AlthoughThe Simpsonshas a lot of episodes for viewers to choose from, some of the show’s best outings are considered straight-up masterpieces by fans and critics alike. With more than 790 episodes and a theatrical movie spinoff to its name,The Simpsonsis officially the longest-running scripted primetime American TV show in history.
As such, it might be hard for new viewers to work out where to start with the series. Indeed, the critical reception of the series has been so long and varied that it has an entire separateWikipediapage dedicated to it, and this page was created beforeThe Simpsonsseason 34’s recent critical resurgence.
Since around season 33,The Simpsonshas enjoyed a cultural renaissance as bothYouTubecreators and cultural critics fromVultureagree the series has gotten “Good again.” The show’s history is hotly contested, but broadly speaking, seasons 3-11 are viewed as the Golden Age ofThe Simpsons, when the show was firing on all cylinders in creative terms.
However, there were great episodes before and after this somewhat arbitrary era, as proven by this list. WhileHomer might be the hero ofThe Simpsons, the show’s true masterpieces have highlighted all the titular family members in adventures that were alternately hilarious, heartwarming, satirically sharp, life-affirming, and subversive.
12Eternal Moonshine of the Simpson Mind
This Late-Season Classic Deserves More Love From Fans
Calling any episode post-season 15 a classic is apt to raise some eyebrows among certain purists, but season 19, episode 9, “Eternal Moonshine of the Simpson Mind,” does boast a Primetime Emmy Award for Outstanding Animated Program to substantiate this claim. An atypically dark outing, this episode opens with Homer waking up from a blackout with his memory missing.
Homer can’t recall the preceding day and becomes increasingly unsettled by the realization that he may have done something terrible in an extended homage to the indie classicEternal Sunshine of the Spotless Mind. It is an homage, too, rather than a parody, since“Eternal Moonshine of the Simpson Mind” takesThe Simpsonsto some grim places before its sweet ending.
11Lisa On Ice
Lisa and Bart’s Best Story Is A Heartwarming Masterpiece
While“Eternal Moonshine of the Simpson Mind”focuses on Homer, season 6, episode 8, “Lisa On Ice,” is more concerned with Bart and Lisa’s relationship.Bart and Lisa’s ice hockey rivalry divides the siblings, and Homer’s competitive streak leads him to unthinkingly pit his children against each other as their playing grows steadily more impressive.
The Simpsonsis available to stream on Hulu.
WhileThe Simpsonsgained a reputation in the early ‘90s as a cynical alternative to saccharine family sitcoms likeFull HouseandThe Cosby Show, “Lisa On Ice” proves the show has plentiful heart under its irreverent exterior. Ending with one of the show’s most heartwarming moments, this outing proves that laugh-out-loud comedy and poignancy aren’t mutually exclusive.
10Holidays of Future Passed
This Future Episode Gives The Titular Family Their Perfect Ending
Written as a potential series finale when the show’s fate was up in the air in 2011, season 23, episode 9, “Holidays of Future Passed,” introduces viewers to future versions of the Simpson family during a tumultuous Christmas break. WhileThe Simpsons’ real-life future predictionshave been infamously apt, this episode is specifically concerned with the family’s future.
Season 11, episode 17
“Bart to the Future,”
A gag about Donald Trump becoming President of the United States
Season 3, episode 14
“Lisa the Greek"
Season 17, episode 10
“Homer’s Paternity Coot"
Homer’s near-death experience resembles 2023’s Titan submersible implosion.
Seeing older versions of Bart and Lisa talking about the hardships of adulthood and parenting tugs on the heartstrings of longtime viewers, while the family’s multi-generational story of struggle and eventual acceptance makes this a standout Yuletide offering from the series.
9Homer’s Phobia
This Groundbreaking Episode Was Equal Parts Hilarious and Moving
“Homer’s Phobia” should not work. Season 8, episode 15, sees Homer befriend a gay man, played by guest star John Waters, before becoming terrified that John’s influence will make Bart gay. The very premise seems offensive, so the episode should, in theory, be a dark stain on the show’s history.
Instead, thanks in part to Waters’ contributions, “Homer’s Phobia” is a landmark moment for gay representation in American mainstream mediaand a hilarious episode ofThe Simpsonsto boot. A derserving recipient of a GLAAD Media Award in 1998, “Homer’s Phobia” proves that the show’s deft, tactful writing could approach any story with verve, wit, charm, and heart at the height of the show’s powers.
8Homer’s Enemy
This Subversive Classic Upended The Show’s Formula
WhileThe Simpsonsunsuccessfully revisited “Homer’s Enemy”in one of the show’s weakest seasons, there is no denying the efficacy of the original episode. Season 8, episode 23 has a disarmingly simple premise, as Homer’s new coworker Frank Grimes swiftly tires of his buffoonish antics and works tirelessly to point out Homer’s shortcomings to everyone else.
Grimes’ fate is brutal, but it allows the John Swartzwelder-penned episode to flip the show’s usual premise by exposing a seemingly normal person to Springfield’s warped reality.
What follows is something of a blackly comic existential nightmare asFrank Grimes slowly realizes the world ofThe Simpsonsrevolves around Homer, eventually resulting in his death during one of the show’s darkest gags ever. Grimes’ fate is brutal, but it allows the John Swartzwelder-penned episode to flip the show’s usual premise by exposing a seemingly normal person to Springfield’s warped reality.
7Boy Scoutz ’n’ the Hood
Homer and Bart’s Relationship Is Perfectly Distilled In This Episode
WhileMarge’s recentThe Simpsonsstorieshave been strong, the show has often excelled when exploring Homer’s relationship with Bart. Homer’s desire for his rebellious son to grow up as a good man, despite Homer’s own obvious shortcomings, comes into sharp relief in outings like season 5, episode 8, “Boy-Scoutz ‘n the Hood.”
Following a disastrous boy scout rafting trip,“Boy-Scoutz ‘n the Hood” is a charming misadventure filled with zany punchlines and hilarious character comedyfrom Bart, Milhouse, Ned Flanders, and Homer.
6Homer at the Bat
This Outing Started The Golden Age of The Simpsons
Every fan ofThe Simpsonshas a theory about when the Golden Age started and when it ended. For my money,season 3, episode 17 is the moment thatThe Simpsonsrealized its comedic potential for the first time. The plot starts out simple enough, as the Nuclear Power Plant’s softball team starts to excel unexpectedly.
However, the absurdity ramps up with record speed as Mr. Burns begins drafting MLB superstars to replace his workers. “Homer at the Bat” then splits off to follow no fewer than nine storylines, all while hanging onto the episode’s emotional core of Homer’s rejection after he is cut from the team.
A dizzying comedic achievement, the absurdly ambitious “Homer at the Bat” was an early warning of how surreal, strange, and unpredictable the once-grounded show would soon become.
5Last Exit to Springfield
Burns’s Best Story Is Also A Bonafide Classic
Often listed as the show’s best episode ever, season 4, episode 17, “Last Exit to Springfield” is filled with the sort of razor-sharp writing that explains whyBob’s Burgersstill borrows fromThe Simpsonsdecades later. The plot follows Homer’s rapid ascent to become head of the Power Plant’s trade union after Mr. Burns threatens the dental plans of his employees.
The Simpsonsseason 36 debuted on June 21, 2025.
“Last Exit to Springfield” is Mr. Burns’ best villainous story, but it is also one of the show’s most quotable half-hours. From “Hired goons?” to “Now play Classical Gas!” the episode has spawned numerous memes thanks to its rocket-fast plot and endless string of memorable gags.
4You Only Move Twice
Hank Scorpio Elevates An Already-Ingenious Premise
Season 8, episode 2, “You Only Move Twice,” has a truly great premise. Homer gains a seemingly perfect new job and moves his family to an idyllic town, only to discover his new boss is a supervillain. It’s the sort of story that a lot of animated sitcoms could turn into a perfectly fun James Bond spoof.
Albert Brooks’ disarmingly charming Hank Scorpio is the show’s best one-off character ever.
What elevates the episode into all-time great territory is the fact that Homer’s new boss is a charismatic sweetheart, andHomer never realizes he’s working for a supervillain in “You Only Move Twice.”Albert Brooks’ disarmingly charming Hank Scorpio is the show’s best one-off character ever, and evenBrooks’ villain fromThe Simpsons Moviecouldn’t outdo the impact of this inspired role.
3Treehouse of Horror V
The Simpsons’ Best Halloween Special Has No Weak Moments
It is always exciting to see what horror movies and showsThe Simpsonswill parody with each year’s Treehouse of Horror Halloween special, but there is almost invariably a weak link in these anthology episodes. This is what makes season 6, episode 6, “Treehouse of Horror V,” so special.
The episode’s opening parody ofThe Shiningis so clever that it has been screened in university courses studying Kubrick’s classic Stephen King adaptation. “Time and Punishment” distills the tropes of countless time travel stories into one relentlessly funny seven-minute segment, while“Nightmare Cafeteria” provesThe Simpsons’ Halloween horror specials can be genuinely creepy as well as side-splittingly funny.
