Watch + Listen: Top 50 Simpsons Episodes (Pt. 1)

by Kevin on June 24, 2011

I’m extremely excited to be launching my new column on Planet Arbitrary with a look at my favorite episodes of my favorite show. Growing up, The Simpsons was probably the one show I made it a point never to miss, and while the its quality isn’t near what it was in those first eight or nine years, it’s still a significant cultural institution finding new generations of fans all the time.

I make it a point to clarify that these are my “favorite” episodes, not necessarily an attempt at an objective “best episodes ever.” There’s plenty of room for debate, and with so many classic episodes everyone is going to have a different opinion. I think this list captures everything I love about the show, and I had a lot of fun putting it together.

What a scoop!

50. “Rosebud”
(Season 5, Episode 4)
It’s a rare episode that turns the ever-diabolical Montgomery Burns into a sympathetic figure, but “Rosebud” plays its cards well. While the Citizen Kane references are often heavy-handed, the bizarre rivalry between Burns and Maggie Simpson (the show’s oldest and youngest characters?) gets a big push forward in a literal tug-of-war over the stuffed bear Bobo. Bonus points for an extremely creepy Smithers in a bear suit.

49. “Radioactive Man”
(Season 7, Episode 2)
When Hollywood filmmakers arrive in Springfield to film a live-action version of everyone’s favorite superhero, Milhouse becomes the tragic foil exposing the hollowness of celebrity. Bart’s initial jealousy is eventually replaced by acceptance of his role as someone Milhouse can hurl whiskey bottles at when he’s feeling low, but not even Mickey Rooney can save the picture from a disenchanted Milhouse (despite a career spanning two decades).

48. “Worst Episode Ever”
(Season 12, Episode 11)
Another episode in which Bart and Milhouse’s friendship is tested, “Worst Episode Ever” lands the boys temporarily in charge of the Android Dungeon, which is still my favorite name for a comic book store. A fight over a Lenscrafters comic starring Bi-Clops (“a superhero with glasses!”) reveals Comic Book Guy’s secret stash of bootleg videos, which leads to a business decision they can both agree on.

Na na na na na na na na leader!

47. “The Joy of Sect”
(Season 9, Episode 13)
The people of Springfield can turn from peaceful assembly to angry mob with an astonishing quickness, so it makes sense that their sheep-like mentality would make them easy targets for a cult. The Movementarians know this, and they brainwash practically the entire town with promises of paradise on another planet. Eventually it’s up to Homer to set aside his collection of Leader beans and reveal the hoax.

46. “Thirty Minutes Over Tokyo”
(Season 10, Episode 23)
The Simpsons have made a lot of “The Simpsons Go to X” episodes, and not too many of them are on this list. “Thirty Minutes Over Tokyo,” however, works brilliantly at fitting in as many references to Japan as possible — Kabuki, origami, talking toilets, seizure robots — without feeling mean-spirited or over-stuffed. And the episode’s take on Japanese game shows is both hilarious and terrifying.

It's like there's a party in my mouth and everyone's invited!

45. “Homer at the Bat”
(Season 3, Episode 17)
Think about this for a moment: every single player on Burns’ team of ringers has since retired from baseball. If that doesn’t make you feel old, watch this episode now and try to remember a time before Jose Canseco and Roger Clemens were hauled before Congress over steroid use. But this was 1992, a simpler time, when Homer was the brief star of the company softball team and Mattingly’s sideburns were out of control.


44. “Lemon of Troy”
(Season 6, Episode 24)
Throughout this list you’ll see a lot of episodes that feature Springfield itself as a major character, which is something the writers of The Simpsons have done a fantastic job fleshing out over the years. By the end of the sixth season we had a pretty good idea of Springfield’s rivalry with its neighbor Shelbyville, but “Lemon of Troy” is the first to feature that rivalry as a central theme. It’s also a great chance to see Bart in a leadership role, though unsurprisingly he has about as much success as Homer usually does.

43. “Lisa’s Pony”
(Season 3, Episode 8 )
The strained relationship between Homer and Lisa has been used so much on The Simpsons, it’s easy to forget how important that relationship can be to the series. When Homer once again disappoints Lisa and fears he’s lost her love forever, he does what any other desperate father would do for his daughter: he buys her the pony she’s been begging for. Ultimately Lisa must make a sacrifice for her father, another big dumb animal she loves even more.

The doll's trying to kill me and the toaster's been laughing at me!

42. “Treehouse of Horror III”
(Season 4, Episode 5)
The third “Treehouse of Horror” installment features the segments “Clown Without Pity,” “King Homer,” and “Dial Z for Zombies,” three near-perfect parodies that made the “Treehouse” episodes such favorites in the early years. The vignettes are filled with great moments, like Homer’s exchange with the owner of the occult shop and Bart’s stream of magic words (“Trebek” and “Walmart” being excellent picks). And I can’t ignore Carl’s classic description of Candy Apple Island as being full of “apes — but they’re not so big.”

41. “Simpsons Roasting on an Open Fire”
(Season 1, Episode 1)
Although it might seem like I’m including the first episode out of some sense of obligation, watching it still brings back fond memories. I was in on the ground floor of The Simpsons, a show that was funny and endearing from the start. All of the major character concepts are here: Homer’s struggles as a provider and father figure, Bart’s mix of trouble-making and family loyalty, Lisa’s intellectual isolation, and Marge’s glue that holds them all together. Over the years the show would get much, much better, but it’s worth remembering just how good it was from the very first moments.

40. “Selma’s Choice”
(Season 4, Episode 13)
Patty and Selma are surprisingly durable characters, evolving from their one-note origins as “Marge’s sisters who don’t like Homer very much” to tragic figures whose homely looks and sour personalities serve as constant obstacles on their respective roads to happiness. Selma is the twin desperate for a family of her own, but when she finds that she’s unable (or unwilling) to care for children, she settles on the next best thing: an iguana named Jub Jub.

You will respect your new mother!

39. “Secrets of a Successful Marriage”
(Season 5, Episode 22)
It’s often unclear how or why Marge continues to stick with Homer, something that the show’s writers are quick to admit. “Secrets of a Successful Marriage” is the first time Marge becomes so upset with Homer that she throws him out, resulting in Homer’s quick deterioration and the realization how lost he would be without her. Once again they reconcile, at least until the next “marriage on the rocks” episode.


38. “Bart vs. Australia”
(Season 6, Episode 16)
“Bart vs. Australia” is another location episode, more irreverent than “Thirty Minutes Over Tokyo” in its portrayal of the “other.” The Simpsons’ Australia is a land of drunks and ruffians, where the prime minister swims naked and you can’t go anywhere without bumping into a Crocodile Dundee reference. I’m still not sure whether Australians actually punish criminals by booting them, and frankly, I don’t want to know.

37. “And Maggie Makes Three”
(Season 6, Episode 13)
I love flashback episodes, particularly from the first six seasons. “And Maggie Makes Three” tells the story of Maggie’s birth, which came at a difficult to imagine time when Homer was debt-free and had a job he loved. In a touching moment, we find that Homer’s love of his family is his true motivation, and he’s willing to subject himself to the deepest unhappiness to be a good father.

36. “Homer Badman”
(Season 6, Episode 9)
And just a few episodes before “And Maggie Makes Three,” Homer found himself accused of sexual harassment. In a misunderstanding that seems straight out of an episode of Three’s Company, Homer’s innocent (but still really stupid) removal of a piece of candy from the backside of the babysitter makes him a national pariah. The scenes where the media manipulates reality to extend the validity of the rumor are still relevant today, and it’s telling that even after Homer’s experience he hasn’t learned to doubt everything he sees on TV.

You can pinpoint the second his heart rips in half.

35. “I Love Lisa”
(Season 4, Episode 15)
I had to “choo-choo-choose” this episode (see what I did there?) because it’s easily Ralph Wiggum’s finest moment. Milhouse’s eternal attempts to woo Lisa have nothing on Ralph’s damnable persistence, and you can’t help but feel for the poor kid. There’s a sweet, schoolyard innocence to the way Ralph and Lisa interact, right up to the end when they decide to just “bee” friends. If only adult relationships were this simple.

34. “Lisa the Vegetarian”
(Season 7, Episode 5)
Great Lisa episodes are difficult to find, because too often she’s either too abrasive (“Lisa vs. Malibu Stacy”) or too morally obnoxious (“Homer vs. Lisa and the 8th Commandment”). “Lisa the Vegetarian” walks the line perfectly, creating a parallel between Lisa’s inward struggle to embrace vegetarianism and her outward struggle with getting acceptance from her family. The cameos by Paul and Linda McCartney are pretty ripe, though.

33. “Flaming Moe’s”
(Season 3, Episode 10)
The great codependent relationship between Homer and Moe hadn’t been fully explored until “Flaming Moe’s,” which sets the tone for their friendship throughout the series. Moe needs Homer as a customer, and Homer needs Moe to get him drunk; when the dynamic changes and Moe no longer needs Homer, the consequences set both men adrift in their respective seas. Tragedy is inevitable, and Homer’s mental break leads to Moe’s financial ruin — naturally, the status quo returns and all is forgiven.

32. “Lisa the Iconoclast”
(Season 7, Episode 16)
Like “Lisa the Vegetarian,” Lisa the Iconoclast” shows Lisa at her most soul-searching. After Lisa discovers the truth about Jebediah Springfield, the beloved town founder, she does what she does best: tells anyone who will listen. But badmouthing Jebediah gets her in nearly as much trouble as Bart when he removed his statue’s head (“The Telltale Head”), and eventually she realizes that the myth about Jebediah has value too. This wisdom embiggens her to do the right thing and keep her mouth shut.

We were discussing Wittgenstein over a game of backgammon.

31. “The Springfield Files”
(Season 8, Episode 10)
When “The Springfield Files” aired, The Simpsons was a lead-in to The X-Files on Sunday nights, so a crossover episode seemed to make at least a little bit of sense. And when Homer claims to see an alien in the woods, who else could investigate but the intrepid Mulder and Scully? I think my fondness for this episode stems exclusively from my fondness for The X-Files, but it has some pretty strong moments, and another excellent cameo from Leonard Nemoy. And the alien lineup still makes me laugh.

Click here for #30-11.

{ 3 comments… read them below or add one }

Joe June 24, 2011 at 1:33 pm

I wont judge until i see the rest….Fuck it, I’m judging, 31 is far too low for Springfield files.


Anthony June 24, 2011 at 11:11 pm

I love this blog


Pat B June 27, 2011 at 4:39 pm

#35 is my favorite from this section of the list. You picked the perfect image from it too!


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