The best episodes of The Simpsons highlight the brilliance of one of the most beloved television shows of all time. The Simpsons first aired in 1989 and has since become one of the longest-running shows of all time, as well as one of the most influential. The antics of the titular family and its members – Homer, Marge, Bart, Lisa and Maggie – have been providing laughs for more than three decades. Looking at the show’s nearly 800 episodes to date and determining the best is no easy task, but a few examples quickly rise to the top.
The Simpsons subverted expectations of the typical sitcom family with these abrasive, rude, and destructive characters who are relentlessly and reliably hilarious. The endlessly colorful characters that make up the citizens of Springfield only added to the show’s greatness. Although there are many who feel The Simpsons has been past its prime for many years, the best episodes cement its place as one of the greatest television shows of all time, packed with jokes, songs, and iconic characters.
10
Behind the laughter
Season 11, Episode 22
Although there is no sign of The Simpsons Coming to an end soon, ‘Behind the Laughter’ is a rare episode in the long-running series that felt like it could have been a fitting finale. The episode changes the format drastically, revealing the life of The Simpsons is staged, with Homer, Marge and their children acting out a script. The mockumentary offers a behind-the-scenes look at the production of the show, the family’s success, and how they were all torn apart by fame.
The episode is a lot of fun commenting on the legacy of The Simpsons and mocking yourself. The overly serious narration provides plenty of laughs with a deadpan delivery of some ridiculous lines. It’s a bold direction that won’t work for all fans, but it shows that the series’ characters and humor can work outside of the typical format.
9
Treehouse of Terror V
Season 6, Episode 6
The Treehouse of Horror episodes have become annual favorites among fans, so it makes sense that the best installment of these Halloween-themed episodes would end up being one of the best Simpsons episodes of all time. “Treehouse of Horror V” follows the established format of these specials, offering three horror stories — a parody of The Shininga story of Homer’s time travel antics changing his reality, and a gruesome story of Lisa and Bart’s teachers starting to eat the misbehaving students.
The Shining the parody is often considered the best segment in the entire long history of Treehouse of Horror and it’s hard to argue with that. Seeing Homer unleash his own unhinged vision of Jack Nicholson is a delight, as is the recreation of the film’s iconic moments. The time travel episode is filled with quick and hilarious jokes, while the final segment shows just how violent these Halloween episodes can be.
8
Homer the Great
Season 6, Episode 12
The city of Springfield holds many unexpected secrets that often emerge never to be mentioned again. This is the case in “Homer the Great”, in which Homer discovers that his friends, and most of the male population of Springfield, are involved in a secret organization known as the Stonecutters. As Homer fights his way into the organization and is quickly fired, things change when he is revealed to be the prophesied leader.
This episode is a great example of the absurdity that The Simpsons can support each other without ever breaking the reality of the show. The idea of this powerful, ancient society that secretly controlled the world operating in Springfield is just something to accept and enjoy the ride. The episode features an excellent guest role from Patrick Stewart, as well as one of The Simpsons‘ most catchy songs with the music of the Stonecutters.
7
Bart sells his soul
Season 7, Episode 4
Although Bart Simpson has done a lot of shameful things throughout the series, “Bart Sells His Soul” is a great episode that shows the layers of his character. The episode sees Bart selling his soul to Milhouse for money, deciding that a soul is a meaningless thing. However, he soon realizes that his life is falling apart and begins to see the importance of holding on to such an important part of himself.
It’s not often that the audience can feel sorry for Bart, as he usually does whatever destructive thing he wants. However, this is a special episode that shows the human side of the little troublemaker. It also never loses its touch of humor, as Bart’s growing paranoia provides plenty of laughs, as does a subplot in which Moe tries to rebrand his bar as a family establishment.
6
Cape Feare
Season 5, Episode 2
Sideshow Bob is one of TV’s most beloved recurring characters. The Simpsonsbut “Cape Feare” really highlights what makes it so special. The episode shows Bob being released from prison and beginning his mission to get revenge on Bart. To keep the boy safe, the Simpson family enters witness protection and moves to a new house with Sideshow Bob in determined pursuit.
The episode is a detailed parody of Martin Scorsese’s remake of Cape Fearwhich is a funny movie to choose to poke fun at. However, it sets up the perfect episode to highlight the beloved Simpsons villain and is even responsible for the famous Sideshow Bob joke. Kelsey Grammer continues to bring the character to life with great energy and passionmaking him a true threat who can also come across as a pathetic fool.
5
And Maggie makes three
Season 6, Episode 13
There were many flashback episodes throughout The Simpsonsbut ‘And Maggie Makes Three’ is the most effective of the bunch. The episode is the untold story of Maggie’s birth, which came at an inopportune time for The Simpsons. With only two children to raise, the family found their financial situation in a comfortable place and Homer was able to leave his devastating job, only for a new baby and more responsibilities to arise.
“And Maggie Makes Three” is a perfect example of how the rare emotional moments in The Simpsons can really pack a punch. The episode builds into a touching and adorable reveal that recontextualizes Homer as a character in a beautiful way. However, the look at the family’s past is also very fun, filling in some gaps in their history before the show.
4
You only move twice
Season 8, Episode 2
While “Cape Feare” briefly touches on the fun idea of the Simpsons living a life outside of Springfield, “You Only Move Twice” examines that idea even further. The episode shows Homer getting a surprising new job opportunity in a new city. It comes with a fancy new house, some prestigious schools for the kids, and a friendly new boss for Homer. However, it soon becomes clear that Homer is the only one enjoying the new life they have built.
The highlight of the episode is the scene-stealing Simpsons character of Hank ScorpioHomer’s new boss. Although he is a friendly and supportive employer, the episode gradually reveals that he is an international Bond villain-type terrorist, which makes his decent treatment of Homer all the funnier. Watching Homer as an oblivious background actor in an epic action film is a strange and hilarious touch, including the moment where Homer unexpectedly leads to James Bond’s death.
3
Lemon of Troy
Season 6, Episode 24
The Simpsons He often has a lot of fun taking little incidents and turning them into wildly entertaining adventures. “Lemon of Troy” explores the recurring joke about the rivalry between Springfield and its neighboring town of Shelbyville. When some local Shelbyville youths steal Springfield’s lemon tree, Bart assembles a team of his classmates to raid the town and retrieve the tree. Meanwhile, Homer and Flanders organize a rescue mission to find the children.
The episode sets the stage for a genuinely fun team-up mission story complete with Bart identifying who fits the appropriate stereotypical roles, such as Rod being the “quiet religious guy who ends up going crazy”. Seeing how Shelbyville mirrors Springfield is also a fun touch and leads to the hilarious confrontation between Homer and his Shelbyville counterpart.
2
Homer’s enemy
One of the darkest episodes of The Simpsons It’s a bit divisive, but it’s a shining example of how the series takes more risks with its storytelling. The episode unexpectedly takes the focus away from The Simpsons and introduces a completely new character, Frank Grimes, a man who has worked hard his entire life only to end up working alongside Homer Simpson. As Grimes witnesses Homer’s incompetence and the success he achieved despite it, he begins to mentally fall apart.
Although Homer’s life is often seen as a mess, Grimes offers a hilarious new perspective on someone who has had a really difficult life. but he sees the undeserved success of this deeply unqualified man. It’s a clever way to make Homer almost the villain of the story, but also to make him more endearing than usual, since all he wants to do is be friends with Grimes. It all builds to a darkly hilarious climax that showcases the show’s edgy tone.
1
Marge vs. The monorail
While many fans may not know that Conan O’Brien was a writer for The Simpsons for a short period, he delivered the biggest episode of The Simpsons during that time. “Marge vs. the Monorail” features the city of Springfield earning a large sum of money and deciding to spend it on a monorail system sold to them by a shady traveling salesman. However, it soon becomes clear that the seller is a bandit and that the monorail poses a great danger to the city.
As a sign of the episode’s lasting legacy “Marge vs. the Monorail” was remade into the 2022 Simpsons episode “Treehouse of Horror”. It’s an episode full of laughs, from the opening sequence of Mr. Burns’ court case to Homer’s misadventures as a monorail conductor and Leonard Nimoy’s cameo. It also features another classic Simpsons song and a wonderful performance from villain Phil Hartman as salesman Lyle Lanley.