The 10 Greatest Simpsons Episodes

I know I know. This topic's been done over and over again. But eh, who cares? With over 25 years on the air, there were plenty of episodes to consider. But in terms of the greatest, best, most essential or whatever, there are those special episodes (usually in the first 8 seasons or so) that are etched in the hearts of true Simpsons fans everywhere. So while the episodes that made my list aren't necessarily untouchable, these are my favorite episodes.

10.

Home Sweet Home-Diddily-Dum-Doodily

The title of the episode already gives it away – this is a Flanders heavy episode. Due to a series of unfortunate coincidences, Homer and Marge are deemed unfit parents and Bart, Lisa and Maggie are put under the Flanders’ supervision. As much as this episode delivers in laughs, it also delivers in poignancy as Marge and Homer have to deal with an empty home and Lisa and Bart have to adjust to a strange new household and lifestyle. Even though it is clear that life in the Simpson household isn’t perfect, this episode helps highlight the special bond that unites this mess of a family.

Best Moment: Homer and Cletus simulating a domestic situation in their parenting class.

9.

I Love Lisa

This was the episode where Simpsons watchers got to meet Ralph Wiggum the lovable doofus in Lisa’s class. Prior to this episode he was just a background character that went to Springfield Elementary but this episode really fleshed him out as a character. Here Ralph innocently mistakes a friendly gesture from Lisa as something more and proceeds to fall head over heels for her. This puts Lisa in a tough spot as she doesn’t feel the same way. This is one of the best examples of what The Simpsons can do when they combine real laughs with real heart.

Best Moment: Bart pausing and unpausing the moment when Ralph gets his heart broken.

8.

Who shot Mr. Burns (Parts 1 & 2)

It is only right that the only time The Simpsons used a season cliffhanger, it resulted in one of the more memorable episodes in its history. Part 1 mostly centers on Mr. Burns being even more villainous than usual. In the process he ends up pissing off Lisa, Bart, Abe, Seymour Skinner, Homer and even Smithers. Quite a feat - even for Burns. So when Springfield’s oldest billionaire gets shot off screen it sets up the intriguing part 2 expertly. This two parter delivers in laughs, mystery and great storytelling. It also featured the late great Tito Puente with a fantastic musical number.

Best Moment: The aforementioned musical number “Senor Burns”.

7.

The PTA Disbands

The funny thing about this episode’s title is that it references a slightly marginal part of the episode. The PTA doesn’t disband until almost halfway through and before then it isn’t even mentioned. The episode is basically about a standoff between Principal Skinner and the teachers of Springfield Elementary over the lack of funds in the school. When the teachers – ably represented by Edna Krabappel - decide to strike, it is up to local members of the Springfield community to come in and replace them. Of course this only makes things worse and as such the teachers and Skinner have to come up with a creative solution.

Best Moment: That’s a paddling. Nuff said.

6.

Deep Space Homer

One small step for man, one large step for the inanimate carbon rod. As we all know, Homer has had a LOT of jobs over the years, but not many more memorable than his stint as an astronaut. Okay the idea that NASA would pick Homer to go on a space mission is a little far-fetched – even if it is for ratings. But eh, who cares about plausibility? Like most of the other episodes on this list, this episode is filled with classic quotables for the avid Simpsons fan. It also featured famous spaceman Buzz Aldrin (how

many shows has he been on) and folk musician James Taylor.

Best Moment: The speed at which Kent Brockman was willing to sell out his fellow humans in the face of the “insect overlords” was alarmingly hysterical. The speech was gold and is easily one of the most quoted references in Simpsons’ history.

5.

Marge vs the Monorail

Conan O’ Brien’s greatest contribution to Simpsons’ lore. At times this episode plays like a loosely connected series of brilliant mini sketches but that’s only because the 22 minutes is bursting in the seams with some of the most memorable gags in the show’s history. The plot is simple enough – the town of Springfield happen on a $3 million windfall and need to spend the money on something to benefit its citizens. Enter Lyle Lanley, a charming S.O.B who through the magic of song and dance convince Springfield’s citizens to build a monorail. It is rightly considered one of the best episodes in the show’s history.

Best Moment: It has to either be between the Monorail song and Mr. Burns “clever” disguise.

4.

Sweet Seymour Skinner’s Badassss Song

Imagine a Looney Tunes episode where Sylvester isn’t trying to eat Tweety, where Elmer isn’t trying to murder Bugs in cold blood or where the Road Runner and Wil E Coyote get along. Well something similar happens here as mortal enemies Bart Simpson and Principal Skinner actually befriend each other when the latter loses his job. We get to learn more about Seymour Skinner as a character and understand the dynamic he has with Bart. This episode is equal parts touching and hilarious.

Best Moment: Apu showing his utter disgust at Skinner’s ignorance of “Jurassic Park”. But really, what was Skinner thinking?

3.

$pringfield

Also known as the episode where Marge develops a gambling addiction. While many Simpsons episodes center on Marge dealing with Homer’s screw ups, here Homer gets to be the stable one with hilarious consequences. One of the subplots involve Mr. Burns slow descent into madness as he struggles to cope with his new responsibilities as casino owner. The other subplot sees Bart open a casino in his treehouse for the Springfield kids. This episode features some of the most memorable gags and quotes in Simpson’s history as well as a great guest appearance by Richard Goulet.

Best Moment: The entire Simpsons family sans Marge freaking out at the supposed presence of a bogey man (or bogey men).

2.

Lisa’s Rival

Here’s an interesting fact about this episode – Conan O’Brien, a former writer on the show, pitched the idea behind the main storyline years before the episode was produced. The premise was simple. Lisa Simpson, the prodigiously gifted eight year old Simpson would become classmates with an even more prodigiously gifted seven year old. This episode is great because we get to see Lisa (who is so often the voice of reason) cope with her feelings of inadequacy like a real child would. But that’s just the main plot. In the subplot, Homer stumbles onto an abandoned pile of sugar and on a whim decides to be a sugar baron. More than just another “Homer gets random job” plot, this storyline provided some of the funniest lines in the show’s history.

Best Moment: Homer’s Scarfacesque rant. “In America, first you get the sugar, then you get the money…”

1.

Last Exit to Springfield

The most consistently hilarious episode of the Simpsons. There is a reason why this episode always tends to make lists like this. It is eminently quotable, the story moves at a brisk pace and well … it’s just funny. The story centers on a dental plan (LISA NEEDS BRACES!) and a standoff between Mr. Burns and his employees over said dental plan (LISA NEEDS BRACES!). The Simpsons have definitely come up with more emotionally resonant episodes, more creative episodes and more interesting episodes. But they’ve never been funnier than this.

Best Moment: Abe “Grandpa” Simpson’s wonderfully rambling story about the time he took the ferry to Morganville. To fix his shoe you see. (Skip to 2:05)

#simpsons #monorail #homer #marge #bartsimpson