It’s pretty much impossible to pick one favorite Simpsons episode. Try it! You’ll think of one, but then immediately a half-dozen others will spring to mind that you can’t imagine not putting in that top spot. There are just so many classic episodes!
And this feature says a lot about that. I asked a number of Splitsider friends and contributors to write a bit about their all-time favorite episode. I asked them to let me know which episode they picked so I could keep track and make sure there were no duplicates. Amazingly enough, every single person picked a different episode. No two people picked the same one. And a handful of episodes I was sure would be fought over didn’t even get chosen.
So don’t view this as a definitive list of the best episodes. It’s not meant to be! Instead, it’s a collection of people talking about specific episodes that meant a lot to them. I know that there are dozens of episodes that have criminally been left out, and I had to stop myself from writing up more than one myself. But it’s a testament to this show that there are just so many Best Episodes Ever, isn’t it?
Homer vs. the Eighteenth Amendment
From my early adolescence – and now into my bearded late 20s – I have never understood why some people would get so butt-hurt about the alleged bad influence The Simpsons had on impressionable youths. One singularly unfunny elementary school teacher of mine once told us that Bart’s disrespect for authority had, through osmosis, made her job so difficult that she wanted to cry sometimes. (She also crossed the picket line during a teacher’s strike, and if there’s one thing I’ve learned, it’s that there’s no honor among scabs. Anyway.)
But that seemed ridiculous, even then. This was comedy, and comedy, if done well, had much to teach. Take an episode like “Homer vs. the Eighteenth Amendment,” which features a first act in which Bart not only gets (accidentally) drunk at the St. Patrick’s Day parade, but (1) shows no remorse, (2) proudly declares he’s going to Moe’s for a beer the next day and (3) receives no sort of admonishment or parental guidance away from alcohol use whatsoever. Oh, and Springfield outlaws booze, so Bart then helps Homer become a bootlegger, which highlights the uselessness of Chief Wiggum and necessitates hard-ass, hard-boiled Rex Banner coming to town.
Okay, so, yes, Bart’s involvement in the chief plot is the sort of thing that sounds a bit dodgy on paper from a “Won’t somebody please think of the children?” perspective. Which is kind of the point! (The aforementioned line even gets trotted out halfway through.) Because the episode isn’t really a celebration of alcohol as much as it’s about knee-jerk society’s dumb overreactions to isolated non-problems. One of the episode’s best gags is Banner’s cough-gurgle when trying to force a chuckle at a press conference, only to tell the assembled crowd, “Well, you all know what laughter sounds like.” We do! It’s the sound we make when we watch a show that respects its viewers enough to not shy away from difficult or ostensibly age-inappropriate subjects and, in doing so, sacrifice the opportunity to make a sharp point about a culture of blame and shifted accountability.
And thank the Angry Owl God for that, because if a comedy program has ever produced a more wonderful, truthful line than the episode’s closing, “To alcohol! The cause of – and solution to – all of life’s problems,” I’ve yet to hear it. So suck on that, you lousy scab.
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Last Exit to Springfield
Take Arrested Development or 30 Rock on their very best days and they’d still come up short against the frenetic pacing, well-chosen randomness, and generous Laffs Per Minute ratio of vintage Simpsons episodes like “Last Exit to Springfield.” After Mr. Burns does away with the company dental plan, Homer becomes an impassioned union leader by accident. Through a series of misunderstandings, unlikely union dynamo Homer intimidates Mr. Burns into thinking he’s a hardnosed negotiator. These misunderstandings unfold as great comedic set-pieces, such as when Homer interprets Burns’ bribe offering as a sexual come-on. “I don’t go in for these backdoor shenanigans,” Homer deflects, abruptly standing to leave. “Sure, I’m flattered – maybe even a little curious – but the answer is no.”
At the same time that Homer is squaring off against Mr. Burns for a dental plan, daughter Lisa is dealing with a prescription for braces. Unlike in later seasons of the show, here the B-story is directly informed and affected by the A-story, lending a thematic unity to the episode, rather than a sudden unearned convergence in the closing minutes. Even the pop culture references seem vital and necessary, as when Lisa’s first viewing of herself with braces resembles Jack Nicholson’s Joker in the plastic surgeon’s office. Arguably one of the all-time great episodes, “Last Exit to Springfield” bears all of the classic Simpsons hallmarks: cinematic homage, media satire, daydreams wherein donuts figure prominently, celebrity guests willing to poke fun at themselves, absurdity, and heart.
That’s right: heart. Although Homer is motivated by not wanting to pay for Lisa’s braces, he obviously cares about his daughter very much. That’s one of the secret weapons of early Simpsons – before they came to resemble gag-delivery machines, the central characters were family members who clearly loved each other. And that’s the tooth.
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Simpsons Roasting Over an Open Fire
It’s rather hard to separate my love of Christmas specials from my love of “Simpsons Roasting Over An Open Fire.” Even looking back to A Christmas Carol, the most memorable Christmas stories have been built on that familiar feeling of desperation and loneliness around the holidays. “Why is that everyone but me gets the perfect Christmas?”
And that’s why “Simpsons Roasting Over An Open Fire” is my favorite Simpsons episode. It sews familiar themes with characters unlike anything seen on television before: a real family. Sure, sitcoms in the past had realistic characters, but they were more often than not surrounded by wacky figures who created the comedy. Richie Cunningham was real. The Fonz was not.
Yet here we had a real family reacting to hardship around Christmastime. A troublesome son who wanted to show his Mom he loved her. A Mom who just wanted a happy family. A Dad who wants to not be a screw up anymore. A daughter starving to show off for approval. We’ve all seen these figures in our lives, especially around Christmastime, but never on television in the way that first episode showed us.
Every storyline in this episode is touching and interrelated. When Bart makes an impassioned plea to bet all of Homer’s money at the tracks – because TV says Christmas miracles do happen – the show is working on two levels. Comedically, we have a parody of the hokey “Tiny Tim” moment. Dramatically, we have a child who realizes his selfishness has pushed his father to desperation and only wants to see him through.
Am I being too heartfelt? Maybe. But, in my opinion, that’s what The Simpsons has lost in recent years. That feeling of desperation and earnestness behind the jokes. Not to be confused with darkness –- I’m not saying all comedy should come from horrible suffering –- but rather the reality of the everyday struggle which The Simpsons mined for so much hilarious commentary on the average American experience.
A Dad dressing up as Santa Claus and accidentally getting his greedy son on his lap is funny. Having that greedy son’s biggest mistake be realizing “the true meaning of Christmas” is genius.
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Marge vs. the Monrail
My favorite Simpsons episode of all time has long been “Marge vs. the Monorail.” On paper alone it’s a classic waiting to happen: Season 4, written by Conan O’Brien, guest starring Phil Hartman in a non-McClure role and Leonard Nimoy as himself. But what continues to impress me today about the episode is that, through the big concept, the fast-paced action and all the character work, there isn’t a single line that isn’t either a setup or a punchline, and nearly every one hits. Most of the punchlines even double as setups. It’s dialogue running at 100% efficiency, a formula that helped The Simpsons prove that animation wasn’t just an alternative vessel for the jokes in primetime comedy, but a way to surpass them in density, timing, and absurdity. And from the throwaways (“I shouldn’t have stopped for that haircut”) to the banter (Marge and Homer’s “Batman” back-and-forth) to the big Monorail song-and-dance (“The ring came off my pudding can!”/”Use my pen knife, my good man!”), “Marge. vs. the Monorail” is that rare episode that feels so perfectly quintessential while accomplishing more than most other episodes ever dared cram into 23 minutes.
Phil Hartman is at his best as Lyle Lanley, Homer is in top form, Marge gets to play hero, Bart bonds with his father, Quimby and Wiggum fight over the town charter and the mob rule of Springfield is at its sublimely stupidest, the townsfolk traipsing like shrieking lemmings from the town hall to the faulty monorail to the top of the Escalator to Nowhere and over. Front to back perfection.
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Bye Bye Nerdie
Quick. What’s your favorite Simpsons episode? What episode surpasses all others in tone, structure, and one-liners? What episode, if given the choice, would you select to represent the very best of the series’$2 20-year run – thereby dismissing 460-some-odd episodes in favor of a particular 22 minutes?
This is worse than Sophie’s Choice. At least she had an evenly split decision.
The Simpsons is virtually unlike any other show. It’s hit perfection so many times that it would be impossible for me to select a single episode as its best. The monorail. Homer goes to college. Joyriding with Ruth Powers. Marge in Streetcar. Lionel Hutz’s debut. Krusty gets canceled. The Springfield cat burglar. How could you possibly choose just one?
Hell, I can’t even say if the fourth or fifth season is my favorite.
But around Season Nine – when the show started falling short of perfection and became merely great – the slight decline was hard to ignore. The tone began to change. Celebrity cameos became more frequent. The number of B and B-minus episodes began stacking up. And once the series introduced tree-dwelling jockeys, the Loch Ness Monster, and “Armin Tamzarian” into its reality, I did what I never thought possible.
I started losing interest.
Weeks would go by where I would fail to tune in and never bothered to seek out the missed episodes. And what I did catch seemed stale or very forced. I became jaded, bad-mouthing the show, saying it should have ended years ago. And at the risk of losing any credibility I have with roughly half of you, I touted Family Guy as a superior program.
Then in March 2001, after a long hiatus, I sat down to watch The Simpsons. It was “Bye Bye Nerdie,” the episode where Lisa discovers the nerd pheromone that incites bullying. Compared to any random entry from Season Four or Five, no, it doesn’t measure up. But being a former superfan, having signed off on the show and asserting it would never be the same, something clicked. I was laughing. Hard.
Amazing gags from the A-story notwithstanding – Drederick Tatum admitting he has “little recourse” but to beat up Nelson and “Pi is exactly three!” – Homer as Springfield’s child safety manager had me rolling. And while I loved Kent Brockman’s report on how Homer’s toddler-conscious provisions is ruining the Get Well card and baby crutch industries, I rank Homer’s flawed “Safety Dance” – and his frozen position throughout Kent’s segment – in one of the Top Five Biggest Simpsons-Related Laughs I’ve ever had.
“Bye Bye Nerdie” rejuvenated my love for The Simpsons. Yes, I’ve been burned countless times since then, but that episode made me look at the series in a brand new light. I accepted the fact that it’s never going to be like how it was in ‘93, but what’s left can still be pretty good. Technically, “Bye Bye Nerdie” may not be my all-time favorite episode, but amidst Homer traveling into space and Skinner getting fired, it’s the only one I can easily single out.
But if technicality’s an issue, I’ll go with, ummm, Springfield legalizes gambling.
My family used to watch The Simpsons together every Sunday night –- Dad laughing, Mom glancing up every now and then from above whatever biography of whatever early president she was reading at the time. I would sit on the floor, pretending to get the jokes I was too young to understand. The Simpsons is one of those shows that lends itself to selective recall. I’ll refer to an episode as “the one where…” only to stream it on some Russian website and find that the part I’m remembering is 10 seconds long and unrelated to the rest of the plot. That’s definitely what happened with “Selma’s Choice,” the thirteenth episode from season four. It aired on January 21, 1993, which means I was six and my little sister, surely asleep in her bassinette that Sunday night, was only five months old. I re-watched “Selma’s Choice” yesterday; it seems I had forgotten most everything about it.
When Grandma Gladys dies, she leaves a video will, bequeathing Marge her collection of celebrity-look-alike potato chips (Homer eats them) and warning Patty and Selma against the loneliness of spinsterhood. Patty shrugs off the advice, but Selma takes it to heart and decides she wants a baby. Homer falls ill after weeks of eating a rotten sandwich, rendering him unfit to take Bart and Lisa to Duff Gardens, despite earlier promises. Selma steps up and agrees to escort the children to the theme park. It’s a forced maternal gesture that she immediately regrets, and she’s soon restored to her usual disgusting self. In lieu of artificial insemination, Selma chooses instead to adopt Jub-Jub, Gladys’s pet iguana.
Not only had I forgotten the entire preamble, but I had forgotten the basic storyline as well. What I remembered perfectly though was the not-even-full-scene in which Lisa drinks the water from the Little Land of Duff ride. She hallucinates, goes peaked, and gyrates around for a while before going home and coming down. Animated delirium directed at kids is horrifying, and there’s lot of it: “Pink Elephants on Parade” in Dumbo, “Heffalumps and Woozles” from Winnie the Pooh, some movie about an Orca whale and a coral infection that I’ve been trying – unsuccessfully – to find on YouTube for a good half-decade. It’s been about 18 hours now since I saw “Selma’s Choice,” and once again, all I remember is that Sally Cruikshank-y nightmare.
“Homer’s Enemy” ranks among the most singularly dark, heartbreaking and hilarious episodes in the long history of The Simpsons.
It achieves all of this with very little plot or character development and absolutely no lessons learned. At its core the entire episode is really about nothing more than watching Homer drive an innocent (if uptight) man slowly toward madness. It’s an extremely simple episode because the idea behind its creation was as well. It was conceived out of a writer’s room speculation about what would occur if a real human was thrown into Springfield and forced to interact with Homer Simpson.
The character in question here is Frank Grimes, a self-made man born out of a life of tragedy whose inspirational story earns him a job at the nuclear power plant. Grimes slide toward insanity is all driven by Simpson’s normal behavior. He eats Grimes’ “special dietetic lunch”, chews up all of his specially monogrammed pencils, causes him to receive a pay decrease, and hilariously refers to him as “Grimey” despite being asked repeatedly not to.
Upon being tricked into coming to dinner at the Simpson residence as part of Homer’s attempt to win him over, Grimes’s hatred for Homer grows upon realizing that he has “A dream house, two cars, a beautiful wife, a son who owns a factory, fancy clothes and lobsters for dinner.” In contrast, Grimes memorably states that that he lives in “a single room above a bowling alley and below another bowling alley”.
Blinded by his hatred for Homer and his growing, incessant need to expose him for the moron he knows him to be, Grimes tricks Homer into entering a power plant model building contest intended for children. When Homer beats out all of his child competitors, Grimes is overcome with anger and proceeds to storm his way through the power plant -– ultimately coming into contact with high voltage power lines that quite abruptly send him off to the great big animator in the sky.
In the greatest, most beautifully non-sentimental and phenomenally unapologetic endings in the history of The Simpsons, Grimes suffers additional posthumous indignity by being called “Grimey” at his funeral, which ends with Homer dozing off and talking in his sleep -– earning a laugh from the assembled mourners that distracts all attention away from the fact that Grimes’ casket is slowly being lowered into the ground.
Nothing would have been worse for the episode than if Grimes had come to realize that Homer wasn’t such a bad guy or Homer had learned anything at all. I shudder at the thought. Because, while I encounter a dozen Homer-like people everyday of my “real life” that I wish nothing but harm on, for some reason, when it comes those 22 brief minutes I get to spend in Springfield, I prefer my morons to be supremely oafish and the wake of their idiocy to be totally free of compassion or consequences.
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A Streetcar Named Marge
A musical version of A Streetcar Named Desire. That should be enough. With a premise like that, most of the work is done for you. But what makes “A Streetcar Named Marge” the best Simpsons episode of all time isn’t Apu’s plaintive third act solo or Flanders’s 12-pack abs – although all the bits in the episode are killer. And it’s not an inspired guest turn from John Lovitz, or enough culture-nerd catnip to fill a grad school seminar. “Streetcar” stands out not just because it’s indelibly clever, but because it’s incredibly heartfelt.
But let’s talk about the play first. That play! “Oh, Streetcar!” as directed by the unhinged Llewellyn Sinclair. Wiggum and Flanders as the most unlikely Mitch and Stanley you could imagine. Dance sequences. Lasers. A stirring, upbeat musical finale that happens to completely miss the entire point of the original Streetcar. And at the center of it all, Marge Simpson as the long-suffering Blanche DuBois. And there’s the rub.
Homer’s boorishness has been a fixture of The Simpsons since the Tracy Ullman Show shorts, but it’s generally just, well, cartoonish. The reason Marge makes such a great Blanche, though, is that Marge is Blanche: emotionally abused, painfully optimistic, neglected. Llewellyn Sinclair sees it right away, and the main arc of the episode pounds the point home. It’s sympathy by proxy. For the first time, we really care about Marge Simpson, the person. We’re not just laughing anymore. We’re invested.
That makes it sound like the episode’s not funny. It is! Nearly every line kills, from the phrase “jive-talking robots” to Lionel Hutz’s scene-stealing appearance. “Streetcar” is also most reference-heavy episodes of the The Simpsons’ early years, with major nods here to The Birds, The Great Escape, Citizen Kane. Maggie’s daycare center is The Ayn Rand School for Tots, for goodness sake. Alfred Hitchcock makes an appearance.
But by the end, when Marge and Homer reconcile after he sees the Stanley in himself? One hand may be busy patting yourself on the back for being in on the jokes, but the other is reaching for a box of tissues.
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Treehouse of Horror VII
Most Simpsons episodes growing up were a weekly treat, but the “Treehouse of Horror” specials – those were an annual event. They were real push-the-coffee-table-aside nights for the Cassels brothers. Even my mom, on occasion, put down the John Grisham novels and Marlboros that typically marked her evenings and joined us for The Simpsons at its most outrageous.
“Treehouse of Horror” was when the show’s writers, momentarily freed from the shackles of realism, loosened their neckties and unleashed the twisted contents of their brains with three 7-minute horror/sci-fi/fantasy satires, presented Rod Serling anthology style. And one of the specials’ finest installment is VII’s “Citizen Kang,” in which the tentacled, Cold War-era space aliens Kang and Kodos impersonate then-presidential candidates Bill Clinton and Bob Dole.
What’s remarkable is how little “Citizen Kang,” which I recently re-watched, has dated despite focusing on a 14-year-old campaign. It’s not trying to skewer national politics in 1996; it’s really just line after line of damn hilarious ‘50s broken sci-fi English booming from the mouths of two stuffy politicians. (“Tomorrow, when you are sealed in the voting cubicle, vote for me… Bobdole,” Kang shouts.) Any political message just felt like a fortunate side-effect of the show’s greater goal to be funny, which is the way The Simpsons should feel.
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Homer at the Bat
Normally, a slew of celebrity guest stars makes for a stunty, cheap episode of a TV show, made for sweeps and to jack up the ratings with some half-assed cameos. But with “Homer at the Bat,” The Simpsons managed to take nine (!) baseball-playing guest stars and fit them into an episode that was not only incredibly funny, but retained at its heart a classic story about Homer.
It’s incredible that they managed to give every single one of the involved players their own hilarious and memorable gag. From Don Mattingly’s “sideburns” to Steve Sax’s issues with the Springfield Police Department, I think it’s safe to say that there are a whole lot Simpsons fans out there who know these players’ jokes from the show much more than anything they did while actually playing baseball.
Making the episode even more fun to watch for the fifteenth time is some of the info available on the recording sessions from the players. For example: “Ken Griffey, Jr. did not understand his line “there’s a party in my mouth and everyone’s invited” and got quite frustrated when he was recording it. He was directed by Mike Reiss, and his father Ken Griffey, Sr. was also present, trying to coach his son.” It doesn’t get much better than that.
But despite the incredible use of the baseball players, the episode is still clearly about Homer and his Wonderbat. The episode has one of the best endings of any Simpsons episode, too: Homer ends up victorious not because of an amazing hit, but by being knocked unconscious by a pitch. His limp, passed-out body paraded around the field in victory, and then that segues into Terry Cashman’s “Talkin’ Softball” playing over the credits, a song that’s able to be laugh-out-loud funny by just reminding you of things you just watched.