(Some of) Our All-Time Favorite Simpsons Episodes

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.

Jordan Ginsberg

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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.

Joe Berkowitz

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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.

Mike Drucker

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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.

Alden Ford

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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’ 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.

Mike Schuster

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