The 25 best Simpsons episodes you should choo-choo-choose to watch

With season 32 premiering this Sunday, it’s time to take a trip down memory lane and rediscover the best Simpsons episodes from the show’s many, many decades on the air.

But as there’s literally hundreds of episodes to choose from (the vast majority of which are now on Disney Plus), whittling them down to just 25 is a Homer-in-a-muumuu-sized task in and of itself. Ask a dozen Simpsons fans what their #1 pick is and you’re bound to get a dozen different answers.

And speaking of #1, we have a new numero uno, readerinos. We’ve rewatched all the episodes in this list of best Simpsons episodes (plus a few more, shh, don’t tell my boss) and revaluated where they stand on this perfectly cromulent rundown of the best The Simpsons has to offer.

Ready? We’ve sorted through the steamed hams, the sugars (do-do-do-do-do-do), and the saddest, lump-in-your-throat moments from all your favourite Springfield adventures to bring you the definitive list of the best Simpsons episodes… ever! Mmm… controversy.

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 an 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 bang-up 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 two 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 there’s so much more than that too. 

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. Not too bad for a silly animated series, eh?

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: 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.

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