The Top Simpsons Episodes

If you are now in your mid-20s to mid-30s that means you grew up, at least partially, in the 90s–you know, that decade Buzzfeed won’t let us forget about.

The 90s produced a lot of terrible things, but the decade did produce the best Simpsons episodes ever made. Believe me, I know it’s kind of hackey to rag on the show’s newer episodes. I’ve heard from people who say the newest episodes have improved, but I wouldn’t know. I stopped watching 10 years ago.

Maybe it makes me a curmudgeon or a snob, but I firmly believe of the Simpsons as seasons two through 10.  The first season was still working out some of the kinks and, for me, things just started to fall apart after season 10. But, in between, lie some of the cleverest TV ever broadcast.

WFLD, the Chicago FOX affliate, played The Simpsons three times a day–twice around dinner time and then a late episode around 10 p.m. As a kid, I saw pretty much every episode from the golden era…multiple times. It was difficult to choose, but here are my favorite episodes from each season.

Season 2 – “Lisa’s Substitute”

Initially, I was going to select another episode–possibly “The Way We Was,” “Simpson and Delilah,” “Homer vs. Lisa and the 8th Commandment” or “Three Men and A Comic Book”–because I laughed more. I thought about it and realized that, even though this episode has less laughs, it’s better overall. It also has possibly the best cameo of the series: Dustin Hoffman playing Mr. Bergstrom, the substitute.

When Miss Hoover gets Lyme disease, Mr. Bergstrom takes over the class. He’s engaging and interesting and basically the antithesis of all the other teachers at Springfield Elementary. Lisa is immediately taken with the new substitute. Shortly thereafter, she runs into him at a local museum and is embarrassed by Homer’s graceless behavior.

Miss Hoover’s Lyme disease turns out to be psychosomatic, and she comes back to class. Thus, Mr. Bergstrom will be leaving town. Lisa panics and rushes to the catch him before he leaves town for another job, admitting she won’t know what to do without him. Mr. Bergstrom writes her a note and tells her it’s all she’ll need if she’s feeling alone. The note simply says “You are Lisa Simpson.”

Upset by his departure, Lisa takes it out on Homer, calling him a baboon. Homer, in his own clumsy way, is able to console Lisa. He expresses, again clumsily, that he’s never lost anyone like Mr. Bergstrom because all the people he truly cares about and loves are living under the same roof as him.

This episode is great and unique because it doesn’t really follow the conventional path of a sitcom. The story arch is more like a drama with a few laughs thrown in here and there. It didn’t need a bunch of Homer or Bart’s shenanigans or goofball one-off characters to make a memorable TV. It was done in a way that only The Simpsons (or possibly Futurama) could have pulled off.

If you were exactly the right age to see this episode when it aired (pre-teen/teenager) or even in reruns, I can’t help but think it would be extremely comforting to see someone like Lisa–smart and resourceful but not necessarily popular–on  a popular TV show go through many of the same things you might be feeling.

Perhaps The Simpsons wasn’t the menace to society that talking heads in the media depicted it as.

Season 3 – “Lisa’s Pony”

This episodes starts with Homer letting down Lisa, which isn’t all that unusual. She needs a new reed for her saxophone because she’s due to perform in the school talent show. Naturally, Homer stops to have a beer first but eventually gets the reed. However, he’s too late. To win back Lisa’s affection, Homer gets a loan and buys a pony for Lisa without really thinking about the maintenance costs.

I picked this episode because lots of people who aren’t Simpsons fans (idiots mostly)  like to think of it as a show about kid disrespecting his parents or just a series of undecipherable pop culture references.

It’s not either of those things, though. There are a lot of references, but, at its core, it’s a comedy with a lot of heart. This episode is a prime example of that. Homer feels so guilty about letting Lisa down, he kills himself at a second job at the Kwik-E-Mart to bring joy to his daughter.

It also has some of the best exchanges, jokes and references of the series. Some of the best being: The Godfather reference with the horse head as well as the 2001: A Space Odyssey  reference with Homer as a monkey in front of the monolith.

It contains the quote I always think about when people discuss personal finance, too.

Marge: We’re just going to have to cut down on Luxuries

Homer: Well, you know, we’re always buying Maggie vaccinations for diseases she doesn’t have.

Marge: Actually, I was thinking we could cut down on your beer.

Homer: Nah, we’re not going to be doing that.

Also, the kid singing “My ding-a-ling” at the talent show always cracks me up.

Season 4 – “Marge vs. the Monorail”

Wow, season 4 was a powerhouse.

There were many  brilliant episodes, including “Mr. Plow,” “I Love Lisa,” “Last Exit to Springfield” and “Kamp Krusty,” but this is hands down my favorite. It might even be my favorite episode of the entire series. Conan O’Brien wrote the episode, so it’s not surprising that it’s amazing.

When Mr. Burns gets caught dumping toxic waste and is subsequently fined $3 million, Springfield is at odds with what to do with the sudden windfall. At a town hall meeting, Marge suggests using the money to fix the pot holes on Main Street. Her thunder is stolen by Lyle Lanley (played by the late great Phil Hartman).

In the end, his idea is chosen with the aid of a fantastic musical number. It’s incredible to think that a show could have such sharp dialogue and then throw in a catchy song-and-dance just because. When most shows do the musical thing, they do it once during the entire series to placate the fans. The Simpsons did it continually throughout the series, seemingly for the hell of it. That’s insane!

Anyway, if you’re a Simpsons fan (and why would you be reading this if you weren’t?) you know the rest. Homer becomes a monorail conductor, Lanley turns out to be a con artist and Marge and Leonard Nimoy must help Homer stop and out of control monorail.

The things that really stick out to me in the episode, and the entire series for that matter, are the sight gags. Even when no one is talking, the show is hitting you with joke after joke. The writers never wasted a single frame. My favorites were the chalkboard in the monorail conductors class and one of many hilarious Homer Simpson file photos. But, really, the whole story arc is just a thing of beauty. I don’t know how else to describe it.

Season 5 – “$pringfield (of How I Learned to Stop Worrying and Love Legalized Gambling)

For Season 5, I was really torn. I landed on this episode, but I was also tempted by “Homer’s Barbershop Quartet,” “Deep Space Homer,” and “Secrets of a Successful Marriage.” In the end, this was the episode I remember quoting the most with friends in high school.

A town hall meeting is also central to this episode. In it, the townspeople suggest legalizing gambling in order to stimulate Springfield’s economy. Seeing an opportunity to exploit the residents, Mr. Burns builds a gaudy waterfront casino. Homer takes a job as a blackjack dealer at the casino, Bart opens his own tree house casino and Marge becomes a “slot jockey.”

This episode was the winner because it’s packed with great jokes from start to end: Homer finding Henry Kissinger’s glasses in the bathroom, Homer’s improvised breakfast, the family freaking out over the boogeyman, Lisa’s Florida costume, Bart’s casino and Mr. Burns going all Howard Hughes.

That’s why this episode has always been one of my favorites–because the comedy came from so many different places. In a lot of sitcoms, the B and C story lines are marginally interesting and have a resolution but they are often forgettable. That’s not the case with the earlier seasons, and specifically this episode. If you weren’t familiar with The Simpsons, I could imagine being skeptical about the tree house casino subplot. It’s better than it has any right to be, though.

This episode also plays with the typical structure of the show, which is appealing. Usually, it’s Homer or Bart who screw up and are irresponsible. However, in this case, it’s Marge who is irresponsible after becoming addicted to gambling and neglecting her family.  It also sets up a nice runner that continues throughout show like when the family goes to IRS Burger in season 7 and Homer asks Marge what her gambling losses were last year.

Season 6 – “Bart of Darkness”

This season was also incredibly strong. There were a lot of other episodes I was tempted to pick including “Homer Badman,” “And Maggie Makes Three,” “Homie the Clown,” and “Two Dozen and One Greyhounds.” But I think “Bart of Darkness” is one of the more iconic episodes of the series.

After a heat wave hits Springfield, Bart and Lisa beg Homer to get a pool. Eventually, Homer relents (leading to my favorite Amish joke of all time (“‘Tis a fine barn, but sure ’tis no pool, English.”), and the family sets up an above ground pool in their backyard.

However, for Bart, the fun is short-lived. Trying to impress the other kids, he jumps from the tree house but missed the pool and breaks his leg. Lisa gets him a telescope to help with his boredom and isolation, but he soon becomes obsessed with spying on the Flanders. He then becomes convinced Ned has murdered Maude (“He’s becoming isolated and weird”).

This episode epitomizes The Simpsons’ ability to create such intelligent homages to pop culture classics. The majority of the episode is a superb take on the Alfred Hitchcock classic Rear Window. Looking back, that was one of the most formative aspects of the show for me.

One of the best gags.

Obviously, when I was a kid, I didn’t get all of the references–especially to older movies. A funny thing started to happen, though. As I kept watching the reruns of old episodes, I started to notice new references each time. A few times I actually sought out the reference or homage in question. It was like a Master’s class in pop culture. For better or worse, it laid the foundation for a high pop culture IQ and for a love for shows with rich and detailed universes.

Season 7 – “A Fish Called Selma”

This episode proved that, often, the many supporting characters in The Simpsons were just as interesting and hilarious as the titular family. Phil Hartman’s characters, Troy McClure, Lionel Hutz, Lyle Lanley, etc… were always my favorite. It’s a shame that he died long before he should have.

Anyway, this was one episode where Hartman really got to shine as McClure, rather than being brought in during one scene for a couple quick laughs. McClure is shown to be down on his luck when he is pulled over by Chief Wiggum. Later, he agrees to a date with Selma, who works at the DMV,  in exchange for a passing score on his vision test.

A picture of the two appear in the paper the next day, which puts to rest rumors of McClure’s less than normal sexual proclivities. Subsequently, McClure’s career is resurrected as he stars in multimillion-dollar musical adaptation of Planet of the Apes (“Ever hear of  Planet of the Apes?” “Uh…the movie or the planet?”).

The catch, and most compelling part of the story, is that McClure agrees to marry Selma and suggests having children strictly because it will further his career. Selma, however, is not aware of this. In the end, she decides not to bring a child into the world as part of a sham. This is another episode with a lot of heart and a solid message for a show that was routinely banned in suburban households by out-of-touch parents.

It had a lot of other things going for it, too. Jeff Goldblum guest starred as McClure’s sleazy agent, which is awesome. And remember that thing I said about musical numbers earlier? Well, this episode has one of the funniest of the entire series (linked above). It’s a parody of “Amedeus,” but why are you still reading this!? Just listen! It also has one of my favorite riffs on the goofy fake movies McClure starred in.

Lisa: Hi, I remember you from such filmstrips as Locker Room Towel Fight:  The Blinding of Larry Driscoll.”

Troy: You know, I was one of the first to speak out against horseplay.

I didn’t know the word horseplay was so funny until I heard it in The Simpsons.

Season 8 – “You Only Move Twice”

Pretty much the only thing you need to know about this episode is that Albert Brooks is in it. Honestly, I could stop right there, but, for the sake of literary congruity, I’ll continue.

Homer accepts a new job in Cypress Creek and moves the family. He really takes to his new boss Hank Scorpio (Brooks) and his new responsibility in a management role. The rest of the family doesn’t fare so well. Marge finds herself with nothing to do in a self-maintaining house, Lisa is allergic to almost everything in the new environment and Bart gets moved to the remedial class with the stone cold dum-dums.

It turns out Hank is a Blofeld-like villain. Homer walks to office, which is under siege and reluctantly resigns to ensure his family’s happiness.

Again, this episode shows what Homer is willing to do for his family. Starting to notice a theme? The Simpsons took a lot of heat from uptight conservatives (“‘Good lord, the rod up that man’s but must have a rod up its butt.”) for contributing to the decay of the nuclear family or some such ignorant garbage. Sure, the Simpsons, as a family, are a little rough around the edges, but, when it comes down to it, Homer and Marge are willing to do almost anything to keep the family together.

Throw in the wall-to-wall jokes and spot-on satire, and it’s easy to see why this is one of the best episodes of the series. This exchange alone:

Homer: Sir, I need to know where I can get some business hammocks.

Scorpio: Hammocks? My goodness, what an idea. Why didn’t I think of that? Hammocks! Homer, there’s four place: There’s the Hammock Hut, that’ on third.

Homer: Uh-huh

Scorpio: There’s Hammocks Are Us, that’s on Third, too.

Homer: Got it.

Scorpio: You got Put Your Butt There…

Homer: Mm-hmm.

Scorpio: …That’s on Third.

Homer: Yes.

Scorpio: Swing Low Sweet Chariot…

Homer: Right.

Scorpio: Matter of fact, they’re all in the same complex…it’s the Hammock Complex, down on third?

Homer: Oh, the Hammock District!

Then there’s this gem:

Scorpio: By the way, Homer, what’ your least favorite country? Italy or France?

Homer: France.

Scorpio: Haha, nobody ever says Italy.

There’s also the paper circles, James Bond, Denver Broncos and a hundred other jokes I can’t begin to cover in this post.

Season 9 – “The City of New York vs. Homer Simpson”

I believe this is the point where the show started to go off the tracks. Sure, there are some great episodes (“The Joy of Sect,” “The Cartridge Family” and “Trouble With Trillions”) this season but certainly not as many as previous seasons.

The episode starts with Moe declaring the regulars at the bar need a designated driver (“The Springfield Police have told me that 91 percent of all traffic accidents are caused by you six guys”), and Barney is the odd man out. After a drunken night, Barney disappears with Homer’s car for two months.

Homer has about given up when he get a letter from the City of New York informing him his car is illegally parked. The rest of the family is excited for the trip to NYC, but Homer is less than thrilled thanks to a bad experience in his youth. It turns out the car is parked between the towers of the World Trade Center. Now, it’s definitely a surreal moment to watch those scenes.

Putting future national tragedies aside, the majority of the comedy from this episode comes from Homer’s ordeal waiting for the parking enforcement officer to arrive. Obviously, the best part is when Homer is forced to eat at the Khlav Kalash cart (admittedly, a pretty broad stereotype) and wash it down with crab juice.

There’s a pretty good musical number as well. While Homer waits with the car, the rest of the family sees a Broadway production about the Betty Ford Clinic.

A lot of shows use this premise–i.e. characters go to big city or some other far off destination–to mixed results. I think cartoons actually do it better than live-action shows (King of the Hill and, yes, even Family Guy have done it a few times successfully). I just remember how desperate it seemed when Boy Meets World went to Disney World and when Everybody Loves Raymond went to Italy. But The Simpsons put together a really fun show, despite the well-worn premise.

Honestly, I wish I had more to say, but, like I said, this was the beginning of the end for The Simpsons as I knew it.

Season 10 – “The Wizard of Evergreen Terrace”

This episode probably isn’t considered one of the classics, but it’s one that I still remember vividly. Homer has midlife crisis, which leads him to become obsessed with Thomas Edison and his inventions. He quits his job, vowing to become a famous inventor like Edison.

Invent yourself some underpants!

This leads to the best part of the episode–Homer’s obsession with Edison’s daily habits and his initial attempts at inventing something useful. The make-up gun was my favorite.

Marge: Homer, you’ve got it set on “whore.”

Homer: Eh, oop. *adjusts gun

Homer: Okay, this time try it with your nostrils closed. *Marge knocks gun away leaving a smeared clown face on the wall

Homer: Oh, look what you did! Now I have to get my cold cream gun.

Lisa: Dad, women won’t like being shot in the face.

Homer: Women will like what I tell them to like.

I also loved when Homer took up smoking cigars because “Thomas Edison smoked several cigars a day,” and Bart notes (holding up an empty notebook) that “He also invented stuff.”

Eventually, Homer does invent something useful–an extra set of legs, attached via hinges, on the back of his chair designed to keep him from falling over while leaning back. However, Homer discovers Edison himself built a similar chair but it was never credited to him.

Homer decides to destroy the evidence at the Edison Museum, inventing an electric hammer to facilitate the smashing. He realized he can’t destroy it, though. Of course, the chair and hammer were discovered after the break-in and are expected to net Edison’s heirs a substantial amount of money.

One thing I appreciated about this episode was the writers’ self awareness. When Homer and Bart drive to the museum, which is in New Jersey, to smash the chair, Bart makes a comment about one of the road signs and the distance. It was small, but it was a nod to the show’s ever malleable geography. I guess it’s not a huge deal, but it was nice to know, at least sometimes, that attention to detail and awareness was still being put into the show.

Oh, also: “Crap, boobs, crap.”


It’s hard to explain to younger people what this show meant to people my age and older. I’m glad that I got to watch it and follow it during its classic period. It’s one of the primary reasons I’m obsessed with comedy and pop culture today, and, for that, I couldn’t be more grateful.


I was going to list a bunch of the runner up episodes, but, frankly, I wrote too much about the nine episodes I picked. So enjoy this instead.

If you put together all the McBain movie clips scattered throughout the series together, it creates a mini movie. Enjoy!

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2 thoughts on “The Top Simpsons Episodes

  1. […] The Top Simpsons Episodes – Smooth Charlie’s Link of the Week is this rundown of favorite episodes, one each from Seasons 2-10.  Plus there’s lots of good Youtube, a healthy dislike of Zombie Simpsons, and a great Hank Scorpio picture.  Well done lists are so much better than slapdash ones. […]

  2. […] The Top Simpsons Episodes – Smooth Charlie’s Link of the Week is this rundown of favorite episodes, one each from Seasons 2-10.  Plus there’s lots of good Youtube, a healthy dislike of Zombie Simpsons, and a great Hank Scorpio picture.  Well done lists are so much better than slapdash ones. […]

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