Full Disclosure: I still have, to this day, 40+ VHS tapes of The Simpsons episodes that I taped off the TV (that’s right, I’m bad) as a young lad. I have all the DVDs up until season 11 where the horrible packaging made it impossible to remove the discs. Most embarrassingly, I have an entire folder full of sheets (almost 100 in total) which perfectly document which episodes are on which tapes (and a brief description), whether or not the episode exists in its entirety or was only half taped, and a grade out of 10 for each. So this list is in honour of that boy who had (and clearly still has) way too much time on his hands.

[Oh dear God. I just found the folder. 100 pages was a VAST understatement. I also have sheets listing exactly (to the second) how long each tape was, a running tally of how many episodes per season are centred around certain characters and a list of who is on each DVD commentary track for the first 10 seasons. In fact I made a top 20 list back then as well which has a bizzare mix of great and mediocre episodes, although certainly there are still epsiodes which I’ve loved since then that aren’t loved by the fandom. Wow my handwriting was markedly better back then].

I am still a member of the NoHomersClub discussion forum so I have a fair idea of what the fandom does and doesn’t like. Notably many feel that the show lost its flair after season 8 and refuse to acknowledge episodes from the much maligned Mike Scully era (seasons 9-12) where things got a little crazier and cartoon-y. I’m significantly kinder to those episodes because they were some of the first that I saw as a young teenager; the time where I truly began to judge content and form preferences. But I’m not going to lie, season 9 onwards represents a different era of The Simpsons, so I’m stopping this list at season 8. I think its was around season 18 when I stopped watching every episode so I still have quite a few favourites all the way through the Al Jean period (Season 13+)***. I’m also a lot less sentimental about the show than hardcore fans. I’ll take hilarious wacky gags over character consistency and heartwarming emotion any day. I take the characters as seriously as the show wants me to take them. Certainly there’s a point where the dumbing down of the characters can make the show deeply unfunny, especially when it’s a character like Marge who is characterised more by cluelessness than stupidity (‘How about we play the basketball? I’m no Harvey Globetrotter’ is an example of a fine clueless Marge line. Having her refer to Frank Gehry as ‘the bestest architect in the world’ is just kinda dumb). And I certainly draw the line at Homer saying he can’t read for a stupid gag in Season 10’s quite awful ‘When I Dish Upon A Star’ but if it makes me laugh, I’m very forgiving. I watch the show for the laffs.

*** I’ll definitely do a ‘post season 8’ list at some point in the near future. But this list only contains episodes up to season 8 (mostly to help me narrow down the list). I’ve also left out the Halloween episodes for another list down the road.

25. Boy Scoutz n the Hood (Season 5)

My favourite seasons of The Simpsons are 4 and 6. Season 5 is a very solid season but it’s also where the show was trying to get crazier while still being tied to what the writers felt an episode of The Simpsons should feel like. For example Bart gets an elephant as a prize from a radio station (crazy no?). Then the rest of the episode tries to deal realistically with keeping an elephant in a suburban household (which just isn’t all that funny).

This episode gets it right by allowing crazy inspiration and weirdness to circle around a relatable father-son story. Sure Bart joins the campers, but through a squishie-bender that leads to an impromptu musical number. Sure Bart is embarrassed with Homer’s antics of losing the map and wasting all their water on cleaning his socks, but Homer saves the day by finding a random Krusty Burger on an off-shore oil rig, while the other other campers and Ernest Borgnine are being eaten by bears (most likely). Crazy? Yes. Hilarious? Uh-huh.

Homer: "Weaseling out of things is important to learn. It's 
what separates us from the animals... except the weasel."

Homer: "Aww $20. I wanted a peanut"
Homer's Brain: "$20 can buy many peanuts"
Homer: "Explain!"
Homer's Brain: "Money can be exchanged for goods and services."

24. El Viaje Misterioso de Nuestro Jomer (Season 8)

Not many shows can take a premise of its main character going on an extended psychedelic drug trip off an extremely hot chilli and turn it into a simple story of a man trying to find his soul mate, but The Simpsons can. This episode is mostly on the list for its gorgeous trippin’ out sequences filled with pissed off turtles and spirit guide Coyotes voiced by Johnny Cash.

McAllister: "Clear sailin' ahead for our precious 
cargo."
Sailor:     "Uh, would that be the hot pants, sir?"
McAllister: "Aye, the hot pants."

Homer: "In your face, Space Coyote!"

Homer: "Oh, everything looks bad if you remember it"

23. Black Widower (Season 3)

The second Sideshow Bob focused episode and the one which acts as the prototype for all following Sideshow Bob episodes  A stylish and cleverly constructed mystery with a satisfying climax. Also Wiggum’s line, ‘Oh right! The gas’ may well be one the funniest moments of the first 3 seasons.

Homer: "Gee, if some snot-nosed kid put me in jail, 
the first thing I'd do when I got out is find out 
where he lived, and tear him a new belly button!.....
Lousy snitch...Yahhhh"
Sideshow Bob "Mr. Simpson, you are forgetting the first
two noble truths of the Buddha"
Homer: "I am not!"

Bart: "After trying four times to explain it to Homer, 
explained it to Mom, and we were on our way!"

TV: MacGyver! MacGyver! MacGyver! MacGyver! (ECHOES)
Bart: Aunt Selma has one hour to live
Homer: Hey, down in front.

22. Secrets To A Successful Marriage (Season 5)

I’m a sucker for episodes of Homer being a well-meaning arsehole or simpleton. This episode stands out mostly for all the quotes and scenes that have stuck in my head since childhood (especially the ‘Something was said. Not good’ sequence). It’s also a nice mix of sincere Homer, who just want to be seen as intelligent and jerkass Homer, who tells his class his wife’s secrets so they’ll continue to pay attention to him. The climax is also both pathetic and kinda touching. The one thing Homer can offer Marge is complete and utter dependence….that’ll have to do for now.

Homer: "But every time I learn something new, it pushes out
something old. Remember that time I took a home wine-making 
course and forgot how to drive"
Marge: "That's because you were drunk!"
Homer: "And how"

21. Duffless (Season 4)

This is a perfect example of a season 4 episode that without any huge gimmicks or a large scale, delivers a solid, hilarious episode of television, with both an A and B story that hit the mark. Much like ‘Homer’s Triple Bypass’ deals with Homer’s overeating, ‘Duffless’ deals with his problem drinking and treats the weight of his sobriety with appropriate exaggeration. While people recovering from drinking problems may feel as though they are constantly surrounded by signs telling them to drink, Homer actually experiences this as Duff beers are thrown at him like bombs as a marketing campaign. The end is appropriately sweet and low key as Homer puts off his first beer in a month to go bike riding with Marge.

The B-story is a solid Clockwork Orange parody as Lisa tries to determine (for science, of course) if Bart is smarter than a hamster by putting him through a bout of humiliating tests. But of course Lisa is too smart for her own good and the plebs around her are more impressed with seeing the hamster ride in a remote-controlled plane despite it having absolutely no relationship to science.

Hans Moleman: "My name is Hans. Drinking has ruined my life. 
I'm 31 years old!"

Lisa: "That'll learn him to bust my Tomata"

Lisa: "How can a hamster write mysteries?"
Store owner: "Well, he gets the ending first, then he
writes backward"

20. Bart of Darkness (Season 6)

Probably the best season opener the show ever did. This episode is both a fantastic evocation of summer vacation as well as a shrewd Rear Window parody. The show succeeds at tying these two story lines together without the episode feeling disjointed or pieced together. I have a particular love for shows and movies that capture the feeling of summer holidays, which is why the ranking is quite generous. But it’s still a classic episode in my book.

Homer: "There's still the little matter of the whereabouts of
your wife."
Maude:"Uh, I'm right here"
Homer:"Oh, I see! Then I guess everything's wrapped up in a neat
little package! Really I mean that ....... Sorry if it sounded
sarcastic.

19. Homer At the Bat (Season 3)

I feel like The Simpsons didn’t really hit their peak until season 4 after the crazier, off-the-wall elements were introduced, but this is one of the better early episodes. It’s also the best example of the ‘multiple guest star’ episode and managed not to be dragged down by the load new of characters the show had to introduce and accomodate. If this episode only gave us the ‘Talkin’ Softball‘ song, it would still be a classic in my book.

Bart and Lisa: "Daryl. Daryl. Daryl".

18. Lisa’s Substitute (Season 2)

As I mentioned before, I’m not as drawn to the sentimental episodes quite as much as other fans. You’ll see no favourites like ‘Mother Simpson’, ‘Bart Sells his Soul’ or even ‘Rosebud’ on this list. Why? They simply never engaged me as much as the other episodes in the list and while I enjoy all 3 mentioned episodes, none are among the show’s funniest, in my opinion. In fact, it seems almost sacrilegious (yes The Simpsons is holy) to have this classic episode so low on the list. It’s a beautiful, poignant and perceptive episode about fatherhood and inspiration, but also……not that funny. Apart from my fairly strong affinity with Lisa (more on that later), the ‘You are Lisa Simpson’ moment is one of the best, most heartfelt moments in the entire series. That moment alone gets it in the list.

Ralph: Dear Miss Hoover, you have Lyme disease. We miss you. 
Kevin's biting me. Come back soon. Here's a drawing of a
spirochete. Love Ralph.

17. Homer’s Triple Bypass (Season 4)

An hilarious episode about a horribly serious medical procedure. Homer was bound to one day require serious medical treatment for his heart, but again this episode doesn’t work because of its realism. It does have some touching passages; the scene where Homer says goodbye to the kids is both exceedingly touching and amusing, but mostly this is about as funny as an episode where the main character has a life threatening heart condition can be. The scene where Homer is fired is particularly inspired. Also this episode has the best use of Dr. Nick in the entire series [Side note: Why is it so hard to find good quality versions of Simpsons clips? Grumble grumble]

Dr. Nick: "Seriously, baby, I can prescribe anything I want."

Dr. Nick: "Why, if it isn't my old friend, Mr. McGreg. 
With a leg for an arm and an arm for a leg."

16. Bart On The Road (Season 7)

I very much enjoy episodes of The Simpsons where the kids are left up to their own devices, because it allows us to follow along with their crazed kid logic (‘Kamp Krusty’ and ‘Das Bus’ are 2 notable examples), which the writers are great at honing in on. Despite the episode following Bart, Milhouse, Nelson and Milton (sorry, Martin) to the World’s Fair in Knoxville, Tennessee, Lisa also plays a significant role, by helping to get them out of trouble. The scene where Lisa tells Homer what Bart has been up to is one of the funniest in the show’s history. But for the most part, this episode takes the road movie tack, except these kids are just doing random shit, as you would if you were a 10 year old with a driver’s license. (-“Can we pick up that Hobo, Bart?” -“Yes!”)

Patty: "Some days we don't let the line move at all."
Selma: "Yeah, we call those week days"

Homer: "Lisa would you like a donut?"
Lisa: "No thank you. Do you have any fruit?"
Homer: "This one has purple. Purple is a fruit"

15. Homer’s Phobia (Season 8)

Beyond the obvious Mr. Smithers hints, this episode was the first real tackling of homosexuality and hilariously explores Homer’s mission to make Bart a man in a world gone gay. It’s most telling about Homer’s character that he likes everything about John (fantastically played by John Waters) until he finds out he’s gay and then he becomes a menace waiting to turn Bart into a mincing fairy. Homer’s extreme offense he takes to everything in the world that doesn’t work for him is both hilarious and yet very true of homophobes who are personally offended by things that don’t effect them.

Homer’s misguided efforts to man-up Bart offer a number of classic set pieces such as the trip to the steel mill, ‘we work hard, and we play hard’, and the shooting trip. Particularly funny is Homer’s attempt to be affectionate with his son, but not in a queer way. Ultimately we all learn that in order to gain a homophobe’s acceptance, a gay person needs to save their lives. It’s a fittingly silly way to get Homer’s acceptance for what is ultimately a silly and misguided distaste towards homosexuality.

Homer: "You know me Marge. I like my beer cold, my TV loud, and
my homosexuals fa-laaaaming."

Homer: "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!"

Homer: "He didn't give you gay, did he?"

14. Homer: Badman (Season 6)

The show’s most pointed bashing of media fear-mongering and sensationalism. David Mirkin’s seasons (5 & 6) were by far the most aggressive in the show’s history in calling bullshit on the media. Everything about ‘Rock Bottom’ hosted by God…….frey Jones is a pinpoint accurate attack on the awful tabloidisation of news media from the slow motion, to the ominous music and careful editing. Homer’s edited interview is again, one of the funniest and cleverest moments of the show. This is certainly one of the sharpest, most quotable episodes of The Simpsons and to think it all starts innocently enough at a candy convention.

This episode plays on Homer’s general good-natured absentmindedness as he gets completely in over his head. Not only does he giggle like a schoolgirl when he hears the word tit-mouse, he also equates sexual harassment to be bitten by a hungry alligator. He has always been reliant on Marge to get him out of trouble but she only has so much power. The only man who can save him is the filthy immigrant pervert (I mean groundskeeper) Rowdy Roddy Peeper (I mean Willie). I love that the moral of the story is both that Homer never learns a thing and that everything will be okay as long as everyone is taping everyone else. When the show is in hardened satire mode, its one of the funniest, most merciless shows you’ll ever see.

Troy McClure: "Simpson scandal update: Homer sleeps nude in an 
oxygen tent which he believes gives him sexual powers!"
Homer: "Hey! That's a half-truth!"

Homer: "So, a graduate student, huh? How come they can send a 
man to the moon but can't make my shoes smell good?"

13. Mr. Plow (Season 4)

Apart from the incredible earworm jingle of the eponymous snow removal service, the first things that comes to mind when I think of this episode are the 2 advertisements that Homer has made for his business. Both are complete opposites in style, tone and message and both are hilarious. They really highlight the different levels of humour the show can evoke by making fun of both under-licensed, one-man business, shoe-string budgeted commercials and pretentious European-styled twaddle that says nothing about the service it is advertising.

At its core though, the episode is about dealing with the self worth of it’s two leads (Homer and Barney) and the rivalry that builds between them. It’s not very substantial, but it carries some of the better gags of the season, such as the old people looking for an excuse not to leave their retirement home and the mountain goat who is not so sure footed.

Insurance man: "Now this place you were at, Moe's, is this a
business of some sort?"
Homer's Brain: "Don't tell him you were at a bar. But what 
else is open at night?"
Homer: It's a pornography store. I was buying pornography.

Homer: "Lenny and Carl suck. Oh, don't tell them I said
that Marge, because if I ever lost them as friends..."

12. Lisa On Ice (Season 6)

Again I love the episodes centred around the kids and episodes (like Bart of Darkness and Summer of 4 ft. 2) where Lisa inexplicably becomes more popular than Bart despite her general social awkwardness. Again, the resolution is a hint of sibling sweetness amongst a violent ice-hockey crowd fight. But what makes this episode truly hilarious is that Homer is just a plain, unrepentant arsehole throughout the entire episode, cherishing the rivalry between Bart and Lisa, whipping Uter, threatening to kill Bart if he loses and preparing himself to boo whoever loses the big ice hockey match.

The episode also continues Mirkin’s attack on media sensationalism in Kent Brockman’s hilarious opening spiel. This is just a plain classic episode. On top of Ralph’s always quotable ‘me fail English? That’s unpossible’ and ‘don’t make me run, I’m full of chocolate’, there is also the hilarious extended sequence of Bart and Lisa NOT hitting each other and Homer NOT eating the blueberry Pie.

Homer: "Wow. Eye of the tiger, mouth of a teamster. And to think
of all the time I wasted on you (point at Bart).....Uh not 
wasted....I love you"

Homer: "Okay Marge, it's your child against my child. The 
winner will be showered with praise. The loser will be taunted 
and booed until my throat is sore."

Marge: "Repeat. You are not in competition with each other"
Homer: "Hey! Apu just called. This Friday, Lisa's team is
playing Bart's team. You're in direct competition! And don't
go easy on each other just because you're brother and sister.
I want to see you both fighting for your parents' love! 
(Flicks light on and off.) Fight! Fight! Fight! Fight!"

11. The Itchy, Scratchy and Poochie Show (Season 8)

The ultimate meta episode of The Simpsons that only draws more power as time goes on and the show continues to grow more tired and further removed from its early peaks of creative and satirical genius. If ‘Homer: Badman’ is a classic example of satirising  bottom feeding tabloids, this episode is an insightful satire of television studio phoniness and pointless buzz words. This is The Simpsons at its most self-aware which season 8 was very good at. However, it’s all somewhat depressing to watch a show foretell its own demise and call out the audience for thinking that the show is slipping in quality (although this episode did coin the phrase ‘Worst episode ever’).

Also at its heart, it’s an episode about Homer wanting to do a good job of something only to have it cruelly taken away. As with all of the 100+ jobs Homer has occupied over the years, he puts infinitely more heart and effort into it than he does with his regular job as safety inspector, but he can’t help that he’s saddled with a character so lame that his banishment from the show is legally binding. The episode ends exactly as Lisa predicted with the kids changing the channel to see what else is on. (Also Roy says goodbye and leaves forever – tear)

Animator: "Excuse me, but "proactive" and "paradigm"? Aren't
these just buzzwords that dumb people use to sound important? 
Not that I'm accusing you of anything like that.
I'm fired aren't I?"

Milhouse: "When are they getting to the Fireworks factory!"

Poochie: "Kids! Always recycle TO THE EXTREME!"

Note: Poochie died on the way back to his home planet.

10. Homer’s Enemy (Season 8)

This episode is without a doubt one of the most bizarre and bravest episodes ever attempted on the show. It’s not very laugh out loud funny, but it contains some of the strongest, blackest humour on the show. The very idea of Homer being so annoying that it leads a good, honest man to accidentally kill himself is completely unnerving and entirely inspired. After all, I’d probably hate to be around a Homer-type figure for more than a few moments. Ending the episode with everyone laughing at Homer’s stupidity as the coffin is being lowered is about as dark as this series gets, but dammit, it’s hilarious. The B-story of Bart owning a factory is appropriately light and silly to offset the A-story but I like the way it plays into that skewed version of the American dream, in that even Homer’s 10 year old son owes property.

The entire episode is a critique on sitcom conventions by way of a scathing critique of the American dream. Most television shows make it seem like living in a spacey 2 storey house in the suburbs is easy even for the lower-middle classes, but the truth is there are probably a lot more people like Frank Grimes, who ‘lives above one bowling alley and below another bowling alley, than people like The Simpsons who live in relative luxury despite having 3 kids, a non-working spouse and an incompetent unqualified provider (I should stop now, I’ve written an entire paper on the episode for a media course).

Frank Grimes: "Can you believe that guy? He fell asleep inside a
radiation suit."
Lenny: "He had three beers at lunch. That would make anyone 
sleepy."

9. Marge Vs. The Monorail (Season 4)

This is episode represents season 4 and The Simpsons in general at its gaggiest. It simply throws as many jokes to the wall as possible, no matter how ridiculous, and a huge percentage sticks. This is one of the funniest ‘Homer gets a new job’ episodes of the show’s run. As usual Homer gets it completely randomly and without the skills actually required to perform the job.

This is an episode that begins with the classic Homer as Fred Flintstone opening and ends with a giant escalator to nowhere sending people to their deaths; everything in between is as equally stupid and inspired including Mr. Snrub trying to get his money back and a teleporting Leonard Nimoy. However the story is surprisingly rich as Marge traces the roots of Lyle Lanley to see the beginning of his monorail enterprise and help Homer survive the disaster movie situation he gets himself in.

Marge: "What if something goes wrong?"
Homer: "Pffft... what if. What if I'm taking a shower and I 
slip on a bar of soap? Oh my god, I'd be killed!"

Kobb: "I shouldn't have stopped for that haircut"

Nimoy: "A solar eclipse. The cosmic ballet continues"
Passenger: "Does anyone want to switch seats?"

8. Lemon Of Troy (Season 6)

Yep, an episode of kids being kids. You knew I’d like this episode. We don’t see enough of the Springfield/Shelbyville rivalry anymore, but this was a potent kick-off for that long-standing feud (in terms of us understanding the extent of the rivalry – apparently Springfield burned down their city hall). This is an incredibly fun adventure story which is both very low stakes from an external standpoint (see Lisa running across the border with ease), but highly tense for the kids involved.

Most of the fun comes from the character pairings this episode: Martin and Nelson (‘Spring forth burly protector and save me’), Milhouse and Milhouse (‘so this is what is sounds like, when doves cry’), even Homer and Flanders. This is also a strong episode for Marge who succeeds in filling Bart with town pride and then assumes Bart has become a tutor when he says he’s gonna teach some kids a lesson (Cue Homer: ‘Tute on, son! Tute on!‘). This is one of those episodes that I enjoy mostly for its ‘kidz adventure’ vibe and its contributions to the sense of who Springfield is than for its quotables, but it is still a highly amusing and refreshing episode.

Jebediah Springfield: "what are you talking about, Shelbyville? 
Why would we want to marry our cousins?"
Shelbyville Manhattan: "Because they're so attractive. I... 
I thought that was the whole point of this journey."

Old Shelbyville man: "Now let's all celebrate with a cool 
glass of turnip juice."

7. 22 Short Stories About Springfield (Season 7)

I’m a sucker for vignette episodes. I’m one of those value for money people; I always preferred cluttered overblown movies, flaws and all, to the overly simplistic and spare (of course, done right, this can be incredibly effective too) and I love shows and movies that are able to offer diversity of style and tone. This episode certainly gives you your money’s worth and shines a brief light on side characters who rarely (sometimes for good reasons – I don’t need a Cletus-heavy episode. Season 18’s ‘Yokel Chords’ was bad enough) get to step into the spotlight and lead an episode.

It’s also a bizarrely faithful Pulp Fiction parody which give the mostly ridiculous happenings a dark, sly edge, especially with Snake and Wiggum tied up in Herman’s weapons store. But mostly the episode is an excuse for random non-sequitors (Lovejoy making his dog defecate on Flanders lawn) and unnecessary yet catchy theme music to go with several vignettes “Most folk’ll never lose a toe, but then again some folk’ll”. My favourite short is probably Skinner and Chalmers, because of Chalmers’ ability to realistically see through all of Skinner’s ridiculous lies (‘and they’re called steamed hams despite the fact that they are obviously grilled?’). I also love the theme music for that particular vignette.

Oakley and Weinstein, the showrunners for seasons 7 & 8 put a lot of effort into creating episodes that were conceptually different from everything that had come before. Whether it was the ‘Simpsons Spin-off Showcase’, the 138th episode Spectacular clip show or the aforementioned Poochie and Grimes episodes, they managed to give the show a bit of life by taking it in strange new directions. This episode is one of the best examples of that.

Chalmers: "The Aurora Borealis? At this time of year? At this 
time of day? In this part of the country? Localized entirely
within your kitchen?"
Skinner: ".....yes"
Chalmers: "May I see it?"
Skinner: "......no"

Smithers: "I'm allergic to bee stings, they cause me to... uh...
die."

6. Who Shot Mr. Burns Part. 1 (Season 6)

Certainly one of the most intricately written episodes the show has done. In fact, it works just as well as a serious mystery as it does a comedy, with real stakes, realistic motives and a real tension as the episode progresses to its foregone conclusion. Mr. Burns has been villainous before, after all one of his earliest character traits was ‘releasing the hounds’ on innocents. But here his villainy has gone too far and he represents the perfect victim for a murder mystery: the man that everyone hates with good reason. The scene leading up to his shooting is very tightly and suspensefully edited, cutting back between all the possible suspects, until the conflict and shooting, all of which takes place in darkness and shadow.

However what I always remember most about this episode is Homer’s crusade to get Mr. Burns to notice him. I recall one of the first times I watched this episode, Homer’s F-bomb (the video link actually has Homer swearing, but it’s still funny) at Mr. Burns forgetting him again had me laughing literally for minutes. However this is probably one of the less gag-filled episodes of the show as it takes its time to establish the conflict and then create realistic motives for a large number of characters while also laying the clues for the reveal in the 7th season premiere. It was hell of a way to close out a season and it succeeds as a very well devised and crafted mystery thriller.

Mayor Quimby: "People, take it easy. We're all upset about Mr. 
Burns' plan to, uh, block out our sun. It is time for decisive
action. I have here a polite but firm letter to Mr. Burns'
underlings, who with some cajoling, will pass it along to him or
at least give him the gist of it.
Also it has been brought to my attention that a number of you 
are stroking guns. Therefore I will step aside and open up 
the  floor."

Groundskeeper Willie: "Aaaaaaaaagh! I'll kill that Mr Burns! 
And wound that Mr Smithers!"

5. Cape Feare (Season 5)

This is perhaps the only Sideshow Bob episode without a core mystery. There is no dastardly scheme that Bart and Lisa will discover and foil at the last minute, and unlike later Sideshow Bob episodes, his family is not involved. No, in this episode, Bob quite simply just wants to gruesomely murder Bart Simpson. This is Bob at his most dogged and vicious.

This episode carries the vaguely surreal feel that many season 5 episodes hold. We have an unmedicated Grandpa turning into a woman, we have Bob trampled on by a number of elephants, as well as Bob’s impromptu musical performance on the boat that concludes with a random lady handing him flowers. But these weird quirks do little to draw away from the eerie tone of the episode or derail the utter hilarity of the proceedings.

This episode contains several moments that are iconic in TV history not just Simpsons history. Firstly there is the rack scene, which has become TV shorthand for a repetitive gag that’s funny at first, then less funny, then funny again (think Peter Griffin hurting his leg in Season 2 of Family Guy. That’s a rake scene). There are also the sequences of Homer barging into to Bart’s room screaming and brandishing a weapon; turns out he only wants offer brownies and show off his hockey gear (“Oh sorry! What am I thinking?”). However in my opinion, the funniest scene by far is when the witness protection people try to convince Homer that his name is now Homer Thompson (“I think he’s talking to you”). That scene will never fail to crack me up.

Wiggum: "Yeah. It's a good thing you drifted by this brothel!"

Homer: "Oh my God! Someone's trying to kill me! Oh, wait, 
it's  for Bart."

Snake: "Use a pen, Sideshow Bob."

4. Lisa’s Wedding (Season 6)

The Simpsons has done a number of future-gazing episodes and while there are others that hold merit (Season 16’s Future-Drama isn’t bad) this is the definitive Simpsons future episode for me. The episode’s success comes both from its hilarious take on the world of 2010 (yeah, I know. We’re all so old) and from the pathos it draws out of Lisa’s relationship with her father.

I’m impressed with how well drawn Lisa’s husband-to-be Hugh is. Like Frank Grimes (although even more patient) he’s a normal guy who just can’t stand to be around Homer and we can completely relate to his predicament. But the scene where Lisa stands up for Homer to Hugh over the ridiculous pig cufflinks is very stirring and a strong moment for Lisa’s character.

But on the laffs side, the opening sequence at the Renaissance Fair has a number of hilarious bits such as Homer wooing Lunchlady Doris for the suckling pig and Wiggum’s magical beasts (see quotes below). Also the very first shot of the future with the frightening metal robot who turns out to be a tin-man auditioning for The Wizard of Oz, is hilarious. My favourite future touches: the holographic tree (in memory of a real tree), Marge constantly forgetting she’s on picture phone and all the robots who for some reason are programmed to cry, but melt and explode when they do.

Homer: "OK, Marge, I'll plan everything: we can have the     
reception at Moe's. Wait. Why not have the whole wedding there?
We'll do it on a Monday morning. There'll be fewer drunks."
Marge: "Homer, don't be offended, but I've obtained a court
order to prevent you from planning this wedding."

Wiggum: "Behold, the rarest of the rare... the mythological two-
headed hound, born with only one head! And here, out of the
mists of history... the legendary Esquilax. A horse with the
head of a rabbit. And the body... of a rabbit!"

3. Last Exit To Springfield (Season 4)

We’ve gotten to the stage in the list where pretty much every scene is classic, over-quoted, sacred script. This episode simply has more classic sequences than any other episode of The Simpsons. 

Rather than discussing them, I’m just going to list them as you remember every hilarious moment: The big book of British smiles, Lisa’s drugged out Yellow Submarine parody, -‘Lisa needs braces’ -‘Dental plan’, Smithers and Burns running the powerplant with their two headed dog, Homer getting a scar demanding a burrito, Homer thinking Burns is coming onto him during union negotiations while he desperately needs to pee, -‘All opposed? Nay’ -‘Who keeps saying that?’, Gummy Joe, Lisa and the workers singing outside the plant + Classical gas, Mr. Burns in Grinch mode, Homer running in circles on the floor ‘Three stooges style’ after he wins, typewriting monkeys, hired goons, ‘I had an onion tied to my belt, which was the style at the time.’ etc, etc, etc. (I’m not even going to find links for these. They should already be indelibly imprinted into your brain)

Worker: "You can't treat the working man this way! One of these
days we'll form a union, and get the fair and equitable 
treatment we deserve! Then we'll go too far, and become
corrupt and shiftless, and the Japanese will eat us alive!"
Burns' Grandfather:"The Japanese? Those sandal-wearing goldfish
tenders? Ha ha! Bosh! Flimshaw!"
Burns: "Oh, if only we'd listened to that young man, instead 
of walling him up in the abandoned coke oven."

Burns: "All right, let's see... "It was the best of times,
it was the BLURST of times?" You stupid monkey."

Burns: "Did you find the bathroom?"
Homer: "Uh...yeahhh"

Dentist: "Why must you turn my office into a house of lies?!"

2. Homer the Heretic (Season 4)

Just seeing the title of this episode makes me smile and this was very nearly at the top of the list. After all, Homer Simpson is probably the funniest character in television history, just putting it out there. Even his greatest flaws (and he has many) are entirely relatable. No one in their family, save for Marge, gets much out of going to church, and especially on a freezing mid-winter Sunday morning. Who wants to gets out of bed to be bored and guilted. Homer is just doing what everyone else in the family wished they could get away with. Is he a good example? God no. Is he selfish and lazy? Most definitely. And yes he can also be rude and quite cruel but he’s not malicious or mean-spirited (at least in this episode). He’s selfish and lazy in ways that many of us can be, and in ways we wish we could get away with. He also utters in this episode one of his greatest, simplest lines, ‘everyone is stupid but me’.

This episode is one of the best showcases for all of Homer’s foibles but also highlights his general good-naturedness. However this is also an episode that underscores the strength of the ensemble and the diversity of the town, while lightly touching upon religious debates (despite the dream-presence of God throughout, the episode is more about being a good and accepting person, than being a devoted Christian). The episode features great moments from the supporting cast including Krusty (“A religious clown thing, yes”), Apu (“Please do not offer my God a peanut”) and Reverend Lovejoy (I particularly enjoy his shock at being asked over for dinner under false pretences). A classic episode of TV’s funniest character at his finest.

Homer: (watching The Three Stooges on TV) "Moe is their leader."

Apu: "Mr. Simpson, please pay for your purchases and get out 
and {brightly} come again"

Homer: "Kids, let me tell you about another so-called wicked 
guy. He had long hair, and some wild ideas, and he didn't always
do what other people thought was right. And that man's name was
... I forget.....but the point is......I forget that too. 
Marge, you know who I'm talking about! He used to drive that 
blue car.

Homer: "There you go again, always taking someone else's side. 
Flanders, the water department, God..."

1. Summer of 4 ft. 2 (Season 7)

Perhaps a controversial choice. As I mentioned above, I love stories that capture the essence of a summer holiday: that time when you are free to do whatever you want, but that’s a little daunting, so you end up filling those long days doing as little as possible. It all makes me very nostalgic. I also mentioned my affinity towards Lisa’s character. Lastly I enjoy when the kids get to be kids and have a healthy rivalry.

Lisa is a character who doesn’t try as hard to be liked as Bart does, but at the end of the day, she doesn’t understand why she’s not more popular (actually this episode is eerily similar to Bart of Darkness). She’s nice to everyone, she tries so hard to do the right thing, she spends hours getting the yearbook published and yet no one wants to sign hers and she doesn’t understand why. I’m not saying that I also feel the world owes me love and lots of it. I’m nowhere near as nice or motivated as Lisa but I think everyone can relate to her desire to just be ‘normal’ and ‘liked’ for once. This is a sweet episode that explores both Lisa and Bart’s character and brings out the best and worst in both; ultimately deciding that they are both good kids who love each other.

The laughs in this episode (and there are plenty)  mostly come from Homer and Marge, particularly the boardgame with Milhouse and Homer’s exploits with buying and lighting fireworks for the holiday. I know I said that I enjoy The Simpsons for its gags more than for its characterisation and pathos, but when all three are firing at once, this show is a wonder to behold and hits the spot so absolutely that you’re left with a smile on your face even long after the credits have rolled.

Homer: "Sweet merciful crap! My car!"

Homer: "Hmm someones travelling light"
Lisa: "Maybe you're getting stronger"
Homer: "Well I have been eating more"

Extra note: I fully expected to include Homer Vs. Australia on this list, but somehow I forgot, which is a bootable offense down here.