I have to be honest....
I struggled with this list. I basically had my top 5 choices, more or less, set in stone and I felt fairly comfortable with them. However, the rest of my top 10 was simply me trying to pick the episodes I felt I was least prone to say something negative about.
I think I may have BARELY pulled together this top 10.
The remarkable thing is how quickly the show seemed to slip, but I suppose a lot of that was due to the writing changeover from Oakley/Weinstein to Mike Scully. In addition to that, two episodes were produced by former showrunners David Mirkin and Al Jean & Mike Reiss.
So, in a way, there are a lot of style shifts within some of these episodes that may seem quite jarring, but the simple truth is that despite writing some solid episodes prior to season 9, Mike Scully would end up being the head of 4 seasons that would make The Simpsons make its descent that it would never truly get out of...even though the show would briefly (and barely) stabilize itself in the 2000s.
I have always said that season 8 was when the show began something of a decline, and I do sort of stand behind that statement. My only difference when examining it more closely is that season 8 had more to offer and still had a few episodes that I considered for the lower half of my top 10.
With season 9, I was struggling to even make the lower half of my top 10.
Well, let's do this, I guess.
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THE TOP 10:
#10 - Girly Edition
Written by Larry Doyle
This episode would be the debut for writer Larry Doyle, who only stayed with the show for a couple of years but managed to write some solid episodes at a time when the show was struggling to maintain a good consistency level.
"Girly Edition" is one of those "Lisa-centric" episodes that these days seems to be lambasted by die-hard fans on the internet. I think these episodes work a lot better when they utilize Lisa for her strong moral beliefs rather than when they try to make her fit in to the latest trends.
Here, we have a true classic Lisa story, but it also contains the classic Bart/Lisa rival dynamic.
We've seen similar ideas to these on a lot of comedy shows over the years: friends or siblings pitted against each other where one wants something more than the other, but the other gets all the glory.
When Lisa gets the opportunity to anchor a small kids news segment on Krusty's show after it is deemed to be not educational enough for children, Bart becomes jealous and manages to fight his way onto the show as a sportscaster.
When his charisma makes him super popular, he gets promoted to co-anchor and Lisa is quietly shifted to the wayside.
Also - this episode contains a totally ridiculous subplot involving Homer becoming obsessed with having a Helper Monkey around to assist with his daily life. It is just one of those silly throwaway gag plots that often work well when the "A" story is strong enough to dominate the majority of the episode.
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#9 - Dumbbell Indemnity
Written by Ron Hauge
Over the years, I think a lot of Simpsons fans have managed to fall in love with Moe and all of his irascible qualities.
We laugh at him and often when he is at his lowest, but there is something very lovely about when things do go his way...even if it'll probably all crash and burn by the end of the episode.
Dumbbell Indemnity manages to give Moe a woman who legitimately likes him...and with some cheeky symmetry considering Moe's voice-actor (Hank Azaria) was married to guest star Helen Hunt at the time.
Based on the episode's title, it shouldn't come as a surprise that insurance fraud is about to come into play. As a means to keep Renee impressed with him, Moe wants to acquire money and decides to commit insurance fraud by staging a car accident with Homer's help. When this backfires and Homer is arrested, Moe refused to bail him out.
In the end, Moe is a loser...but the funny thing is how much we enjoy watching his moments of bliss in the same manner we love watching his life fall apart.
This was certainly one of the funnier episodes of the season quite easily.
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#8 - Natural Born Kissers
Written by Matt Selman
Natural Born Kissers is a key episode in the history of the show in that it was the first episode to be written by Matt Selman.
I call that out because Matt Selman is actually the current showrunner of The Simpsons as of this writing in 2023. He became joint showrunner briefly with Al Jean in 2020 (who had been running the show for 19 years) before Jean decided to finally step down.
I am not saying that the ship has been set on the correct path, so to speak, however...I do feel what Matt Selman has been achieving in the last two seasons has been a bit of a rejuvenation of the series that we actually haven't had in... literally...decades.
I have been knocking the Scully era of seasons 9-12 quite a bit as we've been approaching them, but the truth is, there is still good in seasons 9 and 10...and I would argue that since Selman has taken over fully, the show is seeing a quality bump that is comparable to the late 90s era. I consider that to be a rather impressive feat.
Sorry to go off on that tangent, but let's just say I admire Selman for bringing some freshness to the show that hasn't been seen in over 20 years.
As for his debut episode, this has got to be The Simpsons at its raunchiest. Homer and Marge realize that their lagging sex life is given a boost when they get turned on at the idea of having sex in public places...and that is exactly what they do. This also includes them having sex on the same miniature golf course where Bart was conceived.
The concept was considered so risqué and a bit bold that FOX actually told the writing staff to abandon it early on and then the censors were considered over the sex depictions and the cartoon nudity.
Honestly, the show never really went this far into the sexual content before or, arguably since. I think it works so well as a one-off story and it also goes to show that Matt Selman (who actually said he based a lot of this episode on his own parents...hmm...) would prove to be a writer that the show would so desperately need.
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#7 - The Joy of Sect
Written by Steve O'Donnell
Oh yes, you just got to love when a show dives into religious fanaticism and cults.
I just have to take a moment to say that I absolutely adore the Springfield universe. I would go as far to say that it is my favorite television universe quite easily simply due to the characters within the show and how this whole town is basically bonkers.
It makes total sense that the citizens of Springfield would get swept up into a religious cult...and that it would all begin with Homer.
At the airport no less, Homer comes across a new religious group called the Movementarians. They invite Homer and many residents of Springfield to watch a film narrated by "The Leader", who tells them that they will all be led to the planet of Blisstonia for a life of eternal...well...bliss.
At the time the episode was originally written (by previous showrunner David Mirkin), it was right before the Heavens' Gate movement members committed suicide. Due to many similarities between Mirkin's original draft and the mass suicide and that movement's beliefs, certain elements were tweaked to not appear as offensive.
Perhaps one of my favorite bits of the episode is that Mr. Burns wants to create his own separate religion simply because he wants to become a tax-exempt member of society.
As you would expect from him.
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#6 - This Little Wiggy
Written by Dan Greaney
Writer Dan Greaney was often considered by the writing staff to be the one writer who was best at coming up with the loony non-sequiturs that Ralph Wiggum would provide.
Showrunner Mike Scully had an idea that Marge would naturally force Bart into having a play date with the peculiar Ralph...and naturally tasked Greaney with the episode.
This episode would prove to be the second to prominently feature Ralph Wiggum after the masterful season 4 episode "I Love Lisa". However, in the nearly 5 years since that episode aired, Ralph had become even more nonsensical in his style...so in some ways, this is the first time we get a lot of content devoted to the character in this form.
I think when it comes to Ralph, the writers are always smart to use him sparingly. In a bizarre way, you could say he is similar to Creed on The Office in that when he has a small featured moment, he steals the scene...but if you use him too much, it becomes cumbersome.
In this case, I think Greaney and the team utilize him well and then know to put him on the backburner where he works so well.
Also - it is a great showcase for Nancy Cartwright who gets to act opposite herself as Bart.
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#5 - The Last Temptation of Krust
Written by Donick Cary
I think one of the more interesting things about this episode is that it had a difficult time making it through the network censors.
Keep in mind, this episode was developed in 1997 and aired in early 1998 and it STILL got flagged for what was deemed "offensive" material.
However, if you want to see how not to get yourself cancelled, this is the episode to really show how to write that kind of material.
Krusty the Klown is, without a doubt, a hack. He is old and his material is trapped in the past. Bart still idolizes him and insists that Krusty should appear in a comedy festival organized by Jay Leno.
Krusty hasn't done stand up in years and his material, including a cartoonish depiction of a Chinese man with immensely large buckteeth, leaves the audience stunned.
While this leads to Krusty getting "cancelled" as we would say today, he manages to reinvent himself as a comic that "tells it like it is" similar to that of George Carlin (complete with his hairstyle and outfits).
Although, Krusty can only resist selling out for so long, which leads to him becoming a spokesperson for the new Canyonero (modeled after SUVs)...and I have had the jingle for that commercial in my head now for 25 years.
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#4 - The City of New York vs. Homer Simpson
Written by Ian Maxtone-Graham
Part of me never ever wants to give Ian Maxtone-Graham any kind of good credit when it comes to his writing on The Simpsons.
In truth, he did write several episodes that often had funny/witty moments, particularly "E-I-E-I-(annoyed grunt)" which was one of the very few great episodes of the otherwise paltry season 11.
For reference, Maxtone-Graham was interviewed by The Independent in 1998 in which he talked about how he had never seen the show prior to being hired and then proceeded to insult the show's passionate internet fanbase, calling them "the beetle-browed people on the internet". However, perhaps the worst thing he said was that he felt like women were not suitable writers for the show.
Considering this was a man who also wrote on SNL at a time when a lot of its sketches were based on around themes such as misogyny and homophobia, that comes as no surprise.
As it stands, "The City of New York vs. Homer Simpson" is a fun episode if only for how much I love seeing the whole family trying to vacation in the city while Homer seeks to find his car which Barney drunkenly left on the plaza of the old World Trade Center. The WTC bit actually caused this episode to be pulled from syndication for many years following 9/11. I actually had not seen the episode in almost 15 years before it finally popped back up on streaming services several years ago.
One bit I do love is how Marge calls out various landmarks of NYC that no one ever cares about like "FOURTH AVENUE!" or "THE WILLIAMSBURG BRIDGE!"
We also get another solid musical bit in the episode as the family sans Homer attends a Broadway musical based around The Betty Ford Clinic with the peppy opening number "I'm Checkin' In!".
It serves as a pretty good effort to start the season, but I wouldn't put it on any kind of pedestal when it comes to great character development.
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#3 - Lisa's Sax
Written by Al Jean
Speaking of character development, I do think "Lisa's Sax" manages to give some interesting insight to how young Lisa developed an interest in the saxophone while also throwing in interesting deviations to the show's format, like Homer and Marge singing a variation of "Those Were the Days", the theme song to All in the Family.
Using the flashback motif, which puts the action in 1990, Al Jean gives us references to the time period such as Homer watching Twin Peaks or how the story of Lisa's sax keeps getting interrupted by Bart stories as people wanted "Bart by the barrelful"...which also tracks when you factor in that Bart-mania really began in 1990.
That's really what it comes down to with this episode. It simply manages to combine great and hilarious plot devices along with wonderful and heartwarming character histories.
It is one of the few examples in this stage of the series (and it only gets worse during the Scully era) where we see Homer in a truly lovable state where he does end up doing the right thing for his daughter whom he just never seemed to understand.
This is the beginning of what would become the "Jerk-Ass Homer" era where Scully and the writing staff just seemed to steamroll any sense of stability by making Homer into an invincible and irascible fool.
"Lisa's Sax" does feel like one of those last gasps of the Golden Age...and it sort of makes the singing of "Those Were the Days" truly bittersweet.
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#2 - Lisa the Simpson
Written by Ned Goldreyer
So yeah...she might not be as beloved of a character these days as people tire of the frequency in which new episodes have focused on her, but I have always been fond of the energy that Lisa brings to the table.
As the "straight man" and the "brains" of the family, Lisa could often provide laughs as she responds to lunacy as the "voice of reason", even over Marge at times.
In the first dozen or so seasons, I feel like any episode involving Lisa would be bound to be a winner in my book...and this one visits an idea that was sort of delicately planted back in Season 7's "Mother Simpson".
In that episode, the passionate and liberal mindset of her long-lost grandmother shows that maybe her own beliefs make sense compared to the more simplistic views of her mother or her oafish and lackadaisical father.
When it is discovered that Bart's grades have been in freefall with each passing school year, Lisa fears she is doomed to become stupid before she even reaches the age of 10.
Homer, to his credit, does try his best to help Lisa and manages to round up every Simpson relative in the tri-state area and the discovery is truly made: the Simpson women are smart and immensely successful; the men are basically all some variation of Homer.
So yes, Lisa will find success. Bart will follow in the path of his father and the many Simpson men who may take pleasure in wearing stainless steel pots on their head.
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#1 - Miracle on Evergreen Terrace
Written by Ron Hague
I can be a sucker for a good Christmas episode, and when it comes to episodes based around those themes, I always stand by "Miracle on Evergreen Terrace" as being one of the best that the show has produced.
When it first aired, I remember it standing out for the darker tone it took.
Bart is being as mischievous as ever as he disobeys Marge's rule that they will not open presents until 7am the next morning...and when he opens up a remote controlled fire truck that sprays water onto an electrical socket, it causes a fire which ignites the fake plastic tree and destroys all of the presents.
How does Bart try to get out of this?
He buries the big plastic blob of evidence under snow in the front yard and claims that robbers took their tree and their presents.
Springfield, in an act of kindness, gives them a new tree and presents and pools a huge sum of money as if this were a new reincarnation of the George Bailey saga in It's a Wonderful Life.
However...Bart won't get out of this so easily, and the truth is made known to all of Springfield.
Not surprisingly, the citizens of Springfield handle this news about as well as you would expect the citizens of Springfield to handle it.
I stated at the beginning that my top 4 episodes were pretty much solidified before making this list...and I think this was a very easy selection for my favorite of the season. It was, perhaps, the only episode of season 9 that I felt was on par with some of the true classics of the seasons that proceeded it.
It contains some elements of previous Bart episodes, particularly season 7's Christmas outing "Marge Be Not Proud", which work very well in its favor.
The ending of the itself manages to take such a bleak outcome and make it rather joyful and bittersweet. A true gem from the Scully era.
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FINAL THOUGHTS:
As I stated before, I had a hard time coming up with a top 10 for this season. I don't think that feeling is going to get any better when I start to tackle season 10....
To put this into perspective, I was born in 1988 while The Simpsons premiered in late 1989 so I literally grew up with the show and aged along with it.
I turned nine when Season 9 premiered and despite my young age, I was an avid fan of the show. This was also when I began looking at message boards online discussing the show, and even being only nine, I picked up on a lot of the weird shifts in tone and storytelling that other people did.
This feeling of concern over the show's direction didn't get any better once we got to season 10...and I won't even address season 11 just yet.
Having said that, I do feel that my opinions of season 9 are a little more positive than they used to be. I wouldn't rope this season in with the Golden Age by any means, but there are a couple of really great episodes and even a couple that I would consider classics.
Even if the season does feel like it has managed to stand the test of time a little better, I still feel this strange sense of sadness once I reach it on a rewatch. It just loses a little bit of zest/
I think a lot of this does with the infamous elephant in the room which I will go ahead and discuss now:
"The Principal and The Pauper".
So much has been labored and discussed over this episode online and in articles that I am not even sure I should go into it fully here, but this is one of those episodes where I feel like the vitriol it receives is mostly justified.
For years, I avoided this episode. In fact, I only watched it once, MAYBE twice but avoided it for nearly 20 years. Earlier this year, I finally rewatched it.
As an episode, it isn't badly written...it even contains some witty dialogue and jokes. Even the worst episodes of the show have at least one or two good lines so that isn't shocking.
The problem with the episode is strictly the content.
In short, the character of Principal Seymour Skinner is revealed to be a fraud. He is actually a man named Armin Tamzarian, a con man from Capital City who enlists in the Army to fight in Vietnam to avoid a potential prison sentence. While there, he befriends a Sergeant named Seymour Skinner whose dream once the war is over is to become an Elementary School principal.
When Skinner is believed to be dead, Tamzarian goes to tell Skinner's mother Agnes who seemingly just thinks that Tamzarian is somehow her son and he just goes along with it.
This all comes to light when the real Skinner (voiced by guest star Martin Sheen) comes back to Springfield and forces Tamzarian to reveal the truth.
When Tamzarian flees Springfield to try to return to his rapscallion life in Capital City, Agnes realizes that her real son will not let her treat him like a doormat. He wants his own social life and his own hobbies...and this leads to Springfield making the real Skinner go away (by tying him down to a train flatbed) and having Tamzarian resume the life of Skinner.
From here on out, despite a couple of brief cursory mentions, the show essentially forgets the storyline. Frankly, considering the intense hatred the episode has received, I think that is for the best.
I think what is so ridiculous about this episode is how it manages to take a supporting character that has been with the show since its first season, had been developed a lot more as a character than most over the past 8 seasons, and had been such a prominent foil to Bart...and promptly tells us it was all a lie. It just hit in such an unsatisfying way that it left a bad taste in my mouth then and even when I rewatched the episode recently, it STILL felt like a really jarring shift.
At best, I would say the episode got a marginal shift if only for having a few good lines, but after giving it another chance, I don't think I will ever watch the episode again. I would rather just brush it under the rug and consider it to not be part of the canon.
And frankly, with how the end the episode forcing the real Skinner out of town, it is like the writers subtly knew that it needed to happen that way...and yet, it just renders the whole episode pointless.
Strangely enough, after this early series nadir (which is strange to say its early for a show's NINTH season), the show rebounds with "Lisa's Sax" and then goes into a sort of middling slump for 6 episodes until they reach "Miracle of Evergreen Terrace". Despite an erratic start, the show finds some footing as it goes along but it won't be able to sustain it much longer.
Season 10 only further leads to additional cracks to the façade, and perhaps I will force myself to discuss season 11 after the fact.
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