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 70 to 61 of our top-100 ranking. Click here for the entire list.
70. "Mr. Lisa Goes to Washington"
Season 3, Episode 2
Airdate: September 26, 1991
Written by: George Meyer
In which Lisa learns that institutions are corrupt but not beyond saving. After her Springfield Forest–themed patriotic essay wins the Simpsons a trip to Washington, D.C., she’s full of optimism. But while visiting the Winifred Beecher Howe Memorial — "She led the Floor Mop Rebellion of 1910," Lisa says — she witnesses Congressman Bob Arnold taking a bribe from a logging lobbyist. (The timber industry wasn’t happy with how it was portrayed in the Mr. Smith Goes to Washington parody.) Disillusioned, she starts imagining elected officials as fat cats and pigs. At the Patriots of Tomorrow Awards Banquet, she reads a new essay that calls out Arnold. "Cesspool on the Potomac" doesn’t take home first prize, but Lisa’s whistle-blowing leads to the corrupt official’s arrest.
69. "Oh Brother, Where Art Thou?"
Season 2, Episode 15
Airdate: February 21, 1991
Written by: Jeff Martin
In this episode, which ends on the most fittingly bitter note in Simpsons history, Homer discovers that he has a half brother. Voiced by Danny DeVito, Herb Powell is a millionaire auto executive whom Grampa gave up for adoption. Nancy Cartwright, who voices Bart, liked watching DeVito record his part. The actor’s hair, she wrote in her autobiography, was "pointing in more directions than a sundial."
The long-lost siblings hit it off, and Unky Herb taps everyman Homer to design Powell Motors’ newest model. What Homer invents is an $82,000 monstrosity with bubble domes, shag carpeting, and horns that play "La Cucaracha." The car bankrupts Herb, who tells Homer that as far as he’s concerned he has no brother. "His life was an unbridled success," Lisa says, "until he found out he was a Simpson."
Season 7, Episode 24
Airdate: May 19, 1996
Written by: Brent Forrester
"I used to be with it, but then they changed what ‘it’ was. Now, what I’m with isn’t it, and what’s ‘it’ seems weird and scary to me." — Grampa Simpson
In "Homerpalooza," the middle-aged title character begins to feel old when his taste in music embarrasses Bart and Lisa. "Everyone knows rock attained perfection in 1974," he says before a flashback to his high school years. The hilarious Dazed and Confused–inspired scene, which features a strobe-light-equipped van called the Second-Base Mobile and a girl mockingly telling Homer that she thinks he’s cool, ends with Grampa’s episode-defining lament (see above).
Back in the present, Homer scores tickets to music festival Hullabalooza. The lineup includes Cypress Hill, the Smashing Pumpkins, Peter Frampton, and Sonic Youth, the last of whom would agree to a cameo only if Courtney Love — the two bands had clashed at Lollapalooza ’95 — and Hole weren’t on the bill. "If she was going to be involved, we weren’t," Sonic Youth guitarist Lee Ranaldo told Entertainment Weekly in 1996. According to EW, Bob Dylan, Neil Young, and Pearl Jam all turned down the show’s invitation to appear.
Homer temporarily attains coolness by joining the Hullabalooza tour as a freak whose belly can withstand a cannonball shot. Speaking of shots: The show takes plenty at the perceived apathy of Generation X. After a concertgoer calls Homer’s act cool, his friend asks if he’s being sarcastic. "I don’t even know anymore," he replies. Homer eventually quits the gig because, well, it could kill him. "I realized that being with my family is more important than being cool," he says, before Bart reminds him that what he just said was "powerfully uncool."
The episode also contains a fairly rare specimen: a Simpsons joke that badly shows its age. At a record store, Homer mentions the US Festival, which was "sponsored by the guy from Apple Computers." The flannel-clad clerk responds by asking, "What computers?"
67. "New Kid on the Block"
Season 4, Episode 8
Airdate: November 12, 1992
Written by: Conan O’Brien
"New Kid on the Block" is two episodes pleasantly crammed into one. One plot line focuses on Homer suing the Frying Dutchman after the seafood joint throws him out for going overboard at its all-you-can-eat buffet. The other follows Bart’s infatuation with the Sara Gilbert–voiced new girl Laura. After telling Homer that "this is the most blatant case of fraudulent advertising since my suit against the film The NeverEnding Story," Lionel Hutz represents Homer in court. The Remorseless Eating Machine wins his case. Bart is crushed when he finds out that he has no chance with the older, cooler Laura, although he takes solace in the fact that she says she’d date him if he were old enough to grow a bad teenage mustache.
66. "Saturdays of Thunder"
Season 3, Episode 9
Airdate: November 14, 1991
Written by: Ken Levine and David Isaacs
In "Saturdays of Thunder," which originally aired as the lead-in to the world premiere of Michael Jackson’s "Black or White" video, Homer seeks to improve his parenting skills and Bart attempts to defeat Nelson in the soap box derby. The dueling quests make good comedy, but what pushes the episode over the top is that it features a scene from McBain, the action movie starring Arnold Schwarzenegger clone Rainier Wolfcastle.
The writers managed to cram an amazing cop movie parody into the minute-long sequence, which ends with the title character’s partner — who’s about to retire and sail around the world with his wife on their new boat The Live-4-Ever — getting gunned down and McBain cursing the supervillain who ordered the hit. "MENNNNDOOOZZZA!"
65. "Sideshow Bob Roberts"
Season 6, Episode 5
Airdate: October 9, 1994
Written by: Bill Oakley and Josh Weinstein
You’ve heard this story before: an establishment Democrat loses an election to a cartoonish Republican. In this case, the witty, dastardly Sideshow Bob defeats bumbling incumbent Joe Quimby in the Springfield mayoral race. The terrifyingly prescient episode is loaded with late-20th-century political references, including a spoof of the infamous Willie Horton attack ad, henchmen who look like John Ehrlichman and H.R. Haldeman, and a Rush Limbaugh analog named Birch Barlow. When Bart and Lisa expose Bob as the beneficiary of voter fraud, he unleashes a tirade.
"Your guilty conscience may force you to vote Democratic, but deep down inside you secretly long for a cold-hearted Republican to lower taxes, brutalize criminals, and rule you like a king," Bob says as he’s being arrested. "That’s why I did this: to protect you from yourselves." It’s a joke, although these days you can almost picture an elected official saying something similar. "The political discourse now is way more fucked up than the one depicted in the show," Oakley said in 2015.
64. "Homer Loves Flanders"
Season 5, Episode 16
Airdate: March 17, 1994
Written by: David Richardson
What’s it like to be friends with Homer Simpson? Not easy. With his neighbor in his orbit, even nice guy Ned Flanders loses his cool. When Ned surprises Homer with a ticket to the Pigskin Classic, the latter reluctantly accepts. Homer has a blast at the game and then gloms on to Flanders, who enjoys their friendship at first. It’s painfully funny to watch his new pal’s obnoxiousness gradually bring him to his breaking point.
The episode is full of classic jokes: Homer looks up at the ceiling and asks the Lord why he’s mocking him. "That’s just a waffle that Bart tossed up there," Marge says. Homer eats it and says, "mmm … sacrilicious." Homer also buys a nacho hat and sings "Nacho Man." And while trying to catch a fleeing Flanders, Homer turns into T-1000.
63. "Bart’s Comet"
Season 6, Episode 14
Airdate: February 5, 1995
Written by: John Swartzwelder
No sequence in Simpsons history captures both the best and worst of humanity quite like the climax of "Bart’s Comet." Without any other option, the entire cast of the show piles into Ned Flanders’s bomb shelter. Homer eventually casts out poor Ned, calling him "the only useless person here."
As Flanders stands outside alone, singing "Que Sera, Sera," everybody piles out of the crowded bunker to join him. The town’s polluted air breaks up the comet, which in its mostly diminished form demolishes only the empty cinder block structure. "It’s dark in a way," said Dan Ozzi, cohost of Woo Hoo! Classic Simpsons Trivia in Brooklyn. "But it’s so beautiful."
62. "Blood Feud"
Season 2, Episode 22
Airdate: July 11, 1991
Written by: George Meyer
When Mr. Burns needs a transfusion, Bart donates his blood to save the liver-spotted plutocrat’s life. As a thank-you, he sends the Simpson family a measly card. Homer then writes Burns an angry letter, which Marge tells him not to send. Bart ends up sending it anyway, infuriating the old man, who orders a beating for Homer. Smithers advises against it, however, and Burns gifts the Simpsons not cash but rather a giant Olmec colossal head.
The episode ends with the family openly wondering what the hell has just happened. A traditional sitcom might’ve tried to impart a grand lesson when there isn’t one other than that Mr. Burns is irredeemably evil.
61. "Three Men and a Comic Book"
Season 2, Episode 21
Airdate: May 9, 1991
Written by: Jeff Martin
The ponytailed tub of sarcasm known as Comic Book Guy debuts in this episode, which pits Bart, Milhouse, and Martin against one another. After the three boys pool their money to buy Radioactive Man №1 at the Android’s Dungeon (Bart makes $35 doing housework for an elderly lady voiced by Cloris Leachman), they start to bicker about how ownership will be shared. The argument devolves into full-on paranoia, then a physical fight, and then the precious comic flying out of Bart’s treehouse into the rain.
The nostalgic feel of "Three Men and a Comic Book" is heightened by a clever cameo by Wonder Years narrator Daniel Stern, who briefly voices Bart’s inner monologue. (His brother David wrote for The Simpsons.) Also in this episode is my favorite random joke of the entire series: Milhouse wants to buy a Carl Yastrzemski baseball card from 1973, when the Red Sox star had absurdly big sideburns.
Click here for episodes 60 to 51.
Return to The Ringer’s 100 Best ‘Simpsons’ Episodes.