The Simpsons: 50 best episodes

Rob counts down the top 50 episodes of TV's longest-running animated series, The Simpsons...

Since its debut in 1989, across 552 episodes and 25 seasons, The Simpsons has become one of the most revered and beloved TV programmes of all time. It’s a true cultural phenomenon that’s influenced not just animation, but all areas of TV comedy and sitcom. For so many of us, its quotes and catchphrases have permeated our everyday vernacular, from single words like “crisitunity” and “embiggen” to phrases “you don’t win friends with salad” and “everything’s coming up Milhouse.”

Personal opinions may vary, but for me the show’s peak years were from season 4 through to 10. They’re consistently funny, all killer and no filler runs with barely a dud episode to be found between 1992-1998. Past this point the standard becomes a little more mixed, and recent seasons have been distinctly average at best. The beauty of The Simpsons though is that whenever you watch a newer episode that perhaps doesn’t tickle your fancy; you can always go back to the vast catalogue of bona fide classics and be entertained all over again. There’s more gold in those first 10 or 11 seasons than any other show can hope to achieve.

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In theory, selecting fifty of the show’s best episodes from a choice of 552 shouldn’t be all that difficult. In reality, it’s incredibly hard to pick and choose which ones make the cut. So many episodes have a particular line in them that make you want to include it solely for that one moment. Season 10’s Thirty Minutes Over Tokyo almost made it purely for its Rashomon joke, but ultimately, that episode it lost out to more consistently funny outings.  The next challenge was then to try and actually rank them all in order. Was Deep Space Homer funnier than Homer Goes To College? Did I laugh more at Bart Vs Australia or Two Bad Neighbours? It proved almost impossible in certain cases and I’m already regretting leaving several memorable episodes out.  It was a tough job, but someone had to do it. Here they are then, the top 50 episodes of The Simpsons.

50. Burns Verkaufen Der Kraftwerk (S3)

After Mr Burns begins to grow weary of running his beloved power plant, a German Consortium swoops in and buys it for $100 million. This spells bad news for Homer who, as the plant’s safety inspector, is in deep water when the new management team find the plant in dire need of repair. Eventually of course, Mr Burns grows bored of retirement and after realising he no longer has any power, “what good is money if you can’t inspire terror in your fellow man?”, buys the plant back from the Germans who are themselves taken aback at the cost involved in bringing the place up to scratch. There’s plenty of fun to be had throughout the episode poking fun at German stereotypes, plus Mr Burns trying to blend in at Moe’s is a joy to behold. The episode’s highlights however, as is so often the case, come from Homer. His loveable stupidity comes to the fore and inevitably he’s deemed unfit for duty, but not before one of the show’s most memorable sequences where he drifts off into the magical “land of chocolate”, prancing and skipping about with giddy glee.

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49. A Streetcar Named Marge (S7)

An episode that contains a distinctly Simpsons take on the pratfalls of community theatre, coupled with arguably Maggie’s finest hour in a wonderful subplot involving a parody of The Great Escape. The main thrust of the story sees Marge take on the role of Blanche Dubois in musical version of A Streetcar Named Desire with Homer’s unsupportive and selfish ways leading him to become comparable with that story’s lead male character, Stanley Kowalski.  The songs are catchy, even if the New Orleans one (“home of pirates, drunks and whores”) didn’t go down too well with the aforementioned American city. Jon Lovitz meanwhile is perfect as the over-the-top director, Llewellyn Sinclair, delivering such reassuring comments as “I’ve directed three plays in my career and I’ve had three heart attacks. That’s how much I care. I’m planning for a fourth.”

48. Homerpalooza (S7)

A great Homer-centric episode here which focuses on his desperate attempts to remain cool. After embarrassing Lisa and Bart on the school run with his 70s rock music, Homer begins to question how he became so out of touch. In an attempt to reconnect with his kids, he buys them all tickets to the Hullabalooza rock festival. After a projectile blow-up pig inadvertently hits him in the gut and he suffers no visible ill effects, he joins the tour’s freak show and heads out on the road to rekindle his wild spirit.

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The episode is essentially a reflective look at the inevitability of growing old and falling out of touch with modern culture. Modern culture is itself sent up however, with the disillusioned teens at the festival offering a hysterically exaggerated take on the typical Generation-X slackers, “Are you being sarcastic?” “I don’t even know any more.” It had a fairly eclectic line up of bands on the bill, namely Cypress Hill, Sonic Youth, Smashing Pumpkins and Peter Frampton, and these groups actually get some of the episode’s best moments including the now legendary, “Billy Corgan, Smashing Pumpkins” “Homer Simpson, smiling politely” back and forth.  It also includes my all-time favourite Grandpa Simpson line where he warns a young Homer, “I used to be ‘with it’, until they changed what ‘it’ was. Now what I am ‘with’ isn’t ‘it’ and what is ‘it’ seems weird and scary to me…… It’ll happen to you!”

47. Homer’s Triple Bypass (S4)

Some of the best Simpsons episodes deal with quite serious topics and few come more serious than Homer having a massive heart attack. When Mr Burns catches Homer eating on the job (working his way closer to the poison doughnut) he calls him into his office and fires him, an act which proves the final straw and causes Homer’s struggling heart to finally give up. Unable to afford the necessary operation, the family resort to dialling 1-600-DOCTORB and enlisting the help of Dr Nick Riviera. The section where Bart and Lisa stand at their dad’s bedside before the operation is actually very touching, but of course there are plenty of laughs too, the best of which come from Dr Nick who has perhaps his largest ever role in this episode. My personal favourite bit comes as Homer is slowly drifting off as his anaesthetic kicks in, only for the last thing he sees to be a confused Dr Nick pointing at his chest and muttering, “What the hell is that?”

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46. Weekend At Burnsie’s (S13)

This is the newest episode on my list, coming from as recently as 2002. It revolves around Homer being pecked in the eyes by a group of crows, or as he points out to Marge, “a murrrrrder of crows”, and then being prescribed medical marijuana as a means to relieve the pain. Naturally, Fox was worried that the episode might cause some controversy and the writers thus made sure to never actually show Homer smoking weed on screen. The episode deserves great credit for taking a balanced approach to the issue of marijuana use with both its positive and negative effects being shown and never coming across as overly preachy on either side. That being said, there’s no point in denying that what makes this episode so funny is the sight of Homer high as a kite, dispensing such observations as “Marge, I just realised I am the ‘ow’ in the word ‘now’.”

45. Oh Brother, Where Art Thou? (S2)

After Abe has a sudden heart attack, he reveals from his hospital bed that Homer actually has a half-brother, the result of a fling with a carnival floozy who would do things Homer’s mother never would, “like have sex for money.” Homer eventually tracks his brother down and lo and behold, he’s become a millionaire big-shot who owns his own car company. The reunion starts off beautifully, with the Simpsons revelling in their newfound Uncle’s wealth and being treated to a pony ride on a boat and, in Homer’s case, unlimited pork chops. Naturally though, things take a turn for the worse after Herb lets Homer design his company’s next car, believing Homer possesses the common touch his company needs. The end result is a true monstrosity, complete with a car horn that plays ‘la cucaracha’ and with that, Herb’s company is ruined.

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It’s a twist on the traditional view shown in many shows and movies that the working man knows best and can teach the corporate bigwigs a thing or two. Here the common man emphatically ruins everything. It’s actually quite a dark ending to the episode, with Herb blaming Homer entirely and stating he now has no brother, but despite the downbeat ending, the rest of the episode is hilarious. Danny Devito created a wonderful character in Herb Simpson, and Homer’s inability to pick up on the Dr Hibbert-alike orphanage directors’ subtle hints about his brother’s location is a definite highlight.

44. The Cartridge Family (S9)

After a traditional soccer riot descends into a wave of violence, Homer decides he needs to make the family home more secure. Unfortunately the high-tech security systems prove to be more expensive than he hoped, prompting the brilliant line, “surely you can’t put a price on your family’s safety?” “I wouldn’t have thought so either, but… here we are.”  Consequentially, Homer decides instead to buy a gun. Now while the episode does undoubtedly mock gun culture and the NRA in particular, it is far from being a stinging critique. If anything it is fairly balanced in its arguments, emphasising that while someone as dumb as Homer would easily misuse a gun and that restrictions are undoubtedly vital, they did still serve a purpose for other people. It’s of no surprise to learn that this episode was written by John Swartzwelder, the show’s most prolific writer, a staunch Libertarian and an advocate of gun owners’ rights.

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Homer’s gun lust is mined for plenty of laughs, with his succinct description of his new weapon proving especially amusing, “It’s a handgun. Isn’t it great? This is the trigger, and this is the thing you point at whatever you want to die.” Plot-wise it may be a little lightweight, but there are so many choice Homer lines to choose from it remains a very strong episode.

43. Behind The Laughter (S11)

A unique episode here which plays out as a perfect parody of VH1’s Behind The Music series. The episode purports to depict the show’s “origins” and how the family got their big break in showbiz. After eleven seasons, The Simpsons was still hugely popular and had plenty of good episodes left in the tank, but you didn’t really think there was much left for them to do in terms of mixing up a winning formula. The chance to see “behind the scenes” and imagine a world where the family are all just actors playing a part is a clever one however, and they also neatly include numerous references to prior Simpsons episodes. My personal choice for line of the episode comes when Homer turns to address the camera and very earnestly and  apropos of nothing states, “I want to set the record straight. I thought… the cop… was a prostitute.” Eventually, the family all succumb to the pressures of fame and after rehab and an IRS investigation, it takes Willie Nelson to bring the first family of comedy back together. It’s great to see the characters we know so well given a different twist.

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42. Rosebud (S5)

The Simpsons has long had a tradition of parodying famous movies and one of their greatest efforts was this nod to the Orson Welles’ classic, Citizen Kane. The episode’s opening scenes directly mirror the renowned introduction to Welles’ film and the central premise of Mr Burns longing to be reunited with a memento from his lost youth, a symbol of bygone innocence, is likewise a direct reference to Charles Foster Kane’s plight. In this instance, it is Mr Burns’ beloved bear Bobo which is the source of much attention. Bobo comes into Maggie’s possession and despite Burns offering a hefty sum as recompense and making several attempts to swipe the bear, Homer cannot bring himself to part Maggie and her beloved new toy. As well as being a wonderful homage, the episode packs in plenty of laughs, including Homer’s attempts to write his roast of Mr Burns, “now I’m not saying Mr Burns is incontinent…”, as well as a memorable guest appearance by The Ramones. 

41. Flaming Moe’s (S3)

A classic episode from season three here which was also one of the first to feature Moe in a major role. When business at Moe’s Tavern is so bad he can’t even afford to buy beer, Homer shows Moe a cocktail recipe of his own invention which includes the magic ingredient, Krusty Non-Narkotik Kough Syrup, and is then topped off by being set alight. The drink becomes a smash hit and Moe takes credit for its invention. Moe’s becomes the most popular drinking hole in Springfield and Homer finds himself a stranger in his own bar and grows frustrated at receiving no credit for his creation. Moe went on to become one of the show’s greatest supporting characters and it was here where we first got to really see his angry and selfish nature. The best Moe line of the episode being, “Hey, Homer came up with the drink, but I came up with the idea of charging $6.95 for it.” There’s also an excellent cameo by Aerosmith, but my favourite aspect of this episode were the nods to Cheers, including Collette the waitress in the Diane role and the “Where Everybody Knows Your Name” spoof which includes a sullen Homer peering longingly in at his former hangout.

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40. A Fish Called Selma (S7)

Troy McClure is undoubtedly up there with the likes of Moe and Chief Wiggum as one of The Simpsons’ greatest recurring background characters. Voiced by the brilliant Phil Hartman until his untimely death, his regular reminders of where you might know him from never failed to raise a chuckle. This episode marked the only time he was the main focus of the storyline as he attempts to resurrect his flagging career by embarking on a sham marriage with Marge’s sister Selma, “that’s right, boys. Troy’s back from the gutter, and he’s brought someone with him!”. One memorable sequence is the excellent Planet Of The Apes musical in which a resurgent McClure stars that includes such choice lines as “I hate every chimp I see. From chimp-an-A, to chimp-an-Z.” There’s also the bizarre subplot running through the episode regarding Troy’s peculiar fish fetish, a rumour cemented by Fat Tony’s assertion that he “sleeps with the fishes.” For me this episode is all about Hartman’s performance, giving us a wonderful insight into the peculiar private life of the all-too-seldom seen Troy McClure. Despite being primarily focused on Selma and Troy’s struggling marriage, there’s also a brilliant Homer moment early on when the kids ask him what exactly a Muppet is, “Well, it’s not quite a mop, and it’s not quite a puppet, but man… So to answer your question: I don’t know.”

39. Two Bad Neighbours (S7)

A real life feud of sorts between the Bushes and The Simpsons fuelled the idea for this episode in which the former President moves in across the road and Homer takes an instant dislike to George H. Bush. In years gone by, Barbara Bush had herself criticised the show and when running for re-election in 1992, President Bush himself claimed that he wanted, “to make American families a lot more like the Waltons and a lot less like The Simpsons”. Far from being a cutting satire of any kind though, this episode is far more of a playful attack on Bush’s grumpy and gruff demeanour. While an early high point is Homer whipping up the crowd at the Evergreen Terrace yard sale, the episode’s memorable gags really stem from the escalating prank war between Bush and Homer, especially the use of a multi-coloured wig and some super glue. It’s no surprise to find that Bush didn’t provide his own voice for this outing, which was instead expertly provided by Harry Shearer.

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38. Lisa On Ice (S6)

Bart and Lisa’s relationship swings from partners in crime to extreme rivalry dependent on the show’s need and here the latter dynamic of the two is exploited to great effect. After receiving a poor grade in gym class, Lisa winds up playing little league hockey in order to ensure she doesn’t fail. Soon her team comes into direct competition with Bart’s. Naturally, Homer does the sensible thing and emphasises that being good at sports is vitally important and encourages them to compete passionately for their parents love. Homer’s inappropriateness is superb in this episode and I’ve lost count of the number of times I’ve sought to grab the attention of a room by flicking the light switch on and off and chanting “Fight! Fight! Fight! Fight!”. Rude as it may be, it’s also undeniably effective.

This is also the episode where Bart and Lisa goad each other by walking towards one another with arms and legs flailing, and if the other gets in their way, it’s their own fault. I’m sure more than a few siblings have adopted that move after seeing this episode. In the end though it’s a poignant finale as the siblings realise that their love for one another supersedes petty rivalry and they set their differences aside to leave their game a tie. A tender ending to the episode, even if Homer now sees them both as losers.

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37. Homer The Vigilante (S5)

When a cat burglar starts terrorising the residents of Springfield, Homer forms a vigilante posse to track down the assailant. Inevitably, Homer and his gang wind up causing more crime than they solve and it is actually Grandpa Simpson who solves the riddle and identifies his retirement home neighbour Molloy (voiced by Sam Neill) as the culprit. Famously noting, with a Sherlock-esque observation, that “he wore sneakers… for sneaking.” This episode really works thanks to Homer getting drunk on power and then proceeding to throw his weight around town, never really getting any closer to catching the assailant. It’s also perhaps at its core a fairly scathing look at the American obsession with mob justice and the prevalence of firearms in American society. One of the more obscure sequences which still now never fails to cheer me up however, comes when Homer begins rhythmically dancing to Lisa’s jug playing, and his resultant frustration when she stops, “Lisa, never ever stop in the middle of a hoedown!” Kent Brockman is also on fine form, whipping the Springfield natives up into a frenzy, asking the important questions such as, “When cat burglaries start, can mass murder be far behind?”

36. Mr Plow (S4)

A bona fide classic from season four and undoubtedly one of the show’s most iconic episodes. You only need to have seen the episode once to have Homer’s “Mr Plow” jingle stuck engrained in your head. The story involves Homer accidentally crashing the family car and then buying a snow plough as a replacement. He then actually starts up a successful business ploughing the townsfolk’s driveways. Eventually though, Barney decides to emulate Homer and after roping in Linda Ronstadt to help him make an advert that defames Homer (they’d been looking for a project to do together for a while), he begins to steal his friend’s business. As the rivalry begins to escalate, Homer gets revenge by making a phony call and tricking Barney into going to plough the perilous Widow’s Peak. Eventually however, their friendship proves more important than any petty rivalry as Homer realises his mistake and goes to rescues his friend.  Barney’s brazen attempts to destroy Homer are a definite episode highlight, and this episode also features another great movie reference when Bart is mowed down by a hail of snowballs in a clever nod to Sonny Corleone’s demise in The Godfather.  

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35. 22 Short Films About Springfield (S7)

Another break from the norm here as the day-to-day lives of various Springfield residents are interwoven together in a series of short vignettes. There’s plenty of good stuff in there, including the Pulp Fiction parody going down at Herman’s Military Antiques ship and Moe getting robbed by Snake after Barney finally pays his bar tab. However the episode’s crowning glory, and the section that really makes this episode such a classic, is the dinner Principal Skinner hosts for Superintendent Chalmers. After burning the roast he had planned, Skinner passes off food from a nearby Krusty Burger as his own “steamed hams”. There then follows an exchange between the pair which I imagine most Simpsons aficionados know off by heart, culminating in the following moment of brilliance as Skinner trying to explain the apparent fire in his kitchen:

Chalmers: Aurora Borealis? At this time of year? At this time of day? In this part of the country? Localized entirely within your kitchen?

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Skinner: Yes.

Chalmers: May I see it?

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Skinner: Er… no.

It’s testament to the brilliance of this sequence that should I ever get to see the Northern Lights, I’m almost definitely going to run through this entire sketch before I do anything else.

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34. Krusty Gets Cancelled (S4)

I absolutely love Krusty as a character, and while he has prominent roles in plenty of other great episodes, this for me is his finest 22 minutes. After a hot new ventriloquist act called Gabbo becomes a huge TV hit, Krusty’s rating freefall and he is eventually cancelled. Bart and Lisa eventually rally Krusty and gather together his celebrity friends for a big comeback special. This was a great example of how celebrity cameos could be done to great effect when they were still used sparingly and rarely. Here we get the Red Hot Chili Peppers, Johnny Carson, Hugh Hefner and Bette Midler to name but a few, stepping up to help out Krusty in his time of need. Krusty’s futile efforts to revive flagging ratings are entertaining in their terribleness, especially his own terrifying attempts at ventriloquism. He eventually steals the show however with the greatest out-of-tune rendition of Send In The Clowns you will ever hear.

33. Mayored To The Mob (S10)

The Simpsons has always prided itself on high quality movie references and Star Wars especially has been utilised on many occasions. In this episode though, it’s taken to the next level as Mark Hamill guest stars and is only too happy to poke fun at himself. There are plenty of sci-fi nods throughout, but special mention goes to whoever wrote the lyrics “Luke, be a Jedi tonight” (to the tune of ‘Luck Be a Lady’ from Guys And Dolls). They deserve an award all of their own for that one, as does the wit behind the simple but effective “use the forks” gag. The plot itself is fairly light, Homer becomes a bodyguard for Mayor Quimby and protects him from Fat Tony, but the regular sci-fi references and high quality script make the episode incredibly enjoyable. To this day, if lying down outside, I can’t help but ask someone, “is there anything fluffier than a cloud?” If you don’t get the correct reply, you may want to question your friendship.

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32. The Springfield Files (S8)

Agents Mulder and Scully guest star in the episode in which Homer has a drunken alien encounter and is then forced to gather proof in order to make the doubting townspeople believe it really happened. The interaction between the agents and Homer works brilliantly, especially the sequence where a gasping Homer is on a treadmill and Scully describes it as being, “like a lava lamp”. It’s also a neat touch to have The X-Files’ very own “cigarette smoking man” loitering in the background when Homer takes his polygraph test. The ending might be slightly nonsensical, but the X-Files thread works perfectly, as do the array of other pop culture references scattered throughout, including Milhouse’s frustration with the slow moving and expensive Waterworld game. Plus there’s one of the all-time great Homer lines, “I saw this in a movie about a bus that had to speed around the city, keeping its speed over fifty, and if its speed dropped, the bus would explode! I think it was called, ‘the bus that couldn’t slow down.’”

31. The Way We Was (S2)

The Simpsons’ first flashback episode is a teasing glimpse into Marge and Homer’s youth and the story of how they first met at High School. After Marge uncharacteristically gets detention after burning her bra at a feminist rally, Homer immediately falls head over heels for her and embarks on a mission to win her over. After Homer misleads her and causes her to lose sleep ahead of her debate competition, she decides to go to the prom with Artie Ziff instead, he of the “busy hands”. It was great to see a bit of Simpsons family history, and really adds a bit of romantic depth to the saga of lovebirds Marge and Homer. Another choice quote sees Grandpa Simpson offering his lovelorn son typically constructive advice on women, “Oh, son, don’t overreach! Go for the dented car, the dead-end job, the less attractive girl!” Ever one for realistic advice is Abe.

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30. Homer At The Bat (S3)

It’s testament to this episode’s hilarity that even though the star baseball players drafted into the power plant softball team by Mr Burns may be unknown to most people outside of the US, this episode remains a beloved classic. The plot is a simple one, the power plant softball team does well, largely thanks to Homer and his wonder bat (the storyline owes a great debt to Barry Levinson’s 1984 movie The Natural), but Mr Burns becomes so determined to win he drafts in a whole plethora of professional talent. The baseball stars are all put to great use and each given their own unique storyline and downfall, from a mysterious black hole, to a drunken argument with Barney, “And I say England’s greatest Prime Minister was Lord Palmerstone!” Then there’s the ever so catchy “Talkin’ Softball”, a parody of the song “Talkin’ Baseball”, which has no doubt being inadvertently memorised by many a Simpsons fan down the years.  

29. Simpson Tide (S9)

A fairly bonkers episode here, but nevertheless one filled with numerous big laughs. The central plot sees Homer getting fired and then joining the Naval Reserve, inexplicably also joined by Apu, Barney and Moe. When out on War Games, Homer impresses the Captain and is left in charge of the submarine when he goes to check on a torpedo issue. One thing leads to another and before you know it, Homer is in charge of a nuclear submarine and very nearly prompts a return to the Cold War. An amusing subplot meanwhile sees Milhouse getting an earring and thus immediately becoming cool, while Bart’s desperate attempt to equally impress his classmates by doing the Bartman dance does nothing for his own standing. It’s a thin premise but the episode works brilliantly thanks to moments such as Homer’s inability to be scared by his drill instructor, “nucular….it’s pronounced nucular”, and the surreal joke where the Soviet Union reveals it was in fact just lying dormant all these years. All this plus Homer’s fool-proof tactic for getting out of trouble at work, “it’s my first day!”

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28. Lisa The Vegetarian (S7)

An incredibly funny episode here, but also one with a well-delivered message. Lisa’s burgeoning vegetarianism is played for laughs throughout, but at the episode’s climax the message of tolerance and understanding rings clear. There are so many choice bits in this episode it’s hard to know where to begin. To this day, I can’t hear the word salad without humming “you don’t win friends with salad” in my head. Then there’s Troy McClure’s unforgettable Meat Council video, perhaps the very finest of all his segments, remember, “If a cow ever got the chance, he’d eat you and everyone you care about.” Then there’s also Homer’s confusion over what animal his various meats all come from “the same ‘magical’ animal”, as well as his determined chase to rescue his suckling pig after Lisa shoves it away. The jokes come thick and fast and the conflict between Homer and Lisa works perfectly.  The closing sequence in which father and daughter reconcile is sweet and also cuttingly funny as Lisa says to her dad, “I still stand by my beliefs. But I can’t defend what I did. I’m sorry I messed up your barbeque.” To which Homer memorably replies, “I understand honey. I used to believe in things when I was a kid.”

27. The City Of New York Vs Homer Simpson (S9)

Prior to them becoming ten a penny, there were some great Simpsons travel episodes, Bart Vs Australia and Mr. Lisa Goes To Washington to name but two. This ode to New York which launched the show’s ninth season is also up there with the very best. Homer’s hatred of the city is deep-rooted thanks to a painful childhood memory so when he and the family are forced to travel there in order to retrieve his car, there’s a neat juxtaposition between his gruelling experience waiting for the parking officer and the rest of the family having the time of their lives. One of the episode’s best bits is undoubtedly the opening segment where Barney is forced into being the gang’s designated driver in Moe’s. The look of despair on his face when he hears to opening few notes of Oh Yeah by Yello and realises that Duffman is on his way is plain hilarious, “oh no… not tonight…..NOT TONIGHT!” Once in New York, the family’s visit to see “Kickin’ it: A Musical Journey Through The Betty Ford Centre” is definite high point. The song “You’re Checkin’ In”, complete with lyrics as brilliant as “I should put you away where you can’t kill or maim us, but this is LA……and you’re rich and famous”, actually won the show another primetime Emmy too.  

26. Duffless (S4)

After he gets arrested for drunk driving following a visit to the Duff brewery with Barney, Homer loses his driving licence and is asked by Marge to give up beer (not deer) for a month. Like many of the best Simpsons episodes, this is one which has a definite depth to it with the perils of alcoholism and addiction being a central focus. Likewise, Homer’s decision to turn his back on boozing in order to go and spend time with his wife is a particularly touching ending. Highlights include Hans Moleman’s revelation in Homer’s AA meeting, “drinking has ruined my life. I’m thirty-one years old!”, and Homer’s bittersweet ode to youthful drinking sung to the tune of “It Was a Very Good Year”. The episode’s subplot involving Bart wrecking Lisa’s science project is also very funny, with a neat nod to Kubrick’s A Clockwork Orange included in the shot where he reaches up for the cupcakes. There’s also poor Milhouse delivering a particularly weak Science Fair project in which he uses a slinky to demonstrate gravity in all its glory, prompting Edna Krabapple’s inimitable reply, “preeeetty lame Milhouse.” A truly well rounded episode that’s equals parts fun and serious, and one in which Homer’s fight to stay sober is wonderfully rendered, even if it is soon forgotten in the show as a whole.

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.

This article was originally posted in August 2014.