15. Simpsons Roasting on an Open Fire (season 1, episode 1)
The episode: Downbeat and desperate on Christmas Eve, Homer tries to make ends meet by working as a mall Santa.
Why it’s one of the best: Sure, it’s the very first episode – but it’s not on our list for its historical significance alone. The animation may be a little crude even compared to the next season, yet this is classic Simpsons all the way down to the bone: crude humour and a sickly-sweet premise mesh together perfectly to create an opening episode that captured hearts and minds the world over.
The best bit? It has to be Bart’s infantile rendition of Rudolph the Red-Nosed Reindeer, which was probably the soundtrack of schools for months to come, though the introduction of Santa’s Little Helper still makes the hairs stand up on the back of your neck some 30 years later. Yes, a milestone, but a magnificent one at that.
14. Homer at the Bat (season 3, episode 17)
The episode: Locked in a rivalry with the Shelbyville Power Plant owner, Mr Burns makes a $1 million bet that his employees will beat Shelbyville’s team in a game of softball. Burns plays the system by hiring several major league players as workers.
Why it’s one of the best: Trust The Simpsons to assemble a collective all-star team of talent, including then-current baseball stars Jose Canseco, Steve Sax, and Wade Boggs, and have them written off in increasingly madcap ways.
Boggs gets into an argument about 18th Century Prime Ministers with Barney; Don Mattingly is kicked off the team for not shaving his “sideburns”, and Ozzie Smith ends up trapped in another dimension. It’s silly as all hell but all the more hilarious for it. We even get a feel-good ending as Homer, still stuck on the bench thanks to Daryl Strawberry being the only MLB player in his position not to miss the game, goes on to win the contest for Springfield. This episode proved that The Simpsons could treat its guest stars with reverence or as one-note jokes because everyone was just glad to be a part of the now-cultural phenomenon.
13. Lemon of Troy (season 6, episode 24)
The episode: Springfield’s schoolkids engage in all-out warfare with long-time rivals Shelbyville after they steal Springfield’s lemon tree.
Why it’s one of the best: The Simpsons as a show doesn’t often stray from Springfield – even when it does, it’s normally just an excuse to chuck stereotypes at the wall and see what sticks – but there’s something special about the dark mirror that is Shelbyville in "Lemon of Troy."
Like most of the best Simpsons episodes, the episode U-turns after the first act, a brilliant echoed lecture from Marge on Springfield’s importance, and dashes into a breakneck heist to get Springfield’s lemon tree back. It’s made all the better by the likes of Bart and Milhouse being backed up by their parents – and Ned reluctantly tagging along for the ride while Homer abuses the many gadgets and gizmos onboard his neighbourino’s RV is the cherry on top of a lean joke machine of an episode.
12. You Only Move Twice (season 8, episode 2)
The episode: Homer and his family ups sticks after he’s offered a cushy job at a new company, run by not-so-secret supervillain Hank Scorpio.
Why it’s one of the best: Many characters have taken whole seasons to have the sort of impact Hank Scorpio does within 22 of some of the most hare-brained, hilarious minutes ever committed to television.
The B-plot, involving some of the family struggling to fit in to Cypress Creek, can waver slightly, but that hardly matters when every single Hank Scorpio/Homer Simpson interaction is instantly-quotable and razor sharp. The kicker, in which Homer is the only person somehow incapable of realising that Hank Scorpio is almost literally a Bond villain, makes the episode even better upon multiple rewatches, too. It’s a real shame we missed out on a second outing with Hank Scorpio after he was scrapped from The Simpsons Movie, but at least we have this. And the Hammock District (that’s on Third).
11. Cape Feare (season 5, episode 2)
The episode: The Simpsons are forced to enter Witness Protection after Sideshow Bob threatens to kill Bart.
Why it’s one of the best: It’s all in the rakes. The sequence, which sees Sideshow Bob repeatedly step on several of the pointy garden tools, is proof that The Simpsons could do no wrong at this point in the series’ run. Any other show would’ve cut the sight gag down considerably but, here, the elongated runtime – actually used to fill time after a short script – works wonders. Whether it’s the impeccable job done by Kelsey Grammer after every growl, or the eventual zoom out to give the viewer the final punchline that Bob has been surrounded by rakes all this time, this is The Simpsons at its most absurd, creative best. The creative staff had their nuclear family down pat, and now they took that swaggering confidence to the show’s secondary characters – and it showed in spades.
10. Lisa's Substitute (season 2, episode 19)
The episode: After Mrs. Hoover is taken sick, Lisa’s second-grade class is taken over by substitute teacher Mr. Bergstrom.
Why it’s one of the best: "Lisa’s Substitute" shows that a cartoon doesn’t need to go over-the-top to be funny and heartwarming at the same time. At its core, this is a story about a daughter who feels underappreciated by her father, and chooses to find a substitute (yes, every Simpsons episode is pretty much a terrible joke) in Mr Bergstrom, expertly played by Oscar winner Dustin Hoffman.
While there are jokes aplenty, this isn’t an episode that’s carried by belly laughs or barnstorming set-pieces. It all comes down to four little words Bergstrom writes on a piece of paper, ones that would come to define the terrific storytelling of the early years of the show: You are Lisa Simpson. It’s an amazing look at Homer’s pig-headedness and that rare thing in a TV sitcom: an episode where everyone comes out of it a more well-rounded character. This really is essential viewing for any Simpsons fan and, hey, if you’re not a Simpsons fan, this is probably where you should start.
9. Homer's Barbershop Quartet (season 5, episode 1)
The episode: While killing time after breaking down on the way home from a swap meet, Homer recounts the story about the time he was in a barbershop quartet.
Why it’s one of the best: What a way to kick off one of the finest seasons in television history. From the jokey asides of Principal Skinner trying to find the exact helmet from when he was a POW, to the many, many Beatles references littered throughout, everything in this episode is delivered with such pinpoint accuracy that you spend the entire time watching it with a massive grin on your face. The episodes where the Simpsons dive into the past often rank among the show’s best, but this refines that formula to a tee as the show bounces back and forth between the red-hot rhythm of the present-day jokes, and the show’s well-known talent for picking apart a time and place with relentless enthusiasm. It helps that the music, which we could (probably) forgive if it wasn’t all that, is actually some of the catchiest ever produced on the show. All together now: Baby on board…
8. 22 Short Films About Springfield (season 7, episode 21)
The episode: The clue’s in the name: this is a series of vignettes about the weird and wonderful world of Springfield – and the characters who inhabit it.
Why it’s one of the best: This shouldn’t have worked. "22 Short Films About Springfield" chooses to get rid of The Simpsons (for the most part) and instead focus on the wackiness that goes on around them. For any other show, it would have been a death sentence. For this show? Well, there’s a reason it’s this high up on the list. Nearly every secondary character – barring Professor Frink, of course – gets a chance to shine here, but there’s one 90-second moment that will probably live on forever. Yep. Steamed Hams. Despite its newly-found meme status, it’s hard to discount just how incredibly well-pitched the scene is with every moment featuring masterful comic timing, exceptional voice acting, and the ability to be absolutely ridiculous while still remaining grounded in the huge, colourful town that is Springfield. It shouldn’t have worked – but it couldn’t have turned out any better.
7. Marge vs. The Monorail (season 4, episode 12)
The episode: Mr. Burns is fined $3 million and, in their bountiful wisdom, the town of Springfield spends it on a monorail system.
Why it’s one of the best: Yes, here you’ve got your one-liners, amazing songs, and even your celebrity guest appearances – all of which feature in this episode – but it’s the exceptional voice talent of the late Phil Hartman that’s the glue that holds "Marge vs. The Monorail" together. As Lyle Lanley, he oozes both charm and smarm, and is able to smooth-talk his way into selling his faulty monorail system to Springfield because, after all, it put North Haverbrook, Ogdenville, and Brockway on the map. Lanley could have been such an obvious villain, but Hartman plays him with enough loveable arrogance that it’s hard not to be drawn in along with the rest of the town. Sure, this episode isn’t just about Phil Hartman, but it’s a testament to his astounding ability that he turned a very, very good episode into an all-timer. He was (and still is) sorely missed.
6. Deep Space Homer (season 5, episode 15)
The episode: To stop flagging ratings, NASA trains two ‘average’ people with the goal of them becoming astronauts: Homer Simpson and Barney Gumble.
Why it’s one of the best: This is one of the most quotable and memorable Simpsons episodes ever, with each joke and moment seemingly burned into our collective memories thanks to its absurd premise. It’s the insect overlords; Homer finally understanding the ending to Planet of the Apes mid-press conference; the inanimate carbon rod; that beautifully-rendered sequence with Homer floating about in space – it’s all pretty much perfect. But it doesn’t break the top five. Yep, the show is that good that an episode, which would easily rank as an all-time great anywhere else barely makes a dent in the Mount Rushmore of its run. Still, this is The Simpsons firing on all cylinders, even if the plot stretched the rubber-band of believability about as far as it would go before snapping in later years.