Legend has it that when Matt Groening was sitting in James L. Brooks’ waiting room, about to sell away his comic strip to become a TV show, he got cold feet about selling his life’s work and quickly scrawled a family with three kids and when he was called into Brooks’ office, he pitched this family for a TV show instead. That family, of course, became The Simpsons, one of the most beloved and groundbreaking TV series ever to hit the airwaves.The show has been going on for so long that its steady decline in quality has now lasted for longer than the “golden age” did, but those early seasons contain some of the funniest material ever put on television.Updated December 10, 2021 by Mark Sammut: Currently on its 33rd season, The Simpsons has been around the block. Producing hundreds upon hundreds of episodes across four decades, the Fox show has done pretty much everything there is to do. Naturally, the quality of the stories varies greatly, but the cartoon's absolute greatest creations are timeless. They are also not in short supply, as a discussion of The Simpsons' best episodes could realistically include a shortlist of 50 odd entries. To illustrate the classic show's brilliance, a few more episodes have been added to this article.
20 Homer The Smithers (8.9)
- Season 7, Episode 17
Mr. Burns and Smithers' relationship has been a constant source of amusement for decades, and this season 7 episode analyzes that dynamic by throwing Homer into the mix. After a series of blunders, Smithers is forced to go on vacation; consequently, Mr. Burns' assistant picks Homer as his replacement since, in his mind, there is no way the bumbling employee could outshine him.
Homer's disastrous attempt to fulfill this role produces plenty of laugh-out-loud moments while shining a light on the co-symbiotic nature of Mr. Burns and Smithers' relationship.
19 Bart Sells His Souls (8.9)
- Season 7, Episode 4
From the opening sequence that features a hymn rendition of Iron Butterfly's "In the Garden of Eden" to Lisa's nuanced presentation of the concept of owning a soul, this season 7 episode is a tour-de-force of comedic writing and social commentary. As its name suggests, Bart sells his soul to Milhouse for $5, a move that causes the skeptical child's life to take a turn to the worse.
"Bart Sells His Soul" is more than just a hilarious episode, as it makes well-realized observations on religion and commercialism.
18 And Maggie Makes Three (8.9)
- Season 6, Episode 13
"And Maggie Makes Three" is a flashback episode revolving around Maggie's birth and Homer's brief stint as a bowling alley employee. Although not a laugh-riot like most episodes from these seasons, "And Maggie Makes Three" takes audiences on an incredibly emotional journey that showcases Homer's love for his family.
With all his debt paid, Homer leaves the Power Plant and goes to work at a bowling alley, which is his dream job. However, an unplanned pregnancy forces Homer to rethink his priorities.
17 Rosebud (8.9)
- Season 5, Episode 4
Season 5 leans heavily into movie parodies, with this episode taking a stab at Orson Welles' Citizen Kane. Mr. Burns craves his Bobo, a toy he loved as a child that is currently in the hands of Maggie. Dangling a big reward for its return, Mr. Burns almost convinces Homer to sell the toy; however, when that fails, Montgomery takes a different approach.
"Rosebud" has everything someone could want from an episode of The Simpsons: clever humor, subtle references, a whole lot of heart, and the Ramones.
16 Mr. Plow (8.9)
- Season 4, Episode 9
One of those episodes that can be summed up as "Homer makes it big and then loses it all," "Mr. Plow" might be the best example of this formula. Homer starts a snow plowing company that eventually hits it big. While things initially are great, Homer loses his customers to a rival business run by Barney.
Hilarious cameos, intelligent gags at commercials, and a memorable climax that is genuinely riveting, "Mr. Plow" is a stunning comedic work of art from beginning to end.
15 Homer The Heretic (9)
- Season 4, Episode 3
On one faithful day, Homer Simpson did the unthinkable – he opted out of going to church. As the rest of Springfield listened to Reverend Lovejoy slowly spread the word of God, Homer danced in his underwear and turned his Sunday morning into a day of (rather wholesome) debauchery. This proves to be such a hit that Homer decides to repeat the process every Sunday.
Eventually, Homer falls asleep with a cigar and sets the house on fire, prompting Ned Flanders to step in and save the day. "Homer the Heretic" is relatable and ends on a great final act, one that manages to be insightful and hilarious.
14 Homer The Great (9)
- Season 6, Episode 12
Nobody likes to feel left out, and that holds true for Homer. The only difference is that he will not rest until he is allowed to join the club. The Stonecutters is a secret society with its own power structure free from the realities of everyday life. After a big fall, Homer succeeds in joining the group before, naturally, he is revealed to be their long-awaited Chosen One.
From the nuclear plant's massive car park to the creation of a whole new club designed specifically to exclude the Chosen One, "Homer the Great" is laugh-out-loud funny and jam-packed with references.
13 Homer Badman (9)
- Season 6, Episode 9
Homer's love of candy gets him in hot water when an innocent reach for a gummy stuck on a college student's pants is misconstrued for harassment. The media villainizes Homer, attracting a circus of accusations against the Simpsons family.
"Homer Badman" touches a pretty sensitive topic without making anyone seem particularly sinister, as it is easy to see how Homer's actions could be misunderstood. There are also plenty of memorable moments, be it Homer's trip under the sea or the TV film adaptation of the events.
12 22 Short Films About Springfield (9)
- Season 7, Episode 21
A triumphant success, this season 7 classic presents a quick glimpse into the daily lives of nearly every identifiable Springfield citizen. This is The Simpsons at its most slice of life, although not every story is all that mundane.
The highlights of this episode will vary from person to person, but Principal Skinner's disastrous Steamed Hams lunch with Superintendent Chalmers is the most iconic. Other standouts include Nelson meeting his match, Snake robbing Moe's Tavern, and Milhouse's Pulp Fiction-inspired adventure.
11 Who Shot Mr. Burns? Part Two (9)
- Season 7, Episode 1
For a few months, the world discussed who could have possibly shot Mr. Burns. This was the cliffhanger to end all cliffhangers, and the reveal was quite a surprise. Otherwise, this is a strong episode filled with humor, pathos, and angry Homer.
Obviously, this episode cannot be taken on its own as it is very much a two-parter. "Who Shot Mr. Burns? Part Two" does a great job of paying off the first half's setup, and it doesn't take any shortcuts.
10 King Size Homer (9.0)
- Season 7, Episode 7
Homer starts gaining weight more rapidly than usual when he realizes he’s just a few pounds away from qualifying for workers’ comp. Marge has reservations about Homer’s plan and he finds people’s attitudes toward him change.
With a lot to say about obesity, fat-shaming, and the ups and downs of working from home, “King Size Homer” is a primo Simpsons episode.
9 The Springfield Files (9.1)
- Season 8, Episode 10
Crossover episodes are usually a bad idea, but The Simpsons combining with The X-Files was hugely satisfying for fans of both shows. Mulder and Scully travel to Springfield when Homer claims he saw an alien in the woods and nobody in town believes him.
From Scully forcing Homer to exercise to Mulder having a glamor shot on his federal identification, “The Springfield Files” does a terrific job of transplanting The X-Files’ characters into The Simpsons’ world.
8 The City Of New York Vs. Homer Simpson (9.1)
- Season 9, Episode 1
“The City of New York vs. Homer Simpson” is one of The Simpsons’ funniest episodes, but it, unfortunately, became retroactively controversial because Homer spends most of the episode at the World Trade Center. The episode aired in 1997 and was removed from syndication for a while in the wake of 9/11.
The animators painstakingly recreated Manhattan for the episode, which adds a visual supplement to timeless gags like the Khlav Kalash vendor and the “Checkin’ In” number from Kickin’ It: A Musical Journey Through the Betty Ford Center.
7 Marge Vs. The Monorail (9.1)
- Season 4, Episode 12
One of the common picks for The Simpsons’ best ever episode, “Marge vs. the Monorail” begins with Mr. Burns paying a huge fine to the town and Mayor Quimby holding a town meeting to determine what they’ll spend the money on. A snake oil salesman named Lyle Lanley pitches a monorail system and wows the town with a musical number.
However, Marge uncovers the history of Lanley’s monorail scams on the eve of the maiden voyage of Springfield’s monorail – conducted by none other than Homer.
6 Last Exit To Springfield (9.1)
- Season 4, Episode 17
Another regular pick for The Simpsons’ best episode, “Last Exit to Springfield” sees Homer elected the head of his workers’ union after Lisa is told she needs braces and Mr. Burns tries to cut his dental plan.
On top of mining a ton of absurd humor out of the premise of Homer leading a workers’ strike, “Last Exit to Springfield” has a lot to say about the balance of power between workers and their corporate overlords.
5 Who Shot Mr. Burns? Part One (9.2)
- Season 6, Episode 25
The sixth-season finale of The Simpsons set up the show’s first (and, so far, only) two-part episode. “Who Shot Mr. Burns? Part One” sets up beefs between various Springfieldians and Mr. Burns.
In the episode’s final moments, Mr. Burns is shot by an unseen assailant. Fans were left to ponder the titular question for months before the season 7 premiere paid it off.
4 Treehouse Of Horror V (9.2)
- Season 6, Episode 6
Since its second season, The Simpsons has delivered an annual Halloween special under the iconic “Treehouse of Horror” banner. These episodes are anthologies comprised of three spooky shorts and it’s very rare that all three are great, but “Treehouse of Horror V” manages it.
“The Shinning” puts Homer in Jack Torrance’s place in a Shining parody, “Time and Punishment” explores thought-provoking themes as Homer keeps unwittingly altering the course of history, and “Nightmare Cafeteria” plays like a regular episode that takes a dark turn into cannibalism.
3 Cape Feare (9.2)
- Season 5, Episode 2
Sideshow Bob gets out of prison and terrorizes the Simpson family into witness protection in “Cape Feare,” a spot-on parody of Martin Scorsese’s remake of Cape Fear.
From Bob’s hilariously drawn-out rake gag to Homer’s inability to grasp his new identity as Homer Thompson, “Cape Feare” is filled with classic Simpsons moments that’ll never get old. The ending is also excellent and an example of The Simpsons at the absolute peak of its powers.
2 You Only Move Twice (9.3)
- Season 8, Episode 2
Homer uproots the family and moves them to a seemingly idyllic gated community when a supervillain offers him a job in “You Only Move Twice.”
Throughout the episode, the Simpsons are all driven to despise their new lives – all except for Homer, who loves his new boss (and is completely oblivious to his out-in-the-open global terrorism).
1 Homer’s Enemy (9.3)
- Season 8, Episode 23
One of The Simpsons’ most uncharacteristically dark episodes, “Homer’s Enemy” revolves around a hard-working self-made man who is hired at the nuclear plant and is subsequently astounded by the way Homer lives.
As an outsider who is driven out of his mind by the unbelievable world of Homer Simpson, Frank Grimes ranks alongside Hank Scorpio and Jessica Lovejoy as one of The Simpsons’ most memorable one-off characters. Dark, funny, and unforgettable, "Homer's Enemy" is The Simpsons at its very best and came out just as the show was about to exit its Golden Era.