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The Guys From's Top 100 'Simpsons' Episodes: 10-1


The Guys From's Top 100 'Simpsons' Episodes: 10-1

Shaun Cordingley

This is it.

These are the Top 10 Episodes of The Simpsons of all time, according to We have been revealing this list for you guys for the past 10 weeks, and it's kind of sad that it is coming to an end....I mean, I am looking forward to spending some time in the Film and Gaming...and Sports sections again, but there's been something so wonderful about revisiting all of these old episodes so I/We can talk to all of you about one of the greatest television series ever made.

In case you missed any of the other "tens", be sure to check them out here before we wrap this up:


Well, I won't blather on about things you don't care this is going to be a long one, because these are the ten best episodes of the series, so there's a lot to talk about (and highlight). 

Here are the Top 10 Episodes of The Simpsons:

10) Homer vs. the Eighteenth Amendment (Season 8, Episode 18)

"Homer vs. The Eighteenth Amendment" is an episode that has grown on me over time--I don't think I had the same appreciation for the source material (specifically The Untouchables) when this episode came 1997...when I was in Middle School...but now? Now I definitely see this as being deserving of being inside of a Top 10 list.

Essentially, after Bart accidentally gets drunk on St. Patrick's Day, a strong Prohibition movement moves through Springfield and takes hold, with Eliot Ness...I mean...Rex Banner (brilliantly voiced by the awesome Dave Thomas) showing up to take over the police department, after Chief Wiggum proves to not be up to the task. After Banner proves to be super-good at his job, and worming his way into Dave's heart as one of his favorite characters of all-time, Homer, in what must be one of the smartest moments of his life, becomes "the Beer Baron" and keeps liquor in Springfield until Prohibition is inevitably re-lifted.

The more you know about Prohibition-era USA, the more you know The Untouchables and Boardwalk Empire, "Homer vs. The Eighteenth Amendment" just gets better and better, and completely deserves the #10 slot on our list.

My Other Highlights:

  • "2000 Years of Irish Cops" Float
  • All things become riots in Springfield, especially when the fish & chips shop is bombed (which was--not surprisingly--cut in the UK)
  • Helen: Won't somebody please think of the children (so...much...)
  • Old Clerk: There's also a law requiring ducks to wear long pants
    Quimby: Wait a minute, let me see that. Well I'll be darned: long pants
  • Rex Banner reading telegrams
  • Marge: Why do you have some many bowling balls?
    Homer: Aw, I'm not going to lie to you Marge....So Long!
  • Homer's ingenious system to supply Moe with beer
  • Rex Banner's Birthday
  • The Raid on Moe's Pet Shop
  • "Ill find you.."
  • ...I totally want a bathtub mint julip
  • Rex Banner Laughing

9) Lemon of Troy (Season 6, Episode 24)

"Lemon of Troy" is another episode that seems to get better every time I watch it. Essentially, the kids (and to some extent, parents) find that they all have doubles in Shelbyville when the Shelbyvillians steal Springfield's spectacular lemon tree, and Bart leads a group of kids in to get it back. As you can tell from the title, the plan that, in the end, returns the tree to Springfield is largely based on the legend of the sacking of Troy.

Sadly, I always kinda hoped that this episode was actually about Troy McClure...but alas, it's a "historical reference"

Anyway, rather than telling you more about it, I'm just going to get to my Episode Highlights, as that's going to cover pretty much everything else that happens:

8) Treehouse of Horror V (Season 6, Episode 6)

There was absolutely no way that "Treehouse of Horror V" was not going to make it into our Top 10; it is, easily, the best Halloween episode, top to bottom, that The Simpsons ever did. Throughout the weeks on this list, we have gone over why we love these episodes so much, and Dave even put his Top 10 Segments together as I had already done my Top List on

So yeah: we're fans....and there is just something special about this episode. Part of it, is probably the strangely hilarious use of Groundskeeper Willie as a connecting point between all three stories, as well as the fact that the producers were really trying to pull out all of the stops on this one, meaning that this probably is the creepiest, and the goriest of them all. 
I love the opening, with Marge reading that Congress would not let them show the episode (a fight The Simpsons actually had early on, because the internet had not desensitized us all at that point), the 200 Miles to Oregon clip, and the Outer Limits reference...and now, I think it is just prudent that I talk section by section:

1) 'The Shinning'-- The Simpsons, at their best, have always done excellent satire, and parodies of film, and I do not think that anything they have done before or since has the same level of nuance, and humor in it, nor the sheer amount of clever detail for The Shining fans to pick up on than this segment. Homer going to be the caretaker of Burns' creepy, Overlook-style summer house is amazing. From the Opening, repeated attempts for the family to actually drive there without leaving the door open at their house, to the frozen family basking in the TV, this is just the best segment of all-time. 

My Highlights: 

2) 'Time and Punishment' - Often the middle of the episode is a little bit weaker when it comes to "Treehouse of Horror" but 'Time and Punishment' is an exception: somehow, Homer invents a time machine while he is trying to fix the toaster, and due to the butterfly effect, is having an impossible time returning to "his" line of history. Another parody, this time of the Ray Bradbury short 'A Sound of Thunder', this is probably the lightest of the three, but is so oddly funny, and so ridiculous that it really holds the episode together.

My Highlights:

  • Homer's terrifying fight with the toaster
  • The creepy Ned Flanders led dystopia , and Re-Neducation
  • Homer abandoning his dream world too soon (after the sneezing extinction) 
  • The settling.

3) 'Nightmare Cafeteria' - This is a strange, and somewhat disturbing segment that revolves around Principal Skinner coming to the conclusion that there's an "easy" solution to both the over-crowding of detention, and the cafeteria budget cuts: eat misbehaving students. This one is actually a little bit disturbing (even today), though that does not make me love it any less. 

Plus, I love how lazy they are: "Sloppy Jimbo", "Uterbraten"

My Highlights:

  • Jimbo: It's hard for me to scrub this pot if you keep pouring meat tenderizer over me sound of pot lid being plopped on Great, now I have to work in the dark 
  • Skinner trying to be clever and just telling the kids the plot of the segment 
  • Marge refusing to help 
  • Homework: Eat a stick of butter
  • This:
  • Willie is *so bad* at being the hero 
  • The "dream" ending 

7) Cape Feare (Season 5, Episode 2) 

This is yet another example of how during their Golden Age. The Simpsons were able to make absolutely pitch perfect film parodies work as full, and hilarious episodes. Now when I had first seen "Cape Feare" I obviously did not know Cape Fear (neither the original, nor the 1991 remake), but I still loved the episode--now that I have seen both films, and have a much, much stronger grasp on not only musical theater, but Gilbert and Sullivan? There are few episodes that can compare to this one in terms of satire.

Essentially, Sideshow Bob (somehow) gets paroled, and sets about threatening to kill Bart, eventually the Witness Relocation Program gets involved and sends the family off to become the Thompsons of Terror Lake, but unfortunately for Bart, Bob is along for the ride (literally, strapped under the car), and is all set to eviscerate him, only to be foiled by Bart's Final Wish, which is one of my favorite moments in the series, ever: Bob will "send Bart to heaven, before sending him to hell" by singing the entire score of H.M.S. Pinafore

This is the best Sideshow Bob episode, by far, and some of Kelsey Grammar's best work, period, as far as I'm concerned (seriously, he sings Pinafore), and wholly deserves to by considered one of the greatest episodes of The Simpsons.

My Other Highlights (...get ready for a lot of this episode):

  • Up Late with McBain (another low for FOX)
  • Lisa's letter from her pen-pal Anya
  • Abe: I say we call Matlock. He'll find the culprit. It's probably that evil Gavin MacLeod or George "Goober" Lindsay.
    Bart: [dismissively] Grampa, Matlock's not real.
    Abe: Neither are my teeth, but I can still eat corn on the cob, if someone cuts it off and smushes it into a fine paste. Now that's good eatin'!
  • Milhouse[to Bart] I checked around. The girls are calling you "fatty fat fat fat" and Nelson's planning to pull down your pants. But nobody's trying to kill ya.
    Bart: [relieved] Aaah... that's good.
    Nelson[pulls down Bart's pants]
  • Marge[threateningly] Bart, I'm going to get you...[brandishes some scissors]
     ...some ice cream at the store, since I'm saving so much money on Diet Cola! [holds up a coupon]
    Ned Flanders: [menacingly]
    Say your prayers, Simpson... [cheerfully] Because the schools can't force you like they should! Maude, these new finger razors make hedge trimming as much fun as sitting through church!
    Mrs. Krabappel[menacingly] You're going to be my murder victim, Bart... [normal] In our school production of Lizzy Borden, starring Martin Prince as Lizzie!
    Martin[dressed as Lizzie Borden] 40 whacks with a wet noodle, Bart!
  • Moe smuggling pandas?
  • Bob needs to use a pen
  • Bob's parole hearing and:
    Blue-haired Lawyer: What about that tattoo on your chest? Doesn't it say "DIE BART DIE"?
    Sideshow Bob: No that's German for "The, Bart the."
    Parole Officer: No one who speaks German could be an evil man...
  • The Cape Fear to-a-T cinema scene
  • Bob's Workout 
  • Speedbumps, coffee and the ol' cactus patch
  • Originally the episode was a bit short, so the writers added one of the most iconic moments in Simpsons history: Bob and the rakes
  • Homer: Relax, Marge, I tied up all the loose ends before we left.
    [Scene goes to the Simpsons' old house where Grampa is standing at the door]
    Grampa[knocking on the door] 
    Hello-o! Hello-o! You have my pills! Hello-o? I'm cold, and there are wolves after me. [a lone wolf howls]
  • Bob sees nothing wrong with lying in the middle of the street...
  • Bob at the Bates Motel (...random Pyscho reference, that works flawlessly)
  • Homer's totally not threatening Bart
  • Homer...wasn't(?) drugged
  • Abe off his pills

6) Marge vs. the Monorail (Season 4, Episode 12) 

With all due respect to Family Guy, "Marge vs. the Monorail" is the single, best parody/satire/tribute to The Music Man ever made, eventually leaving the reference all-together and becoming a very strange, and fun, Marge-centric story. Lyle Lanley (voiced by Phil Hartman) is one of the greatest one-off characters the show has ever produced (and this is our favorite episode involving Hartman in a major role period). Leonard Nimoy appearing as himself is easily one of the best celebrity cameos that The Simpsons ever had, he's funny, strange, and wonderful all at the same time. "Monorail" may also contain the most throw-away and one-off gags in any episode of the show, ever...and practically nothing falls flat, making "Marge vs. the Monorail" the sixth best episode of the series. 

After being caught illegally dumping toxic waste by the EPA, Mr. Burns pays for the damages and, like a mule with a spinning wheel, Springfield now has 3 million dollars, and does not know what to do with it. Through the excellently musical con by Lanley, the small town decides to build a mass-transit system (monorail) it does not need, and obviously, Homer becomes the conductor. On it's maiden voyage, there are problems caused by cut-corners and the monorail careens out of control, but thankfully by the end, everything is back as it should be...and Springfield never did something silly like that again...Well...kinda...

When it comes down to it, it's also a rather amusing commentary on flash v. substance, and an examination of the often silliness of a mob's mentality. 

My other highlights:


5) Deep Space Homer (Season 5, Episode 15)

Just breaking into the Top 5 is "Deep Space Homer", an episode that took Homer Simpson, and sent him on a space shuttle with real astronauts in order to see if ants could sort tiny screws in space (unofficially, they also were up there to sabotage MIR a bit...). This is one of the best, pure episodes of the Simpsons that again, focuses on a single story--this is also, thankfully, a time when Homer was not at his 100% stupidest, so seeing him compete for the place on the shuttle, and everything else still had tinges of that amazing character that the early seasons really worked on. 

Again, the episode is littered with amazing film references, from The Right Stuff to showing copious love to 2001: A Space Odyssey, but it would be ridiculous not to appreciate how flat out amazing Homer finally realizing that Earth is the Planet of the Apes is ..Oh, and I'm going to point this out now as well, I do not know if there is any single sequence in any episode of The Simpsons, that works on as many levels as Homer eating the potato chips in zero gravity (plus a slightly mean James Taylor in an amazing cameo), leading into Kent Brockman's hilarious speech about ants. 

I think my absolute favorite other thing about "Deep Space Homer" is that NASA loved it; there is now a copy of the episode at the International Space Station for the astronauts to watch. I mean, you cannot get better praise than that. 

My Highlights:

4) El Viaje Misterioso de Nuestro Jomer AKA The Mysterious Voyage of Homer (Season 8, Episode 9)

An insane trip into surrealism, "The Mysterious Voyage of Homer" is an episode that puts Homer through an absolutely ridiculous, soul-searching journey to really nail down whether Marge and he are soulmates. The episode not only explores the ideas, and constructs of community and marriage through Homer and Marge (and the chili festival), but allows for a sentimental twist to ripple through an occasionally bonkers, and often hilarious episode. 

The use of Johnny Cash as Homer's spirit guide (the pictured above 'Space Coyote') was one of the most subtly brilliant pieces of casting that The Simpsons ever pulled off--rumor has it that Bob Dylan was also offered the part, and while I do wonder what that would have been like, there is no denying the depth, and sage-like sound Cash brings to the Space Coyote. 

This is probably one of my most quoted episodes, in the fact that I can probably say all of the lines along with the episode as it goes, so it is fairly easy for me to fit it in when a Simpsons reference is called for...

My Highlights: 

  • All of Marge's attempts to keep Homer from the Chili Cook-off
  •  it's a lazy, dog-dangling afternoon 
  • Homer: What's wrong with you? What are you trying to hide from me? [opens the front door and sniffs]What's that smell? Onions ... chili powder ... cumin ... juicy ground chuck? Oh, my God, I'm missing the Chili Cook-Off! [whining and fidgeting] I'm missing the Cook-Off, it's going on right now, and I'm missing it!
    Marge: All right! I was trying to keep it from you! But I had a good reason. Every time you go to that Cook-Off you get as drunk as a poet on payday! 
    [Flashback to last year's Chili Cook-Off. People are shocked as a naked Homer is cavorting in the cotton candy machine.]
    Homer[drunk, slurred speech]
     Look at me! I'm a puffy pink cloud!
    [Return to present.]
    Homer: Well, of course everything looks bad when you remember it!
  • Marge is a very, very bland cook 
  • The chili cook-off. All of it..including the amazingness of Nashville Smithers. 
  • The insanity trip where Homer breaks the sun (some crossover with the last clip)
  • The tortoise and his spite at being kicked (the little grin on the tortoise when he's nodding after Homer asks "this is because I kicked you, isn't it" gets me every time
  • Homer: What? Golf course? Did I dream that whole thing? Maybe the desert was just this sand trap. Oh, and I bet that crazy pyramid was just the pro shop. [The pro shop is shaped like a giant pyramid.] And that talking coyote was really just a talking dog.
    Dog: Hi, Homer. Find your soulmate!
    Homer: Hey, wait a minute! There's no such thing as a talking dog.
    Homer: Damn straight!
  • Homer's search for help starting at the all-night furniture store
  • The surprisingly sweet montage of Homer looking throughout Springfield (and that bad ass fish) and
  • [Homer is in the lighthouse, and his silhouette is being projected into the sky by the lighthouse's lamp.]
    Bart[looking out a window and seeing the silhouette] 
    Hey, look! Is that Dad?
    Lisa: Either that, or Batman's really let himself go!
  • The incredibly strange, and perfect ending after the sentimental & nice ending ("In Your Face, Space Coyote")

3) The City of New York vs. Homer Simpson (Season 9, Episode 1) 

After a night of drinking, wherein Barney (of all people) is the designated driver, Barney disappears with Homer's car for a two month binge, and Homer and the family are forced to go to New York City in order to get his car back, and thus begins a two-sided adventure that is remarkable for the number of gags, combining into a cohesive and entertaining plot, juxtaposing Homer's experience in New York with Marge, Bart and Lisa's. It's undeniably clever, and the spot-on hilarious (2 minute) Broadway Musical Kickin' It (totally not about Robert Downey Jr.) won a pair of awards on its' own.

There have been a few "vacation" episodes on this lists, taking the family out of their regular element, but I would argue that there are really none better than "City of New York vs. Homer Simpson" because the story of balancing two, very different "a day in the city" stories works so well within the Simpsons format as it does allow for throwaway jokes, while still progressing the story. 

I understand why this episode was pulled from syndication after 9.11, considering the rather large part the World Trade Center plays in the episode (it's where the car is illegally parked after all), but I am glad that the episode has slowly been rolled back out again, as it really does deserve to be seen as one of the greatest episodes of the series. 

My non-Kickin' in Highlights: 

  • It's the first appearance of Duffman! 
  • Barney's return to Springfield 
  • Homer's first trip to New York 
  • Homer: Alright New York, I'm comin' back! But you're not gettin' this! (throws his wallet into the fireplace)
    Lisa: Dad, our baby pictures were in there!
    Homer: Don't you start!
  • Bart sees ZZ Top
  • Homer: Now remember, criminals prey on small town folk like us. So if anybody asks, we're sophisticated millionaires from the Ozarks.
  • Bart(at top of the Statue of Liberty) Hey, immigrants! Beat it! Country's full!
    Sailor: OK people, you heard the lady. Back into the hold. We'll try Canada.
  • Biting the boot, and the excellent phone call with the parking violations bureau 
  • Homer reaching for Pizza, and settling for Khlav Kalash and too much crab juice
  • Flushing Meadows
  • Homer's fight with the boot
  • The Ben Hur through Central Park 
  • The ending, with a literal juxtaposition of the two sides of the family's day in microcosm. 

2) A Streetcar Named Marge (Season 4, Episode 2) 

Number 2 on our list is my personal favorite episode of all time, "A Streetcar Named Marge" is an exploration of Marge and Homers relationship by drawing parallels with Tennessee Williams' A Streetcar Named Desire, while at the same time taking shots at community theatre, musical theater, and delivering what is the greatest B-story in any episode of The Simpsons, not to mention Maggie's crowning moment in the series: the amazing Ayn Rand School for Tots (a parody of The Great Escape capped off with a parody of The Birds). This is my favorite thing in any Simpsons episode, bar-none, and propelled Maggie into being in the conversation (and honestly, usually winning) for who my personal favorite Simpson is (though I do love me some Grampa).

What's amazing is that the A-Story, an almost better than Waiting for Guffman shot at Community Theater, wherein Marge is playing Blanche DuBois to Ned Flanders' Stanley Kowalksi in a bloody brilliant musical version of Streetcar entitled Oh! Streetcar!. This is, without question, the greatest musical moment in The Simpsons--they have never even come close to topping the sheer cleverness, nor the brilliant use of source material than in Oh! Streetcar! again (and they have tried). Jon Lovitz as Llewellyn Sinclair  (the director) AND his sister (running the School for Tots) is one of the greatest one-off characters ever created, and so spot on perfect (having now lived and worked in the theater world) that...there are almost no words. What's more, is that this is yet another example of an episode that placed high on our list here that has a fairly heavy focus on Marge, and a...somewhat realistic, serious look at Marge and Homer's relationship. 

I've said this a lot when discussing parodies, but "Streetcar Named Marge" is a perfect example, and one that I bring up often, to how a show can satirize and parody work, and yet still make it work (and make it funny) for people who have not seen or experienced the material. I had not seen much community theater, nor had I read A Streetcar Named Desire when this episode came out, and I *still* loved it, however it climbed into the upper echelons of my own lists of favorite episodes once I had the grounding in all of the disciplines this densely seeded episode has to offer, and I'm very pleased to see where it settled here on our list. 

My Highlights...outside the Ayn Rand School, and Oh! Streetcar!

  • The ridiculous (well, more than normal) pageant off the top
  • The audition (did I mention I love Llewellyn Sinclair? SO. MUCH.)
  • Lionel Hutz: Lionel Hutz, Attorney at Law, I'm filing a class-action suit against the Director on behalf of everyone who was cut from the play [cheerful] I also play Mitch!
  • Homer at rehearsal
  • Homer's Stanley moment over pudding
  • A beautiful moment between Homer and Marge at the end.

1) You Only Move Twice (Season 8, Episode 2) 

Our consensus number one, the best episode of The Simpsons of all-time is "You Only Move Twice", home of the best one-off character of all-time, Albert Brooks' Hank Scorpio. This episode is as close to perfect as The Simpsons ever got (or will ever get), and that includes my personal favorite episode "Streetcar", because "You Only Move Twice", while satirizing the James Bond franchise, does not need any frame of reference to be hilarious. There's just something so delightful about Homer working for the nicest boss on the planet, who, unbeknownst to Homer, is a supervillain. 

This episode, like "City of New York" allows for the family to each have a different experience in the episode, but Homer moving the family to Cyprus Creek and working at Globex remains the driving force, and retains a stronger plot than many episodes with a narrower focus; think about it, when it comes down to it, "You Only Move Twice" actually has 4 different storylines, working in tandem and weaving to create a cohesive story, something The Simpsons never quite got right again. 

In doing research about this episode, I discovered that Albert Brooks liked to ad-lib and rework a lot of his lines, across his characters, which means a large part of Hank Scorpio is thanks to Brooks himself, coupling his pitch perfect delivery of the nicest Bond-style super-villain ever conceived. Scorpio has roughly 8 minutes of screen time, however there is, somewhere, over 2 hours of Brooks' recordings of him. That type of looseness does not always work, and can lead to editing nightmares, but clearly Brooks is a master at it, and working in tandem with the excellent writers and other actors that The Simpsons had at the time, created a work that is pure comedic genius. 

You can argue with a lot of parts of a Top 100 list, you can disagree with choices, but I feel like it would be impossible for anyone to argue that "You Only Move Twice" is not a deserving number 1. Plus, who doesn't want to work for (or be) Hank Scorpio?

My Highlights:

There we have it; The Guys From's Top 100 Episodes of The Simpsons is finished. Where did your favorite episode end up? Did we miss one that you think we are completely crazy for not including? Let us know in the comments, or you can always chat with us on Twitter!

As for what the next major project will be...I am not too sure, but I do know that Dave and I want to take a little bit of time to enjoy not having anything of this size on the go for a little while...but stay tuned--more lists, big ol' features are coming!

-S (@Shauncord)