The Simpsons top 50 episodes
Rob counts down the top 50 episodes of TV's longest-running animated series, The Simpsons...
25. Lisa’s Substitute (S2)
A really sweet and heartfelt episode here which sees Lisa forming both a romantic infatuation and an intellectual bond with her new substitute teacher, Mr Bergstrom. Lisa-centric episodes can often be very hit and miss affairs as she tends to get lumbered with the more preachy instalments focusing on serious topics, far away from the loveable idiocy of Bart and Homer. Here though the sentimentality works a treat and while the rest of her class find Bergstrom (voiced of course by Dustin Hoffman) to be a bit of a nerd, to Lisa he is the nurturing father figure she feels she never had. While Homer’s oafish attempts to relate to his daughter are genuine enough, it’s a fellow intellect like Mr Bergstrom who is truly able to push and inspire her to be all she can be. The touching ending also shows that while Homer may not be the role model Lisa needs, he’ll always be there for her and the love between the pair remains as strong as ever.
24. Boy-Scoutz N’ The Hood (S5)
Ahhh, the remorse of the sugar junkie. After Bart and Milhouse find $20 and use it to have the night of their lives, Bart wakes up to find out he inadvertently joined the Junior Campers (not at all affiliated with the Boy Scouts of America). The pair’s sugar-fuelled binge is a wonderful parody of a typical boozy-night out movie montage, but the episode really comes into its own once Homer joins Bart on a father/son river-rafting trip. Homer is on top idiotic form as his attempts to one-up Ned Flanders serve only to put him and his raft-mates in greater danger. Homer is often at his funniest when he’s being as selfish and impolite as possible and this is him at his very worst. The sub-plot involving celebrity dad Ernest Borgnine is also excellent and the fairly random climax which sees him and the surviving Junior Campers attacked by an unseen slasher movie-esque assailant is a welcome addition. I also love the brilliant visual gag where, as Homer watches on from the sofa, Lisa reminds Bart that cartoons don’t have to be realistic, just as a second Homer saunters past the window.
23. A Star Is Burns (S6)
If we ignore the fact that this episode was in effect an ill-advised advert for short-lived animated series The Critic, a decision which perturbed Matt Groening so much he had his name removed from the credits, it’s still an incredibly funny outing. When Marge decides to organise a film festival in Springfield in order to try and raise their cultural standing, several Springfield regulars decide to enter movies, including Mr Burns. Burns is in great form in this episode as he appears determined to overcome his poor public perception. “People see you as somewhat of an ogre,” he is told by Smithers, “I ought to club them and eat their bones!” is his measured reply. He goes on to demand Steven Spielberg’s “non-union Mexican equivalent” in order to make the most self-aggrandising movie of all time. This is also the episode that produced one of the most commonly used Simpsons quotes where Smithers tries to convince Mr Burns the unhappy crowd were saying Boo-urns rather than booing his shambolic movie. To which comes Hans Moleman’s immortal reply, “I was saying Boo-urns”. The movies themselves are perhaps the episode’s stand outs, with Barney’s “Pukahontas” and Moleman’s “football in the groin” proving the pick of the lot.
22. Radioactive Man (S7)
Jiminy Jilikers. Things just never go right for poor Milhouse. When Hollywood comes knocking at Springfield’s door and the new “Radioactive Man” movie is made in their town, he somehow lands the part of the hero’s sidekick, Fall Out Boy. At first Bart is jealous of his friend, but he soon becomes increasingly happy for him, even if he remains completely oblivious to his pal’s growing disenchantment. There’s plenty of fun to be had at the expense of the apparent exploitative nature of the movie industry and the tedium of movie-making itself is also liberally lampooned throughout. There are also choice moments from Krusty, namely where he tries to show off his acting ‘range’, and of course Rainer Wolfcastle’s legendary performance as Radioactive Man, complete with the unforgettable line as a torrent of toxic waste floods his way, “the goggles, zay do nothingggg”. The episode combines the endearing storyline surrounding Bart and Milhouse’s friendship with the unashamedly cynical Hollywood satire to expert effect.
21. Bart Of Darkness (S6)
Milpooooool. Klassic Krusty. St Swythens Day. This episode is loaded with great sequences and it builds to one of the show’s all-time great film homages as Hitchcock’s Rear Window is parodied wonderfully. The plot revolves around the Simpsons getting a swimming pool and the kids experiencing fleeting popularity as a result, “Isn’t it amazing that the same day you got a pool is the same day we realised we liked you?”. Unfortunately, Bart lets it go to his head and after showing off for his adoring public, he winds up with a broken leg. Confined to a wheelchair for the summer, he grows isolated in his bedroom and after grudgingly using the telescope he is bought to pass the time; things take a turn for the sinister. The kids begin to suspect Ned Flanders may have killed his wife and while we know this won’t actually be the case, its fun watching the evidence mount up. The nods and winks to Hitch’s movie are moulded into the traditional Simpsons comedy seamlessly, and the full on musical Fantasia-esque routine that Bart jealously watches from his window is another nice touch.
20. Lemon Of Troy (S6)
One of the greatest Bart-centric episodes here in which he has a sudden surge of civic pride, kick-started in no small part by some no good Shelbyville kids stealing Springfield’s beloved lemon tree. The intense rivalry between Springfield and Shelbyville is a recurring gag throughout The Simpsons and here we learnt that the great irony is that the two towns are almost identical. Typically, one of the most memorable moments of the episode comes from Homer. As Bart races out of the Simpson family home telling his parents he’s going to teach some kids a lesson. “I choose to take that literally” says a hopeful Marge, before we hear Bart yell “death to Shelbyville!!” as he runs away. “Yes, Bart’s a tutor now. Tute on, son! Tute on!” replies an oblivious Homer. The adventure into the badlands of Shelbyville is great fun, with Milhouse and his doppelganger sharing a touching realisation and Martin and Nelson proving an unlikely double act.
19. The Last Temptation Of Homer (S5)
“Oh Mindy. You came and you found me a turkey.” To the legions of Simpsons fans, Barry Manilow’s Mandy will never be thought of in quite the same way again. When Mindy (Michelle Pfeiffer), an attractive new female employee, starts work at the plant, Homer finds himself increasingly attracted to her. It’s rare that we see Homer being dragged down by the drudgery of domestic life; usually he’s aware that he is punching well above his weight with Marge, but here he becomes uncharacteristically disenchanted with his marriage. Tellingly, the reverse It’s A Wonderful Life daydream Homer experiences (led of course by Colonel Klink from “Hogan’s Heroes” and not Sir Isaac Newton) shows Homer that Marge would actually be much better off without him.
Alongside the main storyline, Bart’s transformation into a stereotypical nerd (“You mean it ain’t me noggin’ it’s me peepers?”) is a funny subplot as well. Poignant in parts and successful in delicately handling a tricky subject matter, this episode also has two stand-out, laugh-out-loud funny scenes. First of all there’s the power plant co-worker with the giant hand, and finally, I’ll simply give you a name: Joey, Jo-Jo Junior Shabadoo.
18. Deep Space Homer (S5)
It’s a fairly outlandish premise, but Homer going into space is a true stroke of genius from the Simpsons team. When NASA tries to rejuvenate public interest in its space programme, it decides to choose a regular American to go up into space, and they don’t come much more regular than Homer. Passed over for employee of the week yet again, this time in favour of the inanimate carbon rod, Homer is desperate to prove his worth and eagerly volunteers for the mission. His training regime alongside Barney is hilarious, as is Barney’s succumbing to his Achilles heel, even if it was non-alcoholic champagne.
Homer is on fine form this episode, whether it’s his glum realisation that Planet Of The Apes is set on Earth all along, or the enchanting 2001: A Space Odyssey tribute where he elegantly drifts through the space shuttle, hoovering up potato chips to the tune of The Blue Danube. The episode also marks perhaps Kent Brockman’s finest hour when he sees footage of an escaped ant looming large near the on-board camera and immediately jumps to the conclusion that an ant invasion is imminent. Cue the immortal line, “And I, for one, welcome our new insect overlords. I’d like to remind them that as a trusted news personality I can be helpful in rounding up others to toil in their underground sugar caves.” It’s truly bizarre, but it’s Kent at his pompous best.
17. El Viaje Misterioso De Nuestro Jomer (The Mysterious Voyage Of Homer) (S8)
Though primarily about Homer and Marge’s relationship and the former’s persistent habit of embarrassing his better half, this episode really hinges on Homer’s trippy chilli-fuelled adventure. After finally finding out about the big chilli cook-off despite Marge’s attempts to keep it secret and avoid inevitable humiliation, Homer descends upon the event, his own spoon in tow (“I heard he carved it himself…from a bigger spoon”). The chilli tasting sequences are hysterical, with Flanders first being embarrassed in front of his sons, and then Chief Wiggum seemingly getting one over on Homer through his Guatemalan Insanity Peppers. Homer however comes back, candle wax covering his mouth and throat, and dutifully eats several of the peppers whole. As he walks away triumphant, he also utters a fantastic line, “Don’t quit your day job Chief… whatever that is.”
There then follows the beautifully realised trip sequence with the surreal animation proving some of the show’s finest to date. Lest we forget, there’s also the legendary Johnny Cash voicing Homer’s Spirit Guide in one of the show’s greatest ever cameo performances. Homer does at one stage begin to doubt he and Marge belong together, but ultimately it’s a feel-good ending, as she comes to his aid and inexplicably figures out he’ll be at the old lighthouse, Homer realises she really was his soul mate after all. “In your face space coyote”.
16. Homer’s Phobia (S8)
The issue of homophobia is dealt with in a typical Simpsons manner as Homer’s total idiocy is made clear before he finally sees the error of his ways. The issue is raised when the family befriend John (played superbly by John Waters), a gay antiques dealer who introduces Homer to the concept of “camp value”. When Homer finds out his new friend is gay, he begins to object to Bart spending time with him, even going so far as to desperately ask his son, “he didn’t give you gay did he?” He and the boys from the bar then decide to take Bart out hunting to make sure he grows up “a real man”.
Homer gets away with this offensive attitude largely because he is such a dolt, and so obviously misguided, that it’s clear how ridiculous his opinions really are. By the end of the episode, the show delivers a genuinely heartfelt lesson in terms of acceptance and tolerance. Homer comes out with some great lines throughout, with “There’s only two kinds of guys who wear Hawaiian shirts: gay guys and big fat party animals. And Bart doesn’t look like a big fat party animal to me!” being a personal favourite. The episode’s highpoint though is the father/son visit to the steel mill where they work hard, and play hard. The unforgettable sounds of Gonna Make You Sweat (Everybody Dance Now) will forever remind me of this glorious visit to a gay steel mill.
15. Homer The Heretic (S4)
Few shows can tackle the thorny issue of organised religion with as much intelligence, warmth and humour as The Simpsons does here. When Homer decides to skip church one Sunday and stay at home instead, he winds up having the morning of his life. He has a quiet, kid-free house where he can pee with the door open, sing in the shower, dance around in his underwear a la Tom Cruise in Risky Business and then to top it all off, there’s a surprise football game on the TV. Meanwhile the family sit shivering in church, the heating broken and the congregation growing increasingly perturbed.
Naturally when Homer tells Marge he never intends to go to church again, she is outraged and worried about the example this sets for the children. Then Homer makes one of his most profound comments ever, noting “What’s the big deal about going to some building every Sunday? I mean, isn’t God everywhere? And don’t you think the almighty has better things to worry about than where one little guy spends one measly hour of his week?” Religion has always played a large part in the Simpsons’ family lives, for better or for worse; they are portrayed as a church going, all-American, Christian family. Homer’s perceived heresy therefore, is understandably a major issue for Marge. Luckily for her, after a near-miss of a house fire, where Homer is recused by Flanders, Krusty and Apu, (as Reverend Lovejoy notes, “Christian, Jew or… miscellaneous”), the Reverend convinces Homer that God was actually acting through his friends who were looking out for him, which proves enough to coax Homer back into his flock. The episode is never offensive and is always respectful of those with faith. The timely lesson at it end is that religion doesn’t have to be one thing or another, what is important is that if you do practice it, it should make you be a better person.
14. The Itchy And Scratchy And Poochy Show (S8)
This episode was the one which saw the Simpsons exceed The Flintstones in terms of the number of episodes for an animated series. Naturally therefore, a storyline revolving around keeping a long running show fresh and interesting to its audience was especially apt. Tongue-in-cheek and very self-aware; the story sees the creators of Itchy and Scratchy introduce a new character, the titular Poochie, in order to revive flagging ratings. The funniest part of the episode though, and comfortably one of my all-time favourite Simpsons moments, is the running joke about Roy becoming a new member of the Simpson household. It still has me in hysterics when he saunters in, “Yo, yo! How’s it hangin’ everybody?” To which Homer barely glances up from his paper and replies “Yeah, hi Roy.” Like he’s an old friend the family has known for years. It’s such a simple touch, but is in itself a neat little jab at the show’s own critics; a clever parody woven in to the broader story. The ill-fated screening at the Simpson home is also brilliant, with Moe’s insistence on calling Marge “Midge” and Carl’s non-committal “yeah, you should be very proud, Homer. You, uh…..you got a beautiful home here” being superb little touches that still crack me up.
13. Homer The Great (S6)
A wonderfully deranged episode which sees Homer join the secret sect known as the Stonecutters (a thinly veiled lampoon of the freemasons) and despite his best intentions, he soon runs them into the ground and prompts the other members to break off and form their own club. The secret revelations, such as Homer’s quicker shortcut to work and the new “real” emergency number (912), are a great touch, as is the fact that despite all the mystery and pomp, all the Stonecutters really want to do is shoot pool and get drunk. It’s Homer that comes in and ruins it all by trying to steer them into a more charitable direction.
An early highlight is Carl’s frustration with Lenny continually letting things slip “shut uuuuuupppp”, and the bizarre bit where a guy in an egg suit runs away from Homer is also strangely brilliant. I will also never get bored of repeating Homer’s failed attempt to come up with a valid excuse to leave the house late at night, “I’m going outside now… to… stalk… Lenny and Carl. Doh.” It’s a wonderful piece of satire and also delivers one of the show’s catchiest ever songs, the magnificent “We do”, complete with such choice lyrics as “Who holds back the electric car? Who makes Steve Guttenburg… a star!” To top It all off, Patrick Stewart has a wonderful cameo as the Stonecutters’ leader, “Number One”.
12. Bart After Dark (S8)
It was no surprise to learn that Homer and Bart can’t be trusted when left to their own devices and sure enough, Marge and Lisa leave them alone for just a short while and the house is soon a tip and Bart is working at the local burlesque house. The opening section where the two Simpsons men adjust to life without women is perfect with Homer’s laziness really shining through, especially when Bart asks if he can go to the park and Homer responds with the classic “do I have to sit up?... then knock yourself out.”
When Bart destroys a valuable gargoyle on the side of an old house, the proprietor of said establishment, Belle, escorts him home. This leads to another classic line as Homer answers the door and she asks “are you wearing a grocery bag?”, the timeless straight-faced Homer reply being, “I have misplaced my pants.” Once Bart starts working at Belle’s burlesque house things get even funnier. The two choice gags are Principal Skinner’s attempts to fudge an explanation to Bart as to why he is there, and then Grandpa Simpson’s seamless entrance and exit when he spies his grandson on the door. Naturally there is eventual moral outrage at the existence of such a house in Springfield, but ultimately all the problems get ironed out in typical Simpsons fashion, with a good sing song. “We put the spring in Springfield” proved to be yet another Emmy award-winning ditty for the show, and it’s one that’s seared into the minds of fans everywhere.
11. King Size Homer (S7)
The level of commitment which Homer demonstrates in his attempt to gain 61 pounds in order to get on disability benefits and thus be able to work at home is truly testament to his commitment to laziness. The mere sight of Homer in his floral muu-muu and white “fat guy hat” is funny in itself, but the sheer joy he takes in embracing his slothfulness is equally hilarious. Perhaps the finest example of this being when he finds out he only needs to press “y” instead of typing “yes” and points out to Marge that he has tripled his productivity. The scenes involving Bart and Homer bonding over the latter’s weight gain are also great, with Bart’s observant banana-split advice really hitting home, “eat around the banana, Dad. It’s just empty vitamins.” Homer and his stupidity always make for the best episodes and this is no exception. The climactic dash to the power plant adds a new dimension to the plot with the visual gag of him zipping past the school bus in an ice cream truck coming perfectly after Lisa defends him against the accusation of being “a food-crazed maniac”. It’s very much a Homer-centric episode in which he gets to let his inherent slovenliness really shine.
10. Cape Feare (S5)
Bart’s ongoing rivalry with Sideshow Bob has delivered some magnificent episodes over the years, but the pinnacle remains this wonderful homage to Scorsese’s remake of Cape Fear. Kelsey Grammer’s Bob is an outstanding recurring character and so many of his best moments come in this very outing. His “DIE BART DIE” tattoo (“The Bart, The”), the silly rake gag that gets funnier the longer it’s drawn out, and of course that triumphant performance of HMS Pinafore. There are almost too many great moments in this episode to start listing them, but I have to single out one of the funniest scenes in Simpsons history when the FBI agents try desperately to make Homer understand his new identity. “Now when I say ‘Hello Mr Thompson’ and press down on your foot, you smile and nod.” “No problem.” “Hello, Mr Thompson.” “… … … I think he's talking to you.” Bob’s dogged pursuit of Bart is of course inevitably doomed but here he is at his most determined and fearsome, even if he does occasionally get defeated by unexpected elephant parades.
9. Last Exit To Springfield (S4)
A truly classic episode here that deftly combines cutting satire, silly humour and a genuine political message. The plot sees Mr Burns taking away his workers’ union’s dental plan in exchange for a keg of beer at their meetings. With Lisa needing new braces, Homer takes a stand and convinces the union to reject Burns’ offer. He then becomes the union leader and is incorrectly mistaken by Mr Burns for a canny political operator. From start to finish, this episode is flawless. It opens with a McBain snippet that is so memorable, “Iced to see you”; I sometime genuinely think it’s an Arnie line from Batman And Robin. There’s another excellent Batman parody later on of course when Lisa gets her rusty old braces put on and duly mimics Jack Nicholson’s The Joker as she demands to see a mirror.
Mr Burns is on fine form throughout, whether gleefully skipping through the deserted power plant with loyal lackey Smithers, or channelling his inner Doctor Seuss as he listens to the strikers’ protest song. He’s a classic TV ogre, and in Homer Simpson, he may have finally met his match. This brilliant tactician of course is the same man who took an abnormal amount of time to figure out the ramifications of losing the dental plan with the “Lisa needs braces”, “dental plan” back and forth proving a particularly memorable moment. It’s a story of worker-power, their triumph over big business, and of courageous defiance. Added to that, there’s also the following unforgettable Mr Burns line: “This is a thousand monkeys working at a thousand typewriters. Soon, they'll have finished the greatest novel known to man. All right, let's see... ‘It was the best of times, it was the BLURST of times?’ You stupid monkey.”
8. Bart Vs Australia (S6)
While this sort of set up has been overdone in more recent Simpsons series, this episode was a prime example of how the ‘Simpsons visit XYZ, get into scrapes and point out local stereotypes’ formula could work if the material was funny enough. The depiction of Australia here is intentionally absurd, the Prime Minister (“AAAAANNNNNDDDDY”) drinking a beer in a floating tyre ring being a prime example. The plot sees the Simpsons flying to Australia after Bart causes a minor international incident by making a collect call to a young Australian boy. The trip predictably brings out the worst in Homer and Bart, the former being especially annoying even by his standards.
The jibes at Australia’s expense have gone down in Simpsons folklore, from Marge’s inability to order Cof-fee (“Be-er?”), to the Crocodile Dundee parody that has now perhaps overtaken the original in its prominence. To this day “I see you’ve played knifey-spoony before” comes up in my day to day conversation far more than one might expect. Phil Hartman is great as ever, this time as Evan Conover, the America diplomat responsible for getting the Simpsons home safe and negotiating the ridiculous “booting” punishment. Evan is a great one-off character, his crowning glory coming after Marge makes her emotional plea for her son’s safety over the phone, before handing it back to Evan smugly, who we simply hear say, “So we're in agreement. She won't be allowed near the phone again.” It’s over the top and silly from the off, but it’s The Simpsons’ finest “on the road” offering, equally poking fun at the boorish American abroad.
7. Trash Of The Titans (S9)
An Emmy award-winning episode here in which Homer’s stupidity is once again inexplicably overlooked by the Springfield townspeople. After getting into an argument with the “trash-eating stinkbags” who collect their garbage, Homer eventually decides to run for Sanitation Commissioner against the incumbent Ray Patterson. One of the funniest parts of the episode is an incredibly simple bit where Homer yells at Patterson, telling him he’s there to rattle a few cages, only for him to then take that literally and angrily rattle the cage of Ray’s pet bird. That gag sets the tone for the rest of Homer’s campaign as things get progressively sillier and sillier. He makes a lot of empty promises he can’t possibly keep, and even leads a mass sing-song of “The Garbage Man” set to the tune of The Candy Man from Willy Wonka & The Chocolate Factory.
The show’s standout moment for me however comes during the live debate between Homer and Ray in which the entire back and forth is made all the funnier thanks to the former’s smugness and the latter’s total exasperation. The best bit of the exchanges being the inimitable, “Do we want Old Man Patterson here with his finger on the button?”, “WHAT BUTTON?”. When the town eventually turns back to Patterson after Homer’s failure is laid bare, his big ‘I told you so’ blow-off is incredibly satisfying. The ending is utterly ridiculous, as the whole city is uprooted and moved five miles down the road. No lessons are learned and the need for the town to address its litter problem is completely lost on them all. It’s a fitting ending for a wonderfully daft episode.
6. Homer Badman (S6)
Only The Simpsons could start an episode at a candy convention and have it lead into a hilarious satire dealing with sexual harassment and the media’s ability to whip the public up into a frenzy. The openings scenes at the gummy convention are brilliant, with Marge tagging along in a coat laden with hidden pockets as Homer runs around like a kid in some sort of store. The sequence where he approaches the salesman selling the fake lips, “the candy of a 1000 uses”, is superb, as is the Die Hard-esque explosion Homer generates in order to escape with the Gummi Venus Di Milo.
When Homer later attempts to peal the Gummi off the butt of the babysitter however, he inadvertently causes a sexual harassment controversy that Kent Brockman and his media cronies exacerbate even further. There follows endless 24-hour coverage of the Simpsons home, a TV movie starring Dennis Franz entitled “Homer S: Portrait of an Ass-Grabber” and then of course, that glorious Rock Bottom (a spoof of Hard Copy) interview. As the earnest interviewer poses his questions to a clearly edited Homer, it just gets more and more ludicrous until Homer’s face is freeze-framed and the interviewer simply recoils in horror. Eventually of course Homer is cleared thanks to Groundskeeper Willie’s secret video tape (“every single Scottish person does it!!!”) and he and TV go back to being best of friends once more.
5. Homer’s Enemy (S8)
Poor Frank ‘Grimey’ Grimes. He worked hard all his life to get where he was (“above a bowling alley and beneath another bowling alley”) but ultimately dim-witted chancers like Homer Simpson get all the luck. Grimey get a job at the nuclear power plant and immediately sees the side of Homer that everyone else on the show is seemingly oblivious to. He sees a lazy, selfish and downright irresponsible man who shouldn’t be allowed to rear children, let alone be in charge of safety at a nuclear power plant.
This is undeniably an incredibly dark episode of The Simpsons, and like several other such darker episodes, it’s written by the enigmatic John Swartzelder, a unique writing talent who is revered amongst his peers and with 59 episodes under his belt, has written more Simpsons episodes than anyone else. The bits I find funniest in this episode aren’t the typical witty lines or clever jokes, it’s the ones where Homer is completely unaware of how annoying he is being. For instance, when Grimey is trying to work and Homer lollops around singing “take me out to the ball game”, or even when he tries to nab one of Grimey’s personalised pencils. The pinnacle though comes when Frank visits the Simpsons’ home and suddenly realises just how good Homer has got it despite his oafish ways. The exasperated way he asks, “You? Went into outer space? You?”, only for Homer to blankly reply, “Sure. You’ve never been?” will never fail to have me in stitches. The episode closes with Frank Grimes’ funeral and the rest of the congregation remain blissfully unaware of Homer’s idiocy. It’s a darkly funny ending to a classic episode.
4. Homer Goes To College (S5)
What makes this episode so great is that Homer’s view of college, Animal House-ish frat parties and elaborate pranks, is evidently wide of the mark, yet he clings to it unremittingly. Forced to return to college after nuclear safety inspectors notice that he is dangerously underqualified, Homer moves in with three nerds (“hey buddy, get a load of the nerd?”) and throws himself into the college lifestyle. Expecting a crusty old Dean like the one he sees in TV movie “The School of Hard-Knockers”, Homer isn’t put off by the fact that his new Dean is a friendly and welcoming guy who used to play bass for The Pretenders. He embroils his nerdy friends in his zany schemes such as stealing a rival school’s pig, as well as his infamous “running the Dean over with a car” prank. There are plenty more great scenes throughout the episode, including the nerds coming across the wallet inspector and the spoof of The Untouchables where Mr Burns attempts to pummel the University admissions board into submission. Going back to college allows Homer to be his most childish and ridiculous and by the episode’s end, he typically hasn’t actually learned any lessons at all. This was the last episode solely written by Conan O’Brien before he left to present late night TV, and alongside the next entry on this list, it represents his very best work on the show.
3. Marge Vs The Monorail (S4)
When Mr Burns gets hit with a hefty fine for illegally disposing of toxic waste, the town of Springfield must decide how to spend their $3 million windfall. After they’ve discounted Mr Snrub’s idea to give it all back to the power plant, it starts to look like they might go with Marge’s idea of filling in the potholes on Main Street. That is until a charming stranger turns up in the form of Lyle Lanley. “You know, a town with money is a little like the mule with a spinning wheel. No one knows how he got it, and danged if he knows how to use it.” The man knows how to make an entrance. He then proceeds to work his magic on the entire town, even leading them in a song tribute to the majesty of the monorail itself. Springfield’s mob mentality is a recurring theme on the show, and here their predilection for mass hysteria is fully taken advantage of. Lanley is another character voiced by the sorely missed Phil Hartman, whose great contribution to some of the show’s best ever episodes cannot be overlooked.
Eventually of course we realise that Lanley is in fact a conman ripping the city off, but not before Homer gets a job as a monorail conductor following his intensive training course, “Mono means one and rail means rail.” The jokes increase as the episode races towards its end, cramming in Leonard Nimoy’s random cameo, Homer’s family of pet possums (“I call the big one Bitey”) and the mysterious scientist (not Batman) who helps him stop the runaway monorail. Another Conan O’Brien-penned classic that doesn’t let up from start to finish.
2. Homer Vs The Eighteenth Amendment (S8)
After Bart accidentally gets drunk at Springfield’s St. Patrick’s Day celebrations, the town government realises that prohibition has actually been in place for years and has just never been enforced. After the new laws kick in however, it takes mere minutes for Moe to turn his bar into a swinging speakeasy/pet store. With Chief Wiggum proving less than capable of ending the supply of illegal liquor, the no-nonsense Rex Banner is sent to the town by the U.S. Treasury Department to take action. Homer meanwhile gets involved in an elaborate bootlegging scheme which sees him hurling balls of hooch into the bowling alley gutter which then roll on into Moe’s. It’s part of the show’s chaotic charm that week to week, Homer can be a dim-witted fool one minute, and then a criminal genius the next. In his guise as The Beer Baron, he continually gets the better of Rex Banner and the law, and even Marge struggles to get angry with him thanks to his ingenuity.
Right from the off, this episode has you in stitches, from Moe’s intolerance of designated drivers “Beat it, I got no room for cheapskates”, to the over-the-top Irish stereotypes at the St Patrick’s Day parade. The cat and mouse chase between Banner and Homer then takes centre stage and the classic back and forth, “You're out there somewhere, beer baron! And I'll find you.” “No, you won't.” “Yes, I will.” “Wooooon't!”, is just one of many classic scenes peppered throughout. There’s also Homer trying to pretend his homemade liquor exploding is merely indigestion, “Kablammo! Excuse me dear”, and the nonchalant way he and Bart tear out of the house, “If we don’t come back, avenge our deaths!” It’s great to see Homer getting one over on the straight-laced Banner, even if the latter doesn’t even really grasp that it’s happening. The final line, “To alcohol! The cause of, and solution to, all of life’s problems”, fits the episode perfectly, a booze soaked ode to both the joy and danger of drinking.
1. You Only Move Twice (S8)
This peerless 22 minutes of comedy gold starts with Homer catching an uncharacteristic break at work and inexplicably being offered a big promotion with Globex Corporation, and soon descends into a James Bond-esque tale involving a maniacal criminal mastermind. This is The Simpsons at its very best, perfectly embracing Bond movie clichés and interweaving them with Homer and the family’s struggles to adapt to life in Cypress Creek. Voiced by the great Albert Brooks, Hank Scorpio is unrelentingly polite but at the same time an arch-villain hell bent on world domination. Without doubt one of the show’s best ever one-off characters. Scorpio’s introduction includes one of the most obscure yet brilliant Simpsons quotes when he asks Homer, “Ever seen a guy say goodbye to a shoe?” To which Homer inexplicably replies “yes… once.”
Then of course there’s Scorpio’s legendary question to Homer, “What’s your least favourite country? Italy or France?” “France.” “Nobody ever says Italy.” Also, to this day, if someone asks where they can get an item from, I can’t resist the urge to do the full “hammocks” bit from this episode. “Matter of fact, they’re all in the same complex; it’s the hammock complex on third.” There’s so much gold crammed in, I’ve not even got time to go into Bart’s experiences in the remedial class, or Homer’s Tom Landry hat.
What makes this episode extra special is that the whole riotous James Bond adventure is just occurring in the background. When Homer thwarts his escape, Bond becomes a mere “interloper” whom he tackled at work. We see things entirely from Homer’s perspective and quite typically, just when he has finally begun to be productive at work, he also inadvertently helps a criminal seize the west coast. Both this and Homer Vs The Eighteenth Amendment were written by the aforementioned reclusive comedy writing genius John Swartzwelder. One famous Swartzwelder story posits that he famously used to sit in the same diner booth when he was writing, chain smoking cigarettes and downing coffee. When smoking was banned in public places, he simply bought the booth himself and had it installed at his home so as to not mess up his routine. He’s an exceptionally talented writer and is the man responsible for not just my two favourite Simpsons episodes of all time, but numerous other classic outings as well.
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