How do you define what constitutes the best episode of a series, especially one that has been on the air since 1987 and spans 33 seasons?
Do you judge based on how many times you laugh out loud? How unique the characters are? How accurately it predicts the future? How absurd the plotline? Or perhaps how true it stays to what made you fall in love with the series, to begin with?
In the case of The Simpsons, even one of the show’s most prolific writers — John Swartzwelder — expressed difficulty in deciding which of his 59 episodes he ranked the highest.
Speaking to The New Yorker in a rare interview, the reclusive Swartzwelder cited Itchy & Scratchy & Marge, Bart the Murderer, Dog of Death, Homer at the Bat, Homie the Clown, Bart Gets an Elephant, Homer’s Enemy, and Homer vs. the Eighteenth Amendment as the episodes that he always enjoys watching.
Because choosing just one felt too impossible, we decided to do what any smart person would do and outsource the task to a diehard group of The Simpsons fans. Here are the episodes they said they loved the best.
Marge vs. the Monorail — Season 4, Episode 12
Written by late-night host Conan O’Brien, the monorail episode is highly regarded among most fans of the Matt Groening series, especially as Star Trek‘s Leonard Nimoy makes an appearance.
Even O’Brien has said that this episode, in which Springfield must figure out what to do with the $3 million Mr Burns has paid the town in fines, is one of his favourites.
The late Phil Hartman also appears in the instalment as Lyle Lanley, the smooth-talking monorail salesman who swindles the townspeople into erecting the transit system through his catchy song.
One Fish, Two Fish, Blowfish, Blue Fish — Season 2, Episode 11
In this early episode, Homer begrudgingly agrees to try something new at Marge’s behest and takes his family to a new all-you-can-eat sushi restaurant.
Having ingested incorrectly prepared blowfish, the Simpsons patriarch is told he only has 24 hours to live and sets about trying to tick everything off of his bucket list.
Deep Space Homer — Season 5, Episode 15
When NASA decides they want to send an “average Joe” on a space mission to boost their telecast ratings, Homer is selected (by default) to join the astronauts on their launch.
After a mishap involving Homer’s smuggled potato chips and a destroyed ant farm, the shuttle is in grave danger with Springfield watching the events unfold over the news. Homer manages to save the day (after he’d nearly destroyed it) and jams the shuttle’s door closed using an inanimate carbon rod — which is then celebrated as a hero and given a Time magazine cover.
Lisa’s Wedding — Season 6, Episode 19
At a Renaissance Fair, Lisa is embarrassed by Homer’s antics and seeks refuge in the tent of a mysterious fortune-teller.
Gazing into her future, it is revealed that Lisa meets a dashing British love interest Hugh (voiced by Mandy Patinkin) and they plan to marry. Still embarrassed by her family, Lisa dreads the day Hugh and his aristocratic parents must meet Marge, Homer, Bart and Maggie.
On their wedding day, Lisa realises that Hugh is not the man for her when he refuses to wear the pig cufflinks Homer had given him as part of the Simpson family tradition.
Scenes from the Class Struggle in Springfield — Season 7, Episode 14
When Marge finds a Chanel suit at her local thrift store for $90, she begins wearing it everywhere, including while vacuuming the lounge and taking the car to the petrol station.
When she attracts the attention of one of her old friends, Evelyn, she is mistaken for someone wealthy and is invited to begin spending time at the Springfield Country Club. Feeling the pressure to appear as though she has more than one Chanel in her closet, Marge begins altering the suit to make it look different each time before splashing out and buying an actual designer ballgown.
Ultimately, the Simpsons matriarch decides that she would rather not be a member of the Country Club because they don’t accept her and her family as they are.
When Flanders Failed — Season 3, Episode 3
Long before Fyre Festival didn’t happen, this Simpson‘s episode was a great example of schadenfreude.
When Ned Flanders decides to quit his corporate job and open a retail store that sells products only for left-handed people, Homer thinks it’s the stupidest thing he’s ever heard.
After wishing on a wishbone that Flanders will fail in his pursuit, Homer is delighted to see that business is terrible for his God-fearing neighbour until he has a crisis of conscience and decides to help the Leftorium succeed.
You Only Move Twice — Season 8, Episode 2
Written by John Swartzwelder (although it was notably absent from his list of favourites), this iconic episode sees Homer accepting a fancy new job at a Power Plant in Cypress Creek, working for a charming new boss, Hank Scorpio.
While Homer thrives in his new role and environment, his family quickly become miserable as Lisa finds herself allergic to everything, Bart is thrown into remedial learning and Marge is bored without any housework to do.
Seeing as the episode is inspired by the James Bond film You Only Live Twice, the whole thing plays out as a Bond parody, right down to the fact that Scorpio is a secret supervillain… who knows an awful lot about where to buy a hammock.
El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer) — Season 8, Episode 9
When the annual chilli cook-off descends upon Springfield, Marge begs Homer not to embarrass her by getting too drunk as he does every year.
After eating a chilli made with Guatemalan insanity pepper, Homer starts to hallucinate and embarks on a psychedelic trip — along with a coyote voiced by Johnny Cash — to find his soulmate.
$pringfield (Or, How I Learned to Stop Worrying and Love Legalized Gambling) — Season 5, Episode 10
Mr Burns opens a casino in Springfield in order to boost the town’s dwindling economy, an idea that even the morally upright Marge is on board with.
Homer takes a job in the casino as a blackjack dealer, prompting Marge to find a coin on the floor while waiting for him to finish his shift. Soon, she is hopelessly addicted to gambling as the Simpson house falls apart in her absence.
Mr Burns, meanwhile, becomes obsessed with watching the casino 24 hours and slowly descends into madness.
Homer vs. the Eighteenth Amendment — Season 8, Episode 18
Another of Swartzwelder’s favourites, Homer vs. the Eighteenth Amendment features Homer as the “Beer Baron” who continues to supply Springfield with illegal booze after prohibition is re-introduced in the town.
Desperate to find out where the “hooch” is coming from, Mayor Quinby’s replacement Rex Banner (voiced by Dave Thomas) patrols the neighbourhood, as Homer makes bootleg liquor right under his nose.
This episode brought us one of the most iconic Simpson’s lines of all time, uttered by Homer at its conclusion: “To alcohol! The cause of… and solution to… all of life’s problems!”
We’ll drink to that.
Read more stories from The Latch and subscribe to our email newsletter.