The Simpsons has been on the air for what FEELS like forever (thirty-five years), but its relevance and significance in pop culture has only grown. Its first 8 seasons are widely considered to be the golden age of the yellow family, with a perceived drop in quality since the late 1990s. It may not be as subversive and edgy as it was then, but the fact that a show can even stay consistently watchable (and dare I say entertaining), for that long, is an achievement all its own.
HONORABLE MENTIONS:
A STREETCAR NAMED MARGE (Season 4)
BURNS’ HEIR (Season 5)
HOMER BADMAN (Season 6)
LISA THE SIMPSON (SEASON 9)
YOU ONLY MOVE TWICE (Season 8)
10. BEHIND THE LAUGHTER (Season 11)
Best line: “The Simpsons’ TV show started out on a wing and a prayer, but now the wing was on fire, and the prayer had been answered— by Satan.”
Unlike any other episode in the canon, “Behind the Laughter” is a mockumentary (specifically spoofing VH1’s Behind the Music) that imagines that the family are real actors starring in a long-running sitcom. The meta rise and fall of the Simpsons is a clever, well-constructed episode that pokes fun at itself and Hollywood’s sensationalistic views of the dark side of fame.
9. RADIO BART (Season 3)
Best line: “Your boy picked a bad time to fall down a well. If he had done it at the beginning of the fiscal year, no problemo.”
Bart decides to prank the people of Springfield into thinking a boy is trapped in a well, garnering the sympathy and international attention. When Bart himself falls into the well and actually gets stuck, the townspeople realize that Bart’s been playing them, and do not extend that same sympathy to him. The episode has heartfelt moments and knee-slappers, but it’s the satire of victimhood and celebrity “heroism” that makes “Radio Bart” shine.
8. HOLIDAYS OF FUTURE PASSED (Season 23)
Best line: “This is a tough time of year for someone who’s allergic to holly, mistletoe, and the red part of candy cane.”
The only entry on this list from the modern era, “Holidays of Future Passed” was initially written as a series finale, and it shows. Taking place thirty years in the future as Bart and Lisa take their children to Homer and Marge’s house for Christmas. Maggie is a renowned pop star in the late stages of pregnancy, while both Bart and Lisa are parents struggling to connect with their children. While it’s always wonderful to see future versions of the characters we know and love, the episode is surprisingly poignant, reflecting on growth and change but maintaining the show’s signature comedic style.
7. HOMER’S PHOBIA (Season 8)
Best line: “I like my beer cold, my TV loud, and my homosexuals FLAMING.”
When Homer finds out his new friend, an antiques dealer named John, is gay, he becomes fearful that Bart spending time with John will turn Bart gay. Homer decides to do hypermasculine activities with Bart in hopes to keep him straight. For 1997, this particular episode’s themes are quite progressive, and still manage to be a delightfully laugh-out-loud Simpson-sized send-up of homophobia and hypermasculinity.
Dedicated to the steelworkers of America— keep reaching for that rainbow!
6. LISA’S FIRST WORD (Season 4)
Best line: “It’s not easy to juggle a pregnant wife and a troubled child, but somehow I managed to fit in eight hours of TV a day.”
A lot of episodes explore historical Simpsons lore, but “Lisa’s First Word” tells the touching story of Bart’s early childhood and Lisa’s birth through flashbacks. Packed full of 80s references and classic Simpsons humor, the sentimental origin story culminates in one of the series’ most unforgettable moments: Maggie’s first word.
5. TWO DOZEN AND ONE GREYHOUNDS (Season 6)
Best line: “Your cable TV is experiencing difficulties. Do not panic. Resist the temptation to read or talk to loved ones. Do not attempt sexual relations, as years of TV radiation have left your genitals withered and useless.”
The Simpson family’s dog fathers a litter of 25 puppies that are soon stolen by Mr. Burns, who plans to make a tuxedo from their fur. It’s up to Bart and Lisa to sneak into Burns’ mansion and rescue the puppies. In addition to its hilarious “Be Our Guest” pastiche (“See My Vest”), the episode is filled with to the brim with gags and one-liners that will have you howling with joy.
4. ITCHY & SCRATCHY LAND (Season 6)
Best line: “Bort?!”
The family visits an amusement park themed after a violent cartoon (“Itchy & Scratchy”), and chaos erupts when the park’s animatronic robots go berserk. The episode is not subtle in its parody of Disneyland a la Jurassic Park and Westworld, critiquing consumer culture and amusement park etiquette, while also bringing the Simpsons’ classic antics to a new setting. The absurdity is only heightened by witty gags and a host of memorable quotes (“Bort?”).
3. TWO CARS IN EVERY GARAGE AND THREE EYES ON EVERY FISH (Season 2)
Best line: “This anonymous clan of slack-jawed troglodytes has cost me the election, and yet if I were to have them killed, I would be the one to go to jail. That’s democracy for you.”
Bart and Lisa encounter a three-eyed fish in the waters by the nuclear power plant, triggering an inspection of the plant. When it’s revealed that power plant owner Mr. Burns has overlooked several safety violations, instead of paying the millions of dollars needed to bring the plant up to code, he runs for governor to cover his ass. A colossal tale of Citizen Kane-sized proportions is shrunk down to 22 minutes in what might be The Simpsons’ best political satire ever; Mr. Burns is a fascinating character whose absurd, egotistical crusade and campaign is, unfortunately, more relevant than ever.
2. SCENES FROM THE CLASS STRUGGLE IN SPRINGFIELD (Season 7)
Best line: “Oh, don’t worry, Marge. Her idea of wit is nothing more than an incisive observation humorously phrased and delivered with impeccable timing.”
Finally— an episode focused on the series’ caring matriarch, Marge, and it just so happens to be the series’ strongest single-character study. When Marge buys a Chanel suit at a discount store, she joins the rich elite of Springfield society, and is determined to be accepted by the town’s country club. The only problem? Her husband and children aren’t as supportive of her social climbing. This episode tackles class aspiration and identity in a fun, witty, and heartfelt manner, subtly criticizing the snobbery of Springfield’s upper echelons.
1. THE ITCHY & SCRATCHY & POOCHIE SHOW (Season 8)
Best line: “No, Homer, very few cartoons are broadcast live. It’s a terrible strain on the animator’s wrist.”
When the Itchy & Scratchy cartoon series’ ratings begins to fall, TV network executives bring in a “cool” new character to shake things up, voiced by Homer Simpson. This perfect episode cleverly skewers lazy revitalization attempts, meddlesome executives and toxic TV fandoms, and takes aim at Simpsons fans who, at this point, were already lamenting the series’ alleged creative decline.
All right, it’s high time I disappear back into my hedge. See you at the next ranking!