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 andquickly scrawled a family with three kidsand when he was called into Brooks’ office, he pitched this family for a TV show instead. That family, of course, becameThe Simpsons, one of the most beloved and groundbreaking TV series ever to hit the airwaves.RELATED:The Simpsons: Best Games Of All Time, RankedThe 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 July 25, 2025 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 ofThe Simpsons' best episodescould 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.
20Homer The Smithers (8.9)
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.
19Bart Sells His Souls (8.9)
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.
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“Bart Sells His Soul” is more than just a hilarious episode, as it makes well-realized observations on religion and commercialism.
18And Maggie Makes Three (8.9)
“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 forcesHomer to rethink his priorities.
17Rosebud (8.9)
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 ofThe Simpsons: clever humor, subtle references, a whole lot of heart, and the Ramones.
16Mr. Plow (8.9)
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.
15Homer The Heretic (9)
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.
14Homer The Great (9)
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.
13Homer Badman (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.
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“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.
1222 Short Films About Springfield (9)
A triumphant success, this season 7 classic presents a quick glimpse into the daily lives of nearly every identifiable Springfield citizen. This isThe Simpsonsat 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 disastrousSteamed Hamslunch with Superintendent Chalmers is the most iconic. Other standouts include Nelson meeting his match, Snake robbing Moe’s Tavern, and Milhouse’sPulp Fiction-inspired adventure.
11Who Shot Mr. Burns? Part Two (9)
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.
