December 17, 1989.
It’s a rather historic day because the first episode of this little animated skit from The Tracy Ulman Show aired on FOX. The animation was crude at best, and no one seemed to know why the characters had yellow skin (later, it was revealed that the skin color was an attempt to get channel flippers to stop to watch the show).
Thirty-two years (and seasons) later, The Simpsons would become a household name worldwide as well as break the record for the longest-running American scripted primetime television show. With 692 episodes having already aired (and more on the way) you might think it would be almost impossible to pick just 20 episodes to be the best. Well, we’re going to give it a shot anyway.
No. 20 – Simpsons Roasting on an Open Fire
We can’t start a “best of” list without including the very first episode. It was certainly something very different back on Dec. 17, 1989, at 8 p.m., when folks were channel surfing, only to see what some a few years later would call the downfall of Western Civilization (all eyes on George H.W. Bush).
The episode revolves around Homer losing the family’s Christmas savings and, after a brief stint as a mall Santa (foiled by Bart), bets all the money he has left at the dog track on what was obviously a sure sign – a dog named Santa’s Little Helper. The dog doesn’t even finish the race and the owner throws him out in the cold. Homer takes him home, where he’s embraced as “a Simpson” and Christmas is saved.
No. 19 – Deep Space Homer
That’s right. Over the years, Homer has held numerous jobs outside of working as the safety inspector at the Springfield Nuclear Power Plant.
As NASA sees the ratings for space launches plummet, they get an irate call from a drunk Homer saying this wasn’t what the average American wanted to watch on TV. NASA, seeing the opportunity, takes barfly Barney and Homer to see which would be the better “average Joe” to send into space. Once Barney stops drinking, he is a perfect choice. One sip of non-alcoholic champagne, though, and Barney is back to his old ways, leaving Homer as the only option.
The two most important things to remember in life, thanks to this episode: 1) if you’re ever in space, don’t open a bag of chips, and 2) always carry an inanimate carbon rod with you at all times. You never know when you’ll need it.
No. 18 – Treehouse of Horror I
Fun fact: Even though we’re in Season 32 of The Simpsons, there are only 31 episodes of Treehouse of Horror. Another fun fact? In the first few seasons, it wasn’t called Treehouse of Horror. It was The Simpson’s Halloween Special. The very first Halloween special took place inside the kids’ treehouse, where they shared candy and scary stories while Homer secretly listened in.
The highlight of this episode is James Earl Jones providing the voice of the narrator for Edgar Allen Poe’s The Raven.
No. 17 – Flaming Moe’s
For all the many, many things Homer does wrong, he never really gets credit for the things he does right. One such instance comes in at our No. 17 spot. While having to listen to his boring sisters-in-law, Patty and Selma, Homer goes into the kitchen and freaks out when he realizes they took his last beer. In a panic, Homer mixes all of the alcohol he can find. In the process, he accidentally pours in Krusty-brand cough syrup. The drink is meh at best … that is, until the ash from a cigarette lights the drink on fire. When Homer blows it out, the drink becomes incredible.
He shares the recipe with Moe, the bartender, who renames it the Flaming Moe. The bar becomes the hottest spot in town, especially when Aerosmith drops by to play (“HELLO ST. LOUIS!”). All the while, Homer is miserable and, in an act of desperation, just as Moe is about to sell the formula for a million dollars, Homer tells everyone what the secret ingredient is. Things quickly go back to normal after that.
No. 16 – A Streetcar Named Marge
Marge isn’t the best actor. In fact, she’s not really good at all. That being said, as Homer acts more and more like the brute Stanley from Tennessee Williams’s A Streetcar Named Desire, it’s easy to see why the director of “Streetcar: The Musical” Llewellyn Sinclair (played by Jon Lovitz) cast Marge as his Blanche.
The musical numbers are hilarious and we definitely learned it’s best not to upset Marge when she has a bottle in her hand. Poor Ned, who plays a completely ripped Stanley, finds out the hard way.
No. 15 – Dead Putting Society
This is one of the earlier episodes of the show where the creators knew they wanted Ned Flanders to be a good, Christian person, but didn’t quite have him in the “always nice, no matter what” bucket. This episode is the only time you’ll hear Ned scream, “FEAR IS FOR THE WEAK, TODD!”
Bart competes in a mini-golf tournament. Everything comes down to Bart facing off against Todd Flanders for the championship. Homer and Ned make a bet that the father of the boy who doesn’t win has to mow his neighbor’s yard in his wife’s Sunday best. The wording there is key as both boys, tied at the 18th hole, decide to call it a draw.
No. 14 – Cape Feare
The Simpsons just wouldn’t be The Simpsons without Sideshow Bob. Voiced to perfection by Kelsey Grammer, Sideshow Bob once again is paroled from jail and sets out to kill Bart.
The family goes into the Witness Protection Program and become the Thompsons (which Homer has a hard time getting his head around). Of course, Sideshow Bob hides under the Simpson’s car and shows up once they reach their new home of Terror Lake.
This episode has so many hilarious moments, from Bob being tramped by a parade celebrating Hannibal’s Crossing of the Alps, to Bob stepping on what seems like a million rakes. And let’s not forget the episode is packed to the gills with Gilbert & Sullivan references.
No. 13 – El Viaje Misterioso de Nuestro Jomer (The Mysterious Voyage of Homer)
Who doesn’t love a chili cook-off? Well, Marge, for one. Every year Homer goes he “gets drunk like a poet on payday” and embarrasses her. After Homer promises he won’t drink, the family goes to the chili cook-off where he stuns onlookers by swallowing several “insanity peppers” Chief Wiggum added to his chili just for Homer. However, the peppers have a rather trippy consequence, as Homer runs off hallucinating, leaving Marge to think he broke his promise and had gotten drunk.
The best part of this episode is the voice cameo of the late Johnny Cash, who plays Homer’s spirit guide, which happens to be a coyote. He then poses a serious question to Homer – is Marge your soulmate?
No. 12 – Stark Raving Dad
There are so many rumors and half-truths about this episode, someone could do a documentary just about it. After Bart’s red hat gets thrown into the wash, Homer’s work shirts come out pink. This is, of course, way back when wearing a pink shirt was very much taboo if you were a guy. Mr. Burns has him locked up in the insane asylum, where they “throw him in there with the big white guy who thinks he’s the little black guy.”
Homer’s roommate/cellmate thinks he’s Michael Jackson. When Homer’s released, Michael comes with him and is swarmed by a crowd expecting Michael Jackson … only to find out it’s a big, bald white guy who sounds like him. The episode features one of the sweetest things Bart has ever done for his sister, Lisa – he and Michael write her a birthday song.
The controversy surrounding this episode stems from the fact that Michael Jackson was not credited for voicing the role. Instead, the credit went to the fictitious John Jay Smith. The big issue revolves around who is actually singing. At the time, Jackson’s label wouldn’t allow him to sing on the show, so they brought in a soundalike, Kipp Lennon, to do the singing parts.
Sadly, because of controversy surrounding Jackson’s life and allegations of sexual abuse of young boys, the episode has been pulled from network and streaming services.
No. 11 – HOMR
Did you know that if you have a crayon stuck in your brain you might not be all that smart? It’s true … at least, according to Homer. This is one of those great and sad episodes of The Simpsons, where Homer finds out he has a crayon stuck in his brain and has been there since he was a child. Once the crayon is removed, Homer’s intelligence increases dramatically. At long last, Lisa has someone intelligent she can look up to and admire.
As this episode is a play on the book Flowers for Algernon, Homer finds out that with great intelligence comes great depression. Being the smartest guy in Springfield isn’t for Homer, so he has Moe hammer a crayon back into his brain. Before he goes back to being his old self, however, he writes Lisa a note, apologizing to her for not being strong enough, but that he understood her now on a completely new level.
No. 10 – Brother’s Little Helper
Apparently, the Simpson men are intelligent, they just have things keeping them from being so. As with the crayon for Homer, Bart is forced to take a radical new ADD drug called Focusyn, which works phenomenally well. Maybe a little too well.
Bart starts taking so much Focusyn that he becomes paranoid that Major League Baseball is spying on everyone. After stealing a tank, he shoots down a satellite and, what do you know? The MLB is spying on everyone. Mark McGwire – who was still the home run champ before admitting to taking performance-enhancing drugs – comes in at the end to say yes, the MLB is spying on everyone around the clock, but wouldn’t you rather watch him hit some dingers? YAY!
No. 9 – Hurricane Neddy
Ever want to see what Ned Flanders was like before he was, well, Ned Flanders? As a hurricane blows through Springfield (because, let’s be honest, who the hell knows where Springfield is anyway), the Simpson’s house is saved. Even though Flanders did everything to protect his house, it was not. In fact, his house was the only house in Springfield that was reduced to rubble.
When the town rallies together to rebuild the house (in a day), Ned has to stand there while he sees his house collapse yet again. That’s the straw that broke Ned’s back. After yelling at everyone in town, he drives off to the insane asylum and commits himself. It’s then we find out Ned was a completely undisciplined child. His parents were beatniks who didn’t believe in rules or discipline. (“You gotta help us, Doc. We’ve tried nothing and we’re all out of ideas.” This line from Ned’s mother still cracks us up to this day.)
So, after being spanked for eight straight months, Ned becomes the Ned we know now. Whenever he gets upset, he rattles off a string of nonsensical words (surely, you can think of a few diddlies). He becomes cured when Homer gets him to admit he hates his parents. And, for good measure, if you really tick him off, he’s going to run you over with his car.
No. 8 – Homer’s Phobia
This Emmy Award-winning episode stars John Waters as John, a character that is the PG version of John Waters. He’s flamboyant, charming, and loveable. All of the Simpsons fall for John’s charms – that is, until Homer finds out he’s gay.
This episode came out in 1997 and really pushed the bar for LGBTQ acceptance by showing how much of an idiot Homer, Moe, and Barney were for hating homosexuals when they didn’t even know why they hated him in the first place. Everything comes to an end when John saves the hateful trio, who realizes the error of their ways.
No. 7 – Brother from Another Series
Fans of the TV show Frasier were in for a treat this episode, as Kelsey Grammer’s TV brother, David Hyde Pierce, appears as Sideshow Bob’s brother, Cecil. This is one of the few episodes where Sideshow Bob is actually the good guy.
After Bob leaves prison on a work-release program, he finds out he will be working for his brother, Cecil. Cecil has become Springfield’s chief hydrological and hydrodynamical engineer (we also find out that only the Cappadocians would say that is a calling in life – it’s that wit that makes the episode very Frasier-esque).
Together, they’re going to build a dam. Bart doesn’t trust Bob, so he’s watching him at every step. That’s when Lisa and Bart together figure out Bob has been embezzling the money for the dam and is going to drown the entire town. Slight problem though, as Bob didn’t handle the money, Cecil did. We learn more about Bob’s backstory here, as it turns out Cecil wanted to be Krusty’s sidekick but had no charisma. When Bob gets hit with a pie, the job goes to him and Cecil has wanted revenge ever since.
Bob ends up saving Bart’s life, but the dam bursts anyway. Thankfully, no one is killed, but Chief Wiggum makes sure both Cecil and Bob are sent to jail.
No. 6 – Lisa On Ice
Lisa might be the smartest person at Springfield Elementary, but that can’t change the F she’s getting in gym class. Given the option to play a sport outside of school, she tries – and fails – at everything. Meanwhile, Bart is crushing it in the town’s pee-wee hockey league. It’s not until after a game that Apu sees the potential for Lisa to become the goalie of his dreams.
And Lisa is GOOD. Scary good. One of the greatest lines in the episode is Lisa yelling out to her teammates that Ralph Wiggum has lost his shin guard and screams, “HACK THE BONE! HACK THE BONE!!” As you might expect, with all eyes on Lisa, Bart feels left out.
It all comes to a head when Bart’s team has to face off against Lisa’s team. The ending is rather sweet as both Lisa and Bart skate off the ice as the arena burns around them from angry fans.
No. 5 – Bart After Dark
Here we are – the final five! Ever wonder who puts the spring in Springfield? Well, that would be Belle and her ladies at Maison Derriere, the town burlesque house.
After accidentally knocking over a stone gargoyle from the house, Belle brings Bart home so that he can be punished. Problem is, Marge, Lisa, and Maggie have left on a 400-mile drive to Baby Seal Beach, which is covered in oil thanks to everyone’s favorite Sea Captain (yar), to help clean up. Homer decides the best way to punish Bart is to make him do something Marge would do – work off his debt for the lady. Of course, Homer doesn’t know it’s a burlesque house.
Once the town’s “Committee on Moral Hygiene” finds out about the burlesque house, they want to have it torn down. Begrudgingly, the town votes to tear it down, but it is saved at the last minute by a catchy song that wows the crowd. It’s a shame we never see the burlesque house again after this episode.
No. 4 – Kamp Krusty
“Hail to thee, Kamp Krusty …” After convincing his father to let him go, even though his grades weren’t good enough, both Bart and Lisa head off to summer camp at Kamp Krusty, where the commercials promise campers (or is it kampers?) will spend time with Krusty and do fun activities.
In reality, the camp is a hellhole. The children are forced into labor and served Krusty-brand imitation gruel. Yeah, that’s how bad this place is. When the camp counselors try to pass off Barney as Krusty, Bart officially loses it. He stages a revolt until the real Krusty, who is living it up at Wimbledon, is brought in. Krusty, being the great guy he is, decides to make it up to the kids by taking them to the happiest place on Earth – Tijuana!
No. 3 – Who Shot Mr. Burns Parts 1 & 2
A two-fer! The writing staff of The Simpsons had a field day with these episodes. Part 1 ended Season 6 and fans had to wait until the first episode of Season 7 to find out who actually shot Mr. Burns. These episodes were a play on “Who Shot JR” from the primetime soap Dallas. The writers threw in so many clues that could go so many different ways, it was impossible to tell.
For good measure, the writers and producers created several alternate endings and never let on which one was the real ending so no one could spoil it before the Season 7 premiere. Even though it turned out to be Maggie, people who weren’t even fans of the show spent the entire time between seasons speculating on who shot Mr. Burns.
No. 2 – You Only Move Twice
We could easily give you many, many reasons why Season 8 was the peak for The Simpsons. In fact, six of the 20 episodes on this list are from Season 8 … it’s just that good.
In “You Only Move Twice,” Homer and the family move to Cyprus Creek after being offered a new job at the Globex Corporation. The CEO, Hank Scorpio, is a likable guy – he greets the Simpsons at their new home, chums it up with Homer, and even gives him sugar for his coffee straight out of his jacket pockets (not in packet form, though). The fact that Scorpio is a ruthless Bond-esque villain doesn’t bother Homer, who is actually oblivious to it all.
The sad part about this episode is that we finally see Homer be really good at his job. That being said, Lisa finds out she allergic to everything there, Bart is stuck in the remedial program in school, and since the house is completely automated, Marge has nothing to do and is worried because she drinks a glass of wine a day. The family, sans Homer, wants to go back to Springfield.
As Scorpio is being attacked by the U.S. government (“Oh, those jerks. Don’t get me started on the government!” – Homer), Homer has to tell his boss his family wants to leave. In the end, though, after telling Scorpio his dream was to one day own the Dallas Cowboys, he finds Scorpio has given him the Denver Broncos to start. Of course, Homer has to explain to Marge why that’s bad.
No. 1 – Homer at the Bat
Interestingly enough, if you look at a lot of so-called “Best Simpsons Episodes Ever” lists, this episode is usually left off. It’s a shame because it’s the best in the bunch.
The Nuclear Power Plant has a company softball team, and Homer has his “Wonderbat” which he carved out of a piece of wood that was struck by lightning. The team kicks butt and takes names game after game, with Homer smacking, well, homers left and right.
When Mr. Burns places a million-dollar bet on the Springfield vs. Shelbyville game, he decides it’s time to call up some ringers. After Smithers explains that the ringers Mr. Burns wants have long since passed away, he’s told to go find good, LIVING players.
The episode features an all-star (literally) cast of Major League Baseball players: Ken Griffey Jr., Ozzie Smith, Mike Scioscia (back when he was a catcher for the Dodgers), Roger Clemens (pre-PEDs), Darryl Strawberry (before we knew about all the cocaine), Steve Sax, Wade Boggs, Don Mattingly (back when he played first base for the Yankees), and Jose Canseco (back before, well, you know).
With the ringers on the team, the actual team is benched. That is, until one by one, mysterious maladies happen to each player – except Strawberry, who plays Homer’s position of right field. When Shelbyville brings in a left-handed pitcher, Mr. Burns decides to pull Strawberry (who had hit nine home runs up to that point) for a pinch hitter, Homer. “It’s called playing the percentages,” Mr. Burns says. Mr. Burns’s team is tied with the bases loaded in the bottom of the ninth inning.
As Homer stands in the box, confused by Mr. Burns’s signals, he gets beaned, which brings in the winning run for the team.
So there you have it! The top-20 episodes of The Simpsons of all time! Don’t agree? What did we miss? Are there episodes you think we should have included? Be sure to leave them in the comments below!
