Image courtesy 20th Century Fox
By EDER CAMPUZANO
The Oregonian/OregonLive
It was just a week before Christmas in 1989 when America was introduced to Bart, Homer, Marge, Lisa and Maggie Simpson outside the confines of their regular appearances on "The Tracy Ullman Show."
Now, Matt Groening's cartoon creations are preparing to begin their 30th season, a landmark that further solidifies "The Simpsons" as television's longest-running scripted comedy. And as the largest newspaper in the state with the only Springfield that matters -- suck it, Springfield, Ohio -- we figured it was our duty to jump on the occasion and proffer our takes on the best episodes the show has to offer.
Of course, we had to set a couple of ground rules to ensure there's a bit of variety in the list:
- We're only including one Sideshow Bob episode in this countdown
- Same rule goes for "Treehouse of Horror." Only the best entry makes it in
So, without further ado, here are the 30 best Simpsons episodes ever:
READ MORE: The Simpsons debuted 30 years ago today. Here are our 30 favorite quotes
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30. Simpsons Roasting on an Open Fire, season 1
Quote of the episode: "I'm Bart Simpson. Who the hell are you?" --Bart
Image via Frinkiac
You've got to give it up for the one episode that started it all.
Six hundred and thirty eight entries follow this one so far, but "Simpsons Roasting on an Open Fire" is still infinitely re-watchable and, we dare say, the best Christmas episode the series has to offer.
Original air date: Dec. 17, 1989
Directed by: David Silverman
Written by: Mimi Pond
29. Lisa the Iconoclast, season 7
Quote of the episode: "Embiggens? I never heard that word before I moved to Springfield." --Mrs. Krabapple
Image via Frinkiac
Years after Homer's "D'oh!" entered the public lexicon, "The Simpsons" gave us another pair of words that have also seen wide adoption: Embiggen and cromulent.
Now if you'll excuse us, it sounds like our johnnycakes are ready.
Original air date: Feb. 18, 1996
Directed by: Mike B. Anderson
Written by: Jonathan Collier
28. Two Bad Neighbors, season 7
Quote of the episode: "The boy's name is Bart ... I don't know the name of the man."--George H.W. Bush
Image via Frinkiac
Before 2016, it was fairly rare for a television show to regularly draw the ire of the man in the White House. Yet 20 years ago, "The Simpsons'" feud with George H.W. Bush came to a head with this episode years after the 41st president urged Americans to be "more like the Waltons and less like the Simpsons."
(Barbara Bush also famously called the show "the dumbest thing I've ever seen.")
Add that trivia to to the fact that this is the first appearance of Disco Stu and "Two Bad Neighbors," and this episode is one for the record books, folks.
Original air date: Jan. 14, 1996
Directed by: Wesley Archer
Written by: Ken Keeler
27. 22 Short Films About Springfield, season 7
Quote of the episode: "That isn't smoke, it's steam! Steam from the steamed clams we're having. Mmmm, steamed clams!" --Seymour Skinner
Image via Frinkiac
The most unique episode of the series is responsible for one of the strangest memes to derive from any TV show ever.
Even without the "Steamed Hams" bit, "22 Short Films About Springfield" is a rapid-fire exercise in brilliant comedy, perfectly punctuated with every short segment that gives us stories about characters doing seemingly mundane things like discussing Krusty burgers, taking short work breaks or having the boss over for dinner.
Original air date: April 14, 1996
Director: Jim Reardon
Writers: Richard Appel, David S. Cohen, Jonathan Collier, Jennifer Crittenden, Greg Daniels, Brent Forrester, Rachel Pulido, Steve Tompkins, Bill Oakley, Josh Weinstein, Matt Groening
26. Mr. Lisa Goes to Washington, season 3
Quote of the episode: "We the purple? What the hell is that?" --Essay contest parent
When a little girl is about to lose her faith in democracy, the Washington, D.C., bureaucracy jumps into action to salvage what's left of it. Where else than in America -- or possibly Canada? -- could such wondrous things happen in the early '90s?
Original air date: Sept. 26, 1991
Directed by: Wes Archer
Written by: Al Jean and Mike Reiss
25. You Only Move Twice, season 8
Quote of the episode: "You don't like these shoes? Then neither do I -- get the hell out of here!" --Hank Scorpio
This episode produces the most memorable one-off character to survive a run-in with Homer. (R.I.P., Frank Grimes.)
You've got to hand it to the writers who gave us Hank Scorpio. Not only does he run off with every scene he appears in, but he seems to have a thorough understanding of the market for one of Cypress Creek's hottest commodities: The hammock.
Original air date: Nov. 3, 1996
Directed by: Mike Anderson
Written by: John Swartzwelder
24. Cape Feare, season 5
Quote of the episode: "Oh, I'll stay away all right. Stay away ... FOREVER." --Sideshow Bob
If we're limiting ourselves to one Sideshow Bob episode, why not the one where he performs Gilbert and Sullivan's "H.M.S. Pinafore" in all its glory?
Original air date: Oct. 7, 1993
Directed by: Rich Moore
Written by: Jon Vitti
23. Lisa on Ice, season 6
Quote of the episode: "Me fail English? That's unpossible!" --Ralph Wiggum
By the time its sixth year came around, sibling rivalry wasn't exactly a new concept for "The Simpsons." The very good second-season episode, "Bart vs. Thanksgiving" set the stage for other episodes like it, and "Lisa on Ice" takes delight in grabbing that dynamic and replacing the eating holiday with the hockey rink.
Original air date: Nov. 13, 1994
Directed by: Bob Anderson
Written by: Mike Scully
22. Radio Bart, season 3
Quote of the episode: "The time has come for finger-pointing, and most of them are squarely aimed at the boy's parents." --Kent Brockman
The classic fable of "The Boy Who Cried Wolf" has never been funnier in any incarnation before or since. Also, who'd have thunk Sting would make such a good digger?
Original air date: Jan. 9, 1992
Directed by: Carlos Baeza
Written by: Jon Vitti
21. Bart Gets Famous, season 5
Quote of the episode: "One day, you're the most important guy that ever lived. The next day, you're just some schmoe working in a box factory." --Krusty the Clown
Mere months separate this episode from "Bart's Inner Child," another product of the show's very excellent fifth season that sees the eldest Simpson kid become an obsession of sorts for the residents of Springfield.
But the box factory and former writer Conan O'Brien's late-night shenanigans make this the superior "all-mighty Bart' entry.
Original air date: Feb. 3, 1994
Directed by: Susie Dietter
Written by: John Swartzwelder
20. Homer's Barbershop Quartet, season 5
Quote of the episode: "Baby on board, something something, Burt Ward. This thing writes itself!" --Homer
By season seven, every living member of The Beatles had guest starred on "The Simpsons." In 1993, it was George Harrison's turn, remarking on the seemingly unremarkable sight of Homer's barbershop quartet staging a reunion show on a rooftop as the rest of Springfield nods along in delight.
Original air date: Sept. 30, 1993
Directed by: Mark Kirkland
Written by: Jeff Martin
19. Bart the Daredevil, season 2
Quote of the episode: "Ladies and gentlemen: The 10-year-old with an attitude! When he's not in class, he's risking his ass. Bart Simpson!" --Announcer
Even after nearly 30 years, one of the show's most iconic sights is that of Homer sailing across Springfield Gorge, hopes high as he stands atop Bart's skateboard. Even more iconic are the grunts of pain the Simpson patriarch utters as he hits every rock on the way down the side of a cliff -- twice.
Original air date: Dec. 6, 1990
Directed by: Wesley Meyer Archer
Written by: Jay Kogen and Wallace Wolodarsky
18. Boy-Scoutz 'n the Hood, season 5
Quote of the episode: "Twenty dollars? But I wanted a peanut!" --Homer
When Bart goes on a Squishee bender, he ends up signing up for Springfield's equivalent of the Boy Scouts.
While the musical number parodying "New York, New York" and Homer's fascination with a lone peanut as $20 dangles in front of him are classic moments on their own, you can never discount the one thing that makes this episode truly roundup-worthy: An appearance by Ernest Borgnine, who you may remember as Sgt. Fatso Jetson in "From Here to Enternity."
Original air date: Nov. 18, 1993
Directed by: Jeffrey Lynch
Written by: Dan McGrath
17. Treehouse of Horror V, season 6
Quote of the episode: "Oh, I wish, I wish I hadn't killed that fish." --Homer
The "Treehouse of Horror" series, at its core, flexes the show's penchant for parody in both its best and worst ways. Fortunately, most of the series' early shots at Halloween-themed comedy -- in this instance, Stanley Kubrick's "The Shining," Ray Bradbury's "The Sound of Thunder" and the film "Soylent Green" -- are spot-on.
R.I.P., Willy.
Original air date: Oct. 30, 1994
Directed by: Jim Reardon
Written by: Greg Daniels, Dan McGrath, David S. Cohen and Bob Kushell
16. And Maggie Makes Three, season 6
Quote of the episode: "Homer, you promised: One night of family time a week. Besides, that back-talking boat sets a bad example." --Marge
One of the greatest strengths of "The Simpsons" lies in its ability to evoke legitimate emotion about its yellow, four-fingered stars. "And Maggie Makes Three" is a great flashback episode on its own, but that final shot of Homer's workspace is enough to melt even the iciest of hearts.
Original air date: Jan. 22, 1995
Directed by: Swinton O. Scott III
Written by: Jennifer Crittenden
15. Bart Sells His Soul, season 7
Quote of the episode: "I want you to clean every one of these organ pipes that you have befouled with your popular music!" --Reverend Lovejoy
The greatest criticism of network comedies and sitcoms is typically the format's insistence on episodes where earth-shaking, character-defining events return to the status quo by the time the credits roll.
"Bart Sells His Soul" is no different, what with the eldest Simpson kid learning a valuable lesson about his own morality and Moe, the eternal sourpuss, discovering there's money to be made by being nice with both returning to the status quo when the credits roll. But if this episode proves anything about the formula, it's that the journey itself is what's important when you're watching 22 minutes of foul-mouthed animated creations.
Original air date: Oct. 8, 1995
Directed by: Wesley Archer
Written by: Greg Daniels
14. Flaming Moe's, season 3
Quote of the episode: "It's like there's a party in my mouth and everyone's invited!" --Moe
By the time "The Simpsons" entered its third season, it had pierced American culture so thoroughly that landing guest stars like Aerosmith was no problem at all. And this wasn't even the biggest cameo of the season.
Original air date: Nov. 21, 1991
Directed by: Rich Moore and Alan Smart
Written by: Robert Cohen
13. Duffless, season 4
Quote of the episode: "The other day I was so desperate for a beer, I snuck into a football stadium and ate the dirt under the bleachers." --Homer
For much of series' run, Homer has been defined by two things: His bottomless appetite for doughnuts and his never-ending thirst for beer.
There's no AA for fried dough, so "Duffless" offered us a glimpse at the Simpson patriarch's gluttonous consumption of his favorite beverage with a delightful side-story featuring Bart, Lisa and a flying gerbil.
Original air date: Feb, 18, 1993
Directed by: Jim Reardon
Written by: David M. Stern
12. Homer the Great, season 6
Quote of the episode: "Who holds back the electric car? Who makes Steve Guttenberg a star? We do!" --The Stonecutters song
Who's been keeping the lost city of Atlantis lost for all of these years? Who's been scuttling the very obvious presence of intelligent life out of sight of us regular humans?
In 1995, "The Simpsons" set out to answer these questions and load all of the conspiratorial answers into one jaunty shanty.
Original air date: Jan. 8, 1995
Directed by: Jim Reardon
Written by: John Swartzwelder
11. Stark Raving Dad, season 3
Quote of the episode: "Doctor, if you just talk to him for five minutes without mentioning our son Bart, you'd see how sane he is." --Marge
Michael Jackson's part in this episode was shrouded in such secrecy that it was only confirmed by Matt Groening recently. The show's third season premiere was so masterful in its use of the celebrity appearance that its subversion of the cameo makes it all the more enjoyable to watch.
And in its final moments, "Stark Raving Dad" offers us one of the most heartfelt moments between the Simpsons kids since season two's "Bart vs. Thanksgiving."
Original air date: Sept. 19, 1991
Directed by: Rich Moore
Written by: Al Jean and Mike Reiss
10. The Cartridge Family, season 9
Quote of the episode: "If I didn't have this gun, the King of England could just walk in here any time he wants and start shoving you around. Do you want that?" --Homer
When "The Cartridge Family" debuted, the show hadn't yet come to rely on cheesy licensed musical numbers to pad their airtime and the use of Tom Petty's "The Waiting" is a master class in how to do it properly, even if the execution is a tad cringe-worthy given recent history.
Still, this episode's skewering of gun fanaticism worked exceptionally well when it originally aired, even earning the ire of the NRA for the way it portrayed the club's members.
Original air date: Nov. 2, 1997
Directed by: Pete Michels
Written by: John Swartzwelder
9. Itchy & Scratchy & Marge, season 2
Quote of the episode: "I told you she was soft on full-frontal nudity." --Maude Flanders
It's funny to think there was a time when cartoon violence and blood in video games was cause for concern and even the subject of congressional hearings.
"The Simpsons" was a little ahead of the curve on the latter, coming in with its commentary on freedom of expression a full two years before parents around the country freaked out about "Mortal Kombat."
Marge's crusade against "The Itchy & Scratchy Show" ends abruptly when Michelangelo's "David" goes on display at the Springfield Museum, offering up a blunt commentary on the idea of what sort of art is allowed to be considered crude.
Original air date: Dec. 20, 1990
Directed by: Jim Reardon
Written by: John Swartzwelder
8. A Milhouse Divided, season 8
Quote of the episode: "Crackers are a family food. Happy families. Maybe single people eat crackers -- we don't know. Frankly, we don't want to know. It's a market we can do without." --Cracker factory boss
Would you know dignity if you saw it?
As "The Simpsons" faced the final stretches of its first decade on the air, the show took to shaking up some of its familiar dynamics (although not in a way that stressed the family itself). In "A Milhouse Divided," Bart and Homer discover divorce as it's presented through the very literal thick lenses worn by their blue-haired friends.
The episode offers a bit of rare, pre-emptive introspection from Homer: For possibly the first time in the series, he trundles off to save his marriage even though it was never in any danger to begin with.
Original air date: Dec. 1, 1996
Directed by: Steven Dean Moore
Written by: Steve Tompkins
7. Homer at the Bat, season 3
Quote of the episode: "Something told me this was a very special, very magical piece of wood ... that I could make a bat out of." --Homer
Crossovers be damned.
Juggling rights to characters across networks is one thing. But recruiting nine Major League Baseball players to voice themselves in a single episode is a whole 'nother beast.
Not only did the show's producers pull off the feat, its writers also gave each and every one of these guys -- from Ken Griffey, Jr. to Jose Canseco -- worthwhile bits of dialogue that are memorable to this day. It may have taken six months to get all their lines recorded, but the result is one of the funniest half hours of television ever produced.
Original air date: Feb. 20, 1992
Directed by: Jim Reardon
Written by: John Swartzwelder
6. The PTA Disbands, season 6
Quote of the episode: "Talking out of turn? That's a paddlin'. Looking out the window? That's a paddlin'. Staring at my sandals? That's a paddlin'. Paddling the school canoe? Ooh. You better believe that's a paddlin'."--Jasper
Just as Spider-Man has the best rogues gallery in comics history, writers for "The Simpsons" have, quite possibly, created the best supporting cast America's favorite four-fingered family could ask for.
"The PTA Disbands" puts some of Springfield's zaniest residents on full display, from Professor Frink and his fascination with bubbly primary colors to Jasper and his archaic understanding of elementary education. One of the show's strongest -- and, curiously, most scant -- bit characters, Leopold, gets some time to shine.
Season six is one the most consistently hilarious collections of "Simpsons" episodes, and "The PTA Disbands" is the feather in its cap.
Original air date: April 16, 1995
Directed by: Swinton O. Scott III
Written by: Jennifer Crittenden
5. Who Shot Mr. Burns? seasons 6 and 7
Quote of the episode: "These fumes aren't as fun as beer. Sure, I'm all dizzy and nauseous, but where's the inflated sense of self-esteem?" --Barney
Yes, this is actually two episodes. Yes, this is cheating. No, nobody cares.
The sixth season of "The Simpsons" was capped with the show's first-ever (and only) cliffhanger. When C. Montgomery Burns pulls off his most cartoonishly diabolical stunt ever -- blocking the sun over the city of Springfield -- he gives everyone in town a motive for trying to do him in.
As the mystery barrels toward its outlandish conclusion, we're pulled along as Clancy Wiggum trundles his way through the clues. The set-up allows some of Springfield's quirky residents to shine, from Groundskeeper Willy's hilarious interrogation to Seymour Skinner's comically anodyne interview.
Original air dates: May 21 and Sept. 17, 1995
Directed by: Jeffrey Lynch (Part 1), Wes Archer (Part 2)
Written by: Bill Oakley and Josh Weinstein
4. Lisa's Substitute, season 2
Quote of the episode: "A vote for Bart is a vote for anarchy!" --Martin's and Bart's campaign posters
From the beginning of the series, Lisa Simpson worked as the show's straight man in tandem with Marge, often butting into Homer and Bart's fun as the voice of reason. The first two seasons of the show give us a well-defined picture of Lisa based on how she's treated by the rest of her family -- from the mother-daughter trevails of "Moaning Lisa" to the sibling rivalry best summarized in "Bart vs. Thanksgiving."
But "Lisa's Substitute" puts the middle Simpson child front-and-center as an assertive player with a firm grip on her own thoughts and emotions.
While Homer and Bart get to play their buffoonery for laughs, Lisa shines as the show's primary source of introspection. And nowhere is it more apparent and moving during "The Simpsons" run as it is when Lisa wrestles with her first crush.
Original air date: April 25, 1991
Directed by: Rich Moore
Written by: Jon Vitti
3. Mr. Plow, season 3
Quote of the episode: "I'm Mr. Plow, that's my name, that name again is Mr. Plow!" --The Mr. Plow jingle
Let me spoil one thing about the last three entries in this list: Every single one of them includes at least one earworm that, I can only assume, wriggled around in the heads of every early Simpsons fan upon first airing for weeks on end. (I was 5 when this episode came out, so, no, I didn't catch it on its initial run.)
The Mr. Plow jingle is one of the series greatest tunes, although it's a shame the Plow King theme hasn't been so etched in the public consciousness nearly as much.
The tunes come at the tail end of an episode that already offers some of the best moments in "The Simpsons" history, from Homer smashing into his own car to God knocking Mr. Plow and the Plow King a peg or two when they decide to join forces.
Original air date: Nov. 19, 1992
Director: Jim Reardon
Written by: Jon Vitti
2. Last Exit to Springfield, season 4
Quote of the episode: "Look at them all, through the darkness I'm bringing. They're not sad at all -- they're actually singing! They sing without blenders. They sing without flungers, capdabblers and smendlers!" --Mr. Burns
"Dental plan? Lisa needs braces."
"Now do 'Classical Gas.'"
"Hired goons?"
More than almost any other episode of the show, "Last Exit to Springfield" is defined by the little moments as much as it is the broad strokes. What began as a simple question in "The Simpsons" writers' room -- what if the Springfield Nuclear Power Plant went on strike? -- turned around one of the series' all-time greats.
In its goofiest moments, the episode plays on parody in grand gesture (think Mr. Burns voicing his frustrations like the Grinch) as well as small flourishes (like a vulture that resembles the evil power plant owner perching on a post right next to him, a la "Citizen Kane.")
There's nary a "Simpsons" fan you'll meet that wouldn't consider "Last Exit to Springfield" among the show's best episodes. Still, there's one entry that rises over the rest ...
Original air date: March 11, 1993
Directed by: Mark Kirkland
Written by: Jay Kogen and Wallace Wolodarsky
1. Marge vs. the Monorail, season 4
Quote of the episode: "I've sold monorails to Brockway, Ogdenville and North Haverbrook and by gum, it put them on the map!" --Lyle Lanley
There isn't a wasted scene in "Marge vs. the Monorail," from the song-and-dance Phil Hartman's Lyle Lanley pulls to sucker the citizens of Springfield to buy into his scheme to the surprise cameo from the one and only Leonard Nimoy.
You could write an entire book dissecting what's arguably Conan O'Brien's finest work -- that's not just my opinion, it's evidenced by the fact that the late night host was recruited to sing "The Monorail Song" during the "Simpsons Take the Hollywood Bowl" show just a few years ago.
The episode's runtime is the perfect summation of everything "The Simpsons" excels at when it's firing on all cylinders: A zany premise backed by memorable music and comedic timing so on-point that it's no wonder the show spread like wildfire in its early goings. This is truly a perfect episode of television.
Original air date: Jan. 14, 1993
Directed by: Rich Moore
Written by: Conan O'Brien
Honorable mentions
The first step in composing this list left us with a whopping 70 entries. Here are the next 10, in no particular order. (Except the first one. That was the hardest to cut.)
"Homer's Enemy," season 7
Quote of the episode: "Frank Grimes, or "Grimey," as he liked to be called, taught us that a man can triumph over adversity." --Reverend Lovejoy
"Homer the Heretic," season 4
Quote of the episode: "Kids, let me tell you about another so-called 'wicked' guy. He had long hair and some wild ideas and he didn't always do what people thought was right. And that man's name was ... I forget. But the point is ... I forget that, too. Marge, you know who I'm talking about. He used to drive that blue car." --Homer
"$pringfield (or, How I Learned to Stop Worrying and Love Legalized Gambling)," season 5
Quote of the episode: "The only monster here is the gambling monster that has enslaved your mother. I call him Gamblor, and it's time to snatch your mother from his neon claws!" --Homer
"Homer the Vigilante," season 5
Quote of the episode: "So I says to the guy, 'Look, pal -- your car was upside-down when we got here. And as for your grandma? She shouldn't have mouthed off like that!"
"Itchy & Scratchy Land," season 6
Quote of the episode: "You know what? You're right -- this is the best vacation our family's ever had. Now let us never speak of it again." --Marge
"Lisa vs. Malibu Stacy," season 5
Quote of the episode: "There sure are a lot of ugly people in your neighborhood. Ooh! Look at that one!" --Grampa
"Bart vs. Australia," season 6
Quote of the episode:"That's not a knife -- that's a spoon," --Bart
"Lemon of Troy," season 6
Quote of the episode: "Yes, eat all of our shirts!" --Flanders
"Home Sweet Homediddly-Dum-Doodly," season 7
Quote of the episode: "Stupid babies need the most attention!" --Child services worker
"Selma's Choice," season 4
"Hey, Surly looks out for one guy: Surly!" --Surly
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