Ali Plumb's Top Five Greatest Simpsons Episodes

So I controversially ranked my top five Friends episodes and lived to tell the tale. And now that the pitchforks have been successfully (if not painlessly) removed from my body, I am feeling strong enough to face down another top five terror: the very best episodes of The Simpsons.

The general rule of thumb is that the show was at its peak from seasons two to eight(ish), with most folk circling season six as the very highest point. Season one the show was just getting its shoes on, with things very much improving from two onwards. And sure, while eight is spotty it does have some classic episodes, there's no denying that's the beginning of the descent, and once we get to ten, that's when things really start to slide.

Then again, compared to what's being released in recent seasons, some of what we turn our noses up at in ten seems to glittering gold in comparison. There, I said it.

But anyway! The trouble with ranking Simpsons episodes is that there are a lot of truly excellent ones. Plus, there are many very good entries that have some incredible moments, such as '22 Short Films About Springfield' with its now iconic "steamed hams" localised aurora borealis sequence.

And of course there's personal preference at play. I don't care for Itchy & Scratchy, so as much as I enjoy the self-referential fun of The Itchy & Scratchy & Poochie Show - "Worst episode ever" - it won't appear below. Some people love the Treehouse Of Horrors but I honestly never cared for them. Sorry about that.

Then there are the more heartfelt, emotional episodes like 'And Maggie Makes Three', 'Lisa's Substitute' and 'Marge Be Not Proud' which I love, sure, but I am here for the laughs, let's be honest. If I were to pick my favourite from this subgenre of sappier Simpsons episodes, it would probably be 'One Fish, Two Fish, Blowfish, Blue Fish' from Season 2, if only for Homer telling Bart he likes his... sheets.

I'm tempted to do an "honorable mentions" as well, just to flag up Season 4's 'Mr. Plow' or the funny-but-just-a-bit-too-dark 'Homer's Enemy' from Season 8... but I must resist. I also have a real soft spot for 'Raging Abe Simpson and His Grumbling Grandson in "The Curse of the Flying Hellfish"', if only for being a Grampa episode that really soars, not forgetting the stellar underwater animation and the way Lisa mistakes Mr. Burns on a cherry picker for Santa. I'm an odd kid, I know.

Anyway, let's do this as I embiggen your mind with Ali Plumb's Five Most Perfectly Cromulent Simpsons Episodes.

Before he was Avery Bullock in American Dad!, Sir Patrick Stewart was Number One in 'Homer The Great' (and some sort of space captain in a sci-fi TV show, I never got round to it, I’m sure it’s fine), a send up of the freemasons, fratboys and pointless traditions. So much gets so beautifully skewered here - sorry, paddled - it even fits some thwacks at the Egg Council, because, well, “YOU'D BETTER RUN, EGG!” I’m getting ahead of myself and being very silly, I apologise.

What I am trying to say here is that Homer The Great is a very funny, very well observed, very well performed poke in the eye to self-serving secret societies, with Patrick Stewart on impeccable form as the one-time leader of the mysterious Stonecutters, all secret signs and bizarre stone-based rituals. It even sneaks in one of the very best Simpsons songs, 'We Do', something that only ended up in the episode at Matt Groening’s request. I mean, there’s a reason this was nominated for an Emmy people: "Who holds back the electric car? / Who makes Steve Guttenberg a star? We do, we do!" You may also be pleased to know there are t-shirts that read "Ancient Mystic Society of No Homers" and I may or may not own one.

Favourite quote:

Homer: "Why won't those stupid idiots let me into their crappy club for jerks?"

For the longest time, I always thought of 'Marge vs The Monorail' as my very favourite episode, what with its catchy song - "The ring came off my pudding can" / "Take my penknife, my good man!" - and pleasingly outlandish snake oil salesman set-up. Then there's Marge's voiceover, Mr. Burns as Hannibal Lecter, Mr. Burns as Mr. Snrub, "'Marlon Brando' as the voice of John Truckasaurus", the popcorn pothole gag, "I call the big one Bitey" (one of Matt Groening's own personal favourite one-liners) and Leonard Nimoy's amazing cameo.

It's notable for being thoroughly bonkers, written by Conan O'Brien himself before he sailed off to the land of late night, and marking a sea change for later episodes: yes, you can go there, you can be that silly, you can bend reality so much that Spock himself can beam out of a scene and it'll somehow still work. It's also - handily for a comedy - stuffed to the rafters with jokes, which has seen it on the top (or near the top) of many Simpsons experts' rankings over the years.

And I suppose that's why it's ended up at number four for me today. I have seen this episode so often. This is the episode I think of when I think of The Simpsons, the one I put on for a bit of comfort food and shots of an up-escalator that leads to nowhere (just think about how dotty an idea that is, and for a season four episode). So as I know it almost by heart, and knowing it's universally regarded as one of the best of the best, here it is at near the bottom of my top, in a tiny attempt to be mildly controversial. Not sure it worked, but hey, I sort of tried.

Favourite quote:

Homer: "Doughnuts - is there anything they can't do?"

As a 007 aficionado and a Simpsons fan, it feels at times like ‘You Only Move Twice' was written specifically for me. The whole concept is just genius: what if Homer was hired by a benevolent Bond villain - itself a brilliant idea - and had to relocate, dog 'n' cat 'n' kitchen sink, to a perfect town full of perfect people. We get to see Marge without housekeeping to define her, Lisa betrayed by nature and Bart in remedial class, longing to return to his old school. All this and an appearance by one - checks notes - "James Bont"? It genuinely feels like a treat every time I watch it.

This most recent go-around, the never-ending series of goodbyes from assorted supporting characters really landed for me, as did the detail in the backgrounds for the too-good-to-be-true Cyprus Creek (something designers had to cook up from scratch after years of always using Springfield). Oh, and the Bond theme parody at the end! Just superb.

The star of course is Albert Brooks as the incredible Hank Scorpio, the amazing boss you very nearly wish you had yourself, if only he could shake the megalomania and penchant for flamethrowers. A semi-regular on The Simpsons, Brooks is utterly sensational here, with many of his lines (including the hammock scene) ad-libbed by the man himself on the spot. Oh, and if you love him as much as I do, make sure you check out his cameo in the season 22 episode '500 Keys' because, yes indeed, that is Brooks back once again as the beloved bearded baddie.

Favourite quote:

Hank Scorpio: "But Homer, on your way out if you want to kill somebody, you would help me a lot."

Your favourite Sideshow Bob episode, my favourite Sideshow Bob episode. The Simpsons outing that introduced you to Gilbert and Sullivan, to the fact that "Die" is German for "The" - remember: "No one who speaks German could be an evil man" - to the realisation that seeing a man, holding on to the underside of a car, being battered to near-death by cactuses, is just plain funny. Cape Feare is one of those Simpsons parody episodes where even if you have no idea about the original films (both the 1962 and 1991 versions of Cape Fear), it’s still so appallingly funny it really doesn’t much matter. Same goes for the Edward Scissorhands / Nightmare On Elm Street / Ned Flanders hedge trimming gag or the amazing Friday The 13th "kiss goodnight" joke - "BARTYOUWANTTOSEEMYNEWCHAINSAWANDHOCKEYMASK?" - it just all works.

And Cape Feare’s success is despite its inherently scrappy origins. Here’s an episode that ran so short they used a longer couch gag fill time, on top of the now infamous extended rake "Urrrrghs" from Kesley Grammer that have now gone down in Simpsons legend, stretched out just to use up time. Grammer has said he only recorded one "Urrrrrgh" so it was as much of a surprise for him as it was for us.

A big part of the joy of his episode is getting to hear The Man Sometimes Known As Frasier Crane singing, beautifully, decent chunks of H.M.S. Pinafore. Bart eating popcorn, Bart joining in, the Union Flag dropping down during 'He is an Englishman', it’s gold, I tells ya, gold. Sideshow Bob is a delicious, delectable character and he’s used no better than here, the Sideshow Bob episode by which all others are measured. And if you’re wondering if you’re the only one who adores this one, know this: it’s Hank Azaria’s favourite too, so you’re in good company.

Favourite quote:

Radio DJ: "All right, this next song is dedicated to Bart Simpson, with the message 'I am coming to kill you slowly and painfully.'" ('Wipeout' plays)

Yep, I went there. The episode "frequently cited as the best the show has ever produced" is the one that I also think is the best ever produced. Really sticking my neck out there, I know. There’s joke after joke after joke, buckets of satire, properly bananas flights of fancy - Lisa’s "purple submersible" Yellow Submarine laughing gas trip always delights me - and it’s all done with no fancy guest stars or particularly outlandish conceits. This is pure, hilarious, unfiltered Simpsons at its very finest.

If the title doesn't ring a bell, let me remind you of the plot: Homer becomes his union representative to fight for a dental plan as Lisa needs new braces. ("Dental plan" / "Lisa needs braces") That’s the whole story in a nutshell, but there’s so much coming along with it: Lisa’s singing and guitar plucking, Grampa’s onion waffling (which was the style at the time), a thousand monkeys at a thousand typewriters ("'It was the best of times, it was the BLURST of times?' You stupid monkey!"), some meta fun in Mr. Burns totally forgetting who Homer is despite all their previous bizarre encounters, plus references and parodies to The Grinch, Moby Dick, Get Smart, Citizen Kane (again) and Tim Burton’s Batman.

It's got cerebral humour, it's got goofy humour, it's got utter nonsense, it's got real heart. It's got a victorious Homer spinning around on the floor and making 'Whoop whoop whoop' noises. It's got the lot. It's everything you want in a Simpsons episode and a little bit more, scratching all your Simpsons itches with little additional help. It's about the family, the job, the town. And it's very, very funny.

Favourite quote:

Kent Brockman: "Ah, Mr. Burns, you said you wanted an opening tirade."

Mr. Burns: "Yes, thank you, Kent. Fifteen minutes from now, I will wreak a terrible vengeance on this city. No one will be spared. NO ONE!"

Kent Brockman: "Ha ha, a chilling vision of things to come."