30 Greatest The Simpsons Episodes Ever, Ranked
Anyone who had access to a TV in the 1990s surely has 10 or more years' worth of Simpsons quotes, characters and episodes burned into their brain like a screensaver.
You may not be able to quote much from the last 10-15 years—nothing could sustain that level of greatness forever—but we can still remember just how incredible The Simpsons has been during its nearly three-decade run.
Picking the very best episodes ever is a task that even McBain would struggle with, but we've tried it anyway. If you only ever watch 30 episodes of The Simpsons ever again, and need to choose an order in which to do so, make them these. And in this order. (So you'll effectively save the best for last.)
30| Bart on the Road (season 7)
A great road-trip episode in which Bart makes his own driver's license, takes out a rental car and has an adventure with Milhouse, Martin and Nelson to Tennessee. After watching Andy Williams in concert, visiting a wig shop and missing the 1982 World's Fair by 14 years, they end up signing up as couriers and go to Hong Kong. Wow, that escalated quickly.
Angry Dad in neighboring car: "If you kids don't keep your hands to yourself, I'm going to turn this car around and there will be no Cape Canaveral for anyone! [Nelson slaps the dad's head through the window from Bart's car] Angry Dad: "That's it, back to Winnipeg!"
29| Stark Raving Dad (season 3)
Just three seasons in and The Simpsons was already big enough to feature Michael Jackson. But instead of the lazy celebrity cameo that we're more used to these days, he played an overweight white dude who Homer meets in a mental hospital after he's sent there for wearing a pink shirt to work. 'Leon''s song for Lisa's birthday from Bart is still a cute and heartwarming moment.
Marge: "Doctor, if you just talk to him for five minutes without mentioning our son Bart, you'd see how sane he is."
Doctor: "You mean there really is a Bart? Good lord!"
28| Bart After Dark (season 8)
Marge and Lisa leave Homer and Bart on their own, and within a few minutes Bart ends up working at a burlesque club. It doesn't take long for moral outrage to take over the town (despite most of the gents visiting regularly), but everything is fine and well once again after a classic Simpsons musical number, which even won an Emmy.
Grandpa Simpson's seamless entrance and departure at the burlesque club once he sees Bart behind the desk:
27| I Love Lisa (season 4)
This was the moment everyone fell in love with Ralph Wiggum. Well, everyone apart from Lisa, who gives him a Valentine's Day card out of pity. He soon becomes besotted and won't leave her alone. It's not long before she breaks his heart, but he channels his feelings into a performance as George Washington at the President's Day pageant. We still choo-choo-choose you, Ralph!
Ralph: "The doctor said I wouldn't have any nosebleeds if I kept my finger outta there!"
26| Deep Space Homer (season 5)
If a real person achieved as much as Homer has over the years, he'd be the President of the World. One such example: going into space. A silly but brilliant episode in which NASA worries about the decline in public interest and selects a regular joe to send into space. Homer is chosen, naturally. And of course this can only mean one thing: utter destruction.
Kent Brockman: "Ladies and gentlemen, uh, we've just lost the picture, but what we've seen speaks for itself. The Corvair spacecraft has apparently been taken over, 'conquered' if you will, by a master race of giant space ants. It's difficult to tell from this vantage point whether they will consume the captive Earthmen or merely enslave them. But, one thing is for certain: there is no stopping them; the ants will soon be here. And I, for one, welcome our new insect overlords. I'd like to remind them as a trusted TV personality, I can be helpful in rounding up others to toil in their underground sugar caves."
25| Itchy and Scratchy Land (season 6)
There's no such thing as a relaxing Simpson family vacation. And the most epic of these has to be their trip to Itchy and Scratchy Land, full of stink bombs, arrests and robots going rogue and attacking the entire park. The tagline 'the violentest place on Earth' was pretty accurate.
Park Announcer: "Attention, Marge Simpson. Your son has been arrested."
Woman: "I'd be terribly embarrassed if I was that boy's mother."
Park Announcer: "Attention, Marge Simpson. We've also arrested your older, balder, fatter son."
24| Great School Confidential (season 8)
A rather sweet episode in which Bart acts as a reluctant gofer so that Principal Skinner and Edna Krabappel can continue a secret affair. Of course, as it's Springfield, this doesn't go to plan and soon the whole town knows about it and they almost lose their jobs – until Skinner admits that he's a virgin and they kinda... let it slide. Bart may think they've broken up, but they still have their closet...
Bart: "I guess we could go to Martin's party."
Milhouse: "I don't know. If we're seen there, it will definitely take our social standing down a notch."
Bart: "We're what now, 3?"
Milhouse: "3 and a half. We get beat up, but we get an explanation."
23| Mother Simpson (season 7)
We finally meet Homer's political-activist mother in this episode, but only after he fakes his own death to get out of work for a day. After she arrives at his "grave", she makes up for lost time with his family before having to out on the run again – creating one of the most genuinely heartbreaking moments as he waves off his mum for what might be the last time.
Homer sitting quietly on his car watching shooting stars after his mother left as the credits rolled.
22| Homer's Phobia (season 8)
This Emmy-winning episode was the show's first to revolve entirely around gay themes, and was a big step towards mainstream TV promoting an anti-homophobia message. (So controversial was it for the time, the Fox network nearly pulled it before broadcast.) Homer is at first wary of new family friend John (voiced by cult director John Waters) after finding out he's gay, worried that he'll have a negative influence on Bart. All is well in the end as Homer realizes the error of his ways (though Bart has no idea of his dad's concerns until the very end).
Bart and Homer accidentally finding themselves in a steelmill-turned-gay-disco.
21| Bart of Darkness (season 6)
One of the best parodies of Rear Window ever made, this episode saw Bart stuck with his leg in a cast, before becoming convinced that Ned Flanders had murdered his wife Maude. In the end, it's merely Ned's plant who "died". Meanwhile, it's Lisa vs Martin in the battle of the pool parties.
Lisa: "Shut up, brain! I've got friends now. I don't need you anymore."
20| King Size Homer (season 7)
After finding out that he can work from home if he's classed as disabled, Homer gains 61 pounds on purpose. Despite this, he's still useless and even uses a drinking-bird toy to press the Y key to say "yes" on the keyboard, whatever the instruction. Of course, this means disaster until Homer (for once) saves the day by getting stuck in the plant's gas store. Homer at his Homeriest.
Automated voice: "The fingers you have used to dial are too fat. To obtain a special dialling wand, please mash the keypad with your palm ... now."
19| 22 Short Films About Springfield (season 7)
Inspired by Pulp Fiction, Short Cuts and the like, this one-off shows us more about the lives of other Springfield folk (although there are in fact only 19 scenes). Highlights include Smithers getting stung by a bee, the police boys discussing Krusty Burger, Lisa getting gum stuck in her hair, an extremely tall man mocking Nelson, and of course...
The entirety of this scene with Skinner and Superintendent Chalmers:
18| Homer Badman (season 6)
Homer may be a lazy and selfish buffoon, but he's not a sleazebag. Most of the time. Here, he innocently rips a yummy sweet off the bottom of his babysitter, only for her to assume he was trying to touch her up. After dealing with an angry mob and a stitch-up appearance on Rock Bottom with God...frey Jones, it's down to Groundskeeper Willie to save his bacon (thanks to Willie's peeping-tom hobby).
Homer gets beaten up by a man on a Penny Farthing after mocking them on TV ("So, you don't like the old-time bikes, ah?").
17| Flaming Moe's (season 3)
One of the early classics, where Moe betrays his old friend Homer by stealing his recipe of alcohol mixed with cough syrup. In no time, Moe's Tavern has become a Cheers-style hangout for celebrities (including Aerosmith, no less) and Homer is banished for good. A traditionally heartbreaking end sees Homer ruin everything just as Moe was about to sign over half of the profits to him. D'oh!
Professor Frink: "All right, according to the gas chromatograph, the secret ingredient is... love?! Who's been screwing with this thing?"
16| Radioactive Man (season 7)
Bart's favorite superhero gets his own film, and lo and behold... it's being filmed in Springfield AND it's starring McBain's Rainier Wolfcastle! Sadly for him, Milhouse gets the part of his sidekick Fallout Boy, but his friend hates acting. It's not long before the production is bankrupt and they head back to Hollywood forever. Not only does it satirize Hollywood in general, but it's a lovely little look into Bart and Milhouse's friendship.
"My eyes! The goggles do nothing!"
15| The Springfield Files (season 8)
Featuring not only Leonard Nimoy, but also David Duchovny AND Gillian Anderson at the height of The X-Files' popularity, this spooky episode saw Homer come face to face with an alien (so he thought, he was pretty drunk). After convincing the entire town, it turns out to just be Mr Burns having undergone longevity treatment in order to "cheat death". Even Chewbacca was in town to celebrate the "alien" call for peace and love.
Leonard Nimoy: "Hello. I'm Leonard Nimoy. The following tale of alien encounters is true. And by true, I mean false. It's all lies. But they're entertaining lies. And in the end, isn't that the real truth? The answer is: No."
14| Lisa the Vegetarian (season 7)
After bonding with a lamb at a petting zoo, Lisa decides to become a vegetarian, much to the horror of her meat-loving dad. What follows is a battle of words between the two Simpsons, which peaks when she ruins his BBQ by sending his prize pig airborne. But thanks to Paul and Linda McCartney (who only agreed to appear if Lisa would remain a vegetarian forever), she learns to accept other people's beliefs and reconciles with Homer via a "veggie back" ride home.
The Simpson family: "You don't win friends with salad! You don't win friends with salad! You don't win friends with salad!"
13| One Fish, Two Fish, Blowfish, Blue Fish (season 2)
Another one of The Simpsons' heartfelt episodes: Homer is told he has 22 hours to live after eating a poisonous fish. In his last day on Earth, he has a man-to-man with Bart, listens to Lisa play her sax, makes a video for Maggie, tells off Mr Burns, has one last drink at Moe's and reconciles with his dad. We remember being genuinely worried that he was going to die when Marge found him the next morning, but of course everything was fine in the end. Not that he actually continued to live life to its fullest after that.
Homer: "Goodbye, Maggie. Stay as sweet as you are. Goodbye, Lisa. I know you'll make me proud. Goodbye, Bart. I like your sheets."
12| Homer's Enemy (season 8)
Probably the darkest ever Simpsons episode. The power plant's latest employee, Frank Grimes, becomes increasingly angry with an oblivious Homer for his lazy behavior yet comfortable existence. Soon after declaring himself Homer's enemy, he is electrocuted to death while temporarily going insane and mocking Homer. Even then, Homer falls asleep at his funeral. It might not be the last we see of Grimey, though...
Grimes: "I'm saying you're what's wrong with America, Simpson. You coast through life, you do as little as possible and you leach from decent hardworking people like me. Ha! If you lived in any other country in the world you would have starved to death long ago."
Bart: "He's got you there, dad."
11| Mr Plow (season 4)
Admit it, you can sing the entire "Mr Plow" jingle, can't you? This episode painted Barney as the villain for once, as he quickly put Homer out of business after stealing his idea for plowing people's driveways. After a fierce back-and-forth, things quickly go back to normal, but Homer will always have that "special" Mr Plow jacket for Marge.
Homer: "Now, we play the waiting game. Ahh, the waiting game sucks. Let's play Hungry Hungry Hippos!"
10| Marge vs The Monorail (season 4)
Another episode featuring Leonard Nimoy, and it's another winner. After Mr Burns is forced to pay the town $3 million (despite his attempts to fool them as Mr Snrub), Springfield impulsively buys a faulty monorail, following a legit-sounding song-and-dance by conman Lyle Lanley. Just as it looked like the town was doomed once more, it's up to Homer and Bart (and a donut shop) to save the day.
Marge: "Homer, there's a man here who thinks he can help you.
Marge: "No, he's a scientist."
Homer: "Batman's a scientist?"
Marge: "It's NOT Batman."
9| Homer at the Bat (season 3)
We might not know much about baseball in the UK, but we sure know who Roger Clemens, Wade Boggs, Ken Griffey Jr, Steve Sax, Ozzie Smith, José Canseco, Don Mattingly, Darryl Strawberry and Mike Scioscia are thanks to this episode. Mr Burns hires a load of ringers from the actual major leagues to play for his plant's team, much to Homer's upset. In the end, all the players suffer various horrific ordeals, allowing Homer to become the hero (thanks to being knocked unconscious).
Bart and Lisa trying to distract Strawberry: "Darryylll, Darryyll"
8| Cape Feare (season 5)
Out of all the Sideshow Bob-trying-murder-Bart episodes, this is the ultimate. The Simpsons are put into Witness Protection as the Thompsons (although Homer couldn't quite understand the change), but Bob still finds them—and is only thwarted thanks to an overzealous performance of HMS Pinafore.
The rakes, always the rakes. The perfect example of a joke going way beyond the point where you think it will be funny, only to get funnier.
7| Last Exit to Springfield (season 4)
So many classic moments in this episode, and it even has a bit of a political message, too. Mr Burns takes away his workers' union's dental plan in exchange for a keg of beer at their meetings. But when Homer discovers he'll need to pay for Lisa's braces, he accidentally takes a stand and becomes union leader. It's one of the best Mr Burns-led episodes, especially when he gets annoyed with his monkeys writing dodgy Shakespeare knock-offs.
The whole "Dental plan! Lisa needs braces!" segment going on in Homer's head.
6| Who Shot Mr Burns? Parts 1 & 2 (season 6 & 7)
Up there with 'Who Shot JR?' and 'Who Shot Phil Mitchell?'. Mr Burns pisses everyone off in town, especially when he launches a sun-blocking device in the town, forcing people to use electricity powered by his plant. Everyone's a suspect from Moe to Smithers to Homer, but we never expected Maggie of all people to have done the deed.
After Homer tries to tell Mr Burns what his name is by spray-painting 'My name is Homer Simpson' in massive letters on his wall, Mr Burns: "Who the devil are you?"
5| Lisa the Iconoclast (season 7)
We finally find out the truth about Springfield's supposed founder Jebediah Springfield, after Lisa finds a confession that he was actually a killer pirate named Hans Sprungfeld. As Lisa is about to spread the word to everyone, she realizes that Jebediah's history is too important to the town, and keeps it to herself. The episode also features a classic appearance by Donald Sutherland as the town's historian, and Homer briefly becomes Town Cryer.
Hollis Hurlbut: "Now get out. You're banned from this historical society. You and your children, and your children's children... for three months."
4| Lisa's Wedding (season 6)
Not all flashforward or fantasy episodes are all that classic, but this one still makes us cry a little. Lisa visits a fortune teller who shows her a vision of her future. She's getting married to a posh British dude (played by Mandy Patinkin of all people), who doesn't quite get Homer and the rest. Back in the real world, she embraces her dad and vows to never take her family for granted.
Homer and Lisa walking off hand in hand after Lisa's vision ends. Still gives us goosebumps.
3| You Only Move Twice (season 8)
They had to do a Bond-inspired episode at some point. Here, Homer befriends Hank Scorpio, and he clearly has no idea that he's an obvious Bond villain. Despite being a baddie, Hank genuinely likes Homer and gives him and his family a cushy life. But in the end, the Simpsons realize they don't quite belong in Cypress Creek. A truly epic episode, a lot of which was ad-libbed by guest star Albert Brooks.
Hank Scorpio: "By the way, Homer, what's your least favorite country? Italy or France?"
Homer: "France." [Scorpio adjusts a giant laser cannon pointing towards the sky]
Hank Scorpio: "Heh heh heh. Nobody ever says Italy..."
2| Homer the Heretic (season 4)
Homer incurs the wrath of Marge (and God), when he decides to skip church and have a ruddy good time being lazy at home on a Sunday while everyone else freezes while listening to Reverend Lovejoy drone on. In time, he starts his own religion but soon decides against his newfound world after accidentally burning the house down, and seeing his fellow Springfieldians helping him out. He returns to church, albeit snoring his way through it. A tad preachy, but a perfect example of what Homer is all about.
Reverend Lovejoy: "Homer, I'd like you to remember Matthew 7:26 – 'The foolish man who built his house upon the sand.'
Homer: And do you remember... Matthew... 21:17?"
Reverend Lovejoy: "And he left them and went out of the city, into Bethany, and he lodged there?"
Homer: "Yeah. Think about it."
1| Homer the Great (season 6)
A downright classic episode of any TV genre. Homer discovers that pretty much every bloke in Springfield apart from him is part of a secret society known as the Stonecutters, led by a man named Number One (Patrick Stewart). Homer being Homer, he is soon kicked out after unwittingly destroying their Hallowed Sacred Parchment. But, his birthmark shaped like their emblem causes them to believe he is their "Chosen One"—only for him to abuse his power and get kicked out once and for all. So the question remains... are the Stonecutters still going?
Plumber to Homer, not realizing he's a Stonecutter: "Yeah, I probably won't be able to get the parts I need for two, three weeks and that's if I order them today—which I won't."
This story originally appeared on Esquire.co.uk.
* Minor edits have been made by the Esquiremag.ph editors.