As television milestones go, it’s tough to top being on the air not just for a period of years but a period of decades. On December 17, Matt Groening’s deathless satirical masterpiece will achieve the remarkable feat of being on the air for three decades. Three decades! Thirty years! That’s real good.
The Simpsons has helped define the comic sensibility of multiple generations of irreverent, pop-culture savvy smart-asses. Its run was first ground-breaking in its eviscerating and dark yet emotionally grounded look at the greed and cynicism at the heart of American society, and then record-breaking in the show’s unprecedented commercial success and staggering longevity.
These 30 essential episodes of the preeminent American pop-culture institution illustrate the comedic perfection of the show during its glorious, radiant prime, and then the long, slow, inevitable slide in quality and relevance that followed. But it’s worth noting that while we may not be in the Golden Age, the series still does hit hard – and funny – on occasion, so you will find some more recent eps in this list.
Let us know your favorite Simpsons episodes in the comments.
You never forget your first time! Accordingly, The Simpsons opened on a painfully relatable note of paralyzing Yuletide economic uncertainty with a special Christmas episode that finds Homer desperate to provide a merry Christmas for his family after being denied a holiday bonus. “Simpsons Roasting on an Open Fire” goes to audaciously dark places for the introductory episode of a cartoon pitched at families. It climaxes with Homer going with his son and alcoholic friend Barney to the racetrack, where he gambles away his money, yet still manages to deliver the requisite happy, or at least bittersweet, ending. From the very beginning, The Simpsons wasn’t just very funny. It was also emotionally real and grounded.
Classic episodes like “Two Cars in Every Garage and Three Eyes on Every Fish” helped establish sinister arch-capitalist and power plant owner Montgomery Burns as a standout supporting player of tremendous depth and surprising complexity. He’s a figure of biblical, almost Satanic evil but also an oddly sympathetic figure when his God-like status is threatened. Burns is poignantly, unexpectedly human here after the discovery of a three-eyed mutated fish causes a government crackdown on the power plant and inspires the evil mogul to run for governor to protect his interests.
(Photo by 20th Century Fox Film Corp.)
“Mr. Lisa Goes to Washington” adroitly typecasts Lisa as its pure-hearted Mr. Smith surrogate in a savagely satirical evisceration of political corruption, patriotic hokum, and the terminally mild song stylings of Mark Russell. As the show’s unyielding paragon of integrity, Lisa is a natural choice to earnestly inhabit the well-worn archetype of the idealistic innocent who uncovers the seedy underbelly of American politics. Lisa is an inherently political little muckraker and “Mr. Lisa Goes to Washington” ranks amongst her finest half hours.
If you were a sports fan at the time, “Homer at the Bat” was no mere television episode: It was a seismic cultural event that brought together the best in entertainment and sports in a riotous riff on The Natural. In “Homer at the Bat,” a magic bat transforms Homer into a dinger-smacking dynamo before Mr. Burns hires a team of major league ringers to help him win a million-dollar bet on a company softball game with a fellow mogul. You don’t need to be a baseball fan to find “Homer at the Bat” hilarious, but it does help.
The perpetually long-suffering Marge gets an opportunity to not only express but sing her pain when she’s cast as Blanche Du Bois opposite a disconcertingly shredded Ned Flanders in a musical version of A Streetcar Named Desire that replaces the tragic melodrama of the original with something peppier and more upbeat. Marge’s onstage drama mirrors her offstage frustrations, which lends the episode surprising emotional weight.
(Photo by 20th Century Fox Film Corp.)
Before he rose to talk show fame, Conan O’Brien wrote his way into The Simpsons history with “Marge Vs. The Monorail.” It’s an instant classic parody of The Music Man with Phil Hartman perfectly cast as its Harold Hill figure, a charismatic flim-flam man with a song on his lips and a scam in his heart who bamboozles the gullible people of Springfield into buying a monorail that causes the problems he promises it will solve.
It’s impossible not to feel poor Ralph Wiggum’s precocious romantic heartbreak when Lisa Simpson humiliates him after he publicly professes his love for her in this painfully hilarious and just plain painful exploration of puppy love gone awry. Watch closely and you can pinpoint the exact moment “I Love Lisa” rips the audience’s heart in half. Who knew Lisa could be such a heartbreaker and Ralph such a convincing tragic romantic hero?
To fans of classic The Simpsons, the words “Lisa needs braces” must always be answered with “Dental plan?” and vice versa thanks to “Last Exit to Springfield.” The episode pitted a deeply overmatched Homer against Mr. Burns in a labor-versus-owner skirmish that develops unexpectedly high, personal stakes that sees Homer’s dim-wittedness facing off against his family and co-workers’ needs.
The stars REALLY come for poor Krusty after his place in children’s hearts is taken by sadistic dummy Gabbo. “Krusty Gets Kancelled” would make it into the pantheon of all-time great episodes on the basis of a guest voice roster that includes Johnny Carson, Elizabeth Taylor, and the Red Hot Chili Peppers alone, but it offers an embarrassment of riches even without a ridiculously stacked guest lineup.
(Photo by 20th Century Fox Film Corp.)
Kelsey Grammer’s sonorously duplicitous sidekick-turned-serial attempted murderer, Sideshow Bob, proved himself a worthy antagonist to Bart Simpson by slipping into the role of a vengeance-crazed ex-con in a Cape Fear spoof that contains the legendary sequence where the frustrated clown steps on a rake nine times – a gag that’s funny, then unfunny, then brutal, then hilarious all over again.
The Simpsons’ famous love for Citizen Kane, and pop culture pastiche in general. reaches a glorious crescendo with “Rosebud,” which re-imagines Charles Foster Kane’s iconic nostalgia for the sled of his youth as miserly Mr. Burns similarly pining for a clumsily symbolic totem of childhood innocence, a ratty teddy bear that Maggie comes to own. “Rosebud” humanized a monster by exposing the child within.
When FOX tried to appease censors by eliminating Itchy & Scratchy, a duo that exists for the sake of gratuitous violence, The Simpsons impishly protested with the most uncompromisingly brutal Itchy & Scratchy episode of all time. “Itchy and Scratchy Land” ratcheted the bloodshed up to hyperbolic and hilarious levels in a gut-buster that riffs merrily on Disney Land, Westworld, and Jurassic Park.
(Photo by 20th Century Fox Film Corp.)
The Treehouse of Horror, The Simpsons’ beloved annual Halloween ramble through treasured terror tales past, was never darker or more hilarious than in this fifth entry that focused on adults murderously terrorizing children. First Homer convincingly inhabits the murderous mind of Jack Torrance in a non legally-actionable parody of The Shining called “The Shinning.” Then Homer ruins things for civilization by futzing around with the timeline before a final segment finds teachers and lunch ladies enjoying a new “miracle meat” made of students that gives a deliciously literal meaning to “Eat my shorts.”
The Simpsons delved into the pulse-pounding world of cliffhangers with “Who Shot Mr. Burns?”, a high-profile, much buzzed-about two-part parody of Dallas’ 1980 ratings bonanza “Who Shot J.R?”. Like the earlier pop-culture phenomenon, “Who Shot Mr. Burns?” focused on the shooting of a mogul so cartoonishly evil that just about anyone with a pulse who has interacted with them has reason to wish them dead.
Not eating meat seems so central to Lisa’s identity that it’s hard to believe she didn’t start out as a non-meat–eater. But introducing Lisa as a carnivore allowed The Simpsons to very publicly convert Lisa to the meat-free lifestyle when she’s unable to reconcile her love for animals with her family’s cartoonishly over-the-top love for devouring formerly living creatures, particularly after discovering that Apu and special guest stars Paul and Linda McCartney share her beliefs.
(Photo by 20th Century Fox Film Corp.)
The dazzlingly conceptual, wildly audacious “22 Short Films About Springfield” took inspiration from Pulp Fiction as well as the more obscure 32 Short Films About Glenn Gould in focusing on not one story but a series of overlapping narratives that collectively capture the soul of Springfield. The episode has proven an enduring gift to memes, most famously Principal Skinner nervously serving up “steamed hams” to a skeptical Superintendent Chalmers.
It’s always a momentous occasion when Albert Brooks, maybe the funniest man alive, guests on The Simpsons. Brooks makes every guest appearance an event, and he’s never voiced a more brilliantly conceived or executed character than Hank Scorpio: outside-the-box thinker, unconventional boss, and, unfortunately for Homer, his newest employee, something of a James Bond-style super-villain. The episode subversively foregrounds changes in Homer’s work life, audaciously limiting the international espionage aspect to the background. “You Only Move Twice” takes the action out of Springfield when Hank Scorpio lures Homer away from Mr. Burns and introduces a Homer that’s productive, competent, and respected by his boss. Don’t worry! It would not last.
“The Itchy & Scratchy & Poochie Show” introduced a sturdy new pop-culture archetype in Poochie, who the writers of Itchy & Scratchy come up with in a desperate attempt to breathe new life into the long-running show. A self-proclaimed “kung-fu hippie from gangsta city”, Poochie represents every half-assed attempt to create a crowd-pleasing new breakout character out of moldy cliches and empty “attitude.”
(Photo by 20th Century Fox Film Corp.)
The eternally game John Waters taught Homer and middle America overlapping lessons about kitsch and tolerance in “Homer’s Phobia” playing John, a delightfully droll bon vivant and lover of all things camp who utterly charms the Simpsons before Homer discovers he’s gay. It’s an episode that, like the later “Mypods and Broomsticks,” walks a fine line between being the proverbial “very special episode” and a knowing parody of television that preaches as well as entertains.
What would Homer’s life look like to a total outsider? That’s the the question at the heart of “Homer’s Enemy.” The famously dark episode introduced and killed off Frank Grimes, a new hire at the power plant and a man of perpetual sorrow whose Dickensian existence makes Homer’s impossibly charmed life seem preposterously perfect by comparison. This uncompromisingly dark episode looks at one of America’s most reassuringly familiar families through a revelatory and bracingly harsh new lens.
Despite its extraordinary success, The Simpsons has not spawned a single spin-off. Yet fans got a glimpse at what might have been in “The Simpsons Spin-Off Showcase,” a knowing deconstruction of television cliches that spit-roasts the spin-off in general and the “colorful” detective show, variety show, and supernatural romance in particular when Troy McClure smarmily takes us through the pilots for “Chief Wiggum P.I.,” “The Lovematic Grandpa,” and “The Simpsons Smile Time Variety Hour,” a pitch-perfect lampoon of the ill-fated Brady Bunch Variety Hour and Laugh-In.
(Photo by 20th Century Fox Film Corp.)
Poor, saintly Ned Flanders lost a soul-diddly-ol-mate but gained new depth when Homer caused a tee-shirt-cannon–related demise for Marge Flanders and then felt obligated to help Ned find someone to help ease his loneliness. “Alone Again, Natura-Diddly” is alternately bracingly cruel in the glib way it dispatches with a major character’s spouse but ultimately surprisingly sensitive in its depiction of Ned’s grief.
The perpetually meta Simpsons has always made a point of shattering the fourth wall. But it’s seldom peeled back the curtain as far as it did on “Behind the Laughter,” which impishly offered an alternate creation story for the Simpsons as a literal mom and pop music and comedy act whose highs and lows mirror those of seemingly every act chronicled on Behind the Music.
Science-fiction has a way of shaking late-period The Simpsons out of its doldrums. “Eternal Moonshine of the Simpson Mind” is no exception. Borrowing a few pages out of the Charlie Kaufman playbook, the trippy mind-bender follows Homer’s attempts to figure out what happened to Marge after taking a “Forget-Me-Shot” at Moe’s that does a number on his memory. Intermittently haunting and beautiful, as well as funny, “Eternal Moonshine of the Simpson Mind” showed that FOX’s trusty animated warhorse had some life in it yet.
The Simpsons got a little preachy with “Mypods and Boomsticks,” an all too timely 2008 exploration of our fear and hatred of others and worshipful, sycophantic love of technology. The episode took on Apple and Islamophobia through the story of Homer suspecting a new Muslim neighbor is a terrorist and Lisa falling under the sway of Steve Jobs’ cult of personality.
(Photo by 20th Century Fox Film Corp.)
In “Once Upon a Time in Springfield,” we get yet another glimpse behind the clown paint at Krusty as a man with needs when professional rivalry gives way to true love and he ends up falling in love with Princess Penelope after she’s shoe-horned into his show to boost ratings. Penelope is sugar and spice onscreen yet talks like a Long Island longshoreman and sings like an angel off it, thanks to Anne Hathaway’s Emmy-winning virtuoso guest turn.
“The Ned-Liest Catch” forever changed the destiny of two of the show’s most important supporting characters when Bart played Cupid and made an unlikely love match between Ned Flanders and Edna Krabapple. Ned is surprisingly hot to trot before Edna’s extensive sexual history gives him second thoughts. FOX had audiences vote on whether Ned and Edna should remain together, a move that highlights the mild desperation that comes with being on the air for decades.
As it lumbered towards its third decade on the air, The Simpsons increasingly chased after trends rather than setting them. 2011’s “The Book Job” peppily took satirical aim at the extraordinary success of J.K Rowling in an episode structured like Steven Soderbergh’s Oceans movies. For the last decade, The Simpsons has distinguished itself largely through the caliber and novelty of its guest stars; this has a pair of doozies in Oceans alum Andy Garcia and a gleefully self-deprecating Neil Gaiman.
Three decades on the air has afforded The Simpsons plenty of time to explore its supporting cast. It accordingly took a mere 24 years for The Simpsons to do a deep-dive into the angst of consummate background fixture Carl Carlson in “The Saga of Carl.” This late-period gem uses Carl bailing on his friends after they win the lottery together to look at Homer, Moe, Lenny, and Carl’s friendship in particular and male friendships in general.
(Photo by 20th Century Fox Film Corp.)
The Simpsons has never been shy about toying with the audience’s sense of reality. The 25th season standout episode “Brick Like Me” blew minds with a gimmicky yet emotionally satisfying story that alternated between two realities, one a Lego world that exists only in Homer’s imagination and reflects his hopes and fears about his relationship with Lisa. Like The Lego Movie, which it unsurprisingly resembles, “Brick Like Me” is a funny but ultimately poignant story about growing up and letting go.
