Mmm... controversy. Ask 100 people what the best Simpsons episode is and there's every chance you'll get 100 different answers. Such is the quality of the golden era of Springfield's Favorite Family, it's a Homer-in-a-muumuu-sized task whittling the best Simpsons episodes down to 25, let alone putting them in some sort of perfectly cromulent order.
Over the years, The Simpsons have battled Presidents, joined secret cults, and even orbited the Earth (sorry Grimey, but Homer did go to space). Across 34 seasons and 750 episodes, Homer, Marge, Bart, Lisa, and Maggie have done it all. But which ones are the best and just as watchable today in 2023 as they were in the Bartman-obsessed '90s?
Let's do it to it – this list, that is. Crack open a Duff and sneak in a super sour ball as we rank the sweet, sweet can...didates for the best Simpsons episode ever. And for more animated goodness, check out the best anime you should be watching as well as our guides to Jujutsu Kaisen season 2 and Demon Slayer season 4.
25. Rosebud (season 5, episode 4)
The episode: Mr Burns appears to have everything, yet he secretly craves the one thing money can’t buy – his childhood teddy bear, Bobo. Inexplicably, it ends up in the hands of one Maggie Simpson.
Why it’s one of the best: The Simpsons often wears its pop-culture references on its sleeve and perhaps none more so than in "Rosebud." Part Citizen Kane-parody, part examination into the mind of Springfield's unloved billionaire, Mr Burns manages to steal the show throughout with a bunch of ridiculous schemes to try and get Bobo back. The highlight, though, has to be the Power Plant owner’s attempt to take over every television station to try and emotionally blackmail Homer. The split-second turn from Homer being worried about the fate of his TV shows to really getting involved in the plight of a fictional Smithers skit ranks as one of the series’ finest gags.
24. El Viaje Misterioso de Nuestro Jomer (season 8, episode 9)
The episode: After a chilli cook-off gone very, very wrong, Homer spends the night hallucinating in the desert and comes to the conclusion that Marge may not be his soulmate.
Why it’s one of the best: Honestly? It’s like nothing seen in the Simpsons either before or since. Director Jim Reardon does a pitch-perfect job with the trippy animation during the hallucination sequences as Homer wanders the desert amid a cacophony of colour and regret – and it’s all topped off by Johnny Cash voicing a space coyote. That’s not a typo.
That’s not to say "El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)" doesn’t bring the laughs. The whole lead-up with the chilli cook-off brings with it some spicy, side-splitting set-ups and the episode is also one of the best case studies into why Marge and Homer, despite their trials and tribulations, just work as a couple. D’aww.
23. Behind the Laughter (season 11, episode 22)
The episode: A parody of VH1’s Behind the Music, the episode re-imagines the Simpsons as a real-life TV show, complete with behind-the-scenes interviews with Homer (the creator of the show) and his supporting cast.
Why it’s one of the best: Ideally, this should have served as the series finale to The Simpsons. A meta deconstruction of everything that was good (and bad) about the show, "Behind the Laughter" captured the lightning-in-a-bottle effect of what made the series’ early years so magical but turned it on its head with the genius concept of giving the origin story of The Simpsons a fictional documentary.
Homer’s a pushy star hooked on drugs, Bart and Lisa tire of the show’s one-note and repetitive plotlines, and narrator Jim Forbes decries the tacky merchandise pushed out in the show’s name. It’s a great commentary of the show, with enough laugh-out-loud moments to rival some of the show’s golden years.
22. Who Shot Mr. Burns? Parts One and Two (season 6, episode 25 and season 7, episode 1)
The episode(s): Mr. Burns goes on a tyrannical tirade and manages to block out the sun. He’s only stopped in his tracks by a mysterious assailant who shoots him just outside Springfield’s town hall.
Why it’s one of the best: Okay, this one is a bit of a cheat. While both episodes aired separately, and make up one of only a handful of serialised stories in Simpsons history, one doesn’t work without the other. To put it mildly, this was a mystery that gripped a nation in the summer of 1995 as even a telephone contest and TV special – with Vegas odds, no less – was set up to try and figure out whodunnit. Then it turns out it was the baby all along. Yeah…
Even with that nonsensical reveal (which would be roundly mocked by the show itself in the years to come), the episode is packed with the crème de la crème of Simpsons hallmarks from this period: obscure references (including a whole Twin Peaks parody that was probably lost on 80% of the audience) and absurd plot beats.
But it's so much more than that. For one thing, it’s a genuine mystery you can still go back and piece together, and its irreverent, offbeat ending - which sees everyone involved brushed off the murder, leaving no consequences for the murderous Maggie Simpson - was unlike anything else at the time. It’s a first-rate episode with the added dimension of it being a more-than-passable crime mystery as well.
21. Treehouse of Horror 5 (season 6, episode 6)
The episode: The fifth instalment of the show’s legendary Treehouse of Horror series, this episode features a parody of The Shining, Homer travelling through time with disastrous consequences, and Springfield Elementary being turned into a Sweeney Todd-style eatery.
Why it’s one of the best: This topped our best Treehouse of Horror episodes list - and for good reason. The Shinning (we don’t want to get sued) is a note-perfect parody of the Stanley Kubrick classic – with a delightfully Simpsons feel to it as Homer goes crazy due to a lack of beer and TV. Nightmare Cafeteria, complete with gross-out ending, also brings the chills and the chuckles, particularly with the outlandish Principal Skinner puns that have no intention of hiding the fact he’s eating elementary school students.
The highlight of the episode, though, is Homer’s time travelling adventures. His reluctance not to touch anything in the past – thanks to, weirdly, his father’s wedding day warning – gives way to Homer going all smashy-smashy with a baseball bat and messing up the timelines for good. Doctor Who, eat your heart out.
20. One Fish, Two Fish, Blowfish, Blue Fish (season 2, episode 11)
The episode: After eating poisonous fugu fish at a Japanese restaurant, Homer is given only 22 hours to live. He sets out to tick off his bucket list before saying goodbye for good.
Why it’s one of the best: Who said The Simpsons needs to tickle your funny bone to create a great episode? Absolutely one of the saddest 22 minutes in television history, Homer’s separate farewells to each of his family tug at the heartstrings but also earn some tough laughs through the tears, including Homer teaching Bart how to ‘shave’, despite bleeding like a stuck pig. It all leads up to, for my money, the best end joke in the show’s history. Homer, inexplicably, survives and vows to live life to the fullest. We end with him stuffing his face on his couch whilst watching bowling, of all things. Brilliant.
19. Homer the Great (season 6, episode 12)
The episode: Homer stumbles upon a Mason-like secret society operating in Springfield and, Homer being Homer, tries to finds a way to try join and (most importantly) fit in.
Why it’s one of the best: This episode is nothing but a minute-to-minute joke machine. From Lenny doing his level best to give away the identity of the Stonecutters in the opening minute to the ‘We Do’ song and the Paddling of the Asses ritual, it’s credit to the writing team that they could even fit a plot into there. And that they do: Patrick Stewart voices Number 1, the Leader of the Stonecutters, until Homer reaches top spot in the only way he knows how: sheer dumb luck. His inevitable fall, by abusing his power, is only made funnier by the fact everyone else goes and makes another secret society that he can’t join.
18. Homer's Enemy (season 8, episode 23)
The episode: The Springfield Nuclear Power Plant gets a new model employee in the shape of Frank Grimes – but he doesn’t last long thanks to the sheer incompetence of Homer.
Why it’s one of the best: Probably the most controversial episode in the show’s history, Homer’s Enemy digs down into some dark territory – most notably, with the ending – but its premise is too fantastic to ignore. Here, we’re given a look at how a quote-unquote normal character would fare in Springfield when faced with Homer’s buffoonery and dumb luck. The answer? Not well. Everything from Homer winning a children’s contest to his repeated calls of ‘Grimey’ make Frank Grimes’ blood boil. He soon spirals out of control; it’s proof that no one can keep up with the show’s cartoonishness. And then he accidentally kills himself while trying to ape Homer. Like I said, dark territory.
17. Mr. Plow (season 4, episode 9)
The episode: Homer finds success by starting up a snow plow business but best friend Barney tries to muscle in on his turf.
Why it’s one of the best: Now we’re reaching classic territory. This episode marked the moment where the show went from a pretty damn good cartoon to one of the all-time greats. Even casual Simpsons fans would do well not to remember the Mr Plow jingle, but it’s the absurdity of the episode’s set-ups that are most fondly recalled.
The entire Mr Plow commercial, especially Grandpa getting bored halfway through, is a treat to watch, and the animation of Homer’s perilous rickety bridge crossing has hardly been beaten in the 26 years since. "Mr Plow" serves as a microcosm of the classic years’ winning formula insomuch as it has a great plot involving secondary Springfield characters, literally a joke every 20 seconds, and reverent guest star appearances, such as the one by the late Adam West. It says a lot that this episode is almost perfect and it doesn’t even break our top 15.
16. The Itchy & Scratchy & Poochie Show (season 8, episode 14)
The episode: Wildly popular TV show Itchy and Scratchy wants to shake things up a bit so it introduces a new character, Poochie – voiced by Homer.
Why it’s one of the best: When in doubt, add something new and screw everything up. If this isn’t the best commentary on meddling network executives, I don’t know what is. The creative team took their frustrations from Fox’s tampering and introduced both Poochie and Roy to The Itchy and Scratchy Show. Two ‘cool’ characters who patently didn’t fit in to the worlds they were entering, it all culminates in an excruciating two minutes (though it feels far, far longer) where Poochie makes his TV debut. It’s both hilarious and harrowing as Poochie quite literally keeps the maniacal Itchy and Scratchy from the path ahead of them – where a fireworks factory lay in wait – and then the episode ends to grumbles and groans from Homer’s friends and family. Still, it was the best episode of Impy and Chimpy Ned Flanders had ever seen. So, that’s something.
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: shock 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.
5. A Star is Burns (season 6, episode 18)
The episode: In a bid to improve the perception of Springfield, the town decides to put on a film festival.
Why it’s one of the best: God, I love this episode. Mr. Burns is at his tyrannical best here, trying his absolute best to rig a small-town film festival by throwing millions of dollars at an ego-fuelled production of his life. If that setup doesn’t make you chuckle, then how about the countless other homemade movies on display which allows half of Springfield to really shine? There’s Man Getting Hit by Football, The Eternal Struggle, and so much more besides that.
Each joke set-up quite easily could’ve been the high point for many a different comedy series. Not so for The Simpsons. Here, it was just another moment before an even bigger and better joke. The episode’s successes are summed up by one small throwaway gag: Boo-urns. It doesn’t make sense – much like a film festival being hosted in Springfield – but it didn’t have to, because the timing, set-up, and execution is all absolutely flawless.
It says a lot that this is an episode you can re-visit at any time, whether you’re watching the whole thing or just fancy a quick 20-second dip, and you’re going to be rolling around on the floor in fits of laughter, guaranteed. That’s the sign of a show at the top of its game.
4. Itchy and Scratchy Land (season 6, episode 4)
The episode: The Simpsons decide to go on a vacation to the newly-opened Itchy and Scratchy Land theme park. Chaos ensues.
Why it’s one of the best: We’ve all had a holiday go very, very wrong – but nothing quite like what goes down in "Itchy and Scratchy Land." Whether it’s Bart dialling up his prank game to 11, the Westworld-style meltdown of the robots, or the creative staff’s barbed digs at Walt Disney’s history, it all comes together to provide us with a riotous episode that allows the family to breathe away from the confines of Springfield.
It helps that every part of the trip is so relatable. You’ll groan along with Bart and Lisa as they pass the Flickey’s sign (probably the best sight gag in the show’s history), you’ll be embarrassed and want to be thrown in a (not-so-literal) hole just as Marge does after Homer and Bart’s shenanigans, and you’ll cheer as the family eventually bond as they come face-to-face with killer robots. Ok, maybe not that last bit. Still, this is one road trip you won’t mind revisiting again and again.
3. Homer Badman (season 6, episode 9)
The episode: Homer undergoes trial by public opinion after allegations of sexual assault.
Why it’s one of the best: Homer Badman deals in serious issues – such as sexual assault and alarmist media coverage – and wraps it all up into a package worthy of being on any 'best of' list, Simpsons or otherwise. It doesn’t take you to one side for a stern lecture, either.
The jokes, inevitably, come thick and fast (Homer’s obviously-edited interview to make him look bad is a definite highlight), but it’s the fact that it’s still as relevant today as it was a quarter of a century ago that sets it apart from all the others. Because that’s what The Simpsons does, and why it's one of the best Simpsons episode ever: it makes you laugh, it makes you cry, and, just sometimes, you can relate to it on a level that other shows daren’t even attempt to reach, let alone pull off with as much grace as The Simpsons does in "Homer Badman."
2. Last Exit to Springfield (season 4, episode 17)
The episode: Homer becomes union leader at the Power Plant and leads a strike to push through better benefits for the workers.
Why it’s one of the best: It was the best of times, it was the blurst of times. Don’t be fooled by the dry-sounding plot. Homer’s union antics very much play second fiddle to a show that decided it wouldn’t let something as flimsy as a plot get in the way of jokes. Often regarded as the show’s best (close here, but no dice), it’s not hard to see why everyone loves it thanks to the many cultural parodies, rambling Grandpa stories, and even some vaudeville-style innuendo.
What other show could mesh The Beatles, Jimmy Hoffa, Batman, and The Grinch into 22 minutes quite so expertly? The Simpsons, in its heyday, was something for everyone, yet this episode’s real skill was spinning so many plates at once and not having it all come crashing to the ground. It all ends with Homer getting one over his boss, too. That’s the dream.
1. Bart's Comet (season 6, episode 14)
The episode: The end is nigh for Springfield as a comet hurtles towards the town.
Why it’s one of the best: It doesn’t appear that way at first – or even up until the episode’s final act, really – but this episode is a perfect marriage of what makes the (relatively) early years of the show so great; it makes your heart swell just as easily as it splits your sides. Everything that comes before the final few minutes, where almost all the town gets crammed into Ned’s bunker, is exceptional (“There’s a 4:30 in the morning now?” Bart quips after being forced into early-morning science work with Principal Skinner), but Ned belting out the first few lines of Que Sera Sera elevates it into something even greater. He’s suddenly joined by the entire town, despite facing certain doom. Is someone chopping onions?