B-plot is a classic status reversal that sees Bart becomes a nerd after glasses and orthopaedic shoes. Honestly, this is more a vehicle for gags than anything else, but there’s some excellent ones, such as when he finally throws away his shoes and they smash through the Flanders’ window.

It’s just an excellently-done episode — not super flashy, but chock full of iconic gags like “Joey Joe Joe Jr Shabadoo”.

Cultural relevance: 4/5
Quotability: 4/5
Musical numbers: 1.5/5
Iconic moments: 4/5
Emotional resonance: 4/5
Laughs: 4/5

Total: 21.5/30

Words by: Patrick Lenton

#15. ‘Summer Of 4 Ft.2’

Season 7, Episode 25

Deep down, we are all Cool Lisa. Saddened by her lack of friends after no one signs her yearbook, our favourite eight-year-old nerd has a tie-dye makeover when the family visits a beach house, and finally makes her first-ever friends. But she’s terrified they’ll find out the truth about her, which Bart is all too happy to share.

Through Lisa, we relive the acute, awkward and perennial pains of adolescence and pressure to fit in, amidst the classic, condescending advice to “just be yourself”. Throw in a dash of sibling rivalry and you’ve got a time capsule for anyone who had a bit of a rough time making friends, or having brothers or sisters, growing up.

The happy ending, of course, proves the hackneyed advice always rings true after all. See you in the car!

Cultural relevance: 4/5
Quotability: 4/5
Musical moments: 0/5
Iconic moments: 4/5
Emotional resonance: 5/5
Laughs: 5/5

Total: 22/30

Words by: Giselle A. Nguyen

(tied) #13. ‘$pringfield (or, How I Learned to Stop Worrying and Love Legalized Gambling)’

Season 5, Episode 10

This episode packs a lot into 23 minutes. We open on an old newsreel, showing the Springfield of yore, full of hope and optimism, then transition to the run-down Springfield of today. The town’s woes prompt a community meeting (run by one of my favourite side characters, Mayor ‘Diamond’ Joe Quimby), where everyone agrees that the best solution is to legalise gambling and build a casino.

What follows is nothing short of the complete breakdown of society. Mr Burns becomes a reclusive, Howard Hughes-esque billionaire who’s terrified of germs. Marge is instantly addicted to gambling, which gives Homer the space to give into his worst parenting instincts. Meanwhile Bart, the wiliest of the family, thrives in the new capitalist paradise, building his own treehouse casino and kidnapping singer Robert Goulet, who delivers a great joke when told that his manger said he should “shut the hell up”. (“Really? Vera said that?”)

The other great celebrity cameo is former US Secretary of State Henry Kissinger, who’s terrified to let people know that he dropped his glasses in the toilet. Homer, of course, fishes the glasses out and starts wearing them.

There are so many iconic moments in this episode: Lisa dressed as the world’s crappiest Florida (next to Ralph “I’m Idaho!” Wiggum); Homer’s recollection of the town meeting, involving a green-haired Marge, a woman with a slinky neck, and a phone call from the President; and the oddly-prohetic moment in which Springfield’s Siegfried and Roy rip-offs, Gunter and Ernst, are attacked by their own tiger.

This episode has it all. Emotional scenes, (“You broke a promise to your daughter”), great celebrity cameos, a moral underpinning, and some iconic, still-quotable moments. Go and watch it now.

Cultural relevance: 4.5/5
Quotability: 4.5/5
Musical numbers: 0/5
Iconic moments: 5/5
Emotional resonance: 3/5
Laughs: 5/5

Total: 22/30

Words by: Rob Stott

(tied) #13. ‘Homer the Great’

Season 6, Episode 12

‘Homer the Great’ — the name says it all. Look, I’m not a Simpsons super-fan, but I’ve always adored Homer. He’s the fat, witless husband/dad with a heart of gold I’ve long pined for. All my favourite Simpsons quotes and memorable moments feature Homer: Homer in a mumu, Homer’s genius glasses, Homer selling his soul for a doughnut; the list is boundless.

In this glorious episode, Homer joins the Stonecutters, an exclusive men’s club based on the Freemasons. It’s revealed the clandestine sect controls Springfield, and Homer revels in the perks, parties and sense of camaraderie. But when he becomes leader, our rotund yellow hero learns it’s lonely at the top.

I partly love ‘Homer the Great’ because my late father was a (pretty undedicated) Freemason. I tried hard to make him tell me what happened at meetings and teach me the secret handshake, but his lips were as sealed as the group’s doors to women and people of colour.

Episode highlights include Prince references, moderate nudity and Patrick Stewart voicing Number One, the Springfield Stonecutters’ incumbent leader. Executive producer David Mirkin has called Stewart’s contribution, “one of the best guest performances” in Simpsons history.

But the best thing about this ep is definitely ‘We Do’ (The Stonecutters’ Song). Sung by a chorus of Stonecutters including Mr. Burns and Principal Skinner, the Emmy-nominated song is as catchy as it is hilarious. Plus, it references Steve Guttenberg, which alone makes it an instant “would recommend, five-stars” from me.

Cultural relevance: 4/5
Quotability: 4/5
Musical numbers: 4/5
Iconic moments: 3/5
Emotional resonance: 3.5/5
Laughs: 3.5/5

Total: 22/30

Words by: Nadine von Cohen

#12. ‘Homer Badman’

Season 6, Episode 9

This season six episode in which Homer is wrongly accused of groping the babysitter is one of the sharpest pieces of satire in the show’s entire run — albeit one that plays a little differently in light of everything that’s been happening in the media industry recently.

There’s no doubt that #MeToo colours a contemporary viewing of ‘Homer Badman’. At the same time, the way the writers skewer the grubby business of tabloid news feels more spot on than ever. There are plenty of laughs to be had here, be it in the opening stanza at the candy convention or Homer’s rendition of ‘Under the Sea’. But in this age of rampant partisanship, sensationalism and so-called fake news, it’s the stuff on the media — Homer’s interview with Rock Bottom in particular — that make this episode so iconic.

To quote Marge: “the courts might not work anymore, but as long as everyone is videotaping everyone else, justice will be done”.

Cultural relevance: 5/5
Quotability: 4/5
Musical numbers: 3/5
Iconic moments: 4/5
Emotional resonance: 2/5
Laughs: 4.5/5

Total: 22.5/30

Words by: Tom Clift

#11. ‘Lisa’s Substitute’

Season 2, Episode 19

Full disclosure: Lisa is my favourite Simpsons character. I know this is a widely unpopular opinion, so if anyone needs me I’ll be in my room.

‘Lisa’s Substitute’ is a perfect example of how the earliest seasons of The Simpsons were deeply invested in story and character development over straight-up gags. A quick rundown: Lisa’s class gets a substitute teacher named Mr Bergstrom (voiced by Dustin Hoffman) after Miss Hoover takes leave. Lisa swiftly develops a crush on Mr Bergstrom; he’s everything Homer lacks as a father figure: smarts, sensitivity, interest in her generally — he’s the Miss Honey to her Matilda.

There’s a B-plot about Bart running for class president against Martin which adds some levity to the episode, but this is, at heart, an origin episode for Lisa and Homer’s strained relationship, which is further explored in episodes like ‘Lisa’s Pony’, ‘Lisa the Greek’ and ‘Lisa the Beauty Queen’ (JUST A FEW EXAMPLES OF GREAT LISA EPISODES GUYS SHE REALLY IS A GREAT CHARACTER.)

‘Lisa’s Substitute’ is so insanely well written, from its little gems of wisdom from Mr Bergstrom (‘That’s the problem with being middle class — anybody who really cares will abandon you for those who need it more’) to the solid landing of its emotional beats.

Cultural relevance: 5/5
Quotability: 3/5
Musical numbers: 1/5
Iconic moments: 5/5
Emotional resonance: 5/5
Laughs: 4/5

Total: 23/30. (But 30/30 in my heart.)

Words by: Michelle Law

(tied) #9. ‘A Streetcar Named Marge’

Season 4, Episode 2

In a series famous for its film and literary parodies, few are as memorable of this spot-on send-up of A Streetcar Named Desire. Of course, anyone familiar with the Tennessee Williams play would know just how ridiculous the idea of a flashy musical adaptation is, but that’s just part of what makes this episode so brilliant.

It’s frightfully easy to imagine Marge as Blanche DuBois, driven to madness by Homer’s brutish, boorish Stanley. The writers do a great job of balancing Streetcar in-jokes (like Homer’s obsession with his bowling video game) with more accessible gags, while also providing some genuinely moving insight into Marge and Homer’s marriage. And that’s to say nothing of the wonderfully ridiculous musical numbers.

Meanwhile, the episode is also home to one of the show’s best ever B-plots, centred around Maggie’s time in a draconian day care centre. Her mission to liberate her pacifier results in two more iconic parodies — first an extended spoof of The Great Escape, before a sudden, masterful pivot into Alfred Hitchcock’s The Birds.

Cultural relevance: 3/5
Quotability: 4/5
Musical numbers: 4/5
Iconic moments: 3.5/5
Emotional resonance: 4/5
Laughs: 5/5

Total: 23.5/30

Words by: Tom Clift

(tied) #9. ‘Who Shot Mr. Burns’

Season 6, Episode 25 and 26

‘Who Shot Mr Burns’ is an iconic episode that honestly changed the way we viewed cartoons. It was pretty dramatic to do a two-episode prestige crime-mystery on an animated comedy, but they did it. Inspired by shows like Twin Peaks, where hundreds of thousands of people waited in suspense to solve the mystery, it was not only a bold move but a hilarious episode.

It’s loaded with hilarious quotes: “Sure I’m dizzy and nauseous, but where’s the inflated sense of self esteem?” Or: “But with him out of the picture, I was free to wallow in my own crapulence.”

It’s also a great story, the revolves around Mr Burns finally going full supervillain, instead of just being a regular amount of evil, as he enacts a plan to block out the sun from Springfield (“Since the beginning of time man has yearned to destroy the sun”).

It was also kinda cool how they actually set up a decent mystery — spoiler: it was Maggie.

Cultural relevance: 5/5
Quotability: 5/5
Musical numbers: 1/5
Iconic moments: 5/5
Emotional resonance: 2.5/5
Laughs: 5/5

Total: 23.5/30

Words by: Patrick Lenton

(tied) #7. ‘The Springfield Files’

Season 8, Episode 10

This X-Files crossover is about as 90s as it gets, and that’s what makes it so delightful, with cameos from Mulder, Scully and Star Trek’s late, great Leonard Nimoy.

The cultural fascination with aliens continues to this day, so even though this episode is over two decades old (with the pop-culture references to prove it) it still feels relevant and fresh. The Simpsons has always done mini-mystery well, and I still remember my surprise at the reveal of this episode when I first saw it as a child — it’s completely ridiculous, but that’s what makes it so endearing.

Stuffed with some of the series’ most memorable visual gags — and a musical ending to boot — The Springfield Files is classic Simpsons.

Cultural relevance: 4
Quotability: 5
Musical moments: 3
Iconic moments: 5
Emotional resonance: 3
Laughs: 4

Total: 24/30

Words by: Giselle A. Nguyen

(tied) #7. ’22 Short Films About Springfield’

Season 7, Episode 21

I tried to write a super meta “22 Short Reasons Why ’22 Short Films About Springfield’ Is The Best Simpsons Episode” list but midway through what must’ve been my 100th rewatch of this spectacular episode, I’d already jotted down more than 50 short reasons.

The format of this episode (one that the series has surprisingly never returned to) is a collection of 30-90 second long shorts that falls just short of the 22 promised in the title. Each short features different characters from Springfield, from series regulars to cult favourite background characters, in a much larger than life gag that you’d see in a regular episode.

In spite of the zany situations featured in each vignette, each short also gets to the bottom of what makes each Simpsons character tick. You could put forward almost every one of the shorts as an all time best character moment for the Springfield resident featured within it: Mr Burns’s bizarre 19th century slang that he yells to motivate an allergic reaction suffering Smithers to cycle himself to hospital, Lisa’s defeated “I smell like a sandwich” as she waits in the sun for the peanut butter and mayonnaise to melt in to her hair.

And of course, one of the most beloved scenes in Simpsons history, Superintendent Chalmers’ steamed ham lunch with Principal Skinner, which almost every person I know between age 25 and 35 can quote verbatim, the inspiration for countless memes and tributes  including an onslaught of steamed ham enquiries to Woolworths’ Facebook page two years ago, which lead to them having to post a Simpsons reference filled official statement. In fact, I could’ve just written the words ‘aurora borealis’ instead of this mess of gushing sentences and it would’ve made just a strong a case that ’22 Short Films’ is the best episode.

I’ve seen every episode from seasons 3 – 8 well over 50 times, and for the most of them I can tell you what’s about to happen for the next 20 minutes after only watching the first. But 22 Short Films random collection of moments with creative visual segues between each of them (something I would also love in HBO’s late 90s sketch comedy Mr Show) don’t really hint at what’s to come next. It’s one of the few Simpsons episodes that catches me off guard with moments that I’d forgotten were in this episode, like the long-legged man in the little car getting his revenge on town bully Nelson Muntz, or Milhouse being forced to buy a used Hamburglar comic in order to use the bathroom at The Android’s Dungeon. (I just wish they were able to include the missing Lionel Hutz short too).

’22 Short Films About Springfield’ is a brilliantly edited, lovingly written summation of what makes The Simpsons so wonderful. It should be the perfect entry point to the series for a newcomer, but really it’s a reward for everyone who’d already fallen in love with Springfield and the characters within it.

Cultural relevance: 3/5
Quotability: 5/5
Musical numbers: 5/5
Iconic moments: 5/5
Emotional resonance: 1/5
Laughs: 5/5

Total: 24/30

Words by: Andrew Levins

#6. ‘You Only Move Twice’

Season 8, Episode 2

“So long, stinktown!”

The Simpsons does parody better than anyone else — instead of doing a straight up spoof of a Bond film, they take a classic supervillain in the form of Hank Scorpio, and transfer him into the role of a charismatic CEO of a suburban business. It’s brilliant, and full of some hilarious moments and brilliant lines (“What’s wrong with this country? Can’t a man walk down a street without being offered a job?!”).

‘You Only Move Twice’ follows the Simpson’s move to Cypress Creek, where in the bowels of a supervillain’s evil corporation, everything works out for Homer for once. Unfortunately that doesn’t hold true for the rest of the family. It’s one of the episodes that highlights just how… sad Marge’s life is, as she starts drinking out of boredom in the perfect suburban utopia.

But probably the highlight of the episode is the character of Hank Scorpio, who is both hilarious and a prophetic foretelling of charismatic tech moguls like Elon Musk.

Cultural relevance: 4/5
Quotability: 5/5
Musical numbers: 3.5/5
Iconic moments: 5/5
Emotional resonance: 2/5
Laughs: 5/5

Total: 24.5/30

Words by: Patrick Lenton

(tied #4) ‘Homer’s Phobia’

Season 8, Episode 15

Growing up, we all knew “those kids” who weren’t allowed to watch The Simpsons because their parents were concerned about the content. The episode I’ve chosen, ‘Homer’s Phobia’ (c’mon you knew I was going to choose the gay episode with a pun title) was probably one reason some of them were concerned.

For an episode that was broadcast in 1997, a few months before Ellen came out on television, it is pretty progressive. It stars John Waters, one of the queerest and most subversive directors of all time as John, a gay storeowner who is introduced to the Simpson family. Huge. But more importantly, John introduces the Simpson family to gay culture, through campness, humour, and grace.

The episode follows Homer’s journey as he is first oblivious to John’s queerness, and then disgusted and scared of it, until he finally has a breakthrough when John saves his life. The main throughline of the episode is that Homer thinks John’s presence will make Bart gay, and this lets us experience a wonderful exploration of masculinity (including the iconic steel mill scene).

But ‘Homer’s Phobia’ is most special to me because we get to see the Simpsons’ life in the suburbs through the lens of queerness. It plays Homer’s homophobia as incredibly stupid, something to be dismissed and laughed, but not preached about. John as a character gets to be the better man, the funny and genuine and gentle soul. The hero. He is clearly superior, and above what is going on around him, and that’s how I feel about the queer community to this day.

‘Homer’s Phobia’ is an excellent episode, and by far The Simpsons’ best attempt at dealing with queerness. Especially since we all know Lisa should have been a lesbian.

Cultural relevance: 5/5
Quotability: 4/5
Musical numbers: 3.5/5
Iconic moments: 4/5
Emotional resonance: 4.5/5
Laughs: 4/5

Total: 25/30

Words by: Bec Shaw

(tied) #4. ‘Marge vs The Monorail’

Season 4, Episode 12

In my opinion (which in this paragraph at least, is the only opinion that matters) Marge-centric episodes are the best episodes. “But wait,” you might be thinking. “This is the one with all the singing about the monorail, right? The monorail that Homer drives? That’s not about Marge!” Well guess what dum dum, it IS, because when the residents of Springfield decide to give Mr. Burns’ $3 million environmental fine to a shady monorail-salesman named Lyle Lanley, she (and later, Lisa) are the only ones to flag, “hey, seems like this thing might kill us all”.

This episode features so many classic moments that it’s hard to narrow them down (Conan O’Brien reckons it’s his favourite of all the episodes he wrote). Marge and scientist/former monorail-builder, Sebastian Kobb, being late for the monorail’s deadly launch because Kobb wanted to stop for a haircut! Leonard Nimoy (“one of the Little Rascals”) launching the monorail and saving the day! (“My job here is done,” — Nimoy. “What do you mean? You didn’t do anything,” — Barney. “Haha… Didn’t I?”– Nimoy *beams into sky*.)

Plus, the Monorail Song. THE MONORAIL SONG! The Monorail Song has to be in the top three all-time greatest Simpsons songs. Maybe the first? Sorry Mom, the mob has spoken!

Cultural relevance: 3/5
Quotability: 5/5
Musical numbers: 5/5
Iconic moments: 5/5
Emotional resonance: 2/5
Laughs: 5/5

Total: 25/30

Words by: Sinead Stubbins

#3. ‘Flaming Moes’

Season 3, Episode 10

Homer tells Moe about a secret cocktail he once accidentally made called the “Flaming Homer”, Moe steals the recipe, renames it the “Flaming Moe” and becomes a huge success. Homer subsequently loses his tiny mind, seeks revenge and wouldn’t-you-know-it by the end everything’s back to normal and we’ve learnt something about friendship and had a great bloody laugh.

This is solid gold Simpsons, from beginning to end. There are so many killer jokes here. From Bart’s chalkboard gag (Underwear should be worn on the outside) to Homer’s stupefied response to Eye on Springfield (“Wow. In-Fo-Tainment.”) to hilariously dark one-liners effortlessly dropped into the dialogue (Moe to Homer: “Increased job satisfaction and family togetherness are poison for a purveyor of mind-numbing intoxicants like myself.”)

Plus there’s goddamn Aerosmith singing ‘Walk This Way’. AND a just-as-good-as-the-real-thing parody of the Cheers theme song. AND Bart crank calls Moe’s asking for “Hugh Jass” and turns out Hugh Jass is a real actual man and he answers the phone and Bart doesn’t know what to do and it is funny.

Legend has it that the plot reflects the tested friendship between co-creators Sam Simon and Matt Groening, and Simon’s frustration with feeling like he wasn’t being given sufficient credit for his work on the series. I prefer to think of it as a cutting morality piece about the lure of greed and fame and how capitalism compels us to devalue things like friendship and loyalty for the sake of amassing material wealth.

Also I like how the guy trying to buy Moe out is from a company called Tippsy McStagger’s Good Time Drinking and Eating Emporium.

All in all: brilliant. I don’t know what else you could want from a 22-minute satirical cartoon, frankly. My thanks and congratulations to all involved, which I’m sure will mean a lot to them.

Cultural relevance: 4/5
Quotability: 5/5
Musical numbers: 4/5
Iconic moments: 5/5
Emotional resonance: 2.5/5
Laughs: 5/5

Total: 25.5/30

Words by: Tom Ballard

#2. ‘Bart Sells His Soul’

Season 7, Episode 4

Is there a better analogy for the current state of The Simpsons than ‘Bart Sells His Soul’? Bart’s as cocksure as ever, so certain that the concept is made up that he’s quite delighted to relieve Milhouse of $5 in return for his very essence.

It’s an all-timer, from that tremendous musical opener to the dazzling array of one-liners (“This sounds like rock and/or roll” and “I am familiar with the works of Pablo Neruda” are particular highlights). There’s sulfur-scented Biblical horror and existential angst and acid wit leavened by sweetness, some of the hallmarks of writer Greg Daniels’ later work in Parks and Recreation and the US version of The Office.

And of course it’s Lisa who gets the soul back. Of course it is. She’s not just the show’s beating heart, she’s always been the small and impossibly huge aspect that makes The Simpsons truly alive, which is why her recent portrayal hurts so much.

That’s the beauty of ‘Bart Sells His Soul’: not the certainty that innocence lost can be regained, but the knowledge that questing after what has gone missing may see you end up a little bit further along and with a little bit more than when you started. Make it so, Matt.

Cultural relevance: 5/5
Quotability: 4/5
Musical numbers: 4/5
Iconic moments: 3/5
Emotional resonance: 5/5
Laughs: 5/5

Total: 26/30

Words by: Hari Raj 

#1. ‘Last Exit To Springfield’

Season 4, Episode 17

The thing I remembered most clearly about this episode, before sitting down to rewatch it, is the iconic “Dental Plan… Lisa needs braces!” scene. But it turns out ‘Last Exit To Springfield’ is packed full of some of the most memorable Simpsons moments ever including McBain’s “Ice to see you” line, the brilliant homage to The Godfather II with Homer playing Don Fanucci, the monkeys coming up with “It was the best of times… it was the blurst of times”, and one of my favourites: Homer answering the door in response to “Goons. Hired Goons”.

Yep, these are all packed into one 23 minute episode.

But it’s not just the individual moments of brilliance that make this one of the best episodes ever. The plot revolves around Homer becoming president of his union and leading the power plant employees on a strike in order to retain the company’s dental plan policy, which has personal relevance for the Simpson family after Lisa’s dentist informs her she needs braces.

It’s one of the rare moments where The Simpsons goes explicitly political and it works perfectly. The heartwarming and progressive story is balanced with exactly the right amount of jokes and self-awareness, and there’s even an amazing strike song to boot.

This episode rules.

Cultural relevance: 5/5
Quotability: 4/5
Musical numbers: 3/5
Iconic moments: 5/5
Emotional resonance: 5/5
Laughs: 4.5/5

Total: 26.5/30

Words by: Osman Faruqi