Fun
Frisky
Nostalgic
Intense
Adventurous
Choked Up
Curious
Romantic
Weird
The fact that The Simpsons has been going on for almost 30 years now (season 29 premieres today) is massively impressive, but it’s gotten less fun to evaluate the show as a series because the line of demarcation between the best years of the show (the first 10 seasons, more or less) and the rest of it is so stark.
Still, 29 seasons on the air is certainly nothing to turn up one’s nose at. Sunday night’s season premiere — a Game of Thrones/fantasy-literature-inspired one-off — is the latest in a long line of Simpsons season premieres, some of which rank among the best Simpsons episodes of all time. We ranked the five best ones so you can screen them today.
"Treehouse of Horror XII"
Season: 13
Air Date: November 6, 2001
Guest Voice(s): Pierce Brosnan, Matthew Perry
Back before FOX figured out its World Series scheduling hurdles, The Simpsons spent a stretch not premiering until after baseball had finished, and thus its “Treehouse of Horror” episodes served as season premieres for a while. And while the law of diminishing returns that has effected The Simpsons as a whole has also done the same to its annual Halloween parodies, the 2001 entry in the series was a high point. The first-third gypsy-curse story is enjoyable enough, and the Harry Potter theme in the final third was certainly on trend, but the middle portion shines the brightest, with the Simpsons getting a Smart Home with the suave voice of Pierce Brosnan that ends up getting sweet for Marge. Sweet and eventually murderous, of course.
"Kamp Krusty"
Season: 4
Air Date: September 24, 1992
Guest Voice(s): n/a
It’s no surprise that the golden age of The Simpsons (seasons 4-9) is well represented on this list. “Kamp Krusty” is a klassic classic, sending Bart, Lisa, and their friends to summer camp, and then following them on a worst-case-scenario of neglect, cruel counselors, and sewing knock-off Gucci wallets to the relentless beat of a tympani drum. There are a billion great gags in this one, from Krusty at Wimbledon to the parents celebrating their children leaving for the summer (“don’t come back!”), to the indelible toast between Mr. Black and the teen counselors.
"The City of New York vs. Homer Simpson"
Season: 9
Air Date: September 21, 1997
Guest Voice(s): n/a
While The Simpsons had previously sent up the big city in the guise of Capital City (“the Windy Apple!”), this was the first time that the show took on New York for real, and and it turned out to be a major nemesis for Homer, whose story of visiting Gotham as a youth was a nightmare of pimps and C.H.U.D.s. So when Barney goes on a bender and leaves Homer’s car illegally parked beneath the World Trade Center, we end up getting a Simpsons road trip and an award reminder of pre-9/11 Manhattan.
Stream "The City of New York vs. Homer Simpson" on Simpsons World
"Homer's Barbershop Quartet"
Season: 5
Air Date: September 30, 1993
Guest Voice(s): George Harrison, David Crosby
Season 5 opened with one of The Simpsons‘ most creative episodes, a reconstructed flashback that imagines a phase in Homer’s past where he, Principal Skinner, Apu, and Barney (after casting Chief Wiggum aside) formed a barbershop quartet called the Be Sharps. “Homer’s Barbershop Quartet” is halfway between a regular Simpsons flashback and a “Treehouse of Horror”-style flight of fantasy, with the Be Sharps tracing the same arc as The Beatles, and jokes about Yoko Ono, Grammy Awards, and surgeon-general C. Everett Koop (“Koo-koo-ka-doop!”).
"Bart of Darkness"
Season: 6
Air Date: September 4, 1994
Guest Voice(s): n/a
While the title of this episode often gets it confused with “Kamp Krusty” (as Bart gets a very Heart of Darkness-y Colonel Kurtz-esque scene in that episode). But no, this is the episode where the Simpsons get a pool, and Bart has to miss out on it because he breaks his leg. While airing such a summer-y episode at the beginning of fall must have felt like quite a tease (in fact, this was intended to be the Season 5 finale, but the 1994 Northridge earthquake caused production delays), the episode is one of the show’s best at depicting classic kids’ behavior. The pool is king at that age, and watching Bart go mad (in an eventual Read Window parody) doesn’t feel totally unreasonable. The episode hits all the right notes, down to Martin’s sad, nude elegy at the end.
