But undertaking that challenge through the form of ranking individual seasons of "The Simpsons" is a more manageable proposition. Such rankings study how a couple dozen episodes can come together cohesively to form themes, reveal the skills of writers, and speak about the year they were produced. It isn't just breaking down the greatest and crummiest episodes of the sitcom, it also puts into perspective how "The Simpsons" has evolved over the years.
Despite frequently meager live ratings, "The Simpsons" can still make some headlines, as fans saw in the May 2021 episode "Panic on the Streets of Springfield," which riled Morrissey while lampooning his perceived hypocrisies. Other standouts of the season included "Undercover Burns" (which had Homer's crusty boss infiltrating the ranks of his employees as "Fred") and a memorable "Treehouse of Horror XXXI" that resulted in a viral clip about the horrors of voting in last November's election. It showed that even at its weakest powers, "The Simpsons" still served a vital satirical role in pop culture.
This long-form storyline was titled "Warrin' Priests" and inspired positive marks from critics, with The A.V. Club commending guest writer Pete Holmes ("Crashing") for returning meaningful discussion of theology to a show that once did it so regularly that an entire book was written about it. The rest of the season, however, offered few standout episodes.
While gimmicks were abundant, thoughtful jokes and touching character beats were largely absent. One of the few memorable episodes of the season was "Steal this Episode," which had Homer setting up a ramshackle movie theater in his backyard that projected pirated movies. It was no "Marge vs. the Monorail," but there were amusing chuckles and guest stars, which was more than could be said for most of Season 25 of "The Simpsons."
The most blatant example of this trend in Season 28 was "Kamp Krustier," an unnecessary sequel to the season four installment "Kamp Krusty." Meanwhile, episodes directly tied to modern pop culture moments, such as the two-part "Empire" homage "The Great Phatsby," didn't fare much better. Instead of blazing new trails, Season 28 of "The Simpsons" grasped at straws.
It's easy to call the most important episode of this season the crossover with Matt Groening's other iconic cartoon, "Futurama." But while "Simpsorama" wasn't terrible, it mostly hinged on a bunch of hollow callbacks to classic "Futurama" episodes. Sure, it was nice to hear Billy West and Joe DiMaggio, among the rest of the cast, inhabit their famous roles again ("Futurama" aired its last episode just a few months before this crossover), but the episode didn't offer much beyond that.
The rest of Season 26 was pretty perfunctory stuff, with a season finale couch gag crossing over the program with "Rick & Morty," reminding some viewers that modern animated cartoons may have supplanted "The Simpsons" in pop culture relevance.
On the whole, the guest stars in this season were pretty disposable, including Seth MacFarlane in the finale as a potential new lover for Marge. The better episodes here tended to eschew star-studded cameos in favor of simpler plotlines, like "A Test Before Trying" and its yarn about the fate of Springfield Elementary School hinging on Bart's test scores. It served as a good reminder that Bart's voice actor, Nancy Cartwright, remains as strong as ever at her comical line deliveries.
Unfortunately, "Splendor" was one of the peak episodes of this flawed season. Among those shortcomings were further examples of "The Simpsons" reaching back into older episodes for tired callbacks, such as "Singin' in the Lane," which reunited Homer's bowling team the Pin Pals from Season 7. Part of the fun of "Splendor" was its willingness to engage in new material, but taken as a whole, Season 29 frequently eschewed such a mindset.
Instead, the season delivered all-time worst candidates like "Saddlesore: Galactica" and "Kill the Alligator and Run." The only real highlight of the season came during its requisite "Treehouse of Horror" installment, which included a segment that featured an amusing turn from Lucy Lawless ("Xena: Warrior Princess") as herself. Otherwise, Season 11 saw a shocking decline from what it was just a year prior, let alone in its glorious heyday.
In Season 23, "The Simpsons" cracked 500 episodes, a feat celebrated with the thoroughly unremarkable episode "At Long Last Leave." Far more memorable from this season was one of the modern high points of the program, "Holidays of Future Passed."
Unfortunately, the disparity in the two aforementioned episodes reflected the erratic nature of the season, which oscillated between enjoyable romps like "The Book Job" to forgettable duds like "Politically Inept, with Homer Simpson." As one of Mr. Burns' monkeys might put it, Season 23 of "The Simpsons" was the best of times and the blurst of times.
Those moments do exist for those who want to go back and watch them, thanks in large part to inspired episodes like "Trilogy of Error" and "Skinner's Sense of Snow." Much of the season, however, was dragged down by plots whose writing process seemed to begin and end with a one-sentence pitch.
"Simpsons Safari," for example, sent the titular family to Africa; a slew of generic "comedic" antics involving Homer's encounters with a Maasai tribe and a Jane Goodall knock-off ensued. The episode lacked both imagination and inspiration, and the same held true for several other installments in the season.
While the best pop culture references in "The Simpsons" have always worked for both novices and experts alike, all the gags in "Housewives" seemed intent only on reminding viewers that "Jersey Shore" was a TV show that existed at the time. It set a low point for a season that had its share of entertaining antics, including the amusing episode "Flaming Moe", which had Moe turning his tavern into a gay bar.
With this particular season, Al Jean returned to the position of showrunner for the first time in nearly a decade. It was a momentous moment in the show's history, given that he has occupied the role for nearly two decades since.
"The Simpsons" opted for a lot of that kind of safe, familiar humor this season, though that doesn't mean viewers were entirely devoid of quality comedy. Most notably, this was the season responsible for an excellent musical episode entitled "The President Wore Pearls," delivering an "Evita" lampoon with some surprisingly catchy ditties.
"24 Minutes," a parody of "24," was without equal among the season's collection of 22 episodes. Much like "The Springfield Files" from a decade earlier, "24 Minutes" parodied a famous FOX drama with remarkable attention to detail, while making sure the episode's gags could stand on their own two feet.
Although the power of Jack Bauer provided the peak of the season, there were still several installments here (like "Moe'N'a Lisa") that proved worthwhile. On the other hand, weaker entries such as "Kill Gil (Volumes 1& 2)" relied on tired jokes and unimaginative pop culture references, indicating the potholes that would take down many late-era "Simpsons" episodes.
True, this is the season with the infamous "That '90s Show" episode that rewrote the mythos of "The Simpsons" in the name of derivative 1990's pop culture references. But at least Season 19 delivered some enjoyable laughs, even in its most lackluster plots.
Sometimes, later seasons of "The Simpsons" have employed contrived plot turns that aim for humor but instead smacked of laziness. One of the better examples of this trend came in the final minutes of "Don't Fear the Roofer."
The episode dealt with the idea that Homer's new best friend, a kindly roofer voiced by Ray Romano, wasn't real. Using some humorously over-the-top methods (complete with a Stephen Hawking cameo) to explain how the character avoided being seen by anyone else, "Roofer" marked an entertaining highlight in one of the stronger post-2000 seasons for "The Simpsons." Other standout episodes for this season included the return of Albert Brooks and his gift for improvised comedy in "The Heartbroke Kid" as well as "Midnight RX," which involved Homer leading a series of pill heists in Canada.
Right after that episode came "The Principal and the Pauper," an infamous one that foreshadowed the gimmicky storytelling which would dominate subsequent seasons. Luckily, that foible would become more apparent later on, as the ninth season remained largely enjoyable if decidedly less so than the last few. Among the most entertaining outings this go-around was "Reality Bites" (featuring the last appearance of Phil Hartman's Lionel Hutz), and Homer's love for firearms in "The Cartridge Family."
The animation was cruder, the characters hadn't gelled into their famous personalities yet, and the stories weren't as daring as later seasons. Yet, there was still something remarkable about this trailblazing season of television. Episodes like "Krusty Gets Busted" had the kind of laughs and storytelling that would turn the series into a pop culture sensation. Other installments like "Moaning Lisa" and "Life on the Fast Lane" contained mature, thoughtful handling of themes like infidelity that even modern-day adult cartoons struggle to capture. The edges in this inaugural "Simpsons" season are rough to look back on now, to be certain, especially in "Some Enchanted Evening." The high moments, however, foreshadowed the pop culture institution "The Simpsons" would become.
Other episodes in the season zeroed in on side characters like Seymour Skinner, while an installment focusing on Itchy & Scratchy further expanded the world of Springfield. Growing pains aside, the second "Simpsons" season showed a promising ability to grow and improve.
This level of confidence resulted in all-time great episodes such as "Like Father, Like Clown" and "Flaming Moe's." Even better, this season's episode "Black Widower" established Sideshow Bob as a recurring antagonist for the entire series rather than just a one-off guest character. It's just one of many foundational elements of "The Simpsons" that was established during this vital season. 2b1af7f3a8