The Top 10 Most Essential Episodes Of The Simpsons

The Simpsons are an institution.  Everybody knows who they are, and in my youth, they were the only reason to watch television on Sunday night.  Their mixture of over-the-top antics, subtle hilarity, and iconic characters has shaped the way people think about animated entertainment.  While there is no denying that The Simpsons have declined in quality in recent years, it doesn’t change the fact that the show is (in my opinion) the greatest show of all-time.  I would agree that it’s about time for Matt Groening to call it a day with the series and focus on different ventures (Futurama, for one, is still excellent), but I would be lying if I said that I wouldn’t be sad when the final episode comes to a close, as they were such an influential part of my life.  The show is still solid these days, and still a good way to spend thirty minutes, but the episodes these days aren’t the kind that I’m going to be text-quoting with my friends during class (more on that later).  I mourn for today’s youth because they just won’t understand how great the show was.  It may not be what it once was, but The Simpsons are to television what Mario is to video games, or what The Beatles are to music.  To put it simply, The Simpsons are timeless.  Being a Simpsons superfan for the majority of my life, I’ve compiled a list of the 10 most essential episodes of The Simpsons.  Even if you’re not a fan of the show, I truly feel these 10 episodes are ones that everyone can watch and enjoy.

Before I start, I would like to mention some episodes that didn’t quite make the cut but deserve honorable mentions:

“The Telltale Head”
“Bart the Daredevil”
“Mr. Plow”
“Marge Vs. The Monorail”
Basically every episode from seasons 5-8.

Now, let’s start the official list.

10) Simpsons Roasting On An Open Fire
Episode Number: 1
Original Air Date: 12/17/1989
Fun Fact: Originally planned to be episode 8 of season one.

What better way to kick off this list and by talking about the episode that started it all?  This episode tugs at my heartstrings every time I watch it, and it’s become a Christmas staple of mine, I watch it every year.  After Bart spies a tattoo parlor in the Springfield Mall, he heads in and gets tatted up.  An angry Marge has to use the money they were saving for Christmas to get the tattoo removed, and plans to use the Homer’s Christmas bonus to pay for presents.  The only problem being that Springfield’s very own Scrooge (and Homer’s boss), Mr. Burns, doesn’t give his employees a bonus that year.



To help pay for Christmas presents, Homer takes a second job as a mall Santa Claus.  After being exposed by Bart, Homer is fired.  Dejected, he goes with Barney to the dog track, using the last of his money to bet on a dog named “Santa’s Little Helper," viewing it as a sign from God.  Unfortunately, the greyhound finishes last.  While leaving the track, Santa’s owner abandons him, and Homer reluctantly takes the dog with him.  As Homer tries to think of a way to break the news to the family that there won’t be a Christmas that year, the family, thinking that Santa’s Little Helper is their Christmas gift, are overjoyed.

This is the very first episode of The Simpsons that ever aired, although it wasn’t originally planned that way.  But, in my opinion, this is the perfect episode to start the series off with, and I couldn’t imagine a world where it wasn’t.  It truly is the best reflection of what the family is: a group of people full of flaws, that despite everything, always know that they have one another.  This is the best episode to try and understand Homer Simpson as a character.  He’s a grotesque man-child, slacker extraordinaire who, at the end of the day, loves his family and will do whatever it takes to make them happy.  He may not always be able to provide them with the extravagant items they desire, but he will go above and beyond what most people would in order to try.



This episode isn’t so much memorable for one-liners and signature gags, but it’s a classic for every Simpsons fan.  Everybody has their Christmas traditions, and watching this episode is one of mine.

9) Treehouse Of Horror V
Episode Number: 109
Original Air Date: 10/30/1994
Fun Fact: Features James Earl Jones as the voice of Maggie.

The Treehouse of Horror episodes are a Simpsons tradition.  The annual Halloween episodes are generally considered to be one of the highlights of every season, and this particular installment from season six is, in my opinion, the best of the bunch, although it is definitely a tough contest.  Treehouse of Horror is always split into three separate stories, usually parodying classic horror cinema or literature.  Sometimes the episodes are book-ended with a story.  For instance, one of them starts with the kids eating too much Halloween candy, causing them to have nightmares, the nightmares being shown as the segments.  Everything from classic horror (Dracula, Night of the Living Dead) to classic literature (War of the Worlds, The Raven) to more recent flicks (A Nightmare of Elm Street, Sweeney Todd) have been the basis for some of the segments.  Alien characters Kang and Kodos are brought out every year for the Treehouse of Horror, usually in one of the sketches, but sometimes only in the opening or closing segments.  One other tradition is the use of “scary names” in the credits.  The easiest example being Matt Groening being billed as “Bat Groening.”

The first segment of this episode is widely considered to be one of the best things not only in the Halloween episodes, but in the entire series, and I would have to agree.  It’s called “The Shinning,” and you can pretty easily figure out what the parody is.  The Simpsons become the caretakers of Mr. Burns mansion, who cuts off the power and removes the beer from the extravagant home to try and ensure hard work from the family.  With Homer’s two favorite things completely removed from the house, he begins to slowly lose his mind.  Groundkeeper Willie discovers that Bart has “the shinning,” and can read his thoughts (but not between 4 and 5 because that’s “Willie’s time”), and tells Bart to use his “shin” to call for Willie if Homer goes crazy.  Homer, while sitting in a vacant bar in the mansion, is confronted by an apparition of Moe, who tells Homer to kill his family for a beer.  Homer does indeed try to off his family, and hilarity ensues.



The second segment is “Time and Punishment.”  While trying to fix a broken toaster, Homer accidentally turns it into a time machine.  Homer travels back in time and remembers his father’s words of “If you go back in time, don’t step on anything…”  Homer accidentally kills a small bug and shortly thereafter is transported back to the present day.  After seemingly nothing has changed, Homer believes he is in the clear, only to discover that Ned Flanders is the ruler of the world.  Homer returns to the past several times, and has a different present day each time he returns.  Homer eventually settles for an exact version of his life, only with a family who has lizard tongues.

Seeing as this particular entry is already running long, I will give you a brief description of the third and final segment, “Nightmare Cafeteria.”  You ever see Soylent Green?  It’s that.  The staff of the school start killing the kids in detention and turn them into food for their own consumption.



Every Treehouse of Horror is great in its own way, but this is definitely one of the standout entries, and like I said earlier, my personal favorite.  “The Shinning” is the standout of the episode, but each segment is solid and offers something completely different from the other two.  It also features the best gag of the Treehouse episodes, with Groundkeeper Willie being stabbed in the back with an ax in every segment.

8) The City of New York Vs. Homer Simpson
Episode Number: 179
Original Air Date: 09/21/1997
Fun Fact: I once wrote a blog about a Simpsons/September 11th conspiracy based on this episode.

Almost every episode that involves the Simpson family doing some traveling is a fantastic one.  They’ve been to every continent except Antarctica.  They’ve gone to Japan, China, Africa, Australia (more on that later), Italy, Brazil, Canada, and so on.  But sometimes they travel within the United States, and when the family traveled to the Big Apple, it was a classic.  The plot is simple: Barney, upset after being chosen as a designated driver, disappears with Homer’s car.  Months later, Homer receives a letter telling him that his car is illegally parked at 1 World Trade Plaza in New York.  Thus, the Simpsons go to New York City to retrieve the car.



The reason that these traveling episodes are always so good is because it’s always fun to see the family confronted with things they don’t see in their everyday lives.  In this particular adventure, the entire family is excited to go, except for Homer, who once had a terrible experience in the city, and just wants to go get his car and come home.  So Homer waits with the car until the boot is removed while the rest of the family explore.  The writers are always able to poke fun at the particular city they’re spotlighting and keep it funny, subtle, and tasteful.  They’re able to exploit the stereotypes of the population without offending, and in most cases, the population laughs along with everybody else.

This episode is the youngest on the list; the first episode of season nine.  That’s not to say that the seasons that follow this one aren’t top-notch, because they are, and if this were a top-20 list, I would probably have a few episodes from seasons ten, eleven, and probably even twelve, because there are some episodes on those seasons that are damn good. If this were a top-10 “favorite” episodes, this list would be different, but I’m listing the top “essential” episodes, and in that case, this is the way the cookie crumbles, and the ten essential Simpsons occur before the new millennium.

7) Homer’s Enemy
Episode Number: 176
Original Air Date: 05/04/1997
Fun Fact: The physical appearance of Frank Grimes is modeled after Michael Douglas in Falling Down.

The basic premise of this episode is to pair Homer with an everyman, the kind of guy who works hard but has very little.  Frank Grimes is that kind of man, a man who grew up poor and worked as a delivery boy who delivered presents to more fortunate children, used his few leisure moments to study science by mail, and lives above a bowling alley and below another bowling alley.  When that kind of person is paired with Homer Simpson, the shining example of a lazy, incompetent employee who somehow lives the “American Dream,” the interactions between the two make for comedy gold.

When Frank Grimes is hired by the Springfield Nuclear Power Plant, he is immediately dumbfounded by the fact that Homer is the safety inspector of the plant, referring to him as an “irresponsible oaf.”  All of Homer’s actions annoy “Grimey.”  Things like stealing and chewing all of Frank’s pencils, eating Frank’s lunch, and getting Frank in trouble after saving Homer from drinking a beaker of sulfuric acid and destroying Mr. Burns’ wall.



Homer, being upset about the fact that Frank hates him, invites Frank over for dinner.  After meeting the rest of the family, Frank becomes enraged at how easy Homer has it and how hard he’s had to work for considerably less, and eventually tells Homer off.  After talking with Marge, Homer decides that the best way to get on Frank’s good side is to become a model employee.  Not buying the charade, Frank alters a flyer for a children’s model power plant competition, tricking Homer into entering the competition and hopefully embarrassing him in the process.  Homer winds up winning the competition, which causes Frank Grimes to go crazy.  Frank goes on a rampage through the plant, trying to demonstrate Homer’s incompetence, but all Frank manages to do is kill himself by electrocution.



This episode is regarded as perhaps the darkest episode of the entire series due to the way it ends.  I, personally, would have loved to have come across Frank in later episodes.  They did have a Frank Grimes Jr. trying to get revenge on Homer later in the series, but Frank Grimes was always meant to be a one-time only character, and he is always brought up when people mention the best guest characters on the show.

6) A Star Is Burns
Episode Number: 121
Original Air Date: 03/05/1995
Fun Fact: Series creator Matt Groening hates this episode, and actually tried very hard to get it pulled.

This is the one and only time an episode of The Simpsons could be considered a crossover.  Anyone my age may remember the cartoon The Critic, which starred Jon Lovitz.  I personally never watched the show, so I can’t speak of its quality.  Matt Groening hated this episode, as I just mentioned, because he viewed it as an advertisement for another show.  He lobbied to get it pulled, and was unsuccessful, and I would like to go on record and give my thanks to whoever it was that stood up to Mr. Groening.  All due respect to you, sir, obviously I’m a big fan, but I love this episode, and I know a lot of other people that do as well.



Springfield is voted as the least cultural city in the United States, and a town meeting is called to find a solution.  Marge proposes the idea of holding a film festival, to which the town jovially agrees, making Marge the head of the festivities.  As another way to draw in tourists for the festival, Marge brings in New York film critic Jay Sherman to be a special celebrity judge.  Homer, feeling like Marge doesn’t respect his opinions, begs her to put him on the judges panel, and she reluctantly agrees.  Meanwhile, Mr. Burns, learning that his wealth has decreased because of his poor image with the public, decides that he will buy his way into the Springfieldians hearts by bribing the judges and winning the contest.  Long-time boozehound Barney Gumble enters a film into the contest as well, which is far superior to Mr. Burns’.  Unable to come to a consensus about the winner (Krusty and Mayor Quimby voting for Mr. Burns, Marge and Jay voting for Barney, and Homer voting for “Man Getting Hit By Football"), Homer gives the films another round of consideration.  After a long and tough debate (Barney’s film had heart but “Football in the Groin” had a football in the groin), Homer eventually chooses Barney’s film.

In addition to some great Rainier Wolfcastle scenes and perhaps the best use of a tumbleweed the television world has ever seen, there’s also a great character in Senior Spielbergo, Steven Spielberg’s non-union Mexican equivalent.  He doesn’t really say much, but his subtle approval of Bumblebee Man to star in Burns’ film I still find funny every time I watch it, and I wouldn’t mind seeing Spielbergo make another appearance in the series.

I understand Matt Groening’s reservations about this episode, but I can’t say that I was ever tempted to watch The Critic, and I’m still not, despite how much I love Jon Lovitz.

5) Homer At The Bat
Episode Number: 52
Original Air Date: 02/20/1992
Fun Fact: Surprising to no one, Jose Canseco was not cooperative, and insisted that his part be re-written.
Bonus Fact: Ryne Sandberg and Carlton Fisk rejected offers to appear in this episode.

The reason this episode is so fantastic is because it mixes one of America’s best television shows with America’s pastime, baseball (or softball if you want to be picky about it).  Mr. Burns makes a bet with Aristotle Amadopoulos (thank you, Wikipedia), the owner of the Shelbyville Nuclear Power Plant, that his plant’s softball team will beat Aristotle’s.  Mr. Burns then hires professional baseball players to be ringers for his team, giving them all jobs at the plant.  If you aren’t a long-time baseball fan, some of these names may not sound familiar, but the players Mr. Burns brings in are: Roger Clemens, Ken Griffey Jr., Steve Sax, Mike Scioscia, Wade Boggs, Don Mattingly, Jose Canseco, Ozzie Smith, and Darryl Strawberry.

With a stroke of bad luck, every player except for Strawberry has to miss the game, and that’s really what makes this episode so fantastic.  The reasons the players miss the game are just so ridiculous, and in some cases completely over-the-top:

-Roger Clemens thinks he is a chicken after being hypnotized.
-Wade Boggs gets knocked out by Barney at Moe’s tavern over an argument about who was Britain’s best prime minister.
-Ken Griffey Jr. develops gigantism after consuming Mr. Burns’ nerve tonic.
-Steve Sax is from New York and is arrested by Springfield Police because they assume he is responsible for every unsolved crime in the city of New York.
-Mike Scioscia develops radiation poisoning from taking his job at the plant too seriously.
-Don Mattingly is kicked off the team by Mr. Burns after repeated requests to shave sideburns that he doesn’t have.
-Ozzie Smith disappears into another dimension at “Sprinfield’s Mystery Spot.”
-Jose Canseco gets stuck rescuing a woman and all her possessions from a house fire.



Homer is downtrodden by the fact that even after everyone else misses the game and is replaced by the original team, his spot is still taken up by Darryl Strawberry.  I must say that Strawberry is my favorite character of all the players because he constantly sucks up to Mr. Burns, pointing out other players’ bad attitudes and referring to Mr. Burns as “Skip.”  However, with the game on the line, with bases loaded in the last inning, and Strawberry due up to bat, Mr. Burns, being the witty baseball man that he is, has Homer pinch-hit for Strawberry.  Homer steps in, ready to knock home the game-winning run…and gets hit in the head with the ball, and the winning run comes home.  Springfield wins!

And for the icing on the cake, the episode ends with an amazing song made for this episode called “Talkin’ Softball.”  I actually find myself listening to that song on my iPod just because it makes me so happy.



4) Bart Vs. Australia
Episode Number: 119
Original Air Date: 02/19/1995
Fun Fact: The staff of The Simpsons received over 100 letters from Australians who were insulted by this episode.

I mentioned earlier how it’s always fun to see the Simpson family outside of their element.  Seeing them in New York City was delightful, but when the family travels to the outback, it makes for one of the best episodes of the entire series.  I happen to think this episode is rather underrated, I don’t usually see it mentioned on too many ‘best of’ lists, but in my opinion, from start to finish, it’s a genuine classic.  It features so many subtle laughs that go unnoticed (like the Australian stamp that boasts: “Australia: 30 Years of Electricity"), and also a great performance by the late Phil Hartman in one of his many non-recurring character roles.  The one-liners are some of the best the writers have ever come up with, the “knifey-spooney” and “chazwozzers” lines being the standouts.



The basic story starts out with Bart and Lisa arguing about the “Coriolus Effect” (go look it up).  Trying to prove Lisa wrong, Bart makes a collect call to Australia and winds up leaving the phone off the hook, resulting in a 9-hour call and a phone bill of 900 dollary-doos.  Bart is then confronted by the United States Embassy and asked to go to Australia to make a public apology.  While Bart and Homer go together to make the apology, Lisa and Marge do some tourism.  The Australians trick Bart, and after his apology, try to punish him by giving him “the boot.”  It may just be a little kick in the bum, but Homer is outraged, disparages the boot (which is a bootable offense), and manages to wrestle it away and using it against the natives to escape back to the U.S. Embassy.

Bart, with a sudden surge of American pride, eventually relents to accept the booting, who then rescinds the offer by mooning the Prime Minister.  The Simpsons then escape on a helicopter.  The final scene of this episode is so good that I’m not going to ruin it, it begs to be viewed.



I mentioned in the fun fact that many Australians were very upset with this episode.  They do poke fun at a lot of Australian things, like Crocodile Dundee, Foster’s beer, and the language in general.  They even make mention of the fact that Australia was founded as a territory to house British convicts, and all the Australian natives are portrayed as a bunch of half-wits.  But you know what?  It’s funny, so lighten up, Australia.

3) Lemon of Troy
Episode Number: 127
Original Air Date: 05/14/1995
Fun Fact: The overall plot of this episode is an allegory to the Trojan War.

This is arguably the most quotable episode of The Simpsons.  I once spent a 3-hour class in college texting this entire episode back and forth with my friend Luke.  The story is basic: Springfield’s youth get into a scuffle with the youngsters of rival town, Shelbyville.  The Shelbyville children steal Springfield’s iconic lemon tree, and Bart and his cohorts must travel to the foreign land (where the fire hydrants are yellow) to get it back.



The episode starts with Marge catching Bart defacing public property, and she attempts to teach him a lesson about town pride.  Soon after the lesson sinks in, the boys of Springfield get into a trash-talking contest with the boys of Shelbyville.  The next day at school, Nelson Muntz interrupts class to inform the kids that the town’s lemon tree has been stolen.  The dream team of Bart, Milhouse, Nelson, Todd Flanders, Martin Prince, and Database go on a journey to their hated rival town to try to find the tree and bring it back where it belongs.  Bart later disguises himself (his wig makes him look just like one of the Beatles) and infiltrates the Shelbyville gang.  After outing himself as Bart Simpson...from Springfield, we have an epic skateboard chase scene that culminates in Bart being trapped in the tiger cage at the Shelbyville Zoo.  After narrowly making his escape, the parents of Springfield find their missing children, where the parents are informed of Shelbyville’s theft.  They come to discover that the tree is being held hostage inside the Shelbyville impound lot.

The plan they come up with is to park Flanders’ RV in a tow away zone to get the RV taken to the impound lot, where they successfully take back the lemon tree.



This is one episode of The Simpsons that you will see on almost everyone’s favorite episodes list.  It’s basically been scientifically proven that season six is the best season of The Simpsons, and quite possibly, the best season of any show, ever.  And this is the best episode of the season.

*Note: all scientific facts for this study were done by me, in my head.

2) Cape Feare
Episode Number: 83
Original Air Date: 10/07/1993
Fun Fact: In the original script, Sideshow Bob was only supposed to step on one rake, but, fearing they wouldn’t reach the minimum run time for the episode, the writers stretched the scene by making him step on nine.



Parodying the movie of the same (differently spelled) name, this episode features Kelsey Grammer reprising his role as Sideshow Bob, the former sidekick of Krusty the Clown and several time convict.  Every time Sideshow Bob comes back, he has some sort of gimmick: Aunt Selma’s husband, Mayor of Springfield, destroying television with terrorism, and even an episode where he is trying to live on the straight and narrow.  This episode, however, is Sideshow Bob doing what Sideshow Bob does best, which is attempting (and failing) to kill Bart Simpson.  Killing Bart is almost always Bob’s underlying motive, as Bart was the person to get Bob captured and locked away in the first place for robbing the Kwik-E-Mart.

In this particular adventure, Sideshow Bob slips through the cracks of the American legal system and is let out on parole.  He wastes no time going after his old nemesis.  After receiving several death threats, Bart and the family are relocated to Terror Lake, only to find that Bob has followed them.  One night on the Simpson’s new houseboat, Bob ties up the family, hijacks the boat, sets sail down the river, and finally, tries his best to rid the world of a one Bart Simpson.

Being the gentleman that he is, Sideshow Bob grants Bart one last wish.  Knowing that he needs to stall for time, his request is to have Bob perform the entirety of the H.M.S. Pinafore.  Just as Bob finishes the opera, ready to strike down the heathen that is Bart Simpson, the ship crashes on the shores of Springfield, where Chief Wiggum and the rest of Springfield’s “finest” are waiting to make the arrest.



Sideshow Bob episodes are always great, and I would say that Bob is the best recurring character in the entirety of the series, and this episode is the standout performance, and also marks the beginning of his now famous rake gag.  There really couldn’t be a better pick than Kelsey Grammer for this role.  Bob is a well-educated, well-spoken, debonair individual, much like the real Kelsey Grammer, only with more homicidal tendencies.

1) You Only Move Twice
Episode Number: 155
Original Air Date: 11/03/1996
Fun Fact: Albert Brooks, who voiced Hank Scorpio, ad-libbed the majority of his lines for this episode.



I will start by saying this:  if Sideshow Bob is the single best recurring character in the history of the series, then Hank Scorpio is the single greatest non-recurring character in the history of the series.  If you think I’m wrong then you haven’t seen this episode.  I’m tempted to not even mention the plot and just talk about him.  This is both the most essential and my personal favorite episode of the show.  I will say minimal about this one because seriously, even if you’re not a fan of the show, you will enjoy this particular episode.  The way Homer and Hank play off each other, the way that Homer is completely oblivious to his super-villain of a boss, the scenes with Bart in the remedial class, and Scorpio’s eccentricities all combine to make this an episode that can be viewed multiple times in a row without ever getting tired.



Long story short, Homer gets a new job with the Globex Corporation in Cypress Creek, working for Hank Scorpio.  That’s all I’m going to give you plot-wise, because anything else I say will just be ruining it.  Everyone owes it to themselves to see this one, and I believe all die-hard Simpsons fans would agree.

There it is, my top ten most essential episodes of The Simpsons.  You may not agree, but I’ve been a Simpsons connoisseur for almost my entire life, so I consider myself at least well-educated on the subject.  The Simpsons are my thing, and if you didn’t like this, then don’t have a cow, man (see what I did there?).

*Note: With the exception of where I thanked Wikipedia, this entire article was done by memory, so if I messed something up, shut up about it.

Thanks for reading!