The Simpsons has been a pop culture staple for a quarter century now so we thought it would be a good time to take a look back at the best of the best when it comes to the nation’s true first family. This is a lot like asking a proud parent to pick his favorite child, but in the end, we persevered and came up with these, the 50 best episodes of The Simpsons ever.
One quick note before we begin: it wasn’t planned this way, but all of these episodes come from the show’s first eight seasons. It’s not that there haven’t been a few gems since, but for the most part, the show has been living off of the reputation of the great episodes of its golden age. That’s how awesome these episodes are. It doesn’t mean the show is bad now, it just can’t quite keep up with what it used to be. But to be fair, not many shows – if any – can. With that out of the way, let’s just get to it. Here are the 50 best episodes of The Simpsons in all their majestic glory.
Summary: Troy McClure meets Marge’s sister, Selma, and the two embark on a ridiculous love affair involving… fish?
Why It Belongs Here: Anytime the show could feature Phil Hartman in a major role, it meant good things. This is one of the weirdest episodes in show history – and one of the funniest – as the big running gag throughout the episode is that Troy McClure likes to bang fish.
Summary: Lisa protests Springfield’s annual tradition of clubbing snakes, a tradition we learn that began as an excuse to beat up the Irish.
Why It Belongs Here: Episodes involving the whole town are almost always good, and really, you can’t go wrong with any episode that features massive snake abuse, Barry White getting the snakes all horny, and jokes about the Irish.
Summary: Worried that their show is growing stale, the producers of Itchy & Scratchy make the bold decision to add a new character, an obnoxious dog named Poochie voiced by none other than Homer J. Simpson.
Why It Belongs Here: Poochie has become a shorthand way for anyone to denigrate a show for getting desperate and tinkering with the formula. The episode itself is extra poignant when you realize in hindsight that The Simpsons itself was only a couple short years away from screwing things up by basically turning Homer into Poochie.
Summary: The Kwik-E-Mart gets robbed, and the chief suspect is beloved children’s clown Krusty, but it turns out that Krusty is being framed by his former sidekick, Sideshow Bob
Why It Belongs Here: This is the episode that introduced Sideshow Bob, and created the golden rule that every Sideshow Bob episode has to be a great one. Watching some of the first season’s episodes can be painful, but you can see the show we all know and love being truly born in episodes like this.
Summary: Mr. Burns retires and sells the power plant to a German consortium, which means that Homer’s lazy idiocy comes face to face with grim German efficiency with hilarious results.
Why It Belongs Here: This whole episode is basically one big excuse for the writers to go nuts on Germans and all their various stereotypes. Meanwhile, we get to see Homer being an irredeemable doofus long before the show decided that was his sole character trait.
Summary: Lisa’s trip to a petting zoo convinces her to go veg, which doesn’t play so well with her meat-loving dad and the rest of Springfield.
Why It Belongs Here: This is the perfect satire of the newly converted vegetarian who decides to turn a personal life choice into a crusade to convert everyone else. Also, it features Homer chasing desperately after an airborne prized ham, which is pretty much the most Homer thing ever.
Summary: A series of vignettes featuring the various whacky characters of Springfield.
Why It Belongs Here: This was The Simpsons take on Pulp Fiction, and it does it brilliantly. And again, anytime the show features the whole town, it means good things.
Summary: Mr. Burns adopts a litter of puppies, only for Lisa and Bart to discover his grim motive: he plans on turning them into a fur coat.
Why It Belongs Here: Mr. Burns centered episodes are almost always good. This one is especially funny because he’s so over the top evil here, and his Disneyesque song about killing animals of every species for their coats is so memorable that I find myself humming it sometimes to this day.
Summary: Bart finds out that Grandpa Simpson belonged to a World War II unit known as "The Flying Hellfish," a unit with a dark secret – they all stole priceless Nazi paintings and made a pact that the last one living got to keep it all, and Grandpa is one of only two Hellfish left. The other? Mr. Burns.
Why It Belongs Here: Anytime the show goes back in time, good things tend to happen. Plus, you get to see the badass side of Grandpa Simpson as he tangles with his old sniveling Private Burns.
Summary: Ralph Wiggum falls head over heels in love with Lisa after she feels sorry for him and gives him a Valentine. Of course, Lisa is caught between trying to be nice and not being able to stand Ralph, and the result is predictably hideous.
Why It Belongs Here: Ralph has always been the show’s secret weapon, and they deploy him here to max effect. Bart replaying the moment over and over again on video tape when “you can actually pinpoint the moment Ralph’s heart rips in half” is both excruciatingly perfect and hilarious.
Summary: During a company retreat, Homer and Mr. Burns become trapped together in a mountain cabin by an avalanche.
Why It Belongs Here: These are arguably the two best characters in the entire show, so sticking them together for an entire episode is bound to be a winner. The highlight is probably the scene of the two hallucinating, leading to – naturally – Burns leading an army of Nazi snowmen.
Summary: Marge catches Bart shoplifting and has a crisis of motherly conscience.
Why It Belongs Here: I could say it is a surprisingly poignant treatise on the natural detachment that occurs between mother and son as he gets older, as well as the power of motherly love to forgive, but really this is all about Homer’s reaction to Bart switching the answering message to the “Hello Mother, Hello Father…” song, which is one of the funniest moments in the show’s history.
Summary: Homer winds up in a mental hospital, where he finds himself incarcerated with a fat, white guy who claims to be Michael Jackson.
Why It Belongs Here: If you’re not humming the “Lisa, It’s Your Birthday” song right now, you have no soul.
Summary: Homer comes *this* close to cheating on Marge with a coworker who inexplicably falls for him.
Why It Belongs Here: Beneath all the oafish dumbassery, Homer is actually a profoundly decent dude, and he recognizes that Marge is, was, and always will be the best thing in his life. The Simpsons has beaten the “Homer and Marge’s marriage is in trouble” theme to death over the years, but this is one of the rare times when it actually feels genuine, and isn’t just Homer being a jackass or Marge being a shrill killjoy.
Summary: Mr. Smithers goes on vacation and in order to ensure that nobody steals his job while he’s away, he appoints the one man sure to make him look good in comparison: Homer Simpson.
Why It Belongs Here: Aside from Smithers’ always hilarious toadying, this is the episode where Homer knocks out the insane Mr. Burns, which hilariously leads to both Homer thinking he accidentally killed his boss, and Burns learning to take care of himself out of fear.
Summary: Bart scoffs at the idea of a soul and sells his to Milhouse for $5, and then things get dark.
Why It Belongs Here: If that description alone isn’t enough to make you laugh, the opening scene in which Bart replaces the organ music with Iron Butterfly will. The townspeople all singing “In-A-Gadda-Da-Vida” like any old church hymn is one of those things that will stick with you forever.
Summary: Mr. Burns decides to whip his employees into shape, but Homer isn’t having any of that and realizes he can just go on disability if he allows himself to get fat enough.
Why It Belongs Here: Homer in a muumuu, Homer’s fingers being too fat to dial a phone, Homer saving the day when his fat ass gets stuck and plugs a nuclear leak...this episode just has classic scene after classic scene.
Summary: Bart’s favorite comic book character, Radioactive Man, is being adapted into a movie, and they’re casting for his sidekick, Fallout Boy. The only problem? His best friend, Milhouse, gets the part instead.
Why It Belongs Here: Rainier Wolfcastle, the show’s resident Arnold Schwarzenegger, constantly stumbling over Radioactive Man’s catchphrase, “Up and at ‘em,” because he refuses to say it any other way than, “Up and at them,” in wooden English is one of those things that becomes funnier the more you see it. Plus, this episode let the show’s writers satirize Hollywood, and naturally, they nailed it.
Summary: Springfield legalizes gambling and naturally, Mr. Burns capitalizes on it by opening a casino. He then goes completely insane. Meanwhile, Marge develops a gambling addiction.
Why It Belongs Here: The Marge stuff is what it is, but really, this episode is all about Mr. Burns going the full Howard Hughes, complete with gross uncut toenails and jars of urine. It practically writes itself.
Summary: Homer decides that church is for suckers, especially when he discovers he can just stay home and watch football all day. Of course, he then almost burns down the house.
Why It Belongs Here: We’ve all been there – the giving up church for football part, not the burning down the house part. Plus, how can you not love any episode that ends with Homer and God just chilling like bros and talking football?
Summary: Bart gets a new radio, which he immediately decides to use to play pranks. You know, because he’s Bart. Naturally, this all ends with him convincing the entire town that a little boy fell down a well.
Why It Belongs Here: Again, this falls under the old rule of “if the whole town gets involved, it’s a good episode.” But aside from that, watching everyone look like hysterical idiots perfectly satirizes the way communities deal with stupid Nancy Graceish "disasters" like this.
Summary: Homer gets drunk and thinks he sees an alien on the way home from Moe’s. Springfield goes crazy, Mulder and Scully from The X-Files show up to investigate, Leonard Nimoy stops by with a TV show about weird phenomena he’s been hosting on his down-time, and after the entire town gathers to capture an alien (but not before accusing Homer of being a drunken ass who just hallucinated the whole thing.), the ‘alien’ turns out to be Mr. Burns all hopped up on goofballs.
Why It Belongs Here: Uh, just read all that again.
Summary: Springfield hosts a film festival (judged by Jay Sherman of The Critic) which leads to exactly what you would expect from the contestants – with one notable exception.
Why It Belongs Here: Burns going full megalomaniac and comparing himself to Jesus in his Ben-Hur knockoff would be enough to get this on the list, but what really makes it is Barney’s beautiful art film about being a drunken lout. Oh, and Homer refusing to vote for his pal’s movie because he wants to vote for the film of Hans Moleman getting hit in the groin by a football.
Summary: Moe steals Homer’s brilliant drink idea and attracts a fancier brand of clientele, but loses Homer’s friendship in the process.
Why It Belongs Here: The Flaming Moe recipe (cough syrup lit on fire) should be enough all on its own to make you laugh, but the episode is especially noteworthy for really developing Moe as a character for the first time. The episode is solid from start to finish, with the rift on Cheers possibly being the highlight, but really, this is one of those episodes with just so many little things that work perfectly that it’s hard to pinpoint any one thing that makes it so good. It all just works.
Summary: Mr. Burns finally goes full-on super-villain and blocks out the sun, leading to a season ending cliffhanger in which someone shoots him. Naturally, the list of suspects is as long as the Springfield phone book.
Why It Belongs Here: The first half of this cliffhanger and most of the second belongs in the top ten. It’s one of those perfectly crafted episodes that involves everyone in town and pays off Burns’ incredible assholery in amazing fashion. Then they went and had Maggie be the one who shot Mr. Burns, which felt like a rip-off and marked one of the first times the show erred in direction. But still, it’s a really, really funny episode.
Summary: The family goes on vacation to Itchy & Scratchy Land, but the animatronic robot cartoon characters malfunction and begin hunting all the tourists.
Why It Belongs Here: Again, this is one of those episodes where the premise pretty much guarantees a home run. Special points go to this episode for introducing the "Bort" license plate in the souvenir gift shop.
Summary: Bart accidentally discovers a comet that is headed straight for Springfield. Naturally, the townspeople handle it with their usual grace and dignity.
Why It Belongs Here: Another episode in which the other citizens of Springfield are allowed to shine, especially Flanders, who gets voted out of his own overcrowded bomb shelter when it’s decided that he’s the most useless man in town. Just a funny, funny episode.
Summary: Homer embarrasses Marge by making an ass out of himself at a chili cook-off, declaring everybody in town’s chili too bland for his master palate. That is until he eats Chief Wiggum’s special hallucinogenic Guatemalan Chili Pepper, trips out, gets lost and is led through the desert by a talking fox voiced by Johnny Cash, who leads him to the realization that the woman who supposedly doesn’t understand him, Marge, is his soul-mate after all.
Why It Belongs Here: Got all that? Good, because I’m not explaining it again.
Summary: Homer meets a flamboyant antique dealer voiced by John Waters who he thinks is the coolest. That is until he belatedly realizes that the dude is gay and then flips out and worries that Bart is becoming sissified thanks to John’s influence.
Why It Belongs Here: Homer is quite rightly made to look like a fool here, and the episode ends with Homer realizing that even manly steel workers get down like that and deciding he’s okay with it after all. It was a smart, in your face episode that wasn’t afraid to both joke about stereotypes and show why they’re ludicrous at the same time. When The Simpsons was at the height of its considerable powers, nobody did social satire better, and this episode is a prime example of it.
Summary: Homer becomes a stand-in for Krusty, and revels in his newfound "fame," at least until the mafia decides he’s the real Krusty and decides to kill him. Whoops!
Why It Belongs Here: Homer impersonating Krusty is good for a solid laugh, especially when he’s forced to do a super-complicated trick in order to amuse the elderly godfather. Again, this is just one of those episodes which is solid from start to finish, with solid gags throughout, and with Homer perfectly riding the line between loveable dimwit and obnoxious buffoon.
Summary: Bart breaks his leg and is forced to spend all summer in his room, looking through his telescope. He soon witnesses what he thinks is Ned Flanders murdering his wife, and hilarity ensues.
Why It Belongs Here: It’s an awesome parody of/homage to Rear Window, with Bart getting increasingly weird in his isolation, and a plot that works only because it plays beautifully on the image of Flanders the show had spent years meticulously building. In the end, of course Flanders didn’t do it, and you will never, ever forget his disturbing, girlish scream.
Summary: NASA flips out because the TV ratings for their launches have sunk to an all-time low and so they decide to send an ordinary dude into space. Naturally, they choose Homer who screws everything up in Homerish fashion.
Why It Belongs Here: Another premise so perfect that it practically writes itself. What’s really amazing is how perfectly the show predicted the rise of the moronic reality show culture that was to come almost a decade later. Also, this episode gave us the sublime scene of Homer floating through zero-gravity, capturing potato chips in his mouth to a classical music score. And if that wasn’t enough, it gave us the Inanimate Carbon Rod as a new national hero.
Summary: Mr. Burns finds out that his long-lost teddy bear, Bobo, has come into the possession of one Maggie Simpson, and stops at nothing to get it back.
Why It Belongs Here: The show was at the height of its powers here, turning Burns into the protagonist of Citizen Kane, which was just such a perfect fit that it was kind of miraculous they didn’t do this episode even sooner. The episode perfectly highlights both his petty villainy and his teetering sanity as he tries to destroy a baby over a ragged old teddy-bear.
Summary: Homer buys a new snowplow and starts his own plowing business, which thrives until a competitor emerges – Homer’s drunken best friend, Barney Gumble.
Why It Belongs Here: The episode is so ridiculous that you can’t help but laugh. Anytime Homer goes to war with one of his cronies, it’s almost always a good episode. And this one is one of the best, loaded with tons of pop culture references and gags – Angela Lansbury being forced to walk on hot coals to win a game-show again accurately nailed the rise of ridiculous reality shows to come – that still stand up today, twenty years later.
Summary: Bart becomes enthralled by a daredevil and much to Homer’s dismay, decides to become a skateboard daredevil himself. Naturally, this leads to Homer trying to jump the Springfield Gorge on a skateboard to save his son and nearly killing himself.
Why It Belongs Here: The sight of Homer falling again and again down the cliff is iconic, one of those scenes that made The Simpsons everything it’s been in pop-culture the last 25 years. This is arguably the episode in which the show hit its stride, and it didn’t slow down for almost seven years.
Summary: Hard worker and model employee Frank Grimes can’t stand that Homer skates by despite the fact that he’s a dimwit, and becomes obsessed with destroying him – to his own detriment.
Why It Belongs Here: This episode played on a truth nobody was really willing to acknowledge: Homer is kind of an asshole. But he’s our asshole, and we’ll always take an affable nitwit over a humorless drone any day of the week. The scene where Grimes – or Grimey, as he liked to be called – goes nuts at the end because Homer can seemingly get away with anything, only to electrocute himself to death, is one of the funniest in the show’s history.
Summary: Springfield invokes an old prohibition law after Bart gets hammered at a parade on St. Patrick’s Day. Naturally, this leads to Homer becoming a bootlegger and feuding with Rex Banner, Springfield’s new hard-ass police chief.
Why It Belongs Here: If you need me to explain why that’s awesome, then there’s not a lot of hope for you.
Summary: The kids find an old record album with Homer’s picture on it, which leads to him explaining his brief run of fame with his buddies as members of The B-Sharps.
Why It Belongs Here: Episodes in which Homer tells the kids stories from the past always work, and this one is the best of the bunch. The flashbacks are funny, the premise is completely ridiculous in a good way, and the reunion at the end is actually heartfelt, which, given the aforementioned ridiculousness, is pretty much insane, but that’s how well the episode was written.
Summary: Homer drives the babysitter home only to notice that she has a gummy Venus de Milo stuck to her ass as she gets out of the car. Naturally, he starts drooling like a fiend because candy, and she assumes that he’s after that babysitter booty. Scandal and hilarity ensues.
Why It Belongs Here: The shot of Homer drooling like a degenerate letch over food finally backfires on him and it’s awesome. Homer spends the entire episode swearing he’s not a pervert while the town turns on him, which is amazingly funny to watch. And finally, who can forget the sleazy news crew outing Willie as Rowdy Roddy Peeper? This episode predicted Chris Hansen a good decade before To Catch a Predator.
Summary: Springfield’s beloved lemon tree is stolen by neighboring Shelbyville, and Bart and his friends declare all-out war to get it back. And then Homer gets involved.
Why It Belongs Here: Bart and his friends coming up against their bizarro doppelgangers is great, but the real highlight of the episode is Martin dancing around Nelson, singing his praises like some medieval minstrel, while Nelson swats at him like he’s swatting an annoying gnat. And let’s not forget Homer abusing poor Ned, and forcing him to use his fancy RV to break into Shelbyville and haul that tree – and their boys – back to Springfield
Summary: Bart causes an international incident when he collect calls Australia to verify Lisa’s tale that the water drains the opposite direction there. This then leads to Bart being summoned to Australia to apologize personally for the exorbitant phone charges.
Why It Belongs Here: There are too many funny things in this episode to name here without it turning into an article of its own. Let’s just say that this episode takes on Australia – and the many, many ridiculous stereotypes that follow that country around – and it ends with Bart mooning everyone and the family having to be airlifted out Saigon style as the country falls apart beneath them.
Summary: Homer leads the plant’s softball team to a matchup with one of Mr. Burns’ rivals. The two bet on the game, so Burns dumps the whole team and brings in ringers, voiced by several real life baseball stars.
Why It Belongs Here: This is the best celebrity stunt-casting in the history of TV. That may be a bold statement, but watch this episode and then try to argue with me. Each player is given his own storyline and all of them work. Talk to any dude of a certain age about this episode and prepare to have him start gibbering on forever about Griffey’s giant head or Mattingly’s sideburns.
Summary: The first of the famous Halloween episodes, this one features the family moving into a haunted house, a takeoff on Edgar Allan Poe’s The Raven, and most famously, the introduction of Kang and Kodos in a parody of the short story “To Serve Man.”
Why It Belongs Here: Honestly, you could put any of the Halloween episodes from the first six or seven seasons on this list, but that would end up making up almost the entire top ten, and so we’ll just pick the best one. And I’ll say it’s still the first one – a lot of people will tell you it’s the one with “The Shinning” which is a worthy choice, but how can you vote against an episode that introduces Kang and Kodos *and* features maybe the single best gag in show history – the constant dusting off of the alien cookbook to reveal either horror or relief from the family? This is like Sophie’s Choice if Sophie were a shallow Gen-X’r/Millennial, but I won’t apologize.
Summary: Homer is forced to go back to college after being fired. Naturally, everything he knows about college is taken from raunchy ‘80s comedies and he behaves accordingly.
Why It Belongs Here: That is the perfect setup for an episode, and this episode doesn’t spoil it. Instead, it takes it and somehow makes it even better and funnier than it already sounds. Homer feuding with the puzzled Dean, Homer leading his geek roommates to ruin, Homer playing Dungeons and Dragons and getting slain by a wood elf… this episode is just great.
Summary: A grifter coasts into town and convinces everyone with much song and dance that they should build a monorail. Naturally, it does not go well.
Why It Belongs Here: This episode brings it hard. Just one kickass joke after the next. And probably more than any other episode, this is the one that does the best job featuring the entire town of Springfield and all its ridiculous characters. It’s just perfect. Incidentally, this is one of only three episodes written by Conan O’Brien. One of the others was “Homer Goes to College.” Good Lord.
Summary: Homer joins the underground Freemason-like Stonecutters and soon finds himself vaulted to a leadership position, which naturally he abuses.
Why It Belongs Here: All you have to say to a fan of the show is “The Stonecutters episode” and they’ll start smiling and nodding knowingly. Also, you’re now humming the Stonecutters song. Don’t deny it.
Summary: A new neighbor moves in – former President George Bush, and almost immediately he begins feuding with both Bart and Homer.
Why It Belongs Here: Once the premise was laid down, all the writers had to do was not screw this one up. It was a guaranteed home run, and somehow the show again made it even funnier than it sounds, with Bush and Homer getting involved in an escalating and vicious prank war.
Summary: Lisa needs braces, and after Homer becomes union leader, he votes to go on strike after Mr. Burns yanks the company dental plan.
Why It Belongs Here: This is the episode everyone points to when they say that The Simpsons wasn’t just funny, but brilliant and important. And they’re not wrong. It’s an amazing satire of both unions and corporate greed, but it doesn’t beat you over the head with it. Instead, the jokes come even faster than in a normal episode. Also, this episode is the first place I heard “Classical Gas,” so it has that going for it too.
Summary: Sideshow Bob gets released from prison and immediately sets about doing what he does best: terrorizing Bart.
Why It Belongs Here: Sideshow Bob episodes are always a highlight of any season, and this is the best of the bunch, as Bob takes on Bart and his family even after they enter the witness protection program. Tying in Sideshow Bob’s revenge with a Cape Fear parody is exactly the sort of brilliant thing that caused this show to be on a completely different level than anything else at the time. Also, the gag with Sideshow Bob vs. the rakes is one of the show’s best ever.
Summary: Homer gets a new job and moves his family to a new town. There, he finds himself in heaven, as his job his perfect and his boss is the coolest, nicest man in the world. Oh, he’s also a Bond style super-villain bent on conquering the world.
Why It Belongs Here: The premise is just so ridiculously weird and amazing at the same time. It’s the sort of thing only an insane genius could come up with. Homer as the unwitting henchman of a super-villain is one of those things that just make you laugh out loud. And Hank Scorpio’s constant politeness and appreciation of Homer even in the face of all-out war and impending disaster puts it all over the top. It’s the perfect episode.
(Previously published on October 2, 2013.)
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