With The Simpsons kicking off its 34th (!!!) season on September 25, we’re once more looking back at the show’s very best episodes.
The Simpsons has been around for three decades now, spawning over 700 episodes and one theatrical movie (Homer voice: one theatrical movie so far!). It wasn’t an easy task considering how many there were to choose from, but these 34 episodes are essential viewing for anyone who enjoys hanging out in Springfield, USA.
Even 34 episodes barely scratches the surface of what the show has given us over the years, of course. Let us know your picks for the best Simpsons episodes of all time in the comments section below.
The Top 34 Simpsons Episodes
34. “Homer the Great” (Season 6)
“Why won’t those stupid idiots let me in their crappy club for jerks?”
“Homer the Great” is a classic, absurdist Simpsons episode of the type only the inimitable John Swartzwelder could write. When Homer discovers that Lenny and Carl are members of a secret society known as the Stonecutters, he winds up joining and bumbling his way into becoming their fabled Chosen One. Power goes to Homer’s head, of course, and the ensuing rise and fall of Springfield’s new god-king is a real hoot. Plus, this episode gets bonus points for its great use of guest star Patrick Stewart and having one of the show’s catchiest original songs in “We Do.”
33. “I Love Lisa” (Season 4)
“Watch this, Lise. You can actually pinpoint the second when his heart rips in half.”
When it comes to all-time great Simpsons one-liners, it’s impossible to top Ralph “Chicken Necks?” Wiggum. But every so often the series will make Ralph the main character rather than the dimwitted comic relief, and never more successfully than in this Season 4 gem. When Ralph is cruelly left out of the class’ Valentine’s Day festivities, Lisa takes pity on him and gives him a card. That, of course, immediately spirals out of control when Ralph decides that “I Choo-Choo-Choose You” means Lisa is madly in love. It’s a sweet look at the pitfalls of young love, and a welcome reminder that Ralph can be a three-dimensional character… when he’s not too busy gluing his head to his shoulder.
32. “Treehouse of Horror VI” (Season 7)
“Lousy Smarch weather… ‘Do not touch Willie.’ Good advice!”
Like the series as a whole, the annual Treehouse of Horror specials peaked fairly early on, back when the emphasis was more on spooky fun than parodying the hot movie franchises of the moment. The sixth special still ranks among the best of the bunch, particularly thanks to its hilarious slasher movie spoof “Nightmare on Evergreen Terrace.” This is also the episode that gave us Homer Cubed, a then-groundbreaking segment that dragged Homer kicking and screaming into 3D.
31. “And Maggie Makes Three” (Season 6)
“Aww… it’s a boy. And what a boy!”
“Uhh… that’s the umbilical cord. It’s a girl.”
Thanks to the perpetually sliding timeline of The Simpsons, the series has given us many conflicting accounts of what life was like when Homer and Marge were younger and learning the ropes of being parents. This episode ranks as the best of that particular formula. It springs from a simple question – “Why are there no baby pictures of Maggie in the house?” – and uses it as a springboard for a surprisingly heartfelt look at Maggie’s origins and Homer’s brief stint as a bowling alley employee. As cynical as The Simpsons can be, this episode truly wears its heart on its sleeve.
30. “Lisa the Iconoclast (Season 7)
“Embiggens? I never heard that word before I moved to Springfield.”
“I don’t know why. It’s a perfectly cromulent word.”
In this episode, Lisa learned the same lesson Batman would come to understand in The Dark Knight – sometimes you need to let a city have its heroes, even if the reality doesn’t actually measure up to the ideal. “Lisa the Iconoclast” is one of the stronger episodes to focus on Lisa’s moral dilemma of the day. Here she makes it her mission to force Springfield to realize the truth about its beloved founder, Jebediah Springfield, only to once again find herself a town pariah. As with a lot of great Lisa-driven episodes, the focus is as much on Homer and the conflict between following his whims and wanting to live up to Lisa’s expectations. A memorable guest performance from Donald Sutherland is the icing on the cake in this episode.
29. “One Fish, Two Fish, Blowfish, Blue Fish” (Season 2)
“I want to share something with you – the three little sentences that will get you through life. Number one: ‘Cover for me.’ Number two: ‘Oh, good idea, boss.’ Number three: ‘It was like that when I got here.'”
While The Simpsons was still honing its voice in Season 2, this unusually dramatic episode offered a glimpse of the golden period that was to come for the series. Here Homer confronts his own mortality in a very real and immediate way, fearing he’s just ingested a poisonous blowfish and has only one day left to live. The result could have been overly sentimental and melodramatic, but this episode toes the line between humor and tragedy easily enough. The scenes of Homer bidding farewell to his family and confronting his imminent demise show an unusually human side of a character who so often comes across as a self-centered, even sociopathic jerk.
At the same time, this episode ends on an appropriately sly note. One minute, Homer is celebrating his second lease on life and promising to live every day to the fullest, the next he’s stretched out on the couch with a half-eaten bag of pork rinds.
28. “Mother Simpson” (Season 7)
“Alright! I admit it, I am the Lindbergh baby! Waah! Waah! Goo-goo! I miss my fly-fly, Dada!”
“Are you trying to stall us, or are you just senile?”
“A little from Column A, a little from Column B.”
While Abe Simpson is always a reliably entertaining supporting character, up to this point the show had never focused much attention on Homer’s *other* parent. Who was Homer’s mother, and what part did she play in raising this dysfunctional goofball? As “Mother Simpson” showed us, there’s actually quite a story to be told there.
This episode introduced fans to Moana Simpson (voiced by Glenn Close), Homer’s long-lost mother who’s spent the last several decades on the lam after running afoul of a (slightly) younger Mr. Burns. The ensuing family reunion is a lot of fun, from Homer’s childish plays at attention to Lisa finally discovering a family member she can look up to. But ultimately, Moana realized she couldn’t outrun her past, and that’s where this episode finds its enduring appeal. Homer and Moana’s tearful goodbye ranks among the most emotional moments of the show. It’s basically The Simpsons’ answer to Futurama’s “The Luck of the Fryrish.”
27. “King-Size Homer” (Season 7)
“Your father can be surprisingly sensitive. Remember when I giggled at his Sherlock Holmes hat? He sulked for a week and then closed his detective agency.”
One of our favorite animated sitcom tropes is the episode where a character goes to extreme lengths to get out of having to perform an annoying task. “King-Size Homer” sees Homer transform into a 300-pound caricature of himself in order to get out of Mr. Burns’ mandatory exercise program and enjoy the pleasures of working from home. But when nuclear meltdown looms, Homer has to race against the clock and his own, uncooperative body in order to save the day.
“King-Size Homer” stands out for many reasons, whether because of its smartly crafted dialogue, the hilarious sight gag of Homer in a mumu or its effective blend of cynicism and sympathy regarding Homer’s plight.
26. “Lisa’s Wedding” (Season 6)
“Oh-ho! An English boy, huh? You know, we saved your ass in World War II.”
“Yeah? Well, we saved your ass in World War III.”
Nothing illustrates just how ridiculous and unprecedented The Simpsons’ multi-decade run is than episodes like “Lisa’s Wedding.” This episode flashes forward to what was then the far-flung, futuristic landscape of 2010 to explore what Springfield looks like 15 years in the future. Apart from the presence of Jetsons-style hover cars and Bart being gainfully employed, not much had changed.
The 2010 humor alone would have been enough to make this episode succeed, but it also hinges on a romance between Lisa and her handsome, wealthy British suitor, Hugh (Mandy Patinkin). As much as Lisa may be embarrassed by her family, she can’t bring herself to marry a man who won’t accept them for who they are. Even though the whole future storyline is just a glorified “What if?” scenario, it serves as one of the more poignant looks at the love between Lisa and Homer.
This would be the first of several times the show has looked into the future of the Simpson clan, but all others pale in comparison to “Lisa’s Wedding.”
25. “Who Shot Mr. Burns Parts 1 & 2” (Seasons 6 & 7)
“Ever since the beginning of time, man has yearned to destroy the sun. I shall do the next best thing: block it out.”
We’re cheating a bit on this one by technically including two episodes, it’s true. To date, “Who Shot Mr. Burns?” remains the only two-part storyline the show has ever tackled. And it was a gleeful parody of the infamous “Who Shot J.R.?” storyline on the 1980’s soap opera Dallas.
The first episode closed out Season 6, as Mr. Burns managed to piss off just about every resident of Springfield by stealing oil, blocking out the sun, firing Smithers and still, through it all, never remembering Homer’s name. The episode ended on a cliffhanger, with Burns shot and dozens of Springfielders as potential culprits. Season 7 continued the drama as Chief Wiggum investigated the crime and Lisa raced to clear her father’s name before he actually killed his boss.
Both episodes were funny, certainly, but we also appreciate their darker edge and the whodunit mystery that kept Simpsons fanatics speculating and debating all through the summer of 1995.
24. “‘Alone Again, Natura-diddly” (Season 11)
“Now, now, now, don’t beat yourself up. I’m the one who drove her out of her seat. I’m the one who provoked the lethal barrage of T-shirts. I’m the one who parked in the ambulance zone, preventing any possible resuscitation.”
Time all but stands still in Springfield, and no one ever actually ages on the show (not even little Maggie). So death is a topic that only comes up rarely. And rarer still does death strike a major recurring character. “Alone Again, Natura-Diddily” was motivated largely by the fact that Maude Flanders’ voice actress had moved away from California, but the writers found a great storyline to explore in Maude’s tragic, T-shirt cannon-induced death.
This was the first major tragedy to strike the Flanders clan since Ned’s brush with financial ruin in Season 1. It upset his comfortable, squeaky-clean world and allowed for an extended character arc to play out over the course of many seasons as Ned adjusted to the single-parent lifestyle and started dating again. It was one of several cases where a key twist has given an old character new life on this show.
23. “Radioactive Man (Season 7)
“My eyes! Ze goggles do nothing!”
With “Radioactive Man,” various characters learned that the glamorous allure of Hollywood doesn’t always live up to reality. The episode saw a Hollywood studio choose Springfield as the location to shoot their big-budget Radioactive Man movie (starring Ranier Wolfcastle, of course). Bart’s dreams of playing Fallout Boy were dashed when the role went to Milhouse. For his part, Milhouse wanted no part of the fame, fortune, and constant hassle that come with child stardom. Meanwhile, production ground to a halt as Mayor Quimby and the rest of Springfield bled the studio dry with bogus taxes and fees. In the end, nobody won, especially not Wolfcastle as he was swept away by a river of toxic waste.
This episode was a great spoof of both Hollywood and superhero films, aiming its barbs at the Batman franchise in particular.
22. “Itchy & Scratchy Land” (Season 6)
“We need more Bort license plates in the Gift Shop. Repeat, we are sold out of Bort license plates.”
How can you not love an episode that simultaneously parodies Westworld, Jurassic Park and the Walt Disney empire? This episode sees the Simpsons travel to the new Itchy & Scratchy theme park for their summer trip. And naturally, it’s only a matter of time before Homer and Bart’s promise not to embarrass Marge completely falls apart. Luckily, a little Chaos Theory causes an uprising of animatronic Itchy and Scratchy robots, providing for some much-needed family bonding. Anyone who has experienced the overwhelming assault of capitalism and corporate mascots that is Disney World can appreciate this episode.
21. “Lemon of Troy” (Season 6)
“Homer, come quick! Bart’s quit his tutoring job and joined the violence gang!”
The Simpsons has always referenced an ongoing rivalry between Springfield and the neighboring city of Shelbyville. But it wasn’t until “Lemon of Troy” that said rivalry truly took center stage. Here we saw Bart lead a crew of misfits (Milhouse, Nelson, Martin, etc.) on a quest to retrieve Springfield’s beloved Lemon Tree from Shelbyville’s miscreants. This in turn forced their parents to pile into Flanders’ RV to rescue them.
“Lemon of Troy” offered a fun glimpse into Shelbyville, which turned out to be an almost Mirror Universe version of Springfield in some ways. But the episode also hit all the right notes in terms of celebrating the peculiar sense of community among Springfielders and their mythologized town history.
20. “Homer’s Enemy” (Season 8)
“Yes, that’s me, and the guy standing next to me is President Gerald Ford… And this is when I was on tour with the Smashing Pumpkins… Oh, and here’s a picture of me in outer space.”
“You? Went into outer space? You?”
“Sure. You’ve never been? Would you like to see my Grammy award?”
As much as Homer is portrayed as an ordinary slob of a lower-middle class guy, he’s had some pretty grand adventures and lucky breaks over the years. “Homer’s Enemy” introduced us to Frank Grimes, the man who was everything Homer isn’t. Grimes was intelligent and ambitious, yet he could never seem to catch a break in life. And all of his pent-up aggression burst forth when he encountered Homer, a happy family man with a house and a decent job and everything Grimes didn’t have. Is it any wonder Grimey snapped?
It was definitely amusing to see Grimey lash out at a man too happily obtuse to realize he had made a mortal enemy. But in some ways, this is one of the darker Simpsons episodes. It showed viewers that sometimes life really is unfair, and some people just don’t get what they want out of life, no matter how hard they struggle.
19. “Homer vs. Lisa and the Eighth Commandment” (Season 2)
“There’s something wrong with that kid. She’s so moral. Why can’t she be more like…well, not like Bart…”
Homer is a well-meaning guy, but sometimes his grasp of right and wrong is a little tenuous. And some of the most memorable conflicts on this show have come when the far more mature and morally pristine Lisa struggles to reconcile her beliefs with her father’s actions. Case in point, this Season 2 episode where Homer became the most popular guy in town after getting an illegal cable TV hookup (this being a time when cable TV was still considered a luxury). Seeing her father so brazenly violate the Eighth Commandment caused Lisa no small amount of distress.
The result was an endearing little drama as Homer struggled to live up to the man Lisa wanted him to be. It says a lot about Homer that he gave in and did the morally correct thing, not because he feared for his own soul, but because he didn’t want Lisa to be unhappy.
18. “Bart the Lover” (Season 3)
“Truly, yours is a butt that won’t quit.”
Edna Krabappel’s romantic misadventures have often been a focus of the series, as have her clashes with Bart, every teacher’s worst nightmare. This episode combined both conflicts as it explored Edna’s sad, lonely existence and the emergence of a bond between teacher and student. Bart pranked Mrs. K with a series of love letters inspired by his parents’ own letters, only to feel a pang of regret when he realized the emotional damage he had caused. Luckily, it all worked out okay in the end.
This episode also benefited from an amusing subplot involving Homer struggling to build a doghouse and accidentally teaching Todd Flanders how to swear. It had to happen sometime.
17. “Flaming Moes” (Season 3)
“Moe, I haven’t seen the place this crowded since the government cracked down on you for accepting food stamps.”
With as much alcohol as Homer consumes, it wasn’t too surprising to learn in “Flaming Moe’s” that he can mix a mean drink or two. Homer’s bizarre creation, The Flaming Homer, brought a new level of success and prestige to Moe’s Tavern. But leave it to Moe to hog all the credit and leave his friend and most loyal customer out in the cold.
“Flaming Moe’s” is just an all-around great episode, with a steady stream of gags and one-liners and some nice character growth for Moe, who up till that point had mostly just been the surly bartender who always fell victim to prank calling. And the episode featured a guest appearance by Aerosmith, which was pretty cool.
16. “Bart of Darkness” (Season 6)
“I’M A MUR-DIDDLY-ER-DLER!!!”
“If that’s not Flanders, he’s done his homework.”
If you’ve ever been trapped in a boring summer vacation without end, you’ll understand what Bart went through in this episode. While Bart was stuck indoors with a broken leg and little but bad TV to keep him entertained (“Ugh… Klassic Krusty…”), Lisa was able to bask in her newfound popularity as the girl with a swimming pool. Seeing Bart descend into madness was funny, but the episode really hit its stride when it launched into a parody of Alfred Hitchcock’s Rear Window, as Bart and Lisa investigated the possibility that Flanders murdered his wife. As with everything on this show, the truth is more bizarre and entertaining.
15. “Kamp Krysty” (Season 4)
“Dear Mom and Dad, I no longer fear hell, because I’ve been to Kamp Krusty.”
You’d think at some point Bart would stop idolizing Krusty the Klown. But even after all the razor-sharp Krusty-Os and the former Krusty sidekicks trying to murder him, Bart still looks to Krusty as his personal hero. The closest he ever came to losing faith was in “Kamp Krusty,” where he and Lisa spent a summer wallowing in misery in “The Krustiest Place on Earth.”
The scenes of kids toiling and suffering while the camp counselors basked in luxury and relished their tyrannical power hit all too close to home for many Simpsons fans. These scenes of camp-induced misery allowed the writers to parody everything from Ben Hur to The French Lieutenant’s Woman. But the highlight came when the children revolted and created a Lord of the Flies-style cult calling out for Krusty’s blood. It was hilarious to watch as one glimpse of Bart on TV was enough to rob Homer of all the health and happiness he had gained in his weeks with no children.
14. “A Fish Called Selma” (Season 7)
“I hate every chimp I see, from Chimpan-A to Chimpan-Z! Oh, you’ll never make a monkey out of me!!!”
“A Fish Called Selma” was a great opportunity for two of the show’s lesser characters to step into the spotlight and grow a little. This episode allowed Selma to do something more than serve as one half of Homer’s evil spinster step-sisters. And it gave Troy McClure the role he was born to play when he starred in Planet of the Apes: The Musical.
The musical is easily the highlight of this episode thanks to its clever song lyrics and winning send-up of the classic sci-fi franchise. But it also featured great character work as McClure struggled to revive an ailing career and Selma wrestled with the question of whether a sham marriage was better than being alone.
13. “Homer at the Bat” (Season 3)
“No, Smithers, I’ve decided to bring in a few ringers. Professional baseballers. We’ll give them token jobs at the plant and have them play on our softball team. Honus Wagner, Cap Anson, Mordecai ‘3-Finger’ Brown…”
Celebrity guest appearances are incredibly commonplace on The Simpsons nowadays, with most episodes featuring at least one Hollywood icon stopping by. But they were used a little more sparingly back in the good old days, and rarely were the celebrity guest stars as integral to an episode’s plot as they were in “Homer at the Bat.” In this episode, Homer found the opportunity for a little athletic glory as the star of the Springfield Nuclear Power Plant softball team. That is, until Mr. Burns decided to cheat and hire a who’s who lineup of MLB players to work at his plant and guarantee total victory on the diamond.
What followed was a hilarious series of increasingly implausible developments as each player was knocked off the board for one reason or another. Ken Griffey, Jr. suffered crippling gigantism. Roger Clemens was hypnotized into believing he was a chicken. Ozzie Smith became trapped in “The Springfield Mystery Spot.” In the end, Homer had his chance for glory. And it all wrapped up with Terry Cashman singing a clever parody of his song “Talkin’ Baseball.”
12. “The Itchy & Scratchy & Poochie Show” (Season 8)
“Are you absolutely sure that’s wise, sir? I mean, I don’t want to sound pretentious here, but Itchy and Scratchy comprise a dramaturgical dyad.”
Too many TV shows wear out their welcome and persist long after the original magic has died away. And sometimes networks try to jazz up an old concept with hip new elements, with predictably disastrous results. That’s exactly what happened when Krustylu Studios tried to spice up the Itchy & Scratchy cartoons with a third member of the group – the wise-cracking, slick-dressing Poochie. Voiced by Homer, no less.
Poochie’s meteoric rise and fall offered winning commentary on Hollywood, especially the scene where network executives struggle to poll a group of children on what they want out of their cartoon heroes. And the writers weren’t afraid to direct the satire inward, as they introduced Roy, a hip college kid inspired by a Fox executive asking for a new Simpson to be introduced.
This episode has only become more relevant as the years have passed. And it seems especially appropriate in hindsight. “The Itchy & Scratchy & Poochie Show” appeared during the tail end of The Simpsons’ Golden Age, and things have never been the same since.
11. “You Only Move Twice” (Season 8)
“I can’t buy that. Only management guys with big salaries like me can afford that… Guys like me! I’m a guy like me!”
Many years ago, we voted Albert Brooks as The Simpsons’ greatest celebrity guest star. He’s played a number of memorable roles over the years, but none better than Hank Scorpio. Scorpio managed to simultaneously be the world’s nicest, most peppy boss this side of Chris Traeger and a secret, megalomaniacal supervillain with dreams of world domination. At one point we even saw him in the process of murdering James Bond with an elaborate death trap.
Scorpio may have been the highlight of this episode, but the Simpsons themselves didn’t disappoint either. It turned out that only Homer was happy with the family’s move from Springfield to the clean, idyllic Cypress Creek. Marge had no house chores to keep her busy, Bart was dumped into the remedial class, and Lisa discovered she was horribly allergic to the local flora. In one of his more fatherly moments, Homer wound up sacrificing his personal happiness in favor of his family. But hey, at least he got an NFL team out of the deal.
10. “Round Springfield” (Season 6)
“What I’m saying is, all we have to do is go down to the pound and get a new jazzman.”
Bleeding Gums Murphy was a fun but largely forgettable character introduced early on in the show’s first season. But he returned in a big way in Season 6. This episode saw Bart wind up in the hospital thanks to a bad box of Krusty-O’s, but it was Lisa who truly suffered when she learned that Bleeding Gums was dying.
This episode offered an effective mix of humor and tragedy (often at the same time, as with the Lion King cloud parody). And it dealt with the pain of death and losing loved ones in a way the show only rarely has before or since. And it allowed Bart to offer a rare gesture of generosity to his sister. Sadly, we never found out if his plan to take advantage of Krusty-O’s with flesh-eating bacteria ever panned out.
9. “Deep Space Homer” (Season 5)
“One thing is for certain: there is no stopping them; the ants will soon be here. And I, for one, welcome our new insect overlords.”
Many, many Simpsons episodes have revolved around Homer getting a new job, usually of the very implausible and temporary variety. The formula is a little played out now, but it certainly wasn’t in Season 5 when Homer was chosen by NASA to blast off into orbit with Buzz Aldrin and Race Banyon.
This premise resulted in one of the most iconic Simpsons scenes of all time, as Homer devoured a bag of chips in zero gravity to the tune of Strauss’ “Blue Danube,” accidentally crashed into the shuttle’s ant farm and caused Springfield’s residents to believe they were being invaded by an army of giant space ants.
In the end, Homer got to realize a personal dream. But in true Simpsons fashion, he didn’t get any fame or credit for saving the shuttle. That honor went to an inanimate carbon rod.
8. “Mr. Plow” (Season 4)
“Mr. Plow, that’s my name! That name again is Mr. Plow!”
Speaking of Homer’s impressive resume, at one point he ran a successful snow plow business and became a minor town celebrity in the process. That is, until Barney decided to hone in on Mr. Plow’s turf by becoming The Plow King. Much like “Flaming Moe’s,” this episode succeeded in fleshing out one of Homer’s drinking buddies and developed a rivalry between the two. Between the jacket and the catchy jingle, this still remains one of Homer’s most memorable side jobs.
7. “Last Exit to Springfield” (Season 4)
“Lisa needs braces.”
“Lisa needs braces.”
“Lisa needs braces.”
One need only utter the phrase “dental plan” to a Simpsons fanatic to bring up memories of this classic episode. “Last Exit to Springfield” fired on all cylinders as it foisted Homer into the role of union president for the power plant workers. Despite his gross incompetence, Homer actually did a pretty good job of sticking up for his co-workers’ rights and ensuring that Lisa would get the braces she needed so as not to wind up looking like a cave troll by age 18.
All the gags were memorable in this installment, from the spot-on spoof of Joker’s debut in Batman ’89 to Homer’s appearance on Smartline to Mr. Burns’ typing monkey room. And compared to most episodes of the day, it was unusually story-driven and surreal.
6. “22 Short Films About Springfield” (Season 7)
“That is a rare photo of Sean Connery signed by Roger Moore; it is worth one hundred and fifty dollars.”
The Simpsons may revolve around the exploits of Homer and his family, but by Season 7 Matt Groening and company had built up a pretty sizable and eclectic supporting cast. This Season 7 premiere allowed the many minor players of Springfield to step into the spotlight for brief adventures of their own.
As the title suggests, “22 Short Films” offered up a number of short vignettes that explored various Springfield residents as they went about their daily lives. The episode focused on everything from Kirk’s quest to find Milhouse a bathroom to Chief Wiggum’s Pulp Fiction-style mishaps to Principal Skinner cooking “steamed hams” for Superintendent Chalmers to Nelson finally bullying the wrong guy. All of it was amusing, and it all fit together into a larger tapestry of absurdity.
There have been rumors in the past of Fox commissioning a Simpsons spinoff that focuses solely on the non-Simpsons characters. This episode proves that there’s plenty of potential in such a concept.
5. “Lisa the Vegetarian” (Season 7)
“Don’t kid yourself, Jimmy. If a cow ever got the chance, he’d eat you and everyone you care about!”
No episode has so successfully explored Lisa’s struggle to reconcile her views and beliefs with the world around her as “Lisa the Vegetarian.” Here, a visit to a petting zoo convinced Lisa that eating meat was wrong. And one tragically sabotaged barbecue later, she managed to turn half of Springfield against her and her vegetarian crusade. She learned the hard way that you don’t make friends with salad.
The conflict culminated in one of the most memorable celebrity guest appearances in the show’s history. Apu teamed up with his friends Paul and Lina McCartney to teach Lisa about the joys of vegetarianism and an important lesson about tolerating other peoples’ viewpoints, even when they annoy you. Not only is this one of the show’s more quotable episodes, it also offers a good life lesson for people of all beliefs and backgrounds.
4. “Treehouse of Horror V” (Season 6)
“What do you think, Marge? All I need is a title. I was thinking along the lines of ‘No TV and no beer make Homer something something…’
“DON”T MIND IF I DO!!!”
We always enjoy the annual Treehouse of Horror Specials, even if the writers have pretty well run out of horror tropes and franchises to spoof by now. But while many of these specials are amusing, none can match the wit and brilliance of the fifth installment.
Treehouse V kicked off with an inspired spoof of Stanley Kubrick’s The Shining, as Homer slowly went insane serving as winter caretaker of Mr. Burns’ TV-less, beer-less summer cottage. That was followed by a segment where Homer repeatedly went back in time and created various comical, alternate futures. And finally, the episode wrapped up with a tale of Springfield Elementary’s staff trying to eat their students.
Not only was each of the three segments hilarious on its own, they all tied together in ways you don’t usually see from these episodes. Treehouse V offered just the right blend of satire, black humor, and gore.
3. “Cape Feare” (Season 5)
“Hey, I’m the chief here! Bake him away, toys.”
It’s become tradition for Kelsey Grammer to return to The Simpsons every few years to reprise his role as Sideshow Bob and continue Bob’s fruitless quest to murder Bart. “Cape Feare” marks the second time Bob escaped justice and resumed his quest. And it set the gold standard as far as Sideshow Bob episodes go.
“Cape Feare” spoofed the classic revenge film Cape Fear and its 1991 remake, as well as slasher films in general. With Bob on the loose and sending Bart death threats, the Simpsons had no choice but to enter witness protection and become “The Thompsons.” But even that wasn’t enough to halt Bob’s warpath. Garden rakes, on the other hand…
Here is another episode where the quality of the writing elevated everything. From Bart seeing potential killers around every corner to Bob being tricked into performing the entirety of The H.M.S. Pinafore, the laughs never let up. And it showcased Bob at his most deliciously evil. Later Bob episodes have given him a family and complicated his relationship with the Simpson family. There’s something to be said for his single-minded obsession in this episode.
2. “Rosebud” (Season 5)
“Look at all the wonderful things you have, Mr. Burns. King Arthur’s Excalibur, the only existing nude photo of Mark Twain and that rare first draft of the Constitution with the word ‘suckers’ in it.”
If The Real Ghostbusters could get away with spoofing Citizen Kane for an entire episode, why not The Simpsons? This episode certainly made good use of the premise, as Mr. Burns launched into a quest to recover the lost innocence of his childhood in the form of a forgotten teddy bear named Bobo. Unfortunately for him, Bobo had already fallen into the hands of one Maggie Simpson.
“Rosebud” succeeded in humanizing the show’s most evil and despicable character. You couldn’t help but feel bad for the poor guy who had everything money could buy except the one thing he actually wanted. And the episode created a great conflict for Homer, who was torn between his desire to appease his boss (and score a hefty financial reward) and ensure his daughter’s happiness. “Rosebud” was an unusually heartwarming episode that fleshed out several key relationships on the show.
1. “Marge vs. the Monorail” (Season 4)
“I’ve sold monorails to Brockway, Ogdenville and North Haverbrook, and by gum it put them on the map!”
It’s not as dramatically rich as something like “Rosebud,” but “Marge vs. the Monorail” might just be the most consistently funny and entertaining Simpsons episode ever. Marge was able to take point in this episode (something that didn’t happen all that often in the early seasons), as she questioned the town’s decisions to spend $3 million on a monorail system. Homer got to add another entry to his ever-growing resume when he became a monorail conductor. And everyone in town got to join in on a monorail-themed musical number that still ranks among the show’s best.
“Marge vs. the Monorail” also boasted a pair of terrific celebrity guest stars. Phil Hartman played his most memorable character not named Troy McClure or Lionel Hutz when he appeared as the monorail-shilling con artist Lyle Lanley. And Leonard Nimoy offered plenty of laughs when he appeared as himself.
From Homer’s opening song spoofing The Flintstones to the climactic runaway monorail chase, this episode delivered the goods.
Note: this article was originally published in 2013 and was updated on September 23, 2022 in honor of the show’s 34th season premiere.
Jesse is a senior writer for IGN when he’s not busy restocking the Bort license plates. Allow him to lend a machete to your intellectual thicket by following @jschedeen on Twitter, or Kicksplode on MyIGN.