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The Best ‘Simpsons’ Episodes #60-51

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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 60 to 51 of our top-100 ranking. Click here for the entire list.


60. "Bart Gets Famous"

Season 5, Episode 12

Airdate: February 3, 1994

Written by: John Swartzwelder

Long before internet memes became popular, Bart Simpson basically became one. After weaseling his way into becoming Krusty’s assistant, he’s given a single line to read on the clown’s show. He botches it, destroys the set, and then squeaks out, "I didn’t do it." To his surprise, the audience erupts in laughter. At that moment, a catchphrase is born.

Bart briefly becomes a national celebrity, although he quickly tires of being a one-line wonder. (When he attempts to boogie with Conan O’Brien on the departed Simpsons writer’s late-night show, the host memorably says, "Only I may dance.") To his dismay, Bart’s fame expires as the episode does. He’s left with nothing but a box of unsold merchandise.

In the real world, Bart’s rise and fall wouldn’t even be that far-fetched. This is a country that fell for "Chewbacca Mom" and "Damn, Daniel." If they can have their 15 minutes, the "I didn’t do it" boy can, too.


59. "Two Dozen and One Greyhounds"

Season 6, Episode 20

Airdate: April 9, 1995

Written by: Mike Scully

"Two Dozen and One Greyhounds" is a crasser, funnier — and dare I say it — cuter version of One Hundred and One Dalmatians. Restless for reasons that Bart and Lisa don’t understand, Santa’s Little Helper runs away to the dog track, where he encounters a new friend: She’s the Fastest. The audience can’t see what’s happening, but Bart is confused. "Looks like he’s trying to jump over her but he can’t quite make it," he says. "Come on boy, you can do it!"

To get the most humor out of the scene, Mike Scully wrote it from the point of view of a kid who has no clue what the hell he’s watching. The writer said that when animation of the episode first came back from the show’s South Korean studio, "there was an incredibly graphic shot that they had put in there not knowing that we couldn’t show it on American television. It left nothing to the imagination."

The Simpsons adopt Santa’s Little Helper’s girlfriend, which makes Bart jealous. "He never wants to play anymore since his bitch moved in," Bart says, angering Marge. Said Scully: "As a kid you love discovering those little language loopholes that allow you to use a swear and not get yelled at." She’s the Fastest has adorable puppies, but before the Simpsons can find them a proper home, Mr. Burns steals the whole litter. Bart and Lisa go on a rescue mission and witness the old man revealing his intention through song. An ode to his exotic-animal-based wardrobe, "See My Vest" is a parody of "Be Our Guest" from Disney’s Beauty and the Beast. Scully wrote the lyrics, he said, and "let the legal department deal with it later." Harry Shearer’s pompous performance helped turn it into one of the best musical numbers in Simpsons history.

Burns chooses to save a single puppy who stands on his hind legs and reminds him of Old Hollywood actor Rory Calhoun. The joke, which writer George Meyer suggested, comes back at the end of the episode. In an attempt to stop Burns from killing the dogs, Bart and Lisa coax all the pups to stand on their hind legs. "They’re so wretchedly adorable," says Burns, who instead of killing them turns them into greyhound racing champions. "Twenty-five little Rory Calhouns."

In hindsight, Scully said with a laugh, "we really banked a lot on Rory Calhoun."


58. "Itchy and Scratchy Land"

Season 6, Episode 4

Airdate: October 2, 1994

Written by: John Swartzwelder

The episode’s take on the Disney World experience works on its own, but that’s not why "Itchy and Scratchy Land" cracks the top 60. The reason it’s so high on this list is due to a single exchange. In the park’s gift shop, Bart can’t find a novelty license plate with his name on it. He does spot one that says "Bort." Then this happens:

Child: Mommy, mommy! Buy me a license plate.

Mother: No. Come along, Bort.

Man: Are you talking to me?

Mother: No, my son is also named Bort.

The gag is emblematic of Simpsonian genius. At its best, the show makes a habit of taking something meaningless and turning it into a memorable joke. For a 2014 Slate article, I talked to people who bought actual Bort license plates. One guy was so afraid that a fellow Simpsons fan would steal the tag that he displayed it inside his car.

See also: Simpsons shitposting.


57. "Homer Defined"

Season 3, Episode 5

Airdate: October 17, 1991

Written by: Howard Gewirtz

When writer Howard Gewirtz first suggested the idea for this episode to Simpsons founding father Sam Simon, a friend from their days working on Taxi, he hadn’t thought it through. In fact, all he had was one line: "Homer nearly destroys the plant because he doesn’t know how to work the controls and becomes the definition of stupid in the dictionary."

"I pitched four or five really complete stories," Gewirtz said. "This one was the Hail Mary pass." Simon liked it. The premise is simple: After Homer averts a nuclear meltdown by guessing the correct button to push, Springfield treats him like a hero. Magic Johnson, the first athlete to appear on the show, even calls to congratulate Homer, who feels like a fraud. There’s also a great subplot involving Milhouse’s mother, Luann, banning her son from playing with Bart until Marge sticks up for her son. (Milhouse’s last name is first mentioned in "Homer Defined." Gewirtz says his wife knew a Van Houten.)

Homer is exposed, but the ignominy comes with a silver lining. His name enters the dictionary; to "pull a Homer" is "to succeed despite idiocy."


56. "Brush With Greatness"

Season 2, Episode 18

Airdate: April 11, 1991

Written by: Brian K. Roberts

While Homer and Bart look for exercise equipment in the attic — after getting stuck in a water slide at Mount Splashmore, the former decides he must lose weight — they come upon portraits of Ringo Starr (who makes a cameo). They’re the work of Marge, who as a schoolgirl sent one of the paintings to the Beatle but never heard back from him. After learning that a teacher squashed her mother’s passion for art, Lisa encourages her to take a community-college painting class.

Impressed with Marge’s work, her professor enters her "Bald Adonis" in the Springfield Art Exhibition. Capturing Homer in his underwear on the couch, the painting wins first prize. That leads Smithers to reach out to her on behalf of Mr. Burns, who’s looking for a portrait artist. Marge agrees to do it, but has trouble finding the inner beauty in the old man. A belated letter from Starr, who’s shown catching up on decades’ worth of fan mail, gives her the inspiration that she needs.

At the painting’s unveiling at the Springfield Palace of Fine Arts, the crowd is shocked to see that it depicts the rich, mean, old man in the nude. Marge then explains that she wanted to show that Burns, despite his ugliness, is "as vulnerable and beautiful as any of God’s creatures." Mr. Burns calls the painting "bold but beautiful." When he thanks Marge "for not making fun of my genitalia," she responds with the episode’s gem of a final line: "I thought I did."

In an example of life imitating art, Starr announced in 2008 that he would no longer be obliging autograph requests. "Even The Simpsons have noted this," he told Surrey Life in 2014. "I’ve signed enough."


55. "Homer vs. the Eighteenth Amendment"

Season 8, Episode 18

Airdate: March 16, 1997

Written by: John Swartzwelder

What’s the appropriate reaction to a little boy getting drunk at the St. Patrick’s Day parade*? Prohibition, of course. After Bart accidentally drinks himself into a stupor, Springfield discovers and enforces an old law banning booze. Homer then turns to bootlegging and gains a nemesis in Rex Banner, an Eliot Ness–like U.S. Treasury agent voiced by Dave Thomas.

There’s always something admirable (and very, very funny) about a not-so-bright guy trying to pull off a complicated scheme. Hell, when Marge finds out Homer has been filling bowling balls with beer and piping them to Moe’s, she even admits as much. "I’ve known your father since high school," she says, "and this is the cleverest thing he’s ever done." Homer is eventually thwarted and nearly expelled from town before its citizens forgive him.

The episode closes with Homer giving a toast: "To alcohol! The cause of, and solution to, all of life’s problems." It may be the single best line in the entire series.

[*Note to fellow native New Englanders: There’s a drunk guy in a Red Sox tank top in the parade scene. Anchor Kent Brockman also says, "Today, everyone is a little bit Irish, except, of course, for the gays and Italians." That’s a reference to the ugly history of the South Boston St. Patrick’s Day parade, which 20 years after "Homer vs. the Eighteenth Amendment" first aired was in the news again.]


54. "Simpson and Delilah"

Season 2, Episode 2

Airdate: October 18, 1990

Written by: Jon Vitti

John Waters was not the first gay icon to appear on The Simpsons. After Homer’s hair grows back thanks to the miracle drug Dimoxinil, Mr. Burns promotes him. Enter Karl, Homer’s handsome, stylish new assistant. The character, played by gravelly voiced actor and playwright Harvey Fierstein, helps him build confidence and succeed as an executive. Things come crashing down when Smithers finds out that Homer has committed insurance fraud to acquire his medicine. (He also loses the last of his supply when Bart spills the bottle while trying to grow a beard.)

Karl valiantly takes the hit for Homer, cutting a check to the plant for the cost of the Dimoxinil. Before he leaves, however, he writes a speech for his once-again bald, soon-to-be-demoted boss, and gives him a final pep talk. "It was never the hair," he says. "You did it. Because you believed you could." And then he plants a kiss on Homer and smacks him on the butt.

Karl’s sexuality is never mentioned, but Fierstein saw no ambiguity in it. "I think what we played with," he said in John Ortved’s book The Simpsons: An Uncensored, Unauthorized History, "was that he was the first openly gay cartoon character."


53. "Homer’s Triple Bypass"

Season 4, Episode 11

Airdate: December 17, 1992

Written by: Gary Apple and Michael Carrington

After writing a well-liked spec Simpsons script about Homer becoming a Wall Street corporate raider (with a subplot about Bart making and selling counterfeit raffle tickets), Gary Apple and Michael Carrington landed this freelance assignment. James L. Brooks came up with the idea of Homer suffering a heart attack, at which the show’s staff balked because the subject matter was so serious.

As usual, The Simpsons manages to play Homer’s peril for laughs. When attempting to finance a $40,000 bypass operation, he visits the Merry Widow Insurance Co. Lisa imagines her sick dad in heaven using a remote to adjust his cloud bed and saying, "Cloud goes up, cloud goes down." And then there’s this exchange in the hospital waiting room:

Homer: Well, I could use some laughter right about now.

Krusty: Well, there’s nothing funny about what you’re gonna go through. I should know, I’m in the zipper club myself.

Homer: You seem OK.

Krusty: Yeah? Well, I got news for you. [Points to his painted face.] This ain’t makeup!

Discount doctor Nick Riviera performs the surgery and Homer wakes up in better shape than Mr. McGreg.


52. "The PTA Disbands"

Season 6, Episode 21

Airdate: April 16, 1995

Written by: Jennifer Crittenden

Springfield Elementary’s teachers go on strike in this decades-old episode that feels like a critique of today’s educational system. Fed up with Principal Skinner’s cost-cutting, Mrs. Krabappel and the teachers go on strike. (The feud is escalated by Bart, who tells Skinner that Krabappel said that he’d "fold faster than Superman on laundry day.")

Paul Kehrer, cofounder of the searchable Simpsons database Frinkiac, loves "The PTA Disbands." "Lisa loses her mind trying to find purpose without school," he said, "Bart embraces his worst aspects initially but realizes he needs the foil of school, Marge good-naturedly tries to keep the family operational, and Homer delivers incredible lines." Like this: "Lisa, if you don’t like your job, you don’t strike: you just go in every day and do it really half-assed. That’s the American way."

To solve the budget issues and end the work stoppage, Skinner rents space in Springfield Elementary to the town’s overcrowded prison system. It’s a disturbing move that these days doesn’t seem so far-fetched. Purple monkey dishwasher.


51. "Homie the Clown"

Season 6, Episode 15

Airdate: February 12, 1995

Written by: John Swartzwelder

Another Swartzwelder classic, "Homie the Clown" is one of my favorite Homer character studies. When Krusty’s extravagant lifestyle causes him to fall into crippling debt, he opens a clown college where he can train regional Krusties. After a billboard persuades him to do so, Homer enrolls, graduates, and becomes Springfield’s Krusty stand-in.

Homie the clown struggles to adjust to his new role. At a Krusty Burger opening, he notices the Krusty Burglar pretending to steal burgers and proceeds to beat the hell out of him. "Stop! Stop!" a kid cries. "He’s already dead!" It’s one of the most gut-bustingly funny (and also visceral) moments in the entire series. Homer soon gets the hang of it, taking advantage of the fact that people think that he’s the real Krusty. "You don’t want to sit with the rest of this a-scum," Italian chef Luigi tells an in-costume Homer, leading him to a private room before reminding the other diners, "I only consider you scum compared to Krusty."

When Krusty loses his newly earned cash betting against the Harlem Globetrotters — "I thought the Generals were due!" — the mob accidentally kidnaps Homer. The real Krusty saves the day, paying off his debt and performing a difficult trick for Don Vittorio, who thanks him and says, "You have brought great joy to this old Italian stereotype."

Click here for episodes 50 to 41.

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

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