A Look Back at Season 8 of THE SIMPSONS: Top 10 Episodes Included

After giving us a season that managed to tackle topics such as faking your death, the meaning of having a soul, and babies shooting evil elderly men, Bill Oakley & Josh Weinstein were now going into their second season as showrunners with a stellar track record. 

However, if you've been following these posts of mine, you already know that things are (for me) all downhill from here.

I have to stress that season 8 of The Simpsons is certainly not bad. In fact, I stand by my opinion that it has far more successes than it does misses. 

I think the biggest thing about season 8 is that after tackling more relationship/character driven storyline in season 7, Oakley & Weinstein opted to go more into plot-driven material here that would put the characters into rather bizarre scenarios...and sure, they were mostly entertaining, but there is a definitely a feeling of the tide changing at times.

I have a few more thoughts about the season, but I will save them for after the top 10.

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THE TOP 10:

#10 - Lisa's Date with Density 

Written by Mike Scully

Out of all of the side characters to have been created in the 30+ year history of The Simpsons, I have something of a soft spot for Nelson Mandela Muntz.

As a bully character, he quickly became something more. It was almost as if he bullied based on principle rather than simply vindictive attack...and he also seemed to have no shame bullying adults. He was an equal opportunity bully. 

In season 7, we got two moments that sort of put Nelson in a unique position.

During "22 Short Films About Springfield", a random adult character that we've never seen before puts Nelson in his place when he mocks him for driving such a small car...and during the moment, he is portrayed and drawn with such vulnerability that you almost feel bad for him despite the hilarity of the moment.

In "Bart on the Road", we learn that Nelson is a fan of crooner Andy Williams, insisting they stop to attend one of his concerts in Branson. 

Seeing these interesting quirky details, the team came up with "Lisa's Date with Density", in which Lisa realizes she might actually have a crush on Springfield's oafish bully.

Lisa does manage to bring out a good side to Nelson, and even if it doesn't last, you leave the episode sort of understanding him a little better...and frankly, I came to love the character a lot more after the episode first aired. 

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#9 - Treehouse of Horror VII

Written by Ken Keeler, Dan Greaney, and David X. Cohen

While I do think "The Genesis Tub" and particularly "The Thing and I" are good segments, a lot of my love of this anthology episode comes from "Citizen Kang", in which longtime alien characters Kang & Kodos kidnap then-current Presidential candidates Bill Clinton and Bob Dole with the goal of taking over their lives and then overtaking planet Earth for themselves. 

Homer is the one directly involved in witnessing this act and in order to make people not believe the story, they choose to soak him in rum so everyone assumes he is a drunk...which...to be fair...is not that far from the truth.

And even when everything could have a happy ending, Homer still manages to ruin civilization as we know it.

Perhaps my favorite aspect of this story is how both Kang & Kodos as Clinton and Dole seem to have no real sense of how these candidates should talk and yet the nonsense they dish out doesn't seem the least bit bizarre to the general public.

The most iconic of these lines would be Kodos as Clinton stating the line in the video clip below:

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#8 - In Marge We Trust

Written by Donick Cary

Marge themed episodes don't always seem to come as often...nor do they often seem to be as popular as those based around other characters.

However, I will always love Marge. 

The writers may not always utilize her to their detriment, but they often can find ways to make her hilarious amongst all the chaos.

"In Marge We Trust" puts her in a role of noble power as she takes over Rev. Lovejoy's help line at the church and she becomes a Christian version of Dear Abby. 

To contrast this, the B-plot is hilariously surreal and proves to be one of the show's more humorous bits of fanciful coincidence.

Homer, Bart, and Lisa make a long overdue trip to the dump to dispose of their Christmas Tree and come across a box of the Japanese cleaner Mr. Sparkle, whose mascot resembles Homer.

Homer is almost scared at why this mascot looks so much like him. 

The actual reveal: that two mascots from two conglomerates came together (a fish and a lightbulb) to make the Mr. Sparkle mascot is merely a coincidence...but it works so well as a B-Plot that I admittedly have forgotten in the past that it came from THIS episode as it felt strongly enough to work as an A-Plot.    

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#7 - Hurricane Neddy

Written by Steve Young

If there was ever a character on The Simpsons that deserved to snap, it was arguably Ned Flanders. By this point, we've watched him 8 seasons taking a lot of heat from his neighbor Homer...and in many ways, a lot of the citizens of Springfield.

Flanders was always cheerful and eager to spread his jovial religious views onto anyone who would listen...and that inner strength and sense of self was always a source of disdain to Homer.

It is no hidden secret that Homer has a dark desire to be more like Flanders...and it is even less a secret that Marge also wishes that she had someone like Flanders. Even all 3 of the Simpson kids have shown a desire to have Flanders as their father figure.

Hurricane Neddy is the moment where we finally get to see Flanders reach the end of his rope. When a hurricane hits Springfield, Flanders' house seems to be the only one somehow destroyed.

Despite a brief moment of despair, it seems like his prayers may have been answered when the citizens of Springfield gather together to rebuild the Flanders' home. 

Not surprisingly, it was a half-assed job and this sends Flanders off the cliff, insulting the entire Simpsons family and calling Homer "the worst person I have ever met".

Though, Flanders seems to know that he snapped and checks himself into a mental institution immediately after...and we discover with the aid of his former childhood psychologist that Ned Flanders was a child filled with rage who didn't take to his chill beatnik parents.

Obviously, I would never take or agree with the strict and devout ways that Flanders leads his life, but within the world of Springfield, he always provides such a great contrast to Homer and the loons around him. The episode simply works because it feels so good to see that Ned Flanders, the Saint, does indeed earn this fit of anger.

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#6 - The Mysterious Voyage of Homer

Written by Ken Keeler

Despite not being to the level of season 7 as I have stated before, I do have to admire that Oakley & Weinstein were willing to experiment.

"The Mysterious Voyage of Homer" was originally an idea pitched by George Meyer in season 3 but a lot of the staff felt it was too odd for the show and it was scrapped. While Oakley & Weinstein truly adored that era of the show, they were looking to find ways to imbue some new dynamics and dusted off the template for this episode. 

The family attends a chili cook-off, much to Marge's dismay, and while eating several hot chili peppers (thanks to the rather dangerous method of coating his mouth with scalding candle wax), Homer hallucinates and thus we get one of the first truly surreal sequences in the show's history. 

Not to mention the guest appearance of Johnny Cash as Homer's cayote spirt guide in one of the best guest star coups the show managed to net.

I also credit this episode for developing my love of Janis Ian's song At Seventeen. You hear it sung in a cheesy ironic way by a bunch of beauty queens way back in Season 4's A Streetcar Named Marge, but here, we get an actual snippet of the real song. 

And then to also tie back to a season 4 moment, the episode ends with the song "Who Wears Short Shorts?" but in a moment where Homer and Marge have yet another sweet reconcillation. 

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#5 - Bart After Dark

Written by Richard Appel

The idea of having Bart work in a burlesque house is slight tip in the direction of showing viewers that the show might be going for more bombastic ideas...but nevertheless, the episode works rather well.

A lot of it has to do with the setup: a classic example of what appears to be a kid losing a toy on someone else's property that seems truly scary, but instead of going for something sweeter and more sentimental, they trick you into having the secluded house actually being a burlesque venue that is quite popular with the men of Springfield.

The madame of Maison Derrière, Belle, has Bart start working there as a way to make up for destroying one of her stone gargoyles. Marge is rather upset by the fact that this venue even exists and in true Marge fasion, seeks for it to close down.

The episode ends with Belle and the citizens of Springfield being won over by a big song-and-dance number, We Put the Spring in Springfield...which ended up winning an Emmy for Best Original Song.

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#4 - Homer's Phobia

Written by Ron Hauge

The YouTube channel TheRealJims is devoted to the history of The Simpsons and if you are a truly fanatic admirer of the show like I am, I would recommend checking it out.

I bring him up because he recently did a video about the concept of "Jerk-Ass Homer", which was a term that was created in the late-90s in various online fan forums due to the distaste of how writers just seemed to make Homer a jerk simply for the case of being a jerk.

I will talk more about that when we get into seasons 9 and 10, but there is a valid point to be made which that particular video brought up: Wasn't Homer ALWAYS kind of a jerk?

Yes, he was.

However, the moments of volatility seemed a lot more sparce OR...and this is the key factor...his worst moments were met with punishments or embarrassments or actual realizations of his faults.

A lot of this came out of character driven storylines, and "Homer's Phobia" is a prime example of how an ignorant viewpoint ends up becoming a moment of character growth for him.

As the first real episode to delve into extensive LGBTQ+ themes, "Homer's Phobia" holds up remarkably well and it helps that they got someone like John Waters to guest star as the gay character John...whom the whole family instantly takes a liking to. If stuffy Marge can accept John, so should Homer...even Bart shows no sign of discomfort with John.

While the reindeer ending is a bit...odd, I do think the rest of the episode works well as a social commentary for its time. 

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#3 - Supercalafragalisticexpiala(annoyed grunt)cious

Written by Al Jean & Mike Reiss

This is another one of those episodes that seemed more based on a silly plot device rather than more character driven stories that would bear some resemblance to reality. Co-writer Mike Reiss actually objected to this episode at first for that very reason and fought hard to keep any real magical moments at a minimum. The final product ended up being one of his favorite episodes he contributed to.

Considering how much I adore Mary Poppins, I can't help but love this episode, too.

I actually considered this my favorite (or at least top 3) episode back around the time it first aired. While I certainly wouldn't rank it anywhere near that level anymore, I still greatly enjoy the episode and each of the beats taken from the plot of Mary Poppins. 

Voice actor Maggie Roswell (who worked on the show doing such characters like Maude Flanders) was tasked with voicing Sherry Bobbins, the Mary Poppins counterpart. She excels in the role by imbuing it with a true Julie Andrews style. It was said that Julie Andrews was lined up to actually perform the role, but scheduling with her run in Victor/Victoria and her infamous surgery that cost her the upper range of her singing voice made her step aside.

Despite it being an unrealistic idea borne out of a fantasy film, this is one of the times (thanks to it being on the earlier side of the shift) that the show nailed it and gave us an episode that is just simply nostalgic and fun.

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#2 - Grade School Confidential

Written by Rachel Pulido

As Sideshow Bob once said, "You only get one shot with Edna Krabappel".

Throughout the last 8 seasons, Edna Krabappel has been a common fixture within the show, but mainly confined to the world of Springfield Elementary where she is Bart's 4th grade teacher.

She is a snarky and surly and often crabby woman...but she also has a wicked and sly sense of humor and tends to be unlucky in love...or she just hasn't found the right man and she won't settle.

Pairing Edna with the ultimate Mama's boy this side of Norman Bates almost seems as right as it does wrong.

Principal Seymour Skinner's squarish tendencies and Edna's penchant for mocking him always made for great laughs, and it was clear that the writers saw immense potential in pairing them.

In fact, there were talks in the writers' room of doing so as early as season 3. Even in an episode from that season, "Bart the Lover", they reference Edna possibly dating Seymour to which she refuses because "his mommy won't let him out to play".

Bart discovering their affair is not surprising, nor is his becoming their gofer so they can exchange messages secretly throughout the school day. 

Even after he ends up exposing them eventually which leads to their temporary firing, he pushes for them to get their jobs back. In the end, despite the antagonistic nature this triangle shares, it is truly amazing the hidden warmth they have for one another.

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#1 - Homer's Enemy 

Written by John Swartzwelder

Yeah, I know...this is a pretty typical choice. Also, it used to be (not sure if it still is) the highest rated episode of The Simpsons on IMDB. 

When it comes to the concept of meta-commentary, there is a lot to unpack with an episode like "Homer's Enemy".

It acts as such a strong attack on the show's lead character and with rather morbid results at the end that when it aired, it divided people intensely.

At the time it aired, I was about to turn 9 but was an avid viewer of the show. I can recall the old Simpsons online forums blowing up because many people considered this the end of the show. Others considered it a bold masterpiece.

I obviously wasn't as astute as a lot of the people on the forum at my age, but I always loved this episode. It doesn't surprise me in the least that it has since gone on to be a classic and also the final masterful episode of the Golden Age as season 8 would come to a close just two episodes after this one.

"Homer's Enemy" is that of Frank Grimes, a character developed just for this episode (which is normally a motif I hate on other shows but leave it to this writing staff to make it work) who grew up having a hard life. Despite many obstacles, he persists. He takes a job at the Springfield Nuclear Plant and is placed in Sector 7G with Homer, Carl, and Lenny.

Almost instantly, Frank takes an instant dislike to Homer and is baffled by his laziness and incompetent behavior...especially considering he is the head of Safety for the plant.

The concept of having an outsider come into this world and instantly call out all of the great things that Homer has around him that he honestly didn't truly earn was a very bold move. The show had never been so blatant in calling attention to itself. 

In many ways, it was a critique on themselves just as much as you could view it as being a metaphor for the American Dream and how no matter how hard you may work at it, some others may just grab more for doing a lot less out of pure luck.

The death of Frank Grimes at the end is easily one of the darkest places The Simpsons goes towards, but I still think it was a brilliant place to go.

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Final Thoughts:

Season 8 is one that I have waffled on. For many years, I stated that the Golden Age ended on a high note with Season 7 and then we were left with a whimper in season 8.

Time has been far more kind to season 8 than I ever anticipated. Sure, there were a few episodes I absolutely loved from this season even back when it first aired (a few of them are on this list), but I didn't respond as strongly to the rather abstract and surreal choices after really loving the whimsical and character driven nature of season 7 and the dark and slick season 6. 

I would say that while there is a noticeable drop in quality compared to seasons 6-7, I would still consider season 8 to be a part of the Golden Age...and it would be the season that officially ends it.

Season 8 does try to change the formula a little bit in the same vein that David Mirkin tried to do in season 5, but I think the big difference between these two seasons are that Oakley & Weinstein just had a more innate understanding of how to blend in a certain warmth and whimsy along with the snark and cynicism...or at the very least, they were able to maintain a stronger consistency level.

Maybe it is unfair to necessarily say it played a factor, but while Mirkin came in as an outside hire for season 5, Oakley & Weinstein were hired as writers prior to Season 4 by then-headwriting duo Al Jean & Mike Reiss, who had been with the show since day one. Not to mention, the original team of Brooks, Groening, and Simon were still strongly present in the writers room at that time.

Even if Mirkin did eventually find his groove and create some truly iconic moments, I just think Oakley and Weinstein were the better fit and they managed to turn out a slightly more successful spin at revitalizing the show than the final results of Mirkin's Season 5.

Sadly though, Oakley & Weinstein step down here and the reins are turned over to Mike Scully.

Scully has written a couple of great episodes (with a couple already being mentioned on my lists so far), but Simpsons fans have some strong feelings about him. In many ways, he is the man who set the show down the path that still has many bemoaning to this day that it should've been cancelled 20 years ago.

But I will go more into that when discussing season 9...