The Simpsons is one of those unique series that broke the mold. Often duplicated, never replicated, the animated comedy has been on the air for decades and is now entering its 27th season on the air. Known for its satire, celebrity guests and loveable four-fingered characters, the series has become a pop culture fixture.

Narrowing 500+ episodes down to 16 was not easy and we are sure we left off some of your favorites (apologies in advance). However, each episode that has been chosen is special in its own right, and holds a special place in our hearts. A lot of these episodes come from the early “golden era” of The Simpsons, including the episodes that were replayed ad nauseum in syndication for years and allowed us to truly appreciate the genius of Matt Groening’s creation.

With that said here’s our list of The 16 Best Simpsons Episodes of All Time.

You Only Move Twice (season 8, episode 2)

simpsons you only move twice 16 Best Simpsons Episodes of All Time


The Simpsons are known for their spoofs on pop culture and this season 8 episode is one of the best. In this episode, Homer is recruited to work for Hank Scorpio’s Globex Corporation, which means moving out of Springfield. While Homer and Hank hit it off right away, the rest of the Simpson crew is miserable (i.e. Lisa is allergic to her new environment, Bart is in the remedial program in school and Marge feels useless in their new self-cleaning house).

But what makes the whole episode genius is that Scorpio is actually a megalomaniac super-villain bent on world domination. Of course, Homer being Homer, he has no clue and inadvertently helps Scorpio in his plans including taking out the show’s version of 007, “James Bont.” The episode ingeniously answers the kinds of questions you might ask while watching SPECTRE later this fall: who are these people working for the bad guys? For his help, Scorpio later gifts Homer the Denver Broncos. Not a bad way to maintain company morale.

Voiced by frequent Simpsons collaborator Albert Brooks, Scorpio is a spot-on James Bond villain, but a likeable one. In fact it’s been rumored Brooks was supposed to reprise his role as Scorpio for The Simpsons Movie, but it was changed because producers felt he was too likable a character to be the main bad guy. They were right.

Who Shot Mr. Burns? (season 6, episode 25 & season 7, episode 1)

simpsons who shot mr burns 16 Best Simpsons Episodes of All Time


The Simpsons don’t do cliff-hangers. They just don’t.

A hallmark of the series is that everything is wrapped up in 22 minutes and most of the action is self-contained to that episode. However when the series announced it was spoofing the popular “Who Shot J.R.?” twist with a “Who Shot Mr. Burns?” episode, the idea of a cliffhanger just made sense.  After all C. Montgomery Burns is one of the best TV villains of all time.  As a result it wasn’t hard to come up with a wide array of reasons why the people of Springfield would want to kill him.

The show introduced the concept at the end of season 6 and wrapped it up in the first episode of season 7. While many felt the ending was a bit of a cop out (Maggie did it!), that was kind of the point. The whole thing was very tongue-in-cheek from the start, and it served its point in that it got people talking about the show.

Itchy & Scratchy Land (season 6, episode 4)

itchy and scratchy land 16 Best Simpsons Episodes of All Time


Itchy and Scratchy are two of the series most well-known supporting characters, even if they’re from a TV series within a TV series. In Season 6, the show increases their presence by sending the Simpsons to a theme park created in the cartoon cat and mouse’s honor.

The episode poked fun at everything from Disney World (park-specific currency, “Parent’s Island,” giant parking lots), to Jurassic Park (complete with helicopter fly-over shot). And, of course, things go horribly wrong when the animatronic characters come alive and turn on the guests. Yet what’s remembered the most? It would have to be the Bort souvenir license plates, which was yet another little jab at capitalism.

From top to bottom audiences could look at this episode and (aside from the murderous robots) relate to what was going on, which is what always makes the show so popular.

Behind The Laughter (season 11, episode 22)

behind the laughter simpsons 16 Best Simpsons Episodes of All Time


Nobody thought The Simpsons would last as long as it has, but its success is because of its creativity. In season 11 the series showcased that with its own version of Behind The Music. The episode came complete with the actual narrator of the popular VH1 program and it hit the right cord with fans, even in the eleventh season, as the show’s quality began to decline overall.

The episode asked the question “what went on behind the scenes of the show?” and depicted a fall from grace for the first family of animated comedies. Homer now had a prescription drug problem, the family had money issues and everyone was feuding with everyone.

What it also showed though was the writers were able to change the formula around and still see great success. The producers won back a lot of fans with this episode as well as an Emmy.  In fact many have said that could have served as the series finale and they would have been content; but that didn’t happen.

Homer’s Enemy (season 8, episode 23)

homers enemy 16 Best Simpsons Episodes of All Time


For all intents and purposes, the incompetent, lazy, unambitious Homer Simpson should be doing as well as a guy who lives in a van down by the river, yet that’s not the case. Instead, Homer has a wife, three kids, a big house and he’s even been to space. You can see why someone would hate him right?

Enter Frank Grimes. Grimes, who worked as hard as he possibly could for his entire life, sees Homer and can’t believe he’s been this lucky in life. The more he tries to prove Homer’s an idiot, the more beloved Homer becomes among the residents of Springfield. It all culminates with Grimes accidentally killing himself and Homer, fittingly, dozing off at his funeral.

While this may be one of the show’s darker episodes, it’s also one of the smartest. The irony is that Frank is right and Homer should not have this level of success, but as lifelong fans can attest, it’s Homer. You just tend to overlook things because Homer is Homer.  At the end of the day he can do no wrong in the eyes of the show’s characters or viewers.

Poor Grimey…he never stood a chance.

Marge vs. The Monorail (season 4, episode 12)

simpsons monorail 16 Best Simpsons Episodes of All Time


You may remember Phil Hartman as the voice of such characters as Troy McClure and Lionel Hutz, but one of the most memorable was Lyle Lanley. Lanley sold monorails to Brockway, Ogdenville, and North Haverbrook before making his way to Springfield to peddle his faulty wares.

Aside from the fun plot, which was a takeoff of The Music Man, it also produced one of the show’s best musical numbers, which became instantly quotable (“What about us brain-dead slobs? / You’ll be given cushy jobs!”). As Lanley convinces the town to spend its new found windfall of cash to build an unnecessary monorail, viewers are reminded of the amazing skills of the writers (which at the time included Conan O’Brien).

Granted, Lanley’s proposition wasn’t a hard sell, as the town has always been a gullible bunch; especially the town’s brain-dead slobs (who were given cushy jobs). Yet the line of episode comes from Homer showing Lisa the family of possums he found in his monorail closet, and telling her he “named the big one Bitey.”

Throw in a cameo from the iconic Leonard Nimoy as himself and you can see why this one’s become a fan favorite.

Homer The Great (season 6, episode 12)

homer the great simpsons 16 Best Simpsons Episodes of All Time


In Season 6 we learned about the great and powerful Stonecutters, a secretive, Freemason-like group that controls the world in weird ways, from rigging the Oscars to making Steve Guttenberg a star. On the surface, all the group really does is get drunk in their secret meeting place, which makes it seem like the perfect place for Homer.

Led by Number One (the brilliantly cast Patrick Stewart) the Stonecutters secret society included nearly every male character on the show.  The genius part was that the group hierarchy was determined by the order joined, so characters like Lenny and Carl could finally turn the tables on Mr. Burns.

Homer found a way to screw it up by using the group’s scared parchment as a bib, but that act of stupidity humorously leads to him being revealed as their “chosen one.”

Homer The Heretic (season 4, episode 3)

homer the heretic simpsons 16 Best Simpsons Episodes of All Time


Homer and Flanders have always been opposites. But no matter what their differences are, they both take their families to church every week. That is, until Homer skips church one Sunday, loves the freedom, and afterwards decides that he’s done.

From Homer’s “Moon Waffles” (waffles wrapped around a stick of butter) to his Risky Business-inspired dance while his family is away, the episode has many iconic moments. Yet topping that list is when Homer finally meets God and in a scene that perfect encapsulates the character, he describes the Lord as “Perfect teeth. A nice smell. A class act all the way.”

What’s also interesting to note is that in the show’s 26 years, only one character has ever been animated with five fingers: God.

Cape Feare (season 5, episode 2)

sideshow bob rake simpsons 16 Best Simpsons Episodes of All Time


Perhaps the most well-known recurring character (not voiced by a series regular) is Sideshow Bob. Voiced by Kelsey Grammer, the former clown turned violent psychopath has long had one goal; kill Bart Simpson. In this parody of the movie Cape Fear he comes close, but is (as always) defeated by his own ego.

The episode aired during the show’s fifth season and remains fresh to this day. Whether it be Sideshow Bob being tormented by rakes to the FBI trying (and failing) to explain to Homer how witness protection works, everything about this episode is essential Simpsons.

What is remarkable is that the series took a well-known dark thriller and found every ounce of humor it could out of the situation. The episode even culminates with a song and dance montage by Bob that shows off the pipes of the multi-talented Grammer.

Deep Space Homer (season 5, episode 15)

deep space homer simpsons 16 Best Simpsons Episodes of All Time


Homer Simpson: Astronaut

And that’s all you really need to know about the episode. Springfield’s lovable oaf finds a way to go to space.

In an attempt to boost interest (and ratings) in the space program, Homer ends up being chosen by NASA for a space mission. Yet of course he causes more trouble than anticipated, and almost kills himself and his fellow astronauts, including one voiced by Buzz Aldrin. The

From Star Trek to 2001: A Space Odyssey, the show doesn’t miss a beat in spoofing popular films or TV shows. The international space station reportedly even has a copy of the episode on board for its astronauts to watch, if they so choose.

A Milhouse Dividend (season 8, episode 6)

a milhouse divided simpsons 16 Best Simpsons Episodes of All Time


Homer is lucky to have Marge. We mean REALLY lucky to have Marge.

Over the years, he’s done a lot to take advantage of their marriage, but in this episode, Homer finaly realizes that he may not appreciate her enough. He comes to that conclusion after Milhouse’s parents have it out at a Simpsons’ hosted dinner party and decide to divorce.  While the Van Houten’s are the center of the episode, it is really about Homer proving to Marge how much he loves her.

Much Apu About Nothing (season 7, episode 23)

much apu about nothing simpsons 16 Best Simpsons Episodes of All Time


A hallmark of the series is that it often starts with a sequence that has little to do with the overall plot of the episode. This time around, it was a bear wandering around Springfield that eventually becomes the catalyst for an episode about immigration.

Watching Apu try to be “All-American” in order to stay in Springfield was both funny and painful (“the NY Mets are my favorite squadron”), but it was also a genius commentary on our society. You also had to feel bad for Apu when it realized that while had the entire Simpson family support, the kids weren’t old enough to vote and Homer’s not even registered.

Of course in the end all works out, but not before the show expertly tackled another hot button topic.

The City of New York vs. Homer Simpson (season 9, episode 1)

The city of new york vs homer simpsons 16 Best Simpsons Episodes of All Time


This is, without a doubt, a brilliant episode, but because New York’s Twin Towers were such a big part of it, the episode was actually shelved after the 9/11 attacks.

We understand the reasoning, but everything about the episode was awesome (Khlav Kalash, “The Betty Ford Musical,” Bart visiting MAD Magazine). After Barney leaves Homer’s car directly between the towers, the family goes to NYC to bring it back. While Marge and the kids have a blast, Homer re-lives all the reasons he hates New York.

Having a character stuck in one location for such a long period of time can be monotonous in certain situations, but not with Homer. These things could only happen to him and watching him exacerbate the situation is what makes these scenes work. This was a underrated episode and reinforces how strong the production team has always been through the years.

Last Exit To Springfield (season 4, episode 17)

Last Exit to Springfield 16 Best Simpsons Episodes of All Time


Mr. Burns has always had a prickly relationship with his workers, while Smithers always has colorful nicknames to describe them (“chair moisteners, carton blobs, fork and spoon operators from sector 7G”).

In this episode, that class battle is on full display as Burns takes on his employees over healthcare with Homer as the union rep. Yes, add labor disputes to the ever-growing list of topics covered by the series. This one was brought on by Lisa needing braces (with the plant’s poor dental coverage) and it served as the perfect backdrop.

While Homer is a buffoon, he’ll do anything for his daughter and that’s part of why we love him. Then again, watching Homer mistake Mr. Burns’s offer of a bribe for an offer for sex is another reason we pull for him every week. He may have gotten to the right answer the wrong way, but give him credit for getting there at all.

Homer’s Phobia (season 8, episode 15)

homers phobia simpsons 16 Best Simpsons Episodes of All Time


As we noted earlier, from immigration to religious tolerance, The Simpsons has never shied away from a sensitive subject. In fact, The Simpsons have always been a little ahead of the curve. In this episode, Homer befriends John, a collectibles shop owner, until he learns John is gay.

This in turn freaks out Homer and makes him go to extreme and ridiculous measures to add some more masculinity to Bart’s life. Yet, this being Homer, each attempt backfires, including a visit to all steel mill, which happens to be staffed by dozens of buff, bronzed gay men, giving us one of the show’s best gags (and yet another memorable musical number).

Voiced by John Waters, the character does eventually help teach Homer to be more accepting of others. It also continued the show’s rich tradition of encouraging its audience to do the same.

$pringfield (or, How I Learned to Stop Worrying and Love Legalized Gambling) (season 5, episode 10)

pringfield 16 Best Simpsons Episodes of All Time


The full title of this episode should tell you everything you need to know.

After Springfield’s unemployment problem causes “useful people to start feeling the pinch” (as Kent Brockman tactfully put it), the town legalizes gambling. Always one to take advantage, Mr. Burns builds a casino and it impacts everyone. Homer gets a job as a blackjack dealer, Marge develops a gambling problem and Bart decides to get in on the action with a treehouse club.

Yet the most amazing parts were (as usual) the references to real-life incidents, which culminate with Mr. Burns slowly becoming a crazed hermit like Howard Hughes. This was really a big storyline for Burns as he becomes more and more unhinged over the entire episode.

Of course, over the span of 26 seasons, there are many more Simpsons episodes that are worthy of consideration. What are your favorites? What do you think should be on this list? LEt us know in the comments!