My Top 10 Episodes of THE SIMPSONS (with 5 Honorable Mentions)

I am going to tackle something that has been tackled hundreds of times before by copious amounts of people…and chances are, I won’t be saying anything new to some extent…though whatever, I felt compelled to talk about it.

THE SIMPSONS is a show that is still on the air as of this writing and will be approaching its 32nd season (though it remains to be seen how much COVID-19 will affect its schedule) and despite the fact that the show can still dish out solid episodes from time to time, it is definitely a shell of what it once was.

Despite the fact that its glory years are far into the past, those years still so shine so brightly and they hold up remarkably well today. I am going to try to narrow down what would be my personal top 10 favorite episodes of THE SIMPSONS along with five honorable mentions to sort of tide me over.

This proved to be incredibly difficult as certain plot lines and characters would come to mind and I would think about how I wanted to include an episode surrounding them…and then not have room for those episodes at all. No matter what, there are dozens and dozens of classic episodes that this small list won’t even get to go into and I think you’ll find several writeups on those episodes online.

What did I come up with?


THE PRESIDENT WORE PEARLS (Season 15): The only post Season 8 episode to make it this high. Lisa runs for Student Body President and ends up becoming an Eva Peron-esque figure.

BLACK WIDOWER (Season 3): The second appearance of Bart’s ultimate nemesis, Sideshow Bob (Kelsey Grammer) who is out to kill Bart after he ruined his plan to frame Krusty the Clown for a crime. In this episode, Bob is out of prison and is trying to marry Bart’s Aunt Selma…and Bart realizes he is intending to kill her.

ONE FISH, TWO DISH, BLOWFISH, BLUE FISH (Season 2): One of the earlier episodes that had a darker tone in which Homer supposedly eats some poisionous sushi and is told he has 24 hours to live and therefore seeks out to complete his bucket list.

MOTHER SIMPSON (Season 7): A very key episode in understanding Homer as he discovers his mother (voiced by Glenn Close) is really alive and on the run from the law (she had exposed Mr. Burns’ plan for Germ Warfare…another hilariously evil plotline about him). His desire to have a relationship with her and the pain when she has to keep running showcases Homer at his most vulnerable and lovable.

CAPE FEARE (Season 5): Perhaps the most famous of the Sideshow Bob episodes, this one parodies the legendary film CAPE FEAR and how the family has to go into Witness Protection on a boat to hide from Bob and his continued quest to murder Bart.


#10-A STREETCAR NAMED MARGE (Season 4) Written by Jeff Martin

The marriage of Homer and Marge is often quite bewildering and it is often difficult to watch Marge put up with the insensitive antics and the lack of awareness constantly put out by Homer. In this episode, she decides to audition for a community theatre production: a musical adaptation of Tennessee Williams’ A STREETCAR NAMED DESIRE…and despite telling Homer, he immediately forgets and she feels ignored by the family.

Marge ends up getting cast as the lead, Blanche, opposite her neighbor Ned Flanders (back before he became TOO religious to participate in such an event) as Stanley when the director, Llewellyn Sinclair sees similarities in Marge’s relationship with the oafish Homer is almost like that of Blanche and Stanley.

The episode is great in giving Marge a backbone and more of a story for herself as opposed to always being the supporting player to the rest of the family.

“A stranger’s just a friend you’ve never met!”

The subplot of the episode involves Maggie being a distraction in rehearsals leading Marge to have to leave her with a daycare: The Ayn Rand School for Tots….which is just pure genius. The daycare forces the babies to not have their pacifiers which is essentially the trademark of Maggie but she and the babies organize a plan to get them back, all to the theme from THE GREAT ESCAPE and ending with a priceless homage to THE BIRDS.

Possibly Maggie’s defining moment.

At the end, Homer does apologize and see the error of his ways but…we know he will return to them next week for better or worse.


#9-HOMER’S ENEMY (Season 8) Written by John Swartzwelder

In many ways, ‘Homer’s Enemy’ addresses the elephant in the room right before the series is about to drown us in an increased level of Homer antics: how does a man like Homer Simpson coast through life with so little consequences?

We meet the character of Frank Grimes (voiced by Simpsons regular Hank Azaria after William H. Macy had to back out at the last minute), a life-long struggling person who has been through obstacle after obstacle and just recently got a job at the same Nuclear Plant as Homer.

Grimes is appalled at Homer’s laziness and incompetence and then things become more volatile when, after saving Homer’s life by hitting a vile of sulfuric acid that he was out about to drink out of hands, Mr. Burns admonishes him for causing damage to the wall (due to the splashed acid) and docks his pay.

This sets Grimes on a frustrating path where he simply cannot understand the life that he has culminating in one of the darker endings in SIMPSONS history:

Skip ahead a minute in for the bulk of it to begin

John Swartzwelder was always one of the best writers on the series as he best captured the more surreal aspects that made the show unique.


#8-THE WAY WE WAS (Season 2) Written by Al Jean, Mike Reiss, & Sam Simon

Flashback episodes are often going to be classics or disasters but an episode like ‘The Way We Was’ falls on the side of true greatness because it shows why the relationship of Homer and Marge actually exists and persists.

Set around the typical backdrop of that a sitcom may use to begin such a story (the TV stops working), Marge and Homer tell the story of how they met in high school.

In the end, I think this episode may not seem as vibrant or as bold or as unique as others…but it is an important episode in establishing how much warmth and admiration was truly involved in their relationship considering all of the trials they’d be put through later on.

Hearing Homer tell Marge that he would be afraid to hug her because he would never want to let go is one of the sweetest things you could ever possibly hear…and whenever I think the show tries to decimate Homer as a character, I always try to remember that THIS Homer is still inside of him.


#7-LEMON OF TROY (Season 6) Written by Brent Forrester

An absolutely delightful episode that goes into Springfield’s often discussed feud with the neighboring city Shelbyville. This time, the main premise is that a group of young boys from Shelbyville have stolen Springfield’s prized and beloved Lemon Tree.

This was one of the episodes during the reign of David Mirkin in which his staff truly found the right balance of the show’s original whismy and his new brand of broader sensibilities. The sense of community in this episode is quite infectious and fun…sort of in that sense of how you don’t let anyone mess with those you love but sure enough, Springfield will have their own battles again.

The final moments show that perhaps Springfield might be better off than Shelbyville…and thankfully the former gets to drink the juice of Lemons.

No wonder the citizens of Shelbyville wanted the Lemon Tree


#6-BART SELLS HIS SOUL (Season 7) Written by Greg Daniels

Before going on to co-create KING OF THE HILL and adapt THE OFFICE for American television, Greg Daniels got his big break writing for THE SIMPSONS. His crown jewel was ‘Bart Sells His Soul’, an episode that was so well received that some Religious Studies and Philosophy courses have cited it as a rather potent approach on analyzing the nature and meaning of a soul.

Before going any further though, this episode surges right out of the gate with one of the best opening bits the show ever did: Bart’s Hymnal Prank.

“This sounds like rock and/or roll”

After getting snitched out for the hilarious prank by Milhouse, Bart is forced to do work around the church…along with Milhouse since he is forced to help. During a round of cleaning, Bart proclaims there is no such thing as a soul. Milhouse then promptly offers to buy his soul for $5 and once Lisa finds out, she expresses concern that Bart will end up regretting it.

Soon after, Bart begins experiencing strange incidents and has a nightmare that prompts him to beg Milhouse for his soul back, but he won’t return it for anything less than $50.

Philosophers have often debated if we are actually born with a soul or if we have to earn one. In some ways, Bart seems to search through himself and comes out perhaps actually gaining more of a soul than he may have had before.

The final moments of the episode are truly classic TV:

Leave it to Lisa


#5-KRUSTY GETS KANCELLED (Season 4) Written by John Swartzwelder

No show has as many great secondary characters as THE SIMPSONS does and near the top of that list is the cantankerous Borscht-Belt-esque Kiddie TV host Krusty The Clown, cynical and raspy-voiced and always ready to push some merchandise for a quick buck.

Bart, in particular, idolizes Krusty and with the help of Lisa they will help Krusty stage a comeback special after his show was cancelled due to competition from a children’s show hosted by ventriloquist Arthur Crandall and his dummy Gabbo.

I think this episode is a prime example of how the show was able to have guest stars on voicing as themselves without having to resort to cheesy gimmicks and bizarre situations just to make it work.

Here, the show is able to get the likes of Johnny Carson (which was impressive as this was post-retirement), Hugh Hefner, Bette Midler, Elizabeth Taylor, and The Red Hot Chili Peppers all based around the fact they are here to help Krusty…well not Elizabeth Taylor, blame her agent for that.

I just felt this was the show’s best attempt at “going Hollywood” and yet keeping it grounded in reality.

Sondheim was proud of the parody of his most popular song


#4-WHO SHOT MR. BURNS Part 1 & 2 (Season 6/7) Written by Bill Oakley/Josh Weinstein & Wes Archer)

Mr. Burns is one of the greatest TV villains of all time and by this point in the series, he had put Springfield through pure an utter hell (hilariously of course). Looking for a way to spruce up the show as he had been doing as a relatively new showrunner, David Mirkin and his staff devised this cliffhanger parody of the legendary storyline from DALLAS: Who Shot J.R.?

I feel like this two-part episode is a masterclass in satirical parody and it plays wonderfully if you were ever hooked into shows like DALLAS and how they played out such stories…but they even go as far to parody other famous TV mysteries such as adding TWIN PEAKS to the mix:

For a TWIN PEAKS superfan, this is pure gold

The actual reveal of the shooter is brilliant because it, too, falls under a typical soap opera trope: the culprit is either expendable as a character or the culprit has reasons that prevent them from facing punishment.

In this case, the shooter (SPOILER ALERT) was Maggie the baby!

And the show will even make meta-references to this silly development for years to come.

No jury in the world is gonna convict a baby…well, except maybe in Texas.”

Pure satirical gold!


#3-LISA’S SUBSTITUTE (Season 2) Written by Jon Vitti

While the earlier seasons of THE SIMPSONS were seen as an attack on the typical American sitcom, they also had something that made them very special: a heart of gold among the cynicism. A lot of this was due to the direct involvement of James L. Brooks, who often only acted as a consultant rather than a writer but also pushed for more heart and stories for Marge and Lisa.

I feel like I am always drawn to Lisa’s episodes and this one is the ultimate for me and it also deals with an issue that can be particularly difficult for children: a disconnect from a parent.

Lisa has never been one to have any kind of similar interests to her father Homer nor does he seem to really enjoy a lot of her favorite things. However, Lisa was always seeking approval and it was obvious she wanted Homer to be a figure to look up to in her life.

Instead, her ideal father figure shows up in the form of a substitute teacher named Mr. Bergstrom, voiced by guest star Dustin Hoffman.

I think one of the biggest successes of the episodes is how delicately the relationship between Bergstrom and Lisa is handled because it could come off as quite creepy but instead, you find it to be incredibly warm and moving…and it helps that Bergstrom goes to the source (Homer) and instead finds him to be hopeless.

This leads to what may be the most touching scene in the show’s history and one of the more iconic when Lisa discovers Bergstrom is living Springfield for another gig:

This scene made me tear up when I first saw it as a 6 year old

In the final moments of the episode, Lisa is still devastated by the departure of Bergstrom and as to be expected, Homer is not the least bit sensitive to the matter and finally sets Lisa off.

Sadly, I cannot find a good quality clip of the ending scene but it starts with Lisa referring to Homer as a “Baboon” and she runs off crying to her room. While the usage of the word ‘baboon’ is humorous as is Homer’s reaction to it, the devastation of Lisa is heartbreaking.

Homer eventually goes to Lisa’s room and in his own silly way (acting like a baboon) he is able to get Lisa back on his side in another really touching moment.

The B-Plot of the episodes is mostly inconsequential but works well as a comedic buffer and that revolves around Bart running for class president against the dorky Martin. One of the funnier images from this story is Bart’s poster, which says “SEX!” in big red font on the top…because it sells after all.


#2-MARGE VS. THE MONORAIL (Season 4) Written by Conan O’Brien

While this episode is often lambasted by the SIMPSONS cast for the same reasons the fans hate many of the later episodes for being too big and bold and not truly based in reality, I have to stick with the majority of the fans on this one and say this is the prime example of THE SIMPSONS excelling when dealing with a truly ridiculous plot.

Writer Conan O’Brien, in his last episode before he would be chosen as the successor to David Letterman’s NBC show, said the basis for this episode came when he saw a billboard in Los Angeles that simply said the word “Monorail”.

With that in mind, he came up with what is easily my favorite absurd plot in the history of the series.

When Mr. Burns is fined $3 million for dumping nuclear waste into a park, the city now has a surplus that Mayor Quimby wants to invest in a town project. Marge lobbies hard for the re-paving of Springfield’s city streets and the town seems on her side until a fast talking salesman appears in the door way. This is Lyle Lanley, voiced by frequent guest star and the sorely missed Phil Hartman, and he has a proposal:

Harold Hill has been reincarnated

Springfield, as a town, is always prone to mobs whether they be joyous or angry…and they all rejoice in having a fancy new monorail system. Marge is the lone holdout as she begins to see right through the cunning ways of Lyle and it is up to her to save Springfield, especially when Homer gets to be the conductor of said monorail.

The final couple minutes of the episode…with a random guest appearance by Leonard Nimoy

In 1995, Yeardley Smith, the voice of Lisa, called this the worst episode of THE SIMPSONS…although I would still be shocked if she felt that way. I can see why she and the cast had issues with this episode because of its abstract and over-the-top story but I still feel this was the best representation of such a story.


#1-LAST EXIT TO SPRINGFIELD (Season 4)-Written by Jay Kogen & Wallace Wolodarsky

Perhaps it is the Socialist in me that likes this episode?

I feel like this is sort of an anti-climatic choice as it is a frequent selection as the best, or at least one of the best, episodes of the series. For me, everything about Last Exit to Springfield is a snapshot of what made THE SIMPSONS truly remarkable when it was at the peak of its powers, and this would be the last episode written by the writing team of Kogen & Wolodarsky…they will be sorely missed.

The main premise of the episode revolves around Homer, of all people, organizing a strike AND becoming president of the Springfield Nuclear Power Trade’s Union once he discovers that his boss, the hilariously evil C. Montgomery Burns, is disposing of the company’s dental plan around the same time that Marge tells him Lisa will need braces…and as expected, they cannot afford them out-of-pocket.

The scene in which Homer makes this connection is classic as is the follow-up:


In the book PLANET SIMPSON, author Chris Turner also shares the opinion of this being the best episodes of the series saying it “should be taught in history, economics, social studies, literature, and art classes. It’s flawless”.

I do agree with him. It is hard to believe that THE SIMPSONS were once considered counter-culture but it’s true. This was a time when the series could tackle such an issue as the importance of Unions and the horror of the American Health Care system (two things that are greatly apparent and relevant in our culture today) and manage to do it with class and also great wit.

THE SIMPSONS could be great with a relatively quick low-blow joke and I quite love one of those that is contained in this episode: The Big Book of British Smiles:


I have always had a fondness for the character of Lisa Simpson and her liberal beliefs and wisdom beyond her years. I do quite enjoy how they utilize that side of her in this episode as she is seen singing and playing the guitar (instead of her saxophone) just like she were someone straight out of the 1960s:

Also: This clip includes scenes with Burns and Smithers which show more of the show’s trademark wit and also how wonderful those two characters are.

The episode contains one of my favorite endings of any SIMPSONS episode, which is able to put a spin on the typical treacly ending that many family sitcoms often have by poking fun at it and tying it in with the plot at hand.

Homer’s response is classic…and then Lisa’s new braces make for a funny ending that mocks cheesy sitcom finale bumpers.

It is truly one of my favorite episodes of any television series ever…but frankly, THE SIMPSONS has dozens and dozens of those among that list.


CONCLUSION: That’s the end of that! I hope you enjoyed my list and that the clips selected helped convey my love for these episodes. Next time, I will probably attempt to rank my top 10 favorite seasons of THE SIMPSONS…though, spoiler alert, it will be a mix of the first ten season more than likely.

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