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The Best ‘Simpsons’ Episodes #20-11

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On April 19, 1987, Homer, Marge, Bart, Lisa, and Maggie made their debut during a short on The Tracey Ullman Show. Two years later, Fox gave them their own program. In the three decades since, The Simpsons has become an American institution. To celebrate the 30th birthday of the greatest set of television characters of all time, let’s look back at the stories behind the 100 best Simpsons episodes.

To compile this list, I sought feedback from both hardcore Simpsons fans and former members of the show’s creative staff. Still, it was an inherently subjective undertaking. "You could choose every other episode from the first 200 episodes for your top 100 and you wouldn’t be too far off," one Simpsons writer told me. I don’t claim to be a scientician, but I tried to be meticulous. So crack open a Duff and enjoy.

Below you’ll find numbers 20 to 11 of our top-100 ranking. Click here for the entire list.


20. "Burns Verkaufen der Kraftwerk"

Season 3, Episode 11

Airdate: December 5, 1991

Written by: Jon Vitti

An already memorable episode about Mr. Burns selling the Springfield Nuclear Power Plant to two German businessmen (hence the slightly mistranslated title) is taken to the stratosphere by an idea suggested by executive producer Sam Simon. When Homer meets his new bosses, he complains about the plant’s wonky candy machine. "We understand, Homer," one says. "After all, we are from the land of chocolate." Homer then drifts off into a daydream about the Land of Chocolate, where everything, including a dog he takes a bite out of, is made of delicious melty goodness.

"Sam said, ‘Let’s show it. Let’s cut to the Land of Chocolate,’" showrunner Al Jean recalled to Entertainment Weekly after Simon died in 2015. "That sort of cut-away style of humor, it’s not like it didn’t exist at all, but he really pioneered it and that was a wonderful example."


19. "Bart the Lover"

Season 3, Episode 16

Airdate: February 13, 1992

Written by: Jon Vitti

"Bart the Lover" is based on a simple theory. "There are people in our culture who are approved targets," writer Jon Vitti said in an email, "and everyone feels fine saying or doing any mean thing they feel like to them." On The Simpsons, Edna Krabappel is one such person. Voiced perfectly by Marcia Wallace, the single and jaded fourth-grade teacher is often the target of what Vitti called "show-approved cruelty." But, he added: "It’s always worthwhile to remind yourself that there’s a human being who’s living the other end of that."

Vitti kept that thought in his mind while writing this episode, in which Edna places a personal ad in Springfield Magazine. After Mrs. Krabappel gives Bart detention, he finds the ad in her desk. Seeking payback, he answers it with a romantic letter, calling himself "Woodrow." Edna writes back, but Bart is stumped on how to respond. He consults Marge, who shows him the only love letter Homer’s ever written, a postcard from a brewery visit. "Maybe it’s the beer talking," he begins, "but you’ve got a butt that won’t quit …" Bart borrows the line. When Mrs. K asks him for a photo, he cuts hockey star Gordie Howe’s picture out of a book and sends it to her.

Edna suggests meeting for dinner and Bart says yes, thinking that it’s time to triumphantly tell his teacher that she’s been had. But when he looks into the window of the Gilded Truffle, he sees her sitting alone and decides against it. The next day in school, when she’s lamenting Woodrow’s no-show, Bart tries to console her. "Bart, you are the closest thing to a man in my life," she says, "and that’s so depressing I think I’m going to cry." Instead of telling the truth, Bart adopts his pen name one more time and writes her a sweet goodbye note. It’s the least he can do for her. "I never saw Mrs. Krabappel as a bad person," Vitti said. "My guess is she was someone who started out with ideals and dreams and had the life beaten out of her by kids like Bart Simpson and administrators like Seymour Skinner."

Wallace, who died in 2013, was never better as Mrs. Krabappel. "Marcia Wallace was such an incredibly sweet person, and I think that inner goodness gave some nice undertones to the character," Vitti said. "She brought a relatable spirit to Bart’s adversary; you could be happy at Marcia’s joyous ‘Ha!’ when she triumphed over Bart."


18. "Krusty Gets Kancelled"

Season 4, Episode 22

Airdate: May 13, 1993

Written by: John Swartzwelder

Krusty the Clown has always been the animated embodiment of celebrity, right down to the philandering, poor financial decisions, and shady product endorsements. And like many big stars, he falls hard. It’s an American tradition.

When a program hosted by a heavily promoted ventriloquist dummy named Gabbo cuts into Krusty’s ratings, the network axes his show. With the help of Bart, Lisa, and a bunch of famous people like the Red Hot Chili Peppers, Johnny Carson, and Bette Midler, Krusty gets his groove back and stars in a comeback special.

Like some of his real-life counterparts, Krusty gets a second chance, which he’ll surely blow. But when he does, the country will support him, or at least be there staring while he’s trying to pick himself up.


17. "And Maggie Makes Three"

Season 6, Episode 13

Airdate: January 22, 1995

Written by: Jennifer Crittenden

Extra sweet but never sappy, "And Maggie Makes Three" is one of the most touching Simpsons episodes ever. Told in a flashback, the tale of Maggie’s birth begins with Homer paying off his final debts and quitting his job at the power plant. (After telling off Mr. Burns and crossing the parking lot bridge, Homer literally burns it.) He celebrates the occasion by taking a job at the bowling alley and spending a romantic evening with Marge, who soon learns she’s pregnant.

Marge keeps the news from her content pin monkey of a husband, but spills the beans to her sisters, who tell the whole town. When everybody starts congratulating Homer, he thinks they’re talking about his new job. Even after Moe flat-out says, "Way to get Marge pregnant," Homer replies, "This is getting very abstract, but thank you." He doesn’t figure things out until stumbling upon Marge’s baby shower. Crestfallen, he asks for and doesn’t receive a raise at the Bowlarama and then attempts to earn one by drumming up business. When firing a shotgun in the air outside the alley doesn’t do the trick, he crawls back to Mr. Burns, who gives Homer back his old job with one caveat. In his office he has to keep a demotivational plaque that reads, "Don’t forget: You’re here forever."

During Maggie’s birth, Homer can’t muster any joy. Then his newborn daughter grabs his thumb and he finally lights up. (He also mistakes the umbilical cord with something else and Dr. Hibbert has to remind him that it’s a girl.) Suggested by writer George Meyer, the episode’s famous last shot is of Sector 7-G. Homer has used photos of Maggie to obscure the letters on the demotivational plaque so that it says, "Do it for her."


16. "Deep Space Homer"

Season 5, Episode 15

Airdate: February 24, 1994

Written by: David Mirkin

By the fifth season of The Simpsons, the show’s universe had expanded. Making Homer an astronaut might’ve seemed preposterous in the early ’90s, but by the time David Mirkin took over as showrunner before Season 5, the show was a cultural phenomenon. It made sense that the stories it told would widen in scope. And as the series got older, its focus shifted from an adolescent protagonist to a middle-aged one. "Bart, to write him accurately as a child, he can only have so much depth at a certain age," Mirkin told the New York Post in 2007. "With Homer, we try to explore all levels of adulthood — or arrested childhood. There are just more places to go."

"Deep Space Homer" isn’t exactly realistic, but the writers imagine what it would be like if a lug like Homer went to space. To drum up interest, NASA recruits two average Americans: Homer and Barney. The latter prevails before a celebratory toast (with non-alcoholic champagne) causes him to fall off the wagon. The launch goes smoothly, but when the shuttle reaches space, Homer opens a bag of smuggled potato chips. As his horrified crewmates look on, Homer floats around eating every chip in sight to the tune of The Blue Danube. "Careful," guest star Buzz Aldrin warns, "they’re ruffled!" The brilliant 2001: A Space Odyssey–inspired sequence, which animator David Silverman directed, ends with Homer crashing into the onboard ant colony. Mission control then pipes in guest star James Taylor, whose rendition of "You’ve Got a Friend" adds to the chaos. To top it off, news anchor Kent Brockman sees a scary-looking close-up photo of an ant from inside the spacecraft and launches into an impromptu address about the arrival of a race of giant space ants.

"One thing is for certain, there is no stopping them; the ants will soon be here," he says. "And I, for one, welcome our new insect overlords." The speech, which Harry Shearer delivers with the ideal level of mock seriousness, has been turned into a meme.

Acting on a suggestion by Taylor, Homer and his crew blow the hatch to rid the ship of debris. Homer then recklessly breaks the door handle and accidentally fixes it with a green bar that he’d ripped off the wall. Back on Earth, Aldrin calls Homer a hero. Americans don’t see it that way, though. They celebrate the inanimate carbon rod.


15. "Kamp Krusty"

Season 4, Episode 1

Airdate: September 24, 1992

Written by: David M. Stern

Like many great Simpsons episodes, "Kamp Krusty" was the product of frantic collaboration. As a kid in suburban Washington, D.C., writer David M. Stern attended summer camp. His original pitch involved Moe owning a haven for kids. Showrunners Al Jean and Mike Reiss, Stern said, replied by suggesting he change the concept to Krusty endorsing one.

The script, Stern remembered, fell flat at the table read. Without any other options, the show’s creative staff stayed up until 4 a.m. reshaping it. "It was the greatest Simpsons writing room experience ever," he said. He called that session the highlight of his career. Added Stern: "Everybody fell off the couch laughing."

The episode is full of classic bits. On the day summer vacation starts, Bart dreams of destroying Springfield elementary to the tune of Alice Cooper’s "School’s Out." When a poison ivy–fearing Marge implores Lisa, "Remember: leaves of three, let it be," Homer chimes in with "Leaves of four, eat some more." Kamp Krusty, it turns out, is actually a knockoff Gucci wallet sweatshop overseen not by its namesake but by bean counter Mr. Black, who feeds the campers Krusty Brand Imitation Gruel. "Gentlemen," he toasts to his cruel counselors, "to evil." Led by Bart, the children revolt and the camp devolves into something out of Lord of the Flies. Krusty returns from Wimbledon, where he’d been heckling Ivan Lendl, and makes up for his absence by taking the kids on a trip to Tijuana.

The episode was so good that James L. Brooks suggested that it be turned into a movie. (It never got made.) Stern just wrote a sequel that aired in March. It’s called "Kamp Krustier."


14. "Duffless"

Season 4, Episode 16

Airdate: February 18, 1993

Written by: David M. Stern

In the early days of The Simpsons, well before the show had burned through hundreds of plot lines, it was relatively easy for the writers to come up with ideas. "The low-hanging fruit was just there," said Stern. An episode about Homer trying to quit drinking was too obvious not to work.

After taking a Duff Brewery tour and getting arrested for DWI, Homer is forced to attend traffic school and Alcoholics Anonymous meetings. He takes neither seriously. At the former, he laughs at a Troy McClure–narrated educational film featuring car crash footage. "Here’s an appealing fellow," McClure says to a horrified audience. "In fact, they’re a-peeling him off the sidewalk." At the latter, he tells the group that he’s only there because the judge made him.

Homer only accepts that he has a problem when Marge calls out his addictive behavior. At her urging, he agrees to give up beer for a month. He begins by pouring a six-pack of Duff down the drain while singing a parody version of "It Was a Very Good Year." (Stern says then-showrunner Mike Reiss likely came up with the lyrics, which recount the time 17-year-old Homer used a fake I.D. to buy beer. His name was Brian McGee.) For the rest of "Duffless," Homer struggles to resist temptation. At Bart and Lisa’s science fair, Ralph Wiggum’s alcohol-fueled car project leads Homer to daydream about Gasohol. He discovers that without booze, baseball is boring. "I would kill everyone in this room for a drop of sweet beer," he says at one point. When the 30 days are up, he rushes to Moe’s for a cold one only to realize he’d rather be doing something more fulfilling. The story ends with Homer and Marge on a bike singing "Raindrops Keep Fallin’ on My Head."

As Moe predicts, Homer falls off the wagon by the next episode. Really, it’s fitting. In terms of identity, Homer Simpson without beer is like Popeye without spinach.


13. "You Only Move Twice"

Season 8, Episode 2

Airdate: November 3, 1996

Written by: John Swartzwelder

One of the most eclectic Simpsons episodes ever, "You Only Move Twice" follows the Simpsons as they move to a Silicon Valley–like town for Homer’s new job. Albert Brooks plays his boss Hank Scorpio, a Bond villain in tech mogul’s clothing. The beloved one-off character isn’t outwardly evil like Mr. Burns, but he’s secretly plotting to take over the world. Homer doesn’t understand this. "It’s just the audience that’s aware of it," said Greg Daniels, who devised the story concept. Still, Homer and Scorpio have a real rapport. In fact, Brooks and Dan Castellaneta, the voice of Homer, spent their recording session ad-libbing back and forth.

The episode has a little bit of everything: there’s action (the climax is a battle scene in Scorpio’s lair), drama (the family struggles to adjust to the lush Cypress Creek), and laughs (Bart’s placement in the school’s "leg-up" program is particularly inspired). It’s also yet another instance where The Simpsons was ahead of its time. Scorpio acts much like today’s New Age billionaires, right down to his choice to buy Homer the Denver Broncos, an extravagant gift he accepts — reluctantly.


12. "Cape Feare"

Season 5, Episode 2

Airdate: October 7, 1993

Written by: Jon Vitti

"Cape Feare" contains one of the most influential jokes of the late 20th century. But before getting to the gag that comedy nerds love, let’s state this fact: this hilarious Cape Fear parody features Kelsey Grammer’s best performance as spiky-haired maniac Sideshow Bob. The idea was Sam Simon’s.

"Sam organized the staff field trip to the movie — the only time we did that — and came out saying, ‘Hey, let’s do Cape Fear,’" writer Jon Vitti said of the 1991 version of the thriller. "Sam’s the only one who could have successfully pitched something that weird. You aren’t supposed to rest an entire episode on a single parody like that; you ruin the episode for anyone who doesn’t like that."

Granted parole despite having sent Bart multiple death threats — Sideshow Bob claims that his chest tattoo reading "DIE BART DIE" is German for "The Bart, The" — the evil genius terrorizes Bart. Then the Simpsons become the Thompsons and move to Terror Lake to join the witness protection program. Bart ends up thwarting Bob by baiting him into singing the entire score of H.M.S. Pinafore. (The musical finish was another Simon idea.)

Anne Washburn, who wrote Mr. Burns, a Post-Electric Play, in which survivors of the apocalypse memorize the lines from "Cape Feare," thinks the episode resonates because of its singular focus. "Although there are six million other references in the episode, ‘Cape Feare’ follows the 1991 film Cape Fear almost from beginning to end," she said in a 2015 interview with Words on Plays. "So people retain it because it contains an intact story."

The aforementioned landmark gag is pretty silly. Sideshow Bob steps on the metal head of a rake, causing the wooden part to smack him in the face. This happens nine times over half a minute, and after each he groans. In the DVD commentary, producer Al Jean said that the sequence only went on so long because the episode was running short. Still, this felt like something new. In a 2013 Harper’s essay, Charles Bock argued that the scene paved the way for an entire generation of meta-comedy. "Televised comedies," he wrote, "weren’t doing humor where the degree of repetition, the overlong extension of the joke, was the joke." And now they are, thanks to Sideshow Bob and his rakes.


11. "The Way We Was"

Season 2, Episode 12

Airdate: January 31, 1991

Written by: Al Jean, Mike Reiss, and Sam Simon

The origin story of the greatest sitcom couple of all time is equal parts sweet and pathetic. In other words, it accurately sums up the two halves of an inexplicably whole marriage. Back in 1974, Marge and Homer are high school seniors. The former is a socially conscious student, the latter is a futureless loser. After they meet in detention (Marge is there for burning a bra), Homer fails to woo her. "Oh, son, don’t overreach," Grampa tells him. "Go for the dented car, the dead-end job, the less attractive girl."

Instead of listening to his father, he asks Marge to tutor him in French, a class he doesn’t even take. They start to hit it off and Marge agrees to go to the prom with Homer. Then he promptly blows it by admitting to her that he only asked for help with his schoolwork as a scheme to get to know her better. Marge smacks Homer and goes to the prom with skeevy overachiever Artie Ziff, yet another character rendered memorable by Jon Lovitz. Homer attends the dance alone. That evening, however, Artie reveals himself to be a creep. ("Marge," he says, "I would appreciate it if you didn’t tell anybody about my busy hands.")

Marge eventually hops in her car, tracks down Homer, picks him up, and tells him that she chose the wrong date. His response is the kind of desperately sincere plea that he’ll forever use as relationship glue. "I got a problem," Homer says. "Once you stop this car, I’m going to hug you, and kiss you, and then I’ll never be able to let you go."

Click here for episodes 10 to 1.

Return to The Ringer’s 100 Best ‘Simpsons’ Episodes.

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