Recently, we ran an article about the 10 worst episodes in the history of The Simpsons. However, let it not be said that we are a negative publication. More to the point, let it not be said that The Simpsons isn’t a good show. In fact, it is a tremendously good show. You could make a list of great Simpsons episodes that would ramble on and on, but we’ve narrowed it down to a top 25. This is the cream of the crop, from arguably the greatest sitcom in the history of the universe. One could argue for several episodes that didn’t crack this list (and feel free to share your favorites in the comments), but here are the elite 25 that we are highlighting. Relive all of the fun as you await the 26th season of this great show.
Come for the jokes about Homer starting a vigilante group to catch a cat burglar, which devolves into a series of heavy sack beatings. Stay for the homage to It’s a Mad, Mad, Mad, Mad World at the end. It’s always fun to watch Homer’s somewhat noble ideas devolve into anarchy.
The most recent episode on this list, and even it would now being considered a classic, having original aired in 2004. The Simpsons has had some excellent episodes since then, but none quite good enough to make the top 25. “All’s Fair in Oven War,” on the other hand, is a very funny episode largely focused on Marge’s quest to win a baking competition, and the lengths to which she is willing to go for the win. Also, Homer accidentally kills a parody of Twinkie the Kid in a hilarious fantasy sequence.
Lisa doesn’t get to have the fun of a Homer or a Bart or a Disco Stu, but she is a crucial part of the show, driving the main plot of this top-notch episode with her rivalry with a new girl who is as smart (if not smarter) than she is. While Lisa is the central focus, it must be acknowledged that what makes this episode an all-time great is Homer’s brief dalliance with life as a sugar baron.
Granted, there is nothing much going on here aside from the wacky antics of Homer founding a bowling team on to which Mr. Burns weasels his way. But there doesn’t need to be anything else—it’s a very funny episode, especially with the instant iconography of the Pin Pals shirts. This is also the one where Mr. Burns drills into Hans Moleman’s brains.
In terms of guest voice-overs, this episode may not have the biggest star power anymore, thanks to appearances from the likes of Tony Blair and J.K. Rowling in later episodes, but it is one of the best uses of guest stars. All baseball players instead of actors, the roster includes Roger Clemens, Wade Boggs, Ken Griffey, Jr., Steve Sax, and José Canseco (and more). All of the comedy is built around them, and it works extremely well.
You probably only need one line from this episode to justify its place in the top 20: “I, for one, welcome our new insect overlords.” Sure, an episode where Homer is shot into outer space may have started the show down the well of increasingly unlikely storylines, but it is justified in a funny, biting way, which was the wont of David Mirkin during his time running the show. “Deep Space Homer” also features the funniest parody of Married…with Children committed to film.
If you are of a certain persuasion, you probably remember this as the episode where John Swartzwelder actually appears on a DVD audio commentary (no matter that it is only over the phone). If you aren’t one of those sad, sad people, it’s just a very funny episode about gun control and soccer, but mostly gun control. The only shame is that such topics no longer have any relevance in our modern society.
This is the sort of story that can only—and should only—be told in animated form, if it’s to avoid coming off as completely absurd and out there. Homer decides to become morbidly obese in order to work from home. That’s a funny enough concept as it is, but the episode hilariously builds up from there. It also features the best appearance of Dr. Nick, alongside Homer in a muumuu.
If any Simpsons character has become problematic over the years, it is Bart. But back in the day he was written as someone who still had some degree of stability and logic in his actions, along with the capacity for being sympathetic. Here, he is presented with a moral conundrum when he skips school and finds himself as the only witness who can clear the (less than) good name of the innocent Freddie Quimby. It’s a great episode for Bart, but also Skinner. Then there’s Homer and his strong desire to watch Free Willy. Of course, the director’s cut ended up being a bit disappointing to him, what with the child being crushed by the whale and all.
There are some hilarious, silly, brilliant episodes of The Simpsons, and then there are more dramatic, emotional outings, like “The Last Temptation of Homer,” that are just as enjoyable and impressive in their own way. The undying love between Homer and Marge is at the center of the show, and here Homer worries about his new, beautiful, donut-and-nap-loving co-worker, voiced excellently by Michelle Pfeiffer. In the end, true love—and turkeys lodged behind the bed—win.
In an episode frequently cited as the best ever, Homer becomes the new head of the union, and finds himself in the crosshairs of Mr. Burns. The two make a dynamic duo, especially with Homer’s ability to flummox and foil Burns despite his general lack of business knowledge. This is a pretty epic episode in terms of scope, with several memorable moments etched in the show’s iconography.
Marge is the secret weapon of The Simpsons, often overshadowed by the bigger, bolder personalities of the show, including her own husband (who happens to be the greatest character in television history). However, Marge is excellent in her own right, and brings a very different energy and morality, to her stories. Here she gets the chance to work as a realtor, but her honesty gets in the way, until she unloads the murder house of Flanders. This is a very strong episode, even before you take into account the fact that Kirk Van Houten gets his arm sliced off while driving a convertible.
This is the episode that sparked the great love of our time: Principal Skinner and Edna Krabappel. Two of the show’s best secondary characters, these sad sacks find something worthwhile in each other, something Bart feels bad about standing in the way of. This is perhaps the best of the Ms. Krabappel episodes, even if it doesn’t quite have the emotional heft of “Bart the Lover.” What it does have is a melting Charlie Brown candle and Skinner being outed as a virgin.
Of all the pointed Mirkin episodes, this is the pointiest. The show takes sensationalist “news” shows, parodied here as Rock Bottom, to task for, you know, everything they stand for. The satire and social commentary work, but they don’t swallow the laughs, and in the end, Homer learns nothing. This is how it must be.
On the one hand, Homer moving to a new town and finding out his boss is a super villain shouldn’t technically work. On the other hand, when the jokes are this funny, and the boss is the legendary Hank Scorpio voiced by the equally legendary Albert Brooks, it doesn’t really matter. Additionally, the show manages to work enough stakes and family dynamics and drama to make it all come together. It’s very silly, but also brilliantly funny in a way that ultimately carries it to its lofty status.
This Conan O’Brien-penned episode did bring The Simpsons to a level of silliness that it had not quite reached before. This was not entirely a good thing, as the show went further down that path in lesser seasons. Still, it is a hilarious episode, with a great performance from Phil Hartman, not to mention the best song in the history of the show.
Your level of enjoyment with this episode may vary depending on how you feel about Milhouse and Kirk Van Houten. If you see them as these bottomless wells of bleak, cosmically unkind hilarity, then you too will consider “A Milhouse Divided” one of the best episodes of this, or any, show. “Can I Borrow a Feeling?” alone is brilliantly pathetic enough to make this a keeper. You don’t even need the stuff with Homer and Marge, although that’s plenty enjoyable as well.
For once, Homer finds success. And all he had to do was become the Beer Baron during Springfield’s shortsighted return to prohibition. It is one of his greatest capers, in an all-around fantastic episode filled with laughs and memorable lines. You’ve heard Homer’s toast to alcohol a million times, but in this episode he really earns his title.
Yes, this is darker than your average Simpsons episode, and it is also fairly unique within the history of the show. Basically, “Homer’s Enemy” asks “What if a real person was dropped into the world of The Simpsons, and had to deal with a character like Homer?” What happens to Frank Grimes—or Grimey as he liked to be called—is that he has a mental breakdown and ends up killing himself. Hilarious, right? In fact, it is.
This is another episode where Homer takes on Mr. Burns, this time over Burns’ beloved childhood bear Bobo. This ranks higher on the list than “Last Exit to Springfield” because it’s just funnier; this ma, in fact, be Burns’ best episode in the history of the show. It’s also nice to see Homer put his family, particularly Maggie, over his own wealth and well-being. Anyway, we can all agree that—at the very least—it’s funnier than Citizen Kane.
George Meyer may be a comedy writing legend, but there are only a handful of Simpsons episodes with his name actually on it. “Bart’s Inner Child” is one of them, and it is tremendous. A somewhat headier episode, it takes sharp shots at self-help gurus and things of that ilk, manifested here by Albert Brooks as Brad Goodman. There are also a couple of amusing meta jokes about the nature of sitcom structure. It is a great episode from top to bottom.
You will learn a valuable lesson watching this O’Brien episode. There are two kinds of people in this world, jocks and nerds, and if you’re a jock, like Homer, it’s your responsibility to give nerds a hard time. Or so goes the logic of Homer, who has gleaned all his knowledge of college from terrible raunchy campus comedies. This leads to many-a-humorous misunderstanding in this silly, but supremely funny, episode.
Speaking of silly, there’s not a lot of emotional heft to “Bart Gets an Elephant,” the tale of a boy and his jerk of an elephant. But the journey is great. And the time Bart and Stampy and the family spend together is great. Even the coda at the wildlife reserve is great, because it involves Homer repeatedly headbutting a guy in the ribs. There’s a smart joke about how we can’t be sure what’s right today “what with all our modern ideas… and products!” but there’s also a great bit where Barney is pulled out of a tar pit and lights himself on fire. He’s mildly annoyed. So, you see, there’s something for everybody.
Again, for folks who like emotion, or family bonding, or any of that stuff in their Simpsons episodes (and the show can certainly do that very well), then “Homie the Clown” may not be your ideal episode. However, if you like Homer… dressed as Krusty… mistaking a Hamburgler type character for a real burger and smashing his head against a rock until a boy cries out, “Stop! Stop! He’s already dead,” then this is pretty much as good as it gets. Homer’s adventures as a Krusty the Clown impersonator are very funny, and give us a nice view of the sleaze that Krusty mires in. Also, the show finally took the opportunity to highlight the fact that Krusty and Homer’s designs are fairly similar.
Okay, this episode may be a bit too meta for some, but if you are into that sort of thing, there is no better episode. There is so much fun stuff in it for longtime, devoted fans of the show… even though some of that stuff takes digs at you and your kind. It’s a fantastic bit of television that pokes fun at television and television viewers. Also, we get introduced to our favorite character; Roy. This is all what makes “The Itchy & Scratchy & Poochie Show” the best episode of The Simpsons of all-time, also making it one of the best things ever in the history of anything.
Chris Morgan is an Internet gadabout who writes on a variety of topics and in a variety of mediums. If he had to select one thing to promote, however, it would be his ’90s blog/podcast, Existential Parachute Pants. (You can also follow him on Twitter.)