The Simpsons’ Top 30 Episodes

Rest assured, the '90s were the greatest time to be in Springfield


    Thirty years ago today, America’s favorite animated family made their debut on Fox. To celebrate, Consequence of Sound is re-broadcasting live from Springfield by revisiting their picks for the top episodes of The Simpsons, a feature which originally ran in 2017. Sounds simple? Oh, if only.

    Hi, I’m Blake Goble. You might remember me from other Consequence of Sound mega-posts such as “A Burns for All Seasons at 20: Cinema’s Citizen Lame?” and “Radiohead: I hate every Kid I see from Kid A to Kid Z.” Today, I have the pleasure of introducing you to one of Consequence of Sound’s latest and greatest efforts in ad-slathered pop culture: a perfectly cromulent ranking of the 30 best episodes of The Simpsons! But where to begin?

    Don’t panic, dear readers! This isn’t a Crisitunity. Sure, The Simpsons’ legacy is massive. There are about a million quotes, anecdotes, personal histories, and so on that could open this piece. We could marvel at the lucky history of Matt Groening hastily pitching The Simpsons as a series of sketches for FOX. We could thank Tracey Ullman for getting TV’s first family on the air. The writers. The voices. The characters. The bootleg t-shirts and universe of product placements. We could talk about this show’s eternal life on TV, the billions it’s made Rupert Murdoch, or how the show has become damn hard to follow since the 14th … well, 12th season.


    But for the sake of expediency, we’re simply here to celebrate Homer, Marge, Bart, Lisa, and Maggie’s 30 years of hilarity and share the best episodes of The Simpsons. Our panel of Simpsons experts (all graduates of Bovine University) have assembled the very finest in Simpsonia. No Frinkiac needed. The best Simpsons episodes were usually the product of unusual ideas, insanely specific humor, and the realization that animation has no limits in terms of the jokes and stories that can be told. Three-eyed fish and monorails, anyone? Oh, and don’t forget an arsenal of Harvard grads writing by committee.

    And don’t be alarmed if the episodes mostly come from the first 10 seasons, aka The Golden Age of The Simpsons. Who in the hell has been watching this show over the past 10 years, anyway, beside Al Jean? (Even Matt Groening has been caught off guard by the fact that his creation is a Guinness record holder.)

    Anyway, The Simpsons have come a long way since a John Ford lookalike turned crude sketches into comic gold to allegedly pay off gambling debts. Who knows what adventures they’ll have between now and the point at which the show becomes unprofitable. And judging by Fox’s constant renewals and that Don Hertzfeldt couch gag, The Simpsons may just last beyond all known life and humanity. Again, I’m Blake Goble, and I’ll leave you with what we all came here to see: hardcore nudity!

    –Blake Goble
    Senior Writer


    30. Burns Verkaufen der Kraftwerk

    Season Three, Episode 11

    Premiere Date: December 5, 1991

    Writers’ Room: Talk about writing by committee. To start, Jon Vitti scribed “Burns Verkaufen der Kraftwerk” with a pitch about the nuclear power plant being bought out by the Japanese. Vitti laid the groundwork, but it seems like everyone pitched in. According to Al Jean on the commentary, the Japanese were dropped for fear of being cliché, and swapped with Germans during the writing process. Phil Hartman knew German, and assisted with dialogue. Sam Simon lobbed the amazing idea of “Homer and the Land of Chocolate.” And according to Mike Reiss, again on the commentary, the writers all had to band together come up with just one suitable Moe’s Tavern phone prank. What went to air was a thematically dense and joke-rich episode.

    Essential Quote: Ever feel like the universe is working against you? “Attention workers, we have completed our evaluation of the plant. We regret to announce the following lay-offs, which I will read in alphabetical order:” Pause. “Simpson, Homer.” Pause. “That is all.”

    D’oh! Moment: Poor Homer is the subject of job evaluations by the Germans. They’re huge on safety, and well, Homer’s never been strict with all that. “Hey, Homer. Aren’t you the safety inspector?” “D’oh.”


    Best Visual Gag: The “Land of Chocolate” daydream fantasy is so classically Homer. The chocolate rain drops. That poor little Poochie that Homer rips a bite out of. And the whimsical fantasy music feels straight out of Wonka. And the best part of the long-form gag is that it’s built off Homer’s fear of getting canned from the power plant, which gives the gag a streak of nervous reality – who wouldn’t want to escape somewhere safe when the fear of the everyday is breathing down your neck? They have gum drop streets and cane sugar lamp posts there!

    Willkommen zu Springfield: Guten tag, Herr Fritz und Hans und Horst! Ja, aber… Apologies, this is a predominantly English publication is it not? Hans, Fritz, and Horst, the German consortium representatives, were created for the episode. Also, the white-haired Horst was played by the late, great Phil Hartman with a jolly German accent. And in a bit of TV dweeb inside referencing, Horst’s look was modeled after Sgt. Schultz from Hogan’s Heroes. Man, these writers loved Hogan’s Heroes!

    Episode as a GIF:

    Analysis: “Burns Verkaufen der Kraftwerk” (which poorly translates to “Burns Sells the Power Plant”) is an episode that operates on a ton of levels. We get some real, in-depth characterization from Monty Burns, and his late-life existentialism. Sell the plant? Life his life? Burns longs for something more, or at least the chance to be and do more — even if it is a short-lived jaunt. But it’s a shade deeper than his usual comic book villainy. And Homer’s lay off produces rich comedy and drama for the Simpsons family. They struggle with being poor. Home haircuts, carrot-stuff cat food, and balls of soap made from little slivers – the Simpsons family’s struggle was downright Chaplinesque. And finally, the German humor, meine güte! Vitti and the writing staff came up with playful, non-offensive jokes that would become a casually defined interest of the series (Hello, Uter!). The consortium’s manners, strictness, and enablement for strolls down Chocolate Lane provide ample, memorable humor. And we’re still trying to figure out where that damn chocolate town is!

    –Blake Goble

    29. Homer’s Triple Bypass

    Season Four, Episode 11


    Premiere Date: December 17, 1992

    Writers’ Room: Nobody in The Simpsons writing room wanted an episode about Homer having a heart attack. The material was too serious, the consequences too grave. But the episode was the brainchild of producer James L. Brooks, who believed enough in the idea to make it a reality. Perhaps because the staff didn’t quite know how to approach the episode, it was instead farmed out to freelancers Gary Apple and Michael Carrington, with Brooks himself helping create the pivotal scene where Bart and Lisa visit Homer pre-surgery.

    Essential Quote: “Well, if it isn’t my old friend Mr. McGregg, with a leg for an arm and an arm for a leg!” –Dr. Nick Riviera

    D’oh! Moment: Homer briefly dies in Mr. Burns’ office, his soul leaving his body. The only thing that brings it back is the revelation that Mr. Burns will be sending Marge a ham. Once Mr. Burns realizes Homer’s alive, however, he cancels the ham. Cue: “D’oh!”


    Best Visual Gag: In the episode’s funniest bit, Homer tailgates and then violently rams into a house on wheels driven by Hans Moleman. Homer’s aggression is funny enough on its own, but the joke’s brilliance is revealed by a sign that distinguishes the house as the “birthplace of Edgar Allan Poe.” Homer runs it off the road and, in true Simpsons fashion, it bursts into flames the moment it veers off-track.

    Welcome to Springfield: While this wasn’t the first appearance of cheapskate M.D. Nick Riviera, it was absolutely his first chance to shine. The episode contains some of his best lines — “The coroner? I’m so sick of that guy!”; “These gloves came free with my toilet brush!”; and, of course, his concerned “What the hell is that?” right as Homer passes out — and offers perhaps the only sympathetic glimpse of the crackpot.

    Episode as a GIF: “Woo! Look at that blubber fly!”

    Analysis: Heart attacks aren’t funny. The staff was right to be wary of Brooks’ idea. But The Simpsons has dealt with inherently tragic content before; just look at its pilot, which finds Homer blowing all of his money at the racetrack right before Christmas. In many ways, “Homer’s Triple Bypass” compensates for its heaviness by taking both its touchstones — humor and heart — and cranking them up to 11. The humor is both zanier and nastier than usual — he runs Hans Moleman off the road — while the moments of sentimentality are elevated that much more. We see Homer pray and potentially say goodbye forever to his family, while the surgery itself is given the stakes such an event deserves. Sure, it’s not like the show was ever going to kill off Homer, but damned if the show didn’t go to every length to make us think they would. It also still resonates today. “Don’t worry, Marge,” Homer says. “America’s healthcare system is second only to Japan. Canada, Sweden, Great Britain … well, all of Europe.” Oof.

    –Randall Colburn

    28. The Springfield Files

    Season Eight, Episode 10


    Premiere Date: January 12, 1997

    Writers’ Room: Producers Al Jean and Mike Reiss, who returned to the series for a short window despite being under contract with The Walt Disney Company, originally conceived of the crossover idea five years earlier at a writers’ retreat when they were showrunners during seasons three and four. Jean had seen The X-Files on the cover of a TV Guide and thought it might be nice to throw a bone to the then-budding series. Half a decade later, Chris Carter’s game-changing sci-fi series had long been a ratings juggernaut for the network, so it was essentially a no-brainer to finally bring Mulder and Scully to Springfield. In fact, Carter thought it was an “honor” to be parodied by The Simpsons.

    Essential Quote: The FBI aren’t the only ones with the goods in this episode; Springfield’s own Chief Wiggum gets in on the action with some lucrative sarcasm as he listens to Homer’s “alien encounter” and tells him, “Your story is very compelling, Mr. Jackass, um, Simpson. Let me just type it up on my invisible typewriter.” That line’s been a go-to for this writer ever since.

    D’oh! Moment: There are two for Homer on this go-around. The first arrives when he scares away the “alien” by stumbling into campfire, and the second pops up when he discovers a nearby vendor selling “Homer Was Right” shirts actually sold out of his supply of “Homer Is a Dope” shirts. Writer Reid Harrison triples down on the joke by revealing that Marge bought one, to which she goes to great lengths explaining its quality, all of which prompts Homer to buy one himself.


    Best Visual Gag: Blame it on the behind-the-scenes excitement over the episode’s blockbuster crossover — you have to remember, The X-Files was at its peak popularity around this time (especially for sci-fi geeks) — but “The Springfield Files” goes H.A.M. on the pop cultural references and most of them are hilarious visual gags. A few of them aren’t very subtle (see: Milhouse pouring 40 coins into an arcade game adaptation of Kevin Costner’s box office mega-flop Waterworld), while others require a sharper eye (Lisa’s reading an issue of Junior Skeptic, undoubtedly a nod to Mulder’s saner half, Special Agent Dana Scully). But really, none of them hold a candle to the ridiculous, speedo-wearing photo that Mulder has in his wallet, which is actually a deep, deep reference to a scene from The X-Files’ iconic season two gem, “Duane Barry”.

    Welcome to Springfield: Given that Homer’s strange encounter sparks interest from everyone in town, “The Springfield Files” features a healthy spread of fringe characters that only come out from time to time. (In some respects, the first 10 minutes feels as if we’re watching a redux of the “22 Short Films About Springfield” as we follow everyone’s average Friday night around town.) However, this episode marks the first and only time that David Duchovny and Gillian Anderson would slum it with Homer, and the two have a ball poking fun at their respective characters, especially when Mulder brushes off Scully’s report of “drugs and illegal weapons coming into New Jersey,” scoffing: “I hardly think the FBI is concerned with matters like that.”

    Let’s also not forget about the return of Leonard Nimoy, who plays himself in the episode’s glorious Plan 9-spoofing bookends:


    Episode as a GIF:

    Analysis: “The Springfield Files” is a pleasant reminder of how a crossover of this magnitude was once the type of Event TV that The Simpsons could parody with aplomb — you know, before they actually succumbed to the medium on a weekly basis. From beginning to end, the episode never removes its tongue from its cheek, radiating with a brand of self-awareness that’s brighter than Mr. Burns’ green, nuclear hue. Sure, it’s not without a glut of dated pop-culture references — though, to be honest, we still chuckle at the nods to Speed and those swampy Bud-weis-er! commercials — but most of the cherry-picked homages are to artifacts that remain just as (if not, even more) popular today. Narratively speaking, the episode’s a little cluttered and wonky — the bonding between Bart and Homer, for instance, does seem shoehorned in — but it’s irreverent chaos done well. At this point, both series were oozing with untouchable confidence, and while “The Springfield Files” was certainly a victory lap for Fox, the episode never once stops sprinting, packing in one essential gag after the other, which is why we also get genius shit like this…

    –Michael Roffman

    27. Homer the Vigilante

    Season Five, Episode 11

    Premiere Date: January 6, 1994

    Writers’ Room: Written by Jim Swartzwelder, the script is notable for how signature it is to his style. He loves slapstick, physical jokes, and the script displays them proudly via Chief Wiggum rubbing himself with a cloth that his scent dog is supposed to trace, Homer sleepwalking and being fed sausages as a distraction in the same manner as Santa’s Little Helper, or the home that sprouts legs to run away from its burglar. Swartzwelder would go on to have one of the most impressive resumes of any of The Simpsons’ writers.

    Essential Quote: “Thank you for coming, I’ll see you in hell!” –Apu and “Now I don’t believe in nothing no more. I’m going to law school!” –Jimbo


    D’oh! Moment: Early in the episode, Homer’s family informs him that they’ve been robbed. He lets out a “woo-hoo” when Lisa says her saxophone has been stolen, but “D’oh!”s at Bart’s revelation that they also lost their portable TV.

    Welcome to Springfield: Though Malloy wouldn’t recur on The Simpsons, Sam Neill’s turn as the elderly cat burglar is a classic guest turn. Malloy serves as an example of how the elderly should not be discounted, with Neill’s silky British accent folding completely into his character.

    Visual Gag: When Malloy breaks into the Simpson house, he goes to pick the lock, only to see Homer’s keys (with a keychain reading “Homer”) already sitting in the lock.


    Episode as a GIF:

    Analysis: “Homer the Vigilante” has a heart and moral, with Homer’s father, Abe, dismissed throughout the episode, only to help catch the cat burglar, who also happens to be a senior citizen. And that bigger message helps to make the joke barrage all the more effective. Because elsewhere, things are much less linear. We see cuts to Chief Wiggum’s incompetence, Kent Brockman’s fear mongering, Professor Frink’s ineptitude, and, most importantly, the town forming a vigilante mob. The jokes are big and frequent — Lisa with the jug! The guns going off at the Simpson’s house! Homer busting the kids for drinking and ending up getting wasted with them! — while allowing the focus to be looser and less plot-driven. In fact, episodes like “Homer the Vigilante” are largely the inspiration for shows like Family Guy that would come later.

    –Philip Cosores

    26. Raging Abe Simpson and His Grumbling Grandson…

    Season Seven, Episode 22

    Premiere Date: April 28, 1996

    Writers’ Room: “Raging Abe Simpson and His Grumbling Grandson in ‘The Curse of the Flying Hellfish'” came about when writer Jonathan Collier kept reading story after story about lost paintings popping up after so many years gone. Given its WWII saving of European art, it has a charm akin to the true story of the later book/movie The Monuments Men. The tontine angle, however, came from an old Barney Miller episode, courtesy of showrunner Bill Oakley. The episode also established a wartime history between Grampa Simpson and Mr. Burns, alongside the fathers of several notable Springfieldians.

    Essential Quote: The Simpson men have a hilarious habit of revealing how serving themselves is a close second to caring for others. They’re each keenly focused on their current pursuit and yet so very easily distracted. So after saving Bart from a watery grave, which allows the treacherous Mr. Burns to escape, Grampa of course reassures his grandson with, “Oh, the fortune doesn’t matter, boy; the important thing is you’re safe. Now let’s get that fortune!”


    Best Visual Gag: In the rainy cemetery, Mr. Burns asks: “Oh, Simpson, can’t you go five seconds without humiliating yourself?” Right on cue, Grampa Simpson’s suspenders instantly pop off with a cartoonish sound, and his pants fall down to reveal polka-dotted underwear. After a moment of mournful evaluation, Simpson asks: “How long was that?” Even without the punchline, that instant failure of clothing gets you in the gut.

    D’oh! Moment(s): The best exclamation of “D’oh” comes from Assassin Fernando Vidal after he fails to kill Grampa in the retirement home. The only reason Grampa even lives — by dodging a thrown dagger, no less — is because he grows highly suspicious about his family supposedly coming to visit him. He’s right on the money, as it’s really Mr. Burns dressed as Marge, Smithers dressed as Bart, and a frustrated Vidal ripping off his Homer costume and dropping a Latin-flavored version of Homer’s catchphrase.

    Meanwhile, the “D’oh” most true to its nature comes from Abe and Bart in unison, when the cemetery light reveals the secret spot of the Flying Hellfish treasure. It starts with a slow pan over the nearby tombstones and then quickly zooms over to a deep body of water.


    Welcome to Springfield: The episode introduces “the world’s most devious assassin,” Fernando Vidal, who Mr. Burns hires to kill Grampa. It’s a misleading title, though, since he fails to even remotely harm his target. In his final attempt, Vidal informs his client: “There is one more way to kill a man, but it is as intricate and precise as a well-played game of chess.” Then he kicks open the door of the retirement home blasting a machine gun. Guy knows how to (almost) deliver.

    Episode as a GIF: Abe’s so badass in this episode…

    Analysis: Like many of the town’s seniors, Grampa Simpson is a playful combination of fully embraced, absent-minded crotchetiness and an unusually high spirit. But he wasn’t always like that. As this episode properly freshens your memory, Abe Simpson was tough as nails in his youth, and he operated with a rather black-and-white moral code. The episode also establishes a strained relationship between Grampa and Bart and resolves the distance between them in the best way the show does, with a debonair plot that’s almost too wild, yet makes so much damn sense by staying true to the characters involved. For added value, there’s a welcome backstory, context, and overall strength to a character who often serves the purpose of an easy laugh. It’s as epic as it is personal, reminding you to never assume that a Simpsons character only has one side. –Jake Kilroy

    25. Bart Gets Famous

    Season Five, Episode 12

    Premiere Date: February 3, 1994

    Writers’ Room: It’s (almost) always fun when The Simpsons goes meta, and “Bart Gets Famous” is no exception. Episode writer John Swartzwelder and the rest of the writers’ room had a bone to pick here. They wanted to show how stupid catchphrases can be and how easily we, as a culture, reward cheap and easy laughs. They underlined how fleeting such fame can be, how little reward it brings, and despite Marge’s assertion that Bart “was making people happy,” that such fame comes at a cost. We swear to god it’s a funny episode.


    Essential Quote: “A powerful tidal wave in Kuala Lumpur has killed 120 people. [changes voice] Ay, chihuahua! Whoa, whoa, whoa!” –Bumblebee Man

    D’oh! Moment: This is the D’oh-est of the “D’oh!”s. After breaking a lamp in the family room, Homer’s standard reply begets a string of Simpsons catchphrases, one that ends only when the assembled characters turn to Lisa, who glowers and says, “If anyone wants me, I’ll be in my room.”

    Best Visual Gag: Let’s go with Bart’s Kriss Kross-inspired album cover…

    Welcome to Springfield: Martha Quimby, the First Lady of Springfield. Her Jackie O. drag is deeply messed up. Also, Conan O’Brien as himself.


    Episode as a GIF:

    Analysis: For such an enjoyable episode, “Bart Gets Famous” sure does get depressing. For Bart, there’s monotony pre-Krusty — they take a field trip to the box factory, again — followed by the monotony of show business, followed by the monotony of fame, then back to the monotony of everyday life. No one’s interested in Bart’s attempts to prove he’s more than a catchphrase, but nor does anyone appreciate Lisa’s refusal to have one. No matter what happens, life’s a drag. Fame just puts a fancier face on it.

    That said, the very existence and longevity of The Simpsons decries this. Bart has gone through a number of catchphrases, had many shorts eaten, and seen many cows had, and yet he’s still there. That’s the point, of course — The Simpsons has always had more substance. “The I Didn’t Do It Boy” may be a hollow shell, but Bart Simpson and company contain multitudes, and that’s why they’re still around. Ay caramba, indeed.

    –Allison Shoemaker

    24. Cape Feare

    Season Five, Episode Two

    Premiere Date: October 7th, 1993

    Writers’ Room: When Wally Wolodarsky caught Scorsese’s remake of Cape Fear in 1991, the writer pitched it as a Bob vehicle and a Max Cady parody, and Jon Vitti would later write the final script. Drawing from the source novel, The Executioners, while also spoofing both Cape Fear films, the episode developed into a calling card for the crazed, revenge-hungry Bob Terwilliger.


    Essential Quote: “No one who speaks German can be an evil man.” And that’s the second knock on Germans in the episode! After Up Late with McBain, with your announcer, Obergruppenfuehrer Wolfcastle!

    D’oh! Moment: It would appear no one said “D’oh” in this episode, but the next best thing was Homer freaking out when he realizes “Ice Cream Ville” is “Screamville.”

    Best Visual Gag: Fudge. The Knox Fair cigar? The “WIDE LOAD” tattoo on Homer’s butt? “Hannibal Crossing the Alps” word by word on trampling elephants? All delirious, but come on. You know it’s the rakes. How does one go about typing the sound Bob makes when thwacked by rakes? And the joke was the product of stretching the episode to pad out time. It’s the classic rule of running a joke long enough that it becomes so unfunny that it becomes even funnier if protracted long enough.


    Welcome to Springfield: It’s worth mentioning the FBI Men just to shout out the great, failed Witness Protection Program interview. “Now, when I say, ”Hello, Mr. Thompson” and press down on your foot, you smile and nod.”

    Episode as a GIF: The episode’s like an adult thriller made by the Looney Tunes…

    Analysis: The three greatest strengths of “Cape Feare” are 01.) Kelsey Grammer, 02.) the level of perfection on display with its parody, and 03.) that rake gag. The cautionary tale of a sick and twisted Southern stalker is perhaps the furthest thing from comedy, but in the land of the spoof, The Simpsons proved it was king. Every grim story beat from the Marty movie gets filtered through countless gags and non-sequiturs, and in the end, “Cape Feare” makes the movie look preposterous if you revisit it. Also, the legend goes something like the staff of The Simpsons loved, loved, loved having Kelsey Grammer come on the show as Bob. Writers on DVD commentaries boast that he’d come up with great stuff, was a chummy presence, and was always a pleasure to work with. Plus, that menacing baritone. When the opportunity for a Bob episode came by way of Max Cady, the idea was perfect. Oh. And that famous, truncated rake gag. Anyone else imagine that going on forever and Bob’s still taking hits to his slender face?

    –Blake Goble

    23. Deep Space Homer

    Season Five, Episode 15

    Premiere Date: February 24, 1994

    Writers’ Room: Season five showrunner David Mirkin toyed with the idea of an episode that spoofed the real-life Teachers in Space Project. NASA’s idea was to spur teachers, students, and other common people to reach space, so Mirkin wondered, Why not let blue collar slobs like Homer Simpson in on the action? (The exact phrasing from the episode: “Sir, how would you like to get higher than you’ve ever been in your life?”) Some of the staff had trepidations. This was too far. There’s nowhere else to go with Homer after this. And Groening himself was a vocal opponent. But Mirkin won out.


    Essential Quote: “The only danger is if they send us to that terrible Planet of the Apes. Wait a minute. Statue of Liberty. That was our planet! You maniacs! You blew it up! Damn you! DAMN YOU ALL TO HELL!!!” It should be noted, Dan Castellaneta screamed this so loud you can hear the reverb of the recording studio. And it slays the writers on the episode commentary. Again – Dan Castellaneta is Homer Simpson.

    D’oh! Moment: Homer, feeling snubbed after losing out on an employee recognition award to an inanimate carbon rod (wow), tries to find solace in television. “TV respects me. It laughs with me, not at me,” he says. But when he turns on a random channel: “You stupid!” followed by audience laughing. “D’oh!”

    Best Visual Gag: Homer’s face transforming in to Nixon and Popeye are choice. So is his deep, terrified sweat after seeing an extremely violent and space-themed Itchy and Scratchy. But for our money, the entire “Blue Danube Waltz” sequence is a perfectly executed gag. Aping the same visual cues from 2001: A Space Odyssey, Homer’s intergalactic ballet of eating the ruffled chips he snuck aboard is divine comedy. And the punchline of Homer crashing in to the ship’s ant farm delivers an all timer of a line: “FREEDOM! HORRIBLE, HORRIBLE FREEDOM!”


    Welcome to Springfield: There were two terrific cameos in Buzz Aldrin and James Taylor. And Mirkin and the writers stammered selling jokes to the two. In the commentary, Mirkin acknowledges clamming up when he asked Aldrin to make light of himself being the second man on the moon. Aldrin, ever the amiable hero, was fine with the line, “second comes right after first.” And then Mirkin admits that he was scared to ask James Taylor to alter “Fire and Rain” for this episode to have space jokes. Taylor was also fine with The Simpsons’ humor and requested revisions. Hm. It’s as if people want to be on The Simpsons, and would do anything the show asks just for the chance to be lampooned. Who’dathunkit?

    Episode as a GIF:

    Analysis: “Hello, is this President Clinton? Good! I figured if anyone knew where to get some Tang, it’d be you. Shut up!” In one way, that joke works as an act of bafflement. How the hell did Homer get Bill Clinton’s number in 1995?? But then hear the joke again. It’s a goof on Tang, which is a short hand for space food and spacier jokes that dates to the Coneheads. Hear the joke one more time? Wow, that’s a dirty euphemism at Slick Willy’s expense! That’s the level that “Deep Space Homer” works on. That’s the referential depth David Mirkin’s absurdist mind and humor works on.

    “Deep Space Homer” is a gold mine of references. The Right Stuff. Planet of the Apes. Mr. T. Popeye. Nixon. The Beverly Hillbillies. Married…With Children. Star Trek. Home Improvement (“Looks like it’s back to jail for me!”). And of course, 2001: A Space Odyssey. Mirkin took a preposterous concept – putting a very dumb and dangerous man in to the space program and letting him make it past lift off – and made a mint of gags, goofs, and all around great bits. Now, if we could just figure out where to get some Tang.

    –Blake Goble

    22. Marge Be Not Proud

    Season Seven, Episode 11


    Premiere Date: December 17, 1995

    Writers’ Room: Episode writer Mike Scully based “Marge Be Not Proud” around some of his own experiences being peer-pressured into shoplifting as a child, and the subsequent fear of disappointing one’s loved ones as a result of doing so. It was also the hook for the first Christmas episode since the show’s series premiere, although we don’t how how “Mr. Plow” isn’t at least a spiritual successor for the holiday somewhere in there. Funnily enough, despite their reluctance, the strong critical and audience reception of “Marge Be Not Proud” is what engendered all those other classic holiday episodes of the show.

    Essential Quote: Among the episode’s many classics, its Troy McClure joke is an all-timer: “Hi, I’m Troy McClure. You might remember me from such public service videos as Designated Drivers: The Life-Saving Nerds and Phony Tornado Alarms Reduce Readiness. I’m here today to give you the skinny on shoplifting, thereby completing my plea bargain with the good people at Foot Locker of Beverly Hills.”

    D’oh! Moment: No D’oh from Homer this outing, actually. Aside from establishing his own chiseled physique in snowman form, Homer’s fairly quiet throughout “Marge Be Not Proud”, given that it’s about parenting and Homer’s best suggestion is that Bart not steal for at least three weeks.


    Best Visual Gag: As Bart struggles with his conscience in the Try-N-Save’s video game aisle over Bonestorm, a knockoff Mario and Luigi appear to tempt him into stealing the game, followed by Donkey Kong and Sonic. The angel on his shoulder encouraging him to deny temptation? Lee Carvallo of Lee Carvallo’s Putting Challenge, who offers some sage advice: “Don’t do it, son. How’s that game going to help your putting?”

    Welcome to Springfield: Lawrence Tierney makes a gruff, hilarious appearance as store security guard Don Brodka: “If I wanted smoke going up my ass, I’d be at home with a pack of cigarettes and a short length of hose.” Tierney only gets a handful of lines, but he makes the most of them with his gravelly delivery. Speaking of gravel: “Someday he’ll be a grown man stealing stadiums…and quarries…”

    Episode as a GIF:

    Analysis: Some die-hards see “Marge Be Not Proud” as a more saccharine offering from the show’s golden years. But while it’s definitely on the sentimental side for The Simpsons during that era, it’s also one of the more emotionally rewarding half hours of the show at large. The simple arc of Bart taking his mother’s “excessive” affections for granted until he screws up badly enough to lose them is heartbreaking, especially when Bart’s expected tuck-in time is replaced with a flat, despondent “good night.” There are a ton of fantastic jokes throughout the episode (WELCOME THRILLHO, the final credits), but it’s heavier on the pathos, down to Bart helping Mrs. Van Houten label Christmas cards just to feel like part of a family again. But the final reveal of Bart’s separate portrait is among the show’s most kindhearted, a moment of skewed family unity when it counts: at Christmastime.

    –Dominick Suzanne-Mayer

    21. Lisa the Iconoclast

    Season Seven, Episode 16


    Premiere Date: February 18, 1996

    Writers’ Room: When you decide to write a part for Donald Sutherland, you had better bring your A-game. In creating Hollis Hurlbut, writer Jonathan Collier certainly did. Hurlbut’s a worthy foil for Lisa, in that they both dive headlong into whatever most interests them. How else could Lisa counter Hurlbut’s “Jebeditis” joke with her own “Chester A. Arthuritis”?

    Essential Quote: “This is nothing but dead white male bashing from a P.C. thug. It’s women like you who keep the rest of us from landing a husband!” –Miss Hoover

    D’oh! Moment: “Congratulations, Ned! You are our new town crier!” “D’OH!”


    Best Visual Gag: The headline of the Springfield Shopper reads thus: “PARADE TO DISTRACT JOYLESS CITIZENRY.” Bonus: “Springfield Historical Society, Where the Dead Come Alive (Metaphorically).” Bonus bonus: “The Copy Jalopy – We Tried to Make Copying Fun.”

    Welcome to Springfield: Well, Donald Sutherland’s Hollis Hurlbut is introduced, but as he’s a one-and-done, let’s welcome “cromulent” and “embiggen.” Both were cooked up for this episode by its writers, and have since gone on to post-Simpsons lives of their own. “Cromulent” has even embiggened the dictionary.

    Episode as a GIF:

    Analysis: Lisa haters, watch and be silenced. The wonderful thing about “Lisa the Iconoclast”—well, besides the fact that it’s particularly rich in throwaway jokes, even by Simpsons standards—is that Lisa’s fight for justice comes up against something that’s equally as important, albeit in a completely different sense. Her realization that, in this case at least, the power of the symbol matters more than the truth behind it ranks among the most grown-up of Lisa’s many discoveries. Many of the best episodes of The Simpsons are pure, demented silliness from start to finish. “Lisa the Iconoclast” has plenty of that—the battle between Springfield and Washington alone is a deranged delight—but it’s also got something to say. Truth matters. So does hope, and sometimes the happiness of others is more important than being right.

    –Allison Shoemaker


    20. Lemon of Troy

    Season Six, Episode 24

    Premiere Date: May 14, 1995

    Writers’ Room: Because The Simpsons only do things in epic fashion, writer Brent Forrester spoofed the Greek mythology surrounding Helen of Troy and the Trojan Horse to give Springfield a bitter rivalry with their neighboring town. In fact, the rivalry goes back to the founding of both towns, when Jebediah Springfield and Shelbyville Manhattan split over the legality of being able to marry a cousin. Shelbyville already had a place in the Simpsons universe, but it hadn’t yet been fully explored as the strange mirror to Springfield. However, as the Simpsons’ hometown is often a mess, Shelbyville gets a darker treatment here while Springfield proves to be more of a paradise by comparison. Plus, who doesn’t love a good history lesson about Springfield?

    Essential Quote: The line that delivers a laugh upon every viewing of the episode—a chortle, a chuckle, or a giggle in the very least, no matter the watch count—is Milhouse tearfully muttering, “So this is what it feels like when doves cry.” It may seem like an anomalous moment for someone as inherently uncool as Milhouse to nail a Prince reference, but the dude’s never had an easy existence; he’s long relied on pop culture as a crutch to deal with the hardships of his world and his own highly emotional nature. Here, he just found out Shelbyville has a Milhouse of its own! The quote’s also made sillier by the fact that, just a moment prior, the dingus was narrating his own potential demise, “Is this the untimely end of Milhouse?” Ugh, classic Milhouse.

    In a similar vein, the runner-up quote for this episode has to be forever-endearing Flanders trying to join in on Bart and Homer’s snarky bellows of “Eat my shorts” during their RV escape, only for it come out as a cheerful, “Yes, eat aaaall of our shirts!” Bless sweet Ned Flanders, even when he’s committing a pretty cool theft, he’s still a dork…


    D’oh! Moment: There aren’t any actual outbursts of “D’oh” in this episode, but there are two moments deserving of the exclamation: first, when Bart attempts to evade the Shelbyville kids by using spray cans as jet boosters, only to destroy his shoes; second, when Homer confidently throws a steak at the impound dog chasing Bart to slow him down, only for the beast to catch the meat and devour it in a single leap.

    Best Visual Gag: This episode has a good helping of visual humor to it, but it’s just too curious to behold Shelbyville’s eerily familiar surroundings during the skateboard chase. The town features a more hip and ponytailed Moe lookalike named Joe and an Asian owner of the Speed-E-Mart (as opposed to Apu and the Kwik-E-Mart). It’s then topped off by Groundskeeper Wilma at Shelbyville Elementary, who is just as annoyed, ginger-haired, and furiously Scottish as Groundskeeper Willie.

    Welcome to Springfield: Shelbyville had long been established in The Simpsons universe by the time this sixth season episode came around. In fact, the town was first mentioned in the second season with the introduction of Homer’s half-brother, who grew up in the Shelbyville Orphanage. But it still hadn’t been properly explored. In this episode, we see the debut of Shelby, his sidekick Milhouse, and their little band of ruffians, along with similarly mirrored characters of Springfield.


    Episode as a GIF: The Shelbyville locals are pretty tough as it turns out…

    Analysis: A lot is revealed about Springfield when its residents operate in the larger world, even if it’s just a nearby town. When left to its own devices, Springfield is wacky regardless, but a broader scope allows us to see how its citizens handle other worlds. In episodes like “The City of New York vs. Homer Simpson”, we get the chance to observe members of the Simpson clan in the real world (more or less). But it’s episodes like this one, which may be the show’s best example, when we behold Springfieldians in true passionate glory, unified in celebrating their history and honoring their like-minded strangeness, all while plotting a legacy for generations to come. With so many oddball locals delivered throughout nearly 30 seasons, it’s easy to think of Springfield as a bigger town than it is. This episode delivers Springfield’s small town charm while packing in its larger-than-life inanity.

    –Jake Kilroy

    19. A Milhouse Divided

    Season Eight, Episode Six

    Premiere Date: December 1, 1996

    Writers’ Room: The sole script of staff writer Steve Tompkins, “A Milhouse Divided” tells the story of Kirk and Luann Van Houten’s divorce and how its after effects ripple throughout the Simpson household. The writers had been hoping to write an episode about divorce, if only so they could have the couple stay divorced, thus further differentiating them from most sitcoms.

    Essential Quote: While I’m partial to Luann’s takedowns of Kirk (“We didn’t all go to Gudger College”), this one goes to Starla, Kirk’s rebound: “Can I have the keys to the car, lover? I feel like changing wigs.” This episode is also home to one of the weirdest Simpsons lines of all time: “You know what you two need?” Homer says. “A little comic strip called ‘Love Is…’. It’s about two naked eight-year-olds who are married.”


    D’oh! Moment: Who needs a “D’oh” when we have Homer’s anguished cries after Bart breaks a chair over him in the bathtub?

    Best Visual Gag: Marge nudging a box of Allied Biscuit under the couch after Luann reveals Kirk’s cracker factory is in a tie with them for least popular cracker.

    Welcome to Springfield: Believe it or not, Luann’s new boyfriend Chase (a.k.a. American Gladiators’ Pyro) would go on to appear a whopping 12 more times.


    Episode as a GIF: “Homer, the only thing I asked you to do for this party was put on your clothes and you didn’t do it.”

    Analysis: For as funny as it is, “A Milhouse Divided” is surprisingly tender. Not only do we see genuine sadness on Kirk’s end, but we get a bracingly honest moment of reckoning for Homer, who’s finally able to recognize how awful he’s been to Marge. That includes a closer look at their actual wedding, which devolves into melancholy as the pair sit on a picnic table next to a highway. The show leads the audience to believe Homer wants a divorce so convincingly that the surprise wedding he organizes at episode’s end truly surprises. Also, the writers achieved the surprise they sought after as well. In any other show, Kirk’s “Can I Borrow a Feeling” serenade would’ve won Luann back; instead, she scoffs at the idea that they should reignite their relationship. It’s a wonderful moment of both real-life honesty and female empowerment, especially in a TV landscape that routinely defined women by their relationship to men.

    –Randall Colburn

    18. Homer Badman

    Season Six, Episode Nine

    Premiere Date: November 27, 1994

    Writers’ Room: To understand the conceit behind “Homer Badman”, you have to understand the time from which it was developed. Back in 1994, the entire country was experiencing a then-unprecedented surge in tabloid journalism, mostly thanks to god awful programs like Hard Copy and all the media hoopla surrounding the O.J. Simpson murder case. Showrunner David Mirkin understood all of that, and opted to take writer Greg Daniels initial pitch about Homer and Lisa’s clashing thoughts on feminism and turn it into a brilliant slam against the new wave of pseudo-journalism that was burying the truth in lieu of sensationalized facts and corrupt narratives. Mirkin reportedly based most of the gags on real-life programming.


    Essential Quote: “Simpson scandal update — Homer sleeps nude in an oxygen tank which he believes gives him sexual powers.

    D’oh! Moment: As an angry mob descends upon the Simpson house, Homer pulls the window’s curtains back, bringing him face to face with their recent babysitter Ashley Grant, who immediately accuses him of sexual harassment. It all happens so fast that Homer has no time to register any of it, which is why he rambles on a little bit (“Oh, for a minute there, I thought I was in big trouble, it’s just…”) before the truth hits everybody (“D’oh!”).

    Best Visual Gag: The whole “Ben” segment serves as an outstanding visual metaphor for the stupidity of daytime television, suggesting that any dope could host a show as long as there’s a microphone and a bunch of idiots watching from the crowd. What ultimately sells this gag, however, is how it over-delivers on the goods. Now, seeing a large grizzly bear walking around with a microphone strapped to its head is more than enough to elicit a laugh or two from any self-respecting fan of animals acting like people, but seeing that same grizzly bear freaking out over the nearby craft service table, only to be tranquilized multiple times as his audience erupts into chaos … well, that’s like finding a box of cereal full of marshmallows.


    Welcome to Springfield: Feminist graduate student Ashley Grant makes her first and last appearance in “Homer Badman”, which is kind of a shame given that Lisa obviously took a liking to her style. Pamela Hayden, who’s voiced everyone from Milhouse Van Houten to Rod Flanders to Jimbo Jones, provided the vocals to take Homer down and send Bart into a wall. Altogether, she’s quite a powerful character.

    Episode as a GIF: “C’mon, I’m a decent guy.”

    Analysis: Very few episodes of The Simpsons hold up as well both socially and politically as “Homer Badman”. At a time when social media and our never-ending news cycle consistently seemingly acts like a real-life version of Shirley Jackson’s The Lottery, Mirkin and Daniels’ hilarious cautionary tale couldn’t feel more prescient. Granted, sexual harassment is no laughing matter, and there are sadly countless real-life Ashley Grants who struggle with horrifying sexual predators on a daily basis across the world, but that’s why The Simpsons never make light of it. Instead, they sensationalize the sensationalized, turning the spotlight on the media and revealing how ugly and how manipulative they can be without any accountability whatsoever. (Case in point: See how Rock Bottom simply rolls out their list of corrections at the end of their program. That happens all the time.) The more over-the-top Mirkin and Daniels go with their script, the better their point comes across, whether it’s talk shows hosted by bears (“No Ben! No!”) or made-for-TV movies starring Dennis Franz (“Now I’m gonna grab me some sweet.”). Though, perhaps no line speaks louder now than Marge’s prophetic two cents: “You know, the courts might not work any more, but as long as everybody is videotaping everyone else, justice will be done.” Amen, Marge.

    –Michael Roffman

    17. Mr. Plow

    Season Four, Episode Nine

    Premiere Date: November 19, 1992

    Writers’ Room: If you had a chance to tweak the circumstances so that you could meet a lifelong hero, wouldn’t you tweak away? Jon Vitti did. “Mr. Plow” would be a classic Simpsons episode even without two of the best celebrity cameos in the history of the series, and one of them came about because Vitti willed it into existence. As a result, you’ve got him to thank for the sight of animated Adam West doing the Batusi. Oh, and it’s also a solid plot, seeing Homer transform into a self-starting town hero before his glory is yanked away, first by Barney, and then by God.


    Essential Quote: “Take it easy, folks. It’s snow picnic out there! Heh heh!” “I snow what you mean, heh heh!” “You’re dead weight, Marty.” –Bill and Marty

    D’oh! Moment: It’s a classic Double D’oh! as Homer rear-ends another car, hits his head on the steering wheel, and gets out, only to see the airbag uselessly deploy (“D’oh!”). He then celebrates the sight of the other guy’s wreck (“At least I got him as good as he got me!”) before realizing it’s Marge’s car, parked in the driveway (giant “D’OH!”)

    Best Visual Gag: As God humbles both Mr. Plow and The Plow King, a heat wave melts the a pair of snowmen in an homage to Raiders of the Lost Ark


    Welcome to Springfield: Adam West’s deranged cameo, referenced above, is a delight, but he’s topped by Linda Ronstadt, who comes aboard to sing the Plow King’s jingle and Barney’s explanation: “Oh, we’ve been looking for a project to do together for awhile.”

    Episode as a GIF:

    Analysis: Sometimes the simplest Simpsons episodes can be the most delightful, and this is near the head of that pack. There are some unusual moments—learning Barney’s backstory, that bizarre West cameo, a quick bit of social commentary in the form of a giggling car show model—but for the most part, this is Homer the fool, Homer triumphant, Homer revenged, and Homer repentant, with a final transition back to Homer the fool. Things aren’t quite back to zero, however—the purest pleasure in “Mr. Plow” comes when Marge suggests that Homer should maybe wear that jacket to bed. Well that, and Homer’s amazing commercial. That jingle’s been stuck in my head for almost 25 years.

    –Allison Shoemaker

    16. Homer’s Phobia

    Season Eight, Episode 15

    Premiere Date: February 16, 1997

    Writers’ Room: The process was scattershot, but “Homer’s Phobia” is the result of several notes and ideas stemming back to a one-line suggestion from George Meyer: “Bart the homo.” Vague, and a potential minefield if spun improperly, the idea managed to find traction with writer Ron Hauge, and the Simpsons team’s desire to make an episode with trash icon John Waters. Additionally, Bill Oakley and Josh Weinstein were looking to have The Simpsons feature a gay character without “silly phoniness” that could be a positive intro to gay culture. After dabbling in themes of camp, developing a gay panic as a learning moment for Homer, and navigating a ton of censor notes that eventually got thrown out due to a change in staff at Fox … the final product was a heartfelt episode.


    Essential Quote: “They ruined all our best names like Bruce, and Lance, and Julian. Those were the toughest names we had!” –Homer

    D’oh! Moment: No “D’oh!”s. But the mere screams, whimpers, and worries of Homer Simpson when presented with the notion of working hard and playing hard.

    Best Visual Gag: Homer’s absolute dismay when Bart chooses a pink Sno Ball over a cupcake? It works perfectly to display the absurd nature of Homer’s fear that Bart is gay, and works as a very curious inside joke of sorts; a great, small gesture gag.


    Welcome to Springfield: “…boy, was it fun to do The Simpsons,” says John Waters in the DVD commentary for “Homer’s Phobia”. Zzzzzap! This would be the first and last appearance of gay shop owner John, voiced by Waters. Sporting a bowling shirt and a curly thin mustache, John was modeled after the director, and it’s a shame the show couldn’t make him a regular.

    Episode as a GIF: Oh, Homer’s not afraid of “hot stuff” in any literal sense. Also, being shirtless and wearing cutoffs in a steel mill must be a huge work violation, no?

    Analysis: Airing two months before Ellen‘s “Puppy Episode” and well over a year ahead of Will & Grace, “Homer’s Phobia” was a big deal for ‘90s TV humor as social commentary. Sure, Archie Bunker had his run-ins, but sweet merciful crap, 1994’s “Don’t Ask Don’t Tell” was repealed only in 2011. No, this episode was a watershed moment, unafraid to skirt around a big part of American life, all the while poking fun at homophobia, playing with stereotypes, and basking in the joys of gay culture. The Anvil looks like a great place to work and dance! John Waters, the king of pervert ‘70s cinema playing family-friendly was such a stroke of genius on the show’s part. He’s not the transgressive provocateur he was once made out to be, but he is, in fact, a fun and funny guy with impressive tastes in kitsch. Homer confronts his own mis-perceptions and naiveté, and tries to change (using “queer” instead of “fruit” is but one small upgrade in Homer’s vernacular). John Waters gets to be the hero. And in the end, the only thing to fear is Bart developing a pack-a-day habit. God, we hope they’re not slims, either.

    –Blake Goble

    15. Last Exit to Springfield

    Season Four, Episode 17


    Premiere Date: March 10, 1993

    Writers’ Room: Although written by Jay Kogen and Wallace Wolodarsky, the show’s initial story came from showrunner Mike Reiss, who was eager to see what screwball antics would ensue if the power plant’s workforce went on strike. The title itself is a play off Last Exit to Brooklyn, a rather gritty and controversial novel by Hubert Selby, Jr. about a corrupt union leader during a strike. It’s a supremely solid episode that maintains as much humor as it does heart, with Lisa showcasing truly horrific braces and Homer winding up in charge of his union so he can save their dental plan.

    Essential Quote: There are a lot of funny moments here, from Homer dreaming of a life as an Italian mob boss to Grampa purposefully telling a story that doesn’t go anywhere, but the most memorable quote comes from a rather sincere Lisa — and in song form. Even though she’s had a rough go of life recently, given that she’s donning the world’s most horrifying braces, the little poet strums a guitar and sings for her father and his striking union comrades. The folk melody is catchy and the chorus is simple: ”So we’ll march day and night by the big cooling tower. They have the plant, but we have the power.” In the end, when the lights go out, the power plant employees join in and that marks the change of heart in Mr. Burns.

    Right before Burns gives up, though, he majestically transforms into Springfield’s version of The Grinch, down to his Seussian movements and expressions. He even yanks on Smithers’ bow-tie like he were Max the Dog and bellows, “Look at them all, through the darkness I’m bringing! They’re not sad at all; they’re actually singing! They sing without juicers! They sing without blenders! They sing without flunjers, capdabblers, and smendlers!”


    Best Visual Gag: While showing Homer around his extraordinary mansion, Mr. Burns reveals his room of a thousand monkeys working at a thousand typewriters, which will surely one day produce “the greatest novel known to man.” When Mr. Burns checks on a monkey’s work, only to reveal it’s pretty much a typo-riddled rip-off of Charles Dickens, we see that some of the monkeys are smoking pipes and cigarettes too. The lives of the wealthy are so curious.

    D’oh! Moment(s): At the meeting for the International Brotherhood of Jazz Dancers, Pastry Chefs, and Nuclear Technicians, Homer’s made president of the union after a fiery speech. Naturally, he immediately asks what the job pays, only to find out the answer is, “Nothing.” His obvious reaction is “D’oh” until Carl clarifies, “Unless you’re crooked.” Then comes Homer’s other catchphrase: “Woo-hoo!” No one can bounce through emotions as seamlessly as Homer Simpson.

    Shortly thereafter, at the kitchen table, Homer tells the family about his new gig. Lisa is especially excited for him, as he explains that it all comes down to who’s a better negotiator, him or Mr. Burns. Bart then suggests that Homer swap out “his crummy old danish” for a “delicious doorstop,” which Homer readily accepts, only to realize the obvious folly with a resounding “D’oh.” Lisa’s hopes are dashed.


    Welcome to Springfield: On the Smartline episode “The Power Plant Strike: Argle-Bargle or Foofaraw?”, host Kent Brockman welcomes three guests: plant owner C.M. Burns, union kingpin Homer Simpson, and talk show mainstay Dr. Joyce Brothers. Brothers voiced herself and only had one line: “I brought my own mic!”

    Episode as a GIF: Burns and Smithers have the time of their life running the plant alone like they’re renovating a damn beach house.

    Analysis: As Springfield’s population has a tendency to assume it’s being grifted—truly, it’s a town stacked with people believing they’ve pulled one over on each other and the world at large—aloofness can be mistaken for cunning, misdirection, or even skill. No one proves this better than Homer Simpson, a scammer with practically no common sense and an oddly anchored morality. He takes one confident step and arguably smarter characters believe he’s already 10 steps ahead. That’s the beauty of The Simpsons, that the world appears eternally for the taking, somewhere you can fall up, while nothing ever really lasts. This episode is a perfect example of that phenomenon. So, of course, Homer initially agrees to trade his dental plan for free beer, only to make the right decision out of self-interest (avoiding the bill for Lisa’s braces), with his union naming him leader and Mr. Burns declaring him a “brilliant tactician.”

    –Jake Kilroy

    14. Lisa’s Substitute

    Season Two, Episode 19


    Premiere Date: April 25, 1991

    Writers’ Room: To many—this writer, at the very least—”You are Lisa Simpson” is one of the show’s most genuinely affecting moments. It’s the kind of thing every lonely, misunderstood, and mercilessly teased kid wants to hear from the teacher that makes them feel special. It’s perfect, and that’s why it’s a little jarring to discover that episode writer Jon Vitti wanted it to end with an exclamation point. The fact that it doesn’t, he tweeted, “haunts me to this day.” It’s one of two lovely moments in an episode that’s among the sweetest The Simpsons has to offer, the other being a last-minute rush of good parenting from Homer, who comforts all his kids, one after the other—”I’m on the biggest roll of my life.”

    Essential Quote: “I’m Mr. Bergstrom, feel free to make fun of my name if you want. Two suggestions are Mr. Nerdstrom and Mr. Boogerstrom.” –Mr. Bergstrom

    D’oh! Moment: In the midst of his overdue heart-to-heart with his daughter, Homer attempts to take a seat. On a dollhouse. It breaks. D’oh.


    Best Visual Gag: Martin’s “Simpson Defeats Prince” photo-op is topped only by the delight of this Graduate parody for Mr. Begstrom, who’s voiced by Sam Etic (ahem, who’s really Dustin Hoffman).

    Welcome to Springfield: “Dear Ms. Hoover, You have Lyme disease. We miss you. Kevin’s biting me. Come back soon. Here is a drawing of a spirochete. Love, Ralph.” Ralph Wiggum! He had shown up earlier as a background character or generic kid, but “Lisa’s Substitute” gives us our first glimpse of this fragile, crayon-eating treasure.

    Episode as a GIF:

    Analysis: There’s a totally solid subplot in “Lisa’s Substitute”—Bart’s impending landslide of a win in the class elections gets thwarted when he and all of his friends forget or don’t bother to vote—but it’s so dwarfed by the A-story that it’s often forgotten. That’s understandable, because The Simpsons makes Lisa’s inappropriate crush both endearing and heartbreaking, a connection that comes from being seen, heard, and appreciated. (Sure, there’s also his “semitic good looks” and perfect eye-teeth, but that’s all just a bonus.) That Vitti and company manage to transition this innocent heartbreak into a chance for Homer to do the right thing for his daughter in his own oafish way makes it all that much more special. Oh, and Dustin Hoffman is an all-time great Simpsons guest star. That helps.

    –Allison Shoemaker

    13. The Itchy & Scratchy & Poochie Show

    Season Eight, Episode 14


    Premiere Date: February 9, 1997

    Writers’ Room: Surprise, surprise, “The Itchy & Scratchy & Poochie Show” was based on real events. In the episode, The Itchy and Scratchy Show has gone stale and the network suggests they add Poochie, a new, hip character the kids can relate to. During its seventh season, Fox suggested the same to The Simpsons who, thankfully, never took the note. Instead, writer David S. Cohen used the story as a means to satirize the tactics of network executives while simultaneously poking fun at the show itself and its most vocal fans.

    Essential Quote: There’s so much great Poochie-related material, especially when the network describes their vision of Poochie thusly: “You’ve heard the expression let’s get busy? Well, this is a dog that gets bi-zay. Consistently and thoroughly.” But this is also the episode that gives us peak Troy McClure: “Hi, I’m Troy McClure, you may remember me from such cartoons as Christmas Ape and Christmas Ape Goes to Summer Camp.”

    D’oh! Moment: It’s a sad one. After realizing nobody, not even his family, likes Poochie, he bows his head and offers a melancholy turn of his signature catchphrase.


    Best Visual Gag: When Homer sneaks into a backroom to spy on a meeting of the network’s executives, there are numerous boxes of mail: “Poochie Death Threats”, “Poochie Hate Mail”, and “Poochie Hate Mail (Foreign)”. Also, when Itchy’s chainsawing Scratchy, a small, hilarious splotch of blood appears in the ice, revealing that Itchy just nicked his opponent before pausing to listen to Poochie.

    Welcome to Springfield: Poochie aside, this episode gives us the first utterance of Comic Book Guy’s endlessly quotable, “Worst. Episode. Ever.” This is one The Simpsons’ writers would turn to, in some form or another, again and again.

    Episode as a GIF: Poochie’s fate, in a nutshell.

    Analysis: This is perhaps the first piece of satire that I, as a young child, actually recognized as satire. It’s so simple, so clear, and so utterly hilarious—that they added “Roy”, a hip teenager who is all of a sudden a member of the Simpson clan is so comically unnecessary that it just emphasizes the episode’s message that much further. Truly, it’s damn near impossible not to recognize this episode as a commentary on TV shows (or even film sequels) that pull cheap tricks in order to stay relevant. After all, we’d seen this shit pulled on nearly all of The Simpsons’ contemporaries, from Full House to Family Matters.


    The episode also allowed the show to take stock of its place in pop culture, and to reckon with the idea that the show was easing out of its place as a cultural phenomenon and into a place of comfortability that too often gives way to complacency. This is why the addition of Comic Book Guy is such a brilliant choice here—the fans are changing now. They’re older now, nostalgic and endlessly critical.

    In a way, they were girding themselves for lists like this.

    –Randall Colburn

    12. Lisa the Vegetarian

    Season Seven, Episode Five

    Premiere Date: October 15, 1995

    Writers’ Room: This episode was Futurama co-creator David X. Cohen’s (then known as David S. Cohen) first full episode for The Simpsons after contributing “Nightmare Cafeteria” to “Treehouse of Horror V”. Clearly a food-obsessed man, Cohen scribbled the idea down while waiting for lunch one day in the writers’ room: “Lisa becomes a vegetarian?” Showrunner David Mirkin, who had recently become a vegetarian, loved the pitch, and other writers inspired ideas. The funniest example? John Swartzwelder had a canned monologue about the wonders of pig meat that endlessly fascinated Cohen, and those rants became Homer’s meat fetishism.


    Essential Quote: “You don’t have to eat meat! I made enough gazpacho for all!” (This ties with Samuel L. Jackson’s use of “Hot-Zpacho” for funniest gazpacho reference.)

    D’oh! Moment: When Principal Skinner tactlessly outs Lisa for her vegetarian leanings, she gives a perfect “D’oh” without even having to make the annoyed grunt.

    Best Visual Gag: “You know, Smithers, I think I’ll donate a million dollars to the local orphanage … when pigs fly!”

    “Will you be donating that million dollars now, sir?”

    “Nooo, I’d still prefer not.”


    Welcome to Springfield: Do Paul and Linda (RIP) McCartney count? It’s just such a sweet-natured cameo from the former couple, and they give Lisa a very humbling bit of support. Also, and this is Beatle-maniac trivia, but Macca’s “Maybe I’m Amazed” plays over the credits, and if you listen carefully, there’s a strange sound in the background. It’s Paul’s voice, played backwards. He shares a lentil soup recipe, then states, “Oh and by the way, I’m alive.” It’s an amazing deep cut gag on the urban legend of “I’m So Tired.”

    Episode as a GIF: If not for this episode, we’d never know where hot dog buns come from.

    Analysis: Lisa Simpson has always been The Simpsons’ secret weapon. She’s the heart and soul of the series, and often acts as a gateway to big philosophical, spiritual, and intellectual quandaries. She challenged Homer’s cable theft, learned hard lessons about loss with Bleeding Gums Murphy, and even asked her aunts to not bash her father in the first episode. She has never been afraid to stand up for what she believes is right. “Lisa the Vegetarian” is Lisa’s best episode, and her fight to no longer eat meat takes on noble, hell, Herculian qualities. It’s a soft fable of intolerance.

    In a world filled with killing floors, “BBBQ’s”, and Independent Thought Alarms, the eight-year old vegetarian stands tall. Yeardley Smith gets her most effective work in this episode, and David Cohen’s script has brilliant jokes on top of a very strong and sentimental through line for Lisa. Only on The Simpsons can you threaten Homer’s life with lighter fluid for comedy, then show a broken Lisa have a panic attack before eating a tofu dog. “Rubber band reality,” Matt Groening once called it. In the end, this was an endearing and downright lovely moment of truth for the Simpson family’s first daughter. Also, who knew Apu Nahasapeemapetilon was the Fifth Beatle! Tough break, Billy Preston and George Martin.

    –Blake Goble

    11. Homer the Heretic

    Season Four, Episode Three


    Premiere Date: October 8, 1992

    Writers’ Room: George Meyer, who at this point had already written stellar episodes like “Blood Feud” and “Mr. Lisa Goes to Washington”, wrote Homer’s spiritually hedonistic chapter, but like most episodes of The Simpsons, it didn’t exactly start with him. Showrunner Al Jean came up with the idea while talking to his co-captain Mike Reiss, suggesting: “We had a lot of luck with Homer stealing cable, which was based on the eighth commandment, so maybe we could look to other commandments. So we thought, ‘Honor the Sabbath’ would be a good one. So the ‘Homer doesn’t go to church’ storyline was given to George Meyer.” Why Meyer? Well, he was a lapsed Catholic and Jean thought he could “bring the proper degree of rage.”

    Essential Quote: “Boy, everyone is stupid except me,” Homer says shortly before burning down the house with a cigar. Classic moment, iconic line, Papa John’s.

    D’oh! Moment: Right after Flanders heroically saves his life, Homer still tries to defend his church-less position by adding: “Flanders is a regular Charlie Church, and god didn’t save his house.” Immediately after saying this, a little rain cloud extinguishes the flames, leaving a cute, friendly rainbow. “D’oh!”, indeed.


    Best Visual Gag: Oh, where to begin? There’s Homer’s “space-age, out-of-this-world moon waffles,” the random polar bear digging through the Simpson trash during the blizzard, the portly Risky Business nod, the entire ’70s cops and robbers car chase between Homer and Flanders that leads to Garbage Island, Apu’s shotgun-toting nephew Jamshed, and yes, those baby ducks that are so cute. But really, the most iconic visual gag here is Homer’s ensuing (albeit dreamy) conversations with God. Now, it should be noted that “Homer the Heretic” marks the first episode where the series worked with animation house Film Roman, who has remained on board ever since, and their work during these sequences, especially when married with the Alf Clausen’s Herrmann-esque score, is simply gorgeous. It’s also downright funny, especially when God says he’ll give Lovejoy a canker sore (and another one from Homer) and insists he has to go and “appear in a tortilla in Mexico.” What a guy!

    Welcome to Springfield: What makes “Homer the Heretic” feel so timeless is how it’s so self-contained. There aren’t any special guests, there aren’t any new locations, it’s just a simple story that wrestles with simple ideas. As such, the only person who could be construed as “new” to Springfield here is … well, God himself. The Almighty (voiced by Harry Shearer) appears to Homer twice in this episode, and only through his dreams, which was something Meyer was very particular about in the writers’ room. He didn’t want to suggest that Homer was actually seeing visions from God, which probably explains why God is more or less a balmy, glowing version of our Sunday morning slacker. Hell, he even prefers a great game of football to a maudlin, snore-y sermon. Over the years, God has occasionally returned to “bless” The Simpsons — specifically, in episodes “Thank God, It’s Doomsday” and “Pray Anything” — and despite Meyer’s claims, Jean has gone on record saying, “The Simpsons is one of the few shows on TV where God is not only very real, but he’s a kind of vengeful Old Testament God.” Who knows what to believe!

    Episode as a GIF: “We interrupt this public affairs program to bring you a football game.”


    Analysis: Part of what makes “Homer the Heretic” so good is how it’s so relatable. Everyone has unanswered questions about the Big Man (or Big Woman) above and that extends to every kind of vocation, something Meyer subtly suggests by touching upon left-field oddities like Krusty’s humorously tragic Brotherhood of Jewish Clowns or Moe Szyslak’s dangerous devotion to snake handling. At the end of the day, though, you just have to be a good person and look out for your friends, family, and neighbors, which is about as timely of a message as you can get. Sacred themes and Hallmark feelings aside, “Homer the Heretic” is also just a smart and funny episode, leaning solely on the strengths of the show’s most basic fundamentals and allowing them to carry the entire weight of the story from beginning to end. It’s a divine slice of primetime television.

    –Michael Roffman

    10. Itchy and Scratchy Land

    Season Six, Episode Four

    Premiere Date: October 2, 1994

    Writers’ Room: The Simpsons writers were brave, man. “Itchy & Scratchy Land” came about after stricter censorship laws came about and Fox threatened to cut Itchy and Scratchy from the show entirely. The writers refused, penning this story of a literal theme park centered entirely around violence as a means of sticking it to the executives and also pointing out the absurdity of these censorship laws. Considering it required an entirely new environment, the animators had to work overtime, resulting in one of the more difficult Simpsons episodes ever to be produced.

    Essential Quote: “See all that stuff in there, Homer?” Marge says when an Itchy bot reveals the chips and wires in its head. “That’s why your robot never worked.”

    D’oh! Moment: “Fasten your seatbelt, kids, we’re on our way to Itchy & Scratchy Land!” Homer cheers as he steers the car onto the on ramp annnnnnd into a traffic jam. The whole family joins Homer in this “D’oh!”


    Best Visual Gag: After Homer declares he’s going to take a shortcut, the episode cuts to the Simpsons’ car, battered beyond repair and festooned with wedged traffic signs, a massive U.S. missile, and, incredibly, a wooden wagon wheel. “Let us never speak of the shortcut again,” Homer says somberly.

    Welcome to Springfield: An informational video at the park gives us our first glimpse of Roger Myers, Sr., the Itchy & Scratchy creator whose journey is comically similar to that of Walt Disney. Obviously, Myers, Sr. will play a big role the following season when it’s revealed he didn’t create his iconic duo, after all.

    Episode as a GIF: “The babies look unhappy. Add more balls.”

    Analysis: “I wonder if this kind of violence really does desensitize us?” Lisa asks at one point in the episode, a question she and Bart immediately shrug off. It’s a question the show investigates now and then throughout the series’ run, but it’s also one it doesn’t have the answer to, not that it even needs to have one. Itchy and Scratchy were never meant to satiate the bloodlust of desensitized children, nor were they there serving as any kind of cautionary tale. Itchy and Scratchy’s role in the show is to satirize all the absurd accusations the stuffed-shirts loved to lob at The Simpsons. By pushing the violence to such comical extremes, The Simpsons was placing their own show in context. And here, by positing Itchy and Scratchy as a creation on par with Mickey Mouse and Disneyland, the writers are satirizing the idea that violence alone could propel entertainment to the heights of the stratosphere. It’s also a clever response to the perils of capitalism, something the series itself was likely struggling with at the time. I wonder how they all feel about the Springfield at Universal Studios Florida?

    –Randall Colburn

    09. King Size Homer

    Season Seven, Episode Seven


    Premiere Date: November 5, 1995

    Writers’ Room: “King Size Homer” was the first entry to what would be a steady run for writer Dan Greany. With the issue of Homer gaining weight being a bit sensitive of a topic, the most effort in developing the episode seemed to be keeping things respectful while also humorous. Part of that is seen in Homer’s attitude throughout the weight gain, and how it is, at least for the character, a goal-oriented task. Among the ideas that didn’t make the cut, though, was a plot point where Homer would do a 180 and become skinny for Marge.

    Essential Quote: “I wash myself with a rag on a stick.” –Bart

    D’oh! Moment: Homer is trying to get injured at work and stands in a hard hat area waiting for falling objects. When a wrench falls near him, Homer moves to that spot, only to have bucket of gravel fall in the spot he had just left. “D’oh” is the only suitable response.

    Best Visual Gag: When Homer goes to the movies, the marquee reads: “Pauly Shore and Faye Dunaway in Honk If You’re Horny.”


    Welcome to Springfield: It’s not a person that’s most memorable as a new edition to the cast, but a talking pig that Homer encounters in a fantasy sequence, urges our portly hero to gain weight. Apparently, the role was written with Cary Grant in mind, but having been long deceased, regular Hank Azaria got the part.

    Episode as a GIF:

    Analysis: “King-Size Homer” is an episode full of contradictions. It’s Homer’s laziness that sets him on a quest that winds up being hard work: getting to 300 pounds. And by episode’s end, he’s forced to do the exercises he was trying to avoid just to get back to his original weight. Homer’s weight leads to a series of classic sequences, including the eating montage where Homer learns to rub food against a surface to see if the surface becomes clear. And, when Homer goes searching for loose-fitting clothes at The Vast Waistband, he settles on a muumuu because he “doesn’t want to look like a weirdo.” The episode hits on a number of issues the obese face, including health problems to ostracizing, and does so without being self righteous. It’s a classic Simpsons move to examine a topic from multiple angles, and one that’s hardly matched in deftness throughout the show’s history.

    –Philip Cosores

    08. I Love Lisa

    Season Four, Episode 15

    Premiere Date: February 11, 1993

    Writers’ Room: “I Choo-Choo Choose You” is literally the perfect Valentine’s Day card, a sentiment that’s both absurdly cheesy and all-too-evocative of the sentiments that passed among grade schoolers. It’s also a real card, one that showrunner Al Jean got when he was in third grade. That seed went on to birth this episode, which finds Lisa having to fend off the advances of a starry-eyed Ralph after she gives him a Valentine’s Day card out of pity.


    Essential Quote: “Now for my favorite part of the show. What does that say? Talk to the audience? Oh, god, this is always death.” –Krusty the Clown

    D’oh! Moment: “Woo-hoo!” Homer cries when Principal Skinner says the schoolchildren’s is almost through. “D’oh!” Homer cries when Skinner says it’s now time for “a thorough retelling of the life of George Washington.” That Lisa plays Martha Washington makes Homer’s misery that much funnier.

    Best Visual Gag: A Krusty Home Pregnancy Test with a warning that it “may cause birth defects.”


    Welcome to Springfield: This wasn’t Ralph’s first episode (see above), but it was most certainly his first showcase. Here, he’s allowed to be more than a vessel for randomness, but rather an awkward goof with a heart of gold. The frame-by-frame breakdown of Ralph’s heart breaking remains one of the show’s funniest, most sorrowful moments.

    Episode as a GIF: Speaking of which…

    Analysis: Hearts are everywhere in this episode. Not only do we witness the destruction of Ralph’s, we also see Scratchy’s get ripped out and a shipment of loose beef hearts that lunch lady Doris blithely orders be dumped on the floor. The Simpsons often explored themes of love and infatuation, both among adults and children, and “I Love Lisa” ranks as one of its best explorations. Here, we see not only Ralph’s efforts to win Lisa’s heart, but, more interestingly, Lisa’s difficult task of rebuffing it without being cold. Furthermore, it explores the deliciously complex theme of a good deed gone wrong; what happens when an act of kindness results in unwanted advances? That’s something adults struggle with, let alone grade schoolers.

    –Randall Colburn

    07. You Only Move Twice

    Season Eight, Episode Two

    Premiere Date: November 3, 1996

    Writers’ Room: What’s perhaps the most interesting aspect of the script for “You Only Move Twice” is what wasn’t written in advance. The writing team knew that guest star Albert Brooks would change most of his dialogue, so very little time was put into perfecting the lines of Hank Scorpio. Instead, Brooks wound up recording more than two hours worth of material for the role, including his best bit in response to Homer Simpson’s query as to where he could buy “work hammocks” for the office.


    Essential Quote: Speak of the devil! Nothing gets better here than this classic exchange: Hank: “Hammocks? My goodness, what an idea. Why didn’t I think of that? Hammocks! Homer, there’s four places. There’s the Hammock Hut, that’s on third. There’s Hammocks-R-Us, that’s on third too. You got Put-Your-Butt-There. That’s on third. Swing Low, Sweet Chariot… Matter of fact, they’re all in the same complex; it’s the hammock complex on third.” Homer: “Oh, the hammock district!” Hank: “That’s right.”

    D’oh! Moment: While showing Homer his new job, Hank Scorpio asks Homer to complete a trust exercise with him. Hank counts down from three, but when the phone rings at one, Scorpio becomes distracted. This results in Homer falling to the ground, and letting out a more pained “D’oh” than usual.

    Best Visual Gag: It’s in the closing moments, when the Simpsons return to Springfield and find the Denver Broncos on their lawn, Hank Scorpio’s final gift to Homer, whose biggest dream was to own, well, the Dallas Cowboys.


    Welcome to Springfield: Hank Scorpio goes down as one of the most beloved single-episode characters in Simpsons history, but it almost wasn’t this way. When Brooks was cast in The Simpsons Movie, there was a week’s time when Brooks was set to reprise his role of Scorpio. The juxtaposition of him being the opposite of Homer’s old boss, Mr. Burns, as well as essentially a James Bond villain, of which Homer is blissfully unaware, make every moment that Scorpio is seen on screen something to treasure. It’s a shame he never came back, but hard to imagine that he’d live up to his first appearance.

    Episode as a GIF:

    Analysis: Aside from Hank Scorpio, there’s still a lot to love in the episode. We see each member of the Simpson family taken out of their natural habitat and put into unfamiliar waters, where they should theoretically thrive. It turns out, though, that Springfield is the most conducive environment for all of them. While you could argue this isn’t true for Homer, in the end, it’s his family’s happiness that suits his own well-being. But the episode thrives most on its use of physical comedy, extended jokes, and cultural references. The Bond-esque scenes that Homer walks into are highlights that snowball over the course of the episode, with Scorpio even asking Homer to kill people for him on his way out of the office. And then there is the moment when the Simpsons leave Springfield, which is used as a montage of many of the show’s supporting characters, all getting their chance to say goodbye. With this installment of the series focused away from their hometown, it serves as a nice way to give fans their fix of Simpsons secondary players.

    –Philip Cosores

    06. Homer at the Bat

    Season Three, Episode 17

    Premiere Date: February 20, 1992

    Writers’ Room: “Homer at the Bat” is one of The Simpsons’ staff’s favorite episodes, with showrunner Al Jean naming it “essential.” It took more than six months to make, too, as the incorporation of nine professional baseball players didn’t make recording very easy. While it seems most were a pleasure to work with, Jose Canseco was (unsurprisingly) a giant dick, complaining about his animation and insisting his character be written to be more heroic. While it was, in many ways, a gimmick episode posited by the producers, it resulted in an episode that, 25 years later, still feels like an event.


    Essential Quote: “How would you like to be a ringer on a small town company softball team?” Smithers asks professional baseball player (and upright bassist) Steve Sax. Sax responds with a hearty, “Would I?!”

    D’oh! Moment: No “D’oh!”s here, though the audience is likely to let one rip after Roger Clemens snaps Homer’s Wonderbat in half with a fastball.

    Best Visual Gag: Mr. Burns’ initial lineup of ringers stopped playing baseball a 100 years previous (“Your right fielder has been dead for 130 years,” Smithers says). Look closely and you’ll see a litany of great names, including “Shoeless Joe” (a real player, actually, by the name of Shoeless Joe Jackson). Mr. Burns’ old-timey baseball getup continues to delight throughout the episode.


    Welcome to Springfield: Aside from the abundance of baseball players, this episode is filled with old standbys. It is a bit odd, however, to see nuclear plant employee Charlie have as much screen time as Lenny and Carl.

    Episode as a GIF: “Darrrryyyllllll, Darrrrryyyyllll….”

    Analysis: “Homer at the Bat” is brilliant because it simultaneously functions as both an inspirational sports narrative and a parody of one. Burns bringing in his ringers addresses the plot point of so many embattled coach movies: “Why don’t you bring in some good players?” That the ringers’ removal from the game is all happenstance (and that Homer only wins the game by getting bonked in the head) is a hilarious subversion of the idea that the misfit team could ever come together to actually overcome adversity. The episode also resonates because, unlike most celebrity-packed TV jaunts, the narrative doesn’t sacrifice its storytelling and character work to cater to the guests. Also, the writers are clearly baseball fans. Since each of the cameoing baseball players are written in continuity with their own careers allows them to serve as more than just a mere celebrity guest. Canseco’s insanely high paydays are referenced, as is Wade Boggs’ legendary drinking and Ozzie Smith’s “The Wizard” nickname. That The Simpsons’ was able to translate those traits into hilarious and occasionally uncanny (“Good lord! Gigantism!”) traits was a testament to the level of heart and devotion the writers had for the material.

    –Randall Colburn

    05. 22 Short Films About Springfield

    Season Seven, Episode 21

    Premiere Date: April 14, 1996

    Writers’ Room: The obvious point of comparison for “22 Short Films About Springfield” is the unconventional 1993 biopic Thirty Two Short Films About Glenn Gould, about the Canadian pianist, but Pulp Fiction and its wandering narrative also influenced the episode, including the extended gag with Chief Wiggum and Snake. It also has roots in The Simpsons itself; the season four episode “The Front” and its climactic non-sequitur “The Adventures of Ned Flanders” was where the seeds of the idea were placed. Instead of trying to shoehorn other random, disconnected cutaways into episodes to fill time, the show went ahead and composed an entire episode of nothing but those.


    Essential Quote: Superintendent Chalmers’ farewell to Skinner after their short-lived meal together: “Well, Seymour, I must say, you are an odd fellow, but you steam a good ham.”

    D’oh! Moment: Homer accidentally locks Maggie in a newspaper bin (how quaintly old-fashioned!), and only worsens matters when he ends up pulling her clothes off while attempting to get her out.

    Best Visual Gag: After Flanders’ best efforts to chill and hammer the gum out of Lisa’s hair fail to pay off, the shot continues shifting as more and more of Springfield’s C-squad residents (Captain McAllister! Sideshow Mel! Lionel Hutz!) crowd into the kitchen to offer increasingly terrible advice on how best to approach Lisa’s problem. Then, after a quick cutaway, the kitchen is flooded with semi-familiar faces, and the absurd visual punchline of the Isotopes mascot flailing around in the center of the shot. The rapid escalation straight into a commercial break perfectly ties the whole gag together.


    Welcome to Springfield: Not this time, actually, aside from perhaps the tall man in the little car who publicly degrades Nelson for his cruelty.

    Episode as a GIF: It’s hard to pin such a wandering episode down, but it’s full of these quick, hilarious transitions…

    Analysis: “You ever think about the people in those cars?” As Bart and Milhouse spend another aimless day harassing commuters from an overpass, The Simpsons raises a question that cuts to the heart of the show’s longevity and obsessive fandom. Springfield has always been populated by a wild cast of characters, but especially at the time of the show’s seventh season, they’d always largely been seen through the prism of whatever the Simpson family happened to be doing at the time. It’s not as though “22 Short Films About Springfield” contains any new information about most of the characters who pop up in its vignettes, but for 22 minutes, the show lopes through its sprawling world and simply glances at how everyone exists when plot isn’t happening around them. The concept might be a direct reference to Glenn Gould, but “22 Short Films” could just as easily be taken as a love letter to Slacker and the wave of talky ‘90s independent cinema that was happening at the same time. Like the best of those films, there are odd moments of heart (Apu finally cutting loose, if just for five minutes) alongside the laughs, and it’s about a lot even as it ultimately might be one of the most plotless Simpsons episodes ever.

    –Dominick Suzanne-Mayer

    04. A Streetcar Named Marge

    Season Four, Episode Two


    Premiere Date: October 1, 1992

    Writers’ Room: When Jeff Martin first pitched this episode, it was Homer who’d be doing some community theater acting, but James L. Brooks rightly recognized the opportunity to tie a masterwork of American drama to the plight of poor, sweet Marge. It’s a great setup, giving us the best of the show’s musical episodes, a terrific sub-plot that sees Maggie take on her Ayn Rand-inspired day care provider, and a genuinely thoughtful look at the abusive nature of Homer and Marge’s relationship. (It also royally pissed off the citizens of New Orleans—check the chalkboard message in the next episode.)

    Essential Quote: “Can’t you hear me yell-a?/ You’re puttin’ me through hell-a!/ Stella! STELLA!” –Ned Flanders as Stanley Kowalski

    D’oh! Moment: Homer inadvertently contributes to Marge’s artistic process when he stages a one-on-one battle with the candy machine as she’s trying to rehearse with Ned. After it eats his change and he can’t force the candy out (D’oh!), he takes a running leap at the thing, and the machine spits out a dozen or so candy bars (Woohoo!). Cue Marge almost stabbing Ned in the face, fueled by white-hot rage.


    Best Visual Gag: The contestants of the Miss American Girl pageant each have a Miss Universe-style costume that represents their state. Some highlights include Miss Idaho (a spud), Miss Kansas (moving tornado headdress, complete with uprooted house), Miss North Carolina (cigarette going through her body), and Misses Alaska and Texas (both oil-themed).

    Welcome to Springfield: We saw abrasive theatrical auteur Llewellyn Sinclair and Ms. Sinclair, his stern sister and the owner of Ayn Rand School for Tots, only a few times, but both made a hell of an impression—no surprise, as they were both voiced by Jon Lovitz. The female Sinclair’s mostly there as a set-up for Maggie’s Great Escape, but Lovitz’s Llewellyn would land near the top of any list of the series’ best guest stars.

    Episode as a GIF:

    Analysis: God, what a gem. While “A Streetcar Named Marge” is funny from start to finish, it’s also one of The Simpsons episodes most packed with pathos. It’s not Marge’s talent that wins her the role of Blanche. It’s her palpable air of sadness and defeat, glimpsed by Llewellyn as she calls Homer to tell him she didn’t get the part (and yes, she’ll bring home a bucket of fried chicken. Yes, with extra skin.) When The Simpsons gets feminist, it’s usually Lisa who takes center stage, but in exploring Marge’s woes, Martin and company forced Homer (and Simpsons fans) to consider how damaging daily neglect and disrespect can be. The fact that Homer actually listens—at least a little—is what makes this episode one of the series’ best.

    –Allison Shoemaker

    03. Homerpalooza

    Season Seven, Episode 24


    Premiere Date: May 19, 1996

    Writers’ Room: Naturally, the seeds for “Homerpalooza” were planted by Perry Farrell’s iconic, once-touring music festival Lollapalooza. To gather intel for the episode, writer Brent Forrester actually went to one of the shows, thinking it would be a fun, spirited experience. Similar to Homer’s initial feelings at Hullabalooza, however, Forrester felt completely out of touch and spiritually removed, but he turned that nightmare into comedy gold. The garish advertising, the search and seizure of expensive cameras, and even charges of being a narc. More importantly, though, he found inspiration for Homer’s cannon ball act from Lolla’s Jim Rose Circus freak show, which is what ultimately set the stage for the episode.

    Essential Quote: This category is damn-near impossible, especially since the episode overflows with juicy music-related barbs, but we’ll give this one a proper tie between Bart’s pragmatic intuition (“Making teenagers depressed is like shooting fish in a barrel”) and Grampa’s all-too-haunting truths (“I used to be with it, but then they changed what it was. Now what I’m with isn’t it, and what’s it seems weird and scary to me. It’ll happen to you…”). Though, we’d be remiss to not include B-Real’s hilarious announcement to the crowd: “Before we start, we have a lost child here. If she’s not claimed within the next hour, she will become property of Blockbuster Entertainment.” It’s even funnier now, seeing how Blockbuster also went the way of the dinosaurs.

    D’oh! Moment: After being falsely dubbed a narc, accused of hate crimes, and tossed aside by a sea of rattled, angsty, alternative-loving fans, our yellow-bellied freak utters a dismissive “D’oh!”. Considering his choice of gear — an out-of-touch Rastafarian hat and a lame “Too Cool For This Planet” pin — it’s a blessing Homer received any butt support at all. Don’t even get us started on his lack of karma … ahem, karma, karma!


    Best Visual Gag: Nothing better explains the dichotomy between the Flower Children and Generation-X than Homer’s sobering trip to Springfield’s local record store…

    Welcome to Springfield: Peter Frampton, Cypress Hill, The Smashing Pumpkins, and Sonic Youth all fill the bill of Hullabalooza 1996 and all made vocal cameos for “Homerpalooza”. (Read more about their involvement here.) However, the original lineup was supposed to be much, much different, as the producers tried to nab Bob Dylan over Frampton and Courtney Love’s Hole over Sonic Youth. In fact, the infamous dialogue between “Billy Corgan, Smashing Pumpkins” and “Homer Simpson, smiling politely” was supposed to be for Love and Homer, to which Love would say “Hi Homer, I’m a big fan, Courtney Love” and Homer would say, “Homer Grateful.” Eh, let’s just say history played out accordingly, especially since we got the image of Frampton having a fit over his step pedal and Thurston Moore stealing watermelon out of his cooler. Ugh, goddamn kids…

    Episode as a GIF: Homer’s endless battle with trying to be cool, in a nutshell.

    Analysis: Despite the obvious ’90s overtones, “Homerpalooza” actually gets better over time, namely because everyone, no matter how hard they try not to, becomes Homer. Cool is a currency that’s always on the decline, evolving with age and every generation, and that evolution traditionally happens while you’re too busy living your own life. As Homer aptly tells Marge, “I used to rock and roll all night and party ev-er-y day. Then it was every other day. Now I’m lucky if I can find half an hour a week in which to get funky.” For a thirty-something writer whose entire life is pop culture, that line hits pretty damn hard, and although we’d be lying if we didn’t admit that the festival-centric episode tickled our festival-based minds, there’s something to be said of its exceedingly clairvoyant meditations on mortality and the inherent struggle of waving good bye to your fleeting feelings of eternal youth. By the end, Homer doesn’t care about the stage show, or his fans, or his fame, he feels that if he walks off the stage, he’s succumbing to the confines of adulthood. The scary thing is that he totally is, and what’s worse, is that nobody, not Lisa, nor Marge, nor Billy Corgan, have an answer for him. It’s just a part of life, and life, as we all learn, sometimes sucks.

    –Michael Roffman

    02. Marge vs. the Monorail

    Season Four, Episode 12


    Premiere Date: January 14, 1993

    Writers’ Room: This big-top episode had humble beginnings, originating when writer Conan O’Brien simply saw a billboard sporting the lone word “Monorail.” He pitched his idea to showrunners Al Jean and Mike Reiss at a story retreat, but, since the show wasn’t as slapstick and grandiose in those days, they felt it was a bit too much and wanted him to flesh out other material in the meantime. In the end, it wasn’t exactly hard to see the people of Springfield—save for a much wiser Marge Simpson—rallying behind a totally flashy idea pitched by a charming con artist with a song. So our beloved rubes got themselves a monorail!

    Essential Quote: The most quotable line in the episode is, of course, “Donuts, is there anything they can’t do?” First of all, even without context, this is a good quote and perspective for life. Honestly, the question could’ve been a backup riddle of the Sphinx. Secondly, this comes just seconds after Homer’s makeshift anchor finally stops the monorail by slamming into the giant donut atop the donut shop. Homer had already more or less come to terms with his impending doom, but, given his affinity for donuts, he doesn’t seem at all surprised that donuts have somehow saved his life.

    Best Visual Gag: It comes at the end, as the camera slowly zooms out to reveal the sprawling town. After Marge declares the Monorail to be “the only folly the people of Springfield ever embarked upon,” it’s revealed that’s not necessarily true. As it turns out, the locals also supported and built a popsicle stick skyscraper, a 50-foot magnifying glass (which torches the skyscraper), and a giant escalator that leads to absolutely nowhere. These people, man…


    D’oh! Moment: Everyone at the Springfield Town Hall gets caught up in the extraordinarily catchy Monorail song—the tune’s so good that O’Brien later performed it at the Hollywood Bowl—all working toward the song’s big finale. The only problem is that Homer doesn’t realize when the song’s over, so he starts another chorus before realizing he’s the only one and exclaims accordingly.

    Welcome to Springfield: The very memorable Lyle Lanley (voiced by the late Phil Hartman) is introduced as the handsome charlatan, a parody of The Music Man’s Harold Hill. Meanwhile, Leonard Nimoy plays himself for the first time, dropping vaguely poetic goodies like, “A solar eclipse; the cosmic ballet goes on.”

    Episode as a GIF: The monorail seems like an even more ludicrous idea when you recall how small the town is.


    Analysis: “Marge Vs. the Monorail” has been lauded by so many reviewers on so many lists for so many years, but, honestly, it belongs there. In early seasons like this one, The Simpsons often meditated on middle class struggles — marital strain (“A Streetcar Named Marge”), unrequited love (“New Kid on the Block”), staying healthy (“Homer’s Triple Bypass”) — but this episode was a play at the gleefully lunacy that would more or less become the show’s hallmark. The Simpsons is a curious pop culture staple that, to this day, absorbs, interprets, and reflects other pop culture. It spoofs and parodies with love. It takes art and asks, “Hey, what if this existed in Springfield?” So in this madcap reimagining of The Music Man, we get to see the whole town of our most beloved goofballs get behind a seriously absurd idea, and it’s times like these when Springfield feels most like home.

    –Jake Kilroy

    01. Homer Goes to College

    Season Five, Episode Three

    Premiere Date: October 14, 1993

    Writers’ Room: When Conan O’Brien came on in the fourth season, apparently, the late night great understood The Simpsons formula faster than anybody. David Mirkin coos at O’Brien’s zany talents and energy in the commentary for “Homer Goes to College”, and loved when O’Brien pitched an episode where Homer’s perception of higher education is primarily informed by really crappy Animal House rip-offs. You know, ones like School of Hard Knockers. With Corey Masterson!

    Essential Quote: “The bee bit my bottom” is classic. Homer asking his class, “Did you see that jerk?!” when his professor drops index cards is also a great. The very long “NNNNNEEEEERRRDDD!!” is so usable in so many ways, too. But for our money, the essential quote wasn’t even scripted: “I am so smart. I am so smart. I am so smart. S-M-R-T. I mean, S-M-A-R-R-T.” Dan Castelleneta gaffed in the recording studio. Or as The Simpsons crew attests, he really was Homer Simpson in that moment.


    D’oh! Moment: There are six sensational “D’oh!”s in “Homer Goes To College,” but the best are a series of them when Homer’s rejected from a ton of schools. Maybe it was the cake photo? Marge: “Homie, here are the responses from the colleges you applied to.” Homer: “D’oh! D’oh! D’oh! Whoo-hoo! A flyer for a hardware store! …D’oh!”

    Best Visual Gag: Speaking of “SMRTs,” at one point on the episode commentary, director Jim Reardon, who went on to co-direct Wall-E, demurely points out that Homer lighting his GED on fire is “the funniest fire ever.” We’d agree.

    Welcome to Springfield: The three nerds, Benjamin, Doug, and Gary, were introduced in this episode. And they all had nosebleeds. O’Brien based them off geeks in his Harvard dorm that would drop phone books on the floor to get the attention of girls below. Clever. Creepy, too. But these three have lasted, and have become fan avatars for the kind of pedantry and nitpickiness that comes with popular franchises like The Simpsons.


    Episode as a GIF:

    Analysis: “This is around the period where we started making Homer way too dumb. Yeah. This began the Homer… forgetting to make his heart beat… cells in Homer’s body being so stupid they forget to divide.” –Conan O’Brien, in the DVD commentary for “Homer Goes College”

    O’Brien couldn’t have characterized it any better, and that’s why we love this episode so much. The dumber Homer got, the funnier this show became, and this episode’s the apex of dopey, jerk-ass humor. It’s the height of The Simpsons’ rapid-fire comedy, the lowest depths of Homer Simpson’s intelligence. How a man that barely finished his high school education got to work around nuclear power is something we still can’t believe, and that’s the improbable genius of the show’s comedy — dumb comedy done super smart.

    And there’s lots to go around: A safety van melting down despite no nuclear material in it. Homer splitting a case of malt liquor with a pig. The terrifying appearance of a very vengeful Richard Nixon (“Don’t think you won’t pay!”). The TV and the rock tumbler. Mr. Burns’ struggling to lift a baseball bat. Bra bombs. Spiked punch. Nerds who say, “Ni!” Even zanier schemes. Curly. Straight. Curly. Straight. And, the infamous “running you over” prank.


    “Homer Goes To College” aces every last gag, ranging from referential to fantastical, and as a pure joke factory, no other episode comes close. O’Brien’s script can’t stop, Reardon’s direction is more than up to the speed of humor, and this episode fulfilled Groening’s animation promises by jamming the episode with zany, blunt, consequence-free hijinks at every turn and it’s still funny as all hell. We could watch Homer moronically chase a squirrel for days because it’s so smartly delivered and designed. Why must our number one be zany? Because why not, stupid head!?!?! Sorry. This episode is our series’ valedictorian.

    –Blake Goble


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