There’s not a moment I can remember when The Simpsons hasn’t been on the air. And for a long time, it’s been a big part of my life. This list took a while to decide upon, but these are my ultimate favorites, ones that represent why I love this show so much. Before we get started, here’s a quick bonus pick.
Best Treehouse of Horror Segment: “Citizen Kang” (Season 8)
Even though the annual Halloween episode is a big tradition, most of them always contain one classic short and two so-so stories. That’s why I can’t devote one entire anthology to a top 10 spot. But of the great shorts, this remains the gold standard. Kang and Kodos abduct Homer, along with presidential candidates Bob Dole and Bill Clinton, replacing themselves as the Republican and Democratic nominees to dominate earth. That leads to one of the series’ best lines, and some of the most accurate statements ever made about politics, including…
Kang: “It makes no difference which one of us you vote for. Either way you’re planet is doomed. DOOMED!”
10. “Behind the Laughter” – Season 11
Poking fun at itself, its parent network and the rest of the TV landscape is well-worn territory for The Simpsons by now. But “Behind the Laughter,” a Behind the Music parody Fox would later steal for its own tawdry tell-all specials about The Partridge Family, is a classic because it imagines the family Simpson as actual actors, telling the behind-the-scenes horrors of performing stunts and receiving anti-hormones to make it look like they stay the same age. The actors grow to hate each other and eventually are reunited by Willie Nelson.
Willie Nelson: “Thank you, Taco, for that moving tribute to Falco.”
9. “Blame it on Lisa” – Season 13
The very best of the “Simpsons go somewhere” episodes, and perhaps the series’ most controversial episode to date. The family head to Brazil to track down an orphan Lisa has sponsored. They arrive to see an array of inappropriate kids shows, colored lines of rats and crime—so much crime. But it’s hard to think of an episode that makes me laugh more, whether it’s Bart watching his new favorite show Teleboobies, or Homer reading a book called How to Loot Brazil. The city of Rio threatened to sue Fox, and it’s not hard to see why. It’s unflattering as hell, but the source of great comedy.
Homer: “I have a bladder the size of a Brazil nut!”
Kidnapper: “Around here we just call them nuts.”
8. “Hurricane Neddy” – Season 8
Ah, religion. One of the show’s favorite points of contention. Tackled head-on in “Homer the Heretic” – which just barely missed the cut – but done in a more genuine way here, “Hurricane Neddy” finds its most religious (and genuinely nice) resident experiencing a real crisis of faith. After a hurricane blows its way through Springfield but only destroys Ned’s house, he relies on the community to help him, but is reaches his breaking point by their sheer ineptitude. This episode never implies that Ned shouldn’t believe in God because of his misfortune, but rather gives him the chance to work out his issues with his Lord.
Ned: “Homer, you are the worst human being I have ever met.”
Homer: “Hey, I got off pretty easy.”
7. “A Fish Called Selma” – Season 7
Undoubtedly, the world would be a better, funnier place if Phil Hartman was still alive. But all we have of him are his weekly pieces of genius on Saturday Night Live and NewsRadio, as well as his many appearances here. Troy McClure is easily one of my favorite characters and this his finest hour, er not, considering what a terrible person he turns out to be. Inspired by his agent to start a family as the key to his career’s re-launch, he snuggles up to Marge’s sister Selma. She’s completely taken by a real-life movie star fawning over her, but it’s all for his image. And it works, too. He gets the lead in Planet of the Apes: The Musical, easily the show’s best musical moment.
Louie: “Troy McClure?! You said he was dead!”
Fat Tony: “No, what I said is that he sleeps with the fishes! You see.”
Louie: “Uh, Tony, please, no. I just ate a whole plate of dingamagoo.”
6. “22 Short Films About Springfield” – Season 7
One of the great things about The Simpsons is its ever-expanding universe. Very few shows (only Lost and Parks and Recreation come to mind) that actually explore the worlds the characters inhabit, adding characters and mythology to the show’s framework. No episode better shows what it’s like to live in Springfield than this wildly inventive series of shorts. Pretty much every inhabitant gets his moment to shine, including people who don’t even have real names like Comic Book Guy and Bumblebee Man. And not one but two Pulp Fiction parodies. If you’ve ever wanted to explore the world beyond 742 Evergreen Terrace, this is the place to start.
Superintendent Chalmers: “Aurora Borealis?! At this time of year? At this time of day? In this part of the country? Located entirely within your kitchen? May I see it?”
Principal Skinner: “No.”
5. “E Pluribus Wiggum” – Season 19
Satire doesn’t get any sharper than this, as Springfield becomes the first municipality to hold the presidential primary. Candidates from both parties descend on the town to pander at the townsfolk while the news media swoops in to declare a winner and move on. Fed up, Springfieldians overwhelmingly choose 8-year-old Ralph Wiggum as their candidate.
Bill Clinton (on the phone with Hillary): “What did I do to deserve this? Oh, right. Never gonna let that go, are you?”
4. “Cape Feare” – Season 5
I tell you, it’s really hard to pick a favorite Sideshow Bob episode. Aside from the pointless “Day of the Jackanapes,” they’re all winners. So I’m going with this Cape Fear parody, which finds Sideshow Bob on parole, tracking down the family who has gone into Witness Protection. Between the now-classic rake scene and hearing Kelsey Grammer belt out the score of the H.M.S. Pinafore, I have to pick this one, especially because it ends with Chief Wiggum’s best line ever: “It’s a good thing you drifted by this brothel.”
BEST LINE (aside from the one above):
Parole Board Member: “No one who speaks German could be an evil man.”
3. “A Milhouse Divided” – Season 8
And that brings us to marriage, one of the few institutions the show seems to respect and honor. While Kirk and Luann van Houten go through a bitter divorce, perhaps the show’s most painfully funny storyline, Homer begins to wonder if his own marriage is doomed. The show commonly brings up how much Marge gave up to be with Homer, and here is one of the few times it seems like they might actually separate. Homer’s stupid-but-heartfelt renewal vows represent what this show does best: it may often be silly, but it’s always sincere.
Kirk: “I sleep in a racing car bed. Do you?”
Homer: “I sleep in a big bed with my wife.”
2. “Marge vs. the Monorail” – Season 4
Perhaps the single best-written episode of the series, courtesy of a script by Conan O’Brien, “Marge vs. the Monorail” features another fine performance by Phil Hartman, as trickster Lyle Lanley, who tricks the town into buying a faulty monorail system through song and dance. Leonard Nimoy guest stars as a doltish version of himself, who proves especially inept in a time of crisis when the monorail speeds up to dangerous levels.
Homer, about the family of opossums who lives in the fire extinguisher compartment of his cabin: “I call the big one Bitey.”
1. “Homer’s Phobia” – Season 8
When it comes down to it, this is ultimately the best episode the show has ever produced. Sincere and hilarious, it tackled a topic so taboo Fox censors initially rejected the whole shebang. When Homer befriends a junk store owner named John (guest star John Waters), he’s thrilled to have a cool new partner in crime. But reverses course once Marge reveals John is gay. Initially uncomfortable around him, Homer becomes paranoid John will “turn” Bart gay and sets out on a masculine course to “save” his son. This episode not only dispels rumors about the LGBT community, it does so in a genuinely funny and understanding way.
Homer: “This man is a fruit. I mean queer! That’s what you like to be called, right?”
John: “Well that or John.”