My Top 10 Simpsons Episodes Ever

Coming up with a top-ten list of The Simpsons episodes ever is, by far, the toughest and most agonizing list I have ever drawn up. At first, coming up with a list to accompany (and compete!) with my homeboy, J-Oro’s list seemed like a terrific, exciting endeavor. Ultimately, it still was, but by the end—after watching and carefully considering at least fourteen episodes for my final four spots—it wasn’t so fun. Coming up with a top 15 list would have been dandy, like a stroll through a verdant park with a pretty girl, but picking only ten best episodes from the entire Simpsons repertoire seemed like an unfair exercise. (And really, I only looked at Seasons 2 – 8.)

So before I get started with my list, let me be explicit about a couple of rules that Justin and I followed:

1) Treehouse of Horror episodes did not qualify (though, for my money, my favorite Halloween episodes are III and IV),
2) Simpsons clip episodes such as “The Simpsons 138th Episode Spectacular” and “Homer’s Triple Bypass” were not considered, and
3) Though I think it’s a hilarious episode, I did not consider The Simpsons “Behind the Laughter” because it is not a typical Simpsons episode.

And since I fancy myself a proponent of transparency (unlike certain current presidents who promise such overtures before being elected to office), let me share with you the simple methodology I used to attempt to help me complete my list. By the end, when I was struggling to pick my final four episodes for the top-ten cut, I graded the episodes I watched on a school-grade system of A+ to F. After scoring each episode segment between commercial breaks with a letter grade, I came up with a cumulative grade. The best ones made the cut.

Now that I have that out of the way, let’s get on to the fun ladies and gents! I offer, with humbleness and confidence, my top 10 Simpsons episodes of all-time:

1) Last Exit to Springfield – Season 4
On more than one occasion, I have told my fellow Simpsons lovers, Maria and Justin, that I could write a thesis about why I believe this is the greatest Simpsons episode ever. And I seriously could. There are so many classic gags from this episode that I can name off the top of my head: The Big Book of British Smiles; Lisa’s dentist (who, arguably, is one of the greatest Simpsons bit characters to ever appear on just one episode); Homer’s interior monologue of “Dental plan! Lisa needs braces.”; Homer’s explanations for the scars on his skull; Burns and Smithers attempting to run the nuclear power plant by themselves; Homer’s fantasy of being a corrupt union boss that is a parody of The Godfather II

I could go on and on—and it’s only one episode!

2) Cape Feare – Season 5
What would a top-10 list be without an episode starring Kelsey Grammer as Sideshow Bob? And this episode, in my humble opinion, is by far his best Simpsons episode (with the “Black Widower” episode as his second best Sideshow performance) and my second favorite Simpsons episode of all-time. Like “Last Exit to Springfield” and every other astounding and immortal Simpsons episode, “Cape Feare” has at least one—or probably a few—gags that I would argue are Simpsons lore; “Bart the Daredevil” has Homer soaring over Springfield Gorge (and the Truckasaurus bit!); “Rosebud” has Smithers daydreaming of a naked Mr. Burns popping out of a cake to sing “Happy birthday” to him ala Marilyn Monroe; and “Marge vs. the Monorail” has quite possibly the greatest Simpsons episode intro with Homer’s exit of the power plant ala The Flintstones.

Cape Feare has so many such moments: all the blood-strewn threatening letters Bart gets while the ominous (now funny) Cape Fear theme plays; The Simpson family’s run-in with Sideshow Bob in the movie theatre; Homer’s inability to respond to "Mr. Thompson”; Sideshow Bob repeatedly stepping on rakes in Terror Lake; and, of course, Sideshow Bob singing the score of the H.M.S. Pinafore to Bart. And then there’s so many other laughs: Homer’s daydream of being John Elway; Sideshow Bob’s rough ride through the cactus patch while tied beneath The Simpsons’ car; and Bart tattooing “WIDE LOAD” on Homer’s butt while the entire family and an impeccably-timed Nelson laugh at him. Top to bottom one of the most entertaining episodes ever.

3) Homer at the Bat – Season 3
In re-watching so many of the golden-era Simpsons episodes, I can’t help but conclude that The Simpsons used to handle celebrity appearances in a more fluid and organic manner than they do now. Starting around the “Homerpalooza” episode near the tail-end of Season 7, I feel like celebrity appearances on The Simpsons became more forced; it’s hard to explain, but “Homer at the Bat” is a great example of how they used to include celebrity appearances with ease and fluidity. Mike Scoiscia’s turn as a wannabe blue-collar stiff is hilarious. Darryl Strawberry’s exchange with Homer over playing right field is funny, as is the way he constantly kisses up to his skipper, Mr. Burns. Even Ken Griffey Jr.’s first line of dialogue is in line with the chipper personality he conveyed during his playing career. Back in the glory days, The Simpsons creators seemed to create situations and dialogue that was in character with their celebrity guests instead of forcing them to say things that wasn’t so in line with their personas.

“Homer at the Bat” has a playful sense of innocence to it that helps it stick out over other terrific Simpsons episode. I think this tone is perfectly captured with the nostalgic jingle and montage that comprises the outro credit sequence (arguably one of the greatest The Simpsons ever produced). It’s a great episode with notable contributions from famous baseball players like Jose Canseco, Ozzie Smith, Ken Griffey Jr. (“It’s like there’s a party in my mouth—and everyone’s invited!), Steve “Saxy Boy” Sax, and Don Mattingly and regular Simpsons characters such as Mr. Burns, Homer, and Apu (who has one of his best lines when he says “Such a mighty wallop” after watching one of Homer’s Wonderbat-driven home runs soar over him).



After “Homer at the Bat,” my final top seven episodes are not meant to be in order of my favorites; it would be hard to impossible to somehow figure out which of these episodes are better than the others (though I suspect my homie, Mr. Goldman, could say a word or two to the contrary). They are simply listed to fill out my list:

4) I Love Lisa – Season 4
Like “Cape Feare” and “Last Exit to Springfield,” this episode is a goldmine of great gags and quotes: Ralph’s “I Choo-Choo-Choose You” Valentine’s card to Lisa; Bart rewinding footage of the Krusty special in slow-mo to show the very second when Lisa broke Ralph’s heart;



Chief Wiggum’s dating advice for Ralph; Ralph’s classic “My cat’s breath smells like catfood” line, and Homer’s advice to Lisa on how to ward off the little Wiggum: “Six simple words: I’m not gay, but I’ll learn.” It’s fucking hilarious.

I love having this episode in my top 10 because it features other characters besides Homer and Lisa (see remainder of my list), like Ralph and good ole’ Chief Wiggum. (“Nothing gets chocolate out, see!”) Plus, it has a tender ending that is cute and cool without being cheesy (though I can be quite the cheesy man).

5) The Last Temptation of Homer – Season 5
Noticing a trend yet with two top episodes from Season 4 & 5? What can I say; I feel like Seasons 2-7 were the golden years of The Simpsons with Seasons 3-5 being the creamy cream of the crop.

If The Dentist in “Last Exit to Springfield” is one of the greatest bit characters to ever have screen time on one of The Simpsons episodes, I think a decent argument could be made for Michelle Pfeiffer’s turn as Mindy in this episode as being one of the best feature characters to ever make one appearance. She is a delicious character to pair Homer with—a female version of him. All the things they happen to share in common—from hamburgers, drinking beer and watching TV, free shower curtains, and the way they both say “Can’t talk; eating”—is hilarious. Between them Homer and Mindy share some classic Simpsons moments: their awkward elevator conversation and—to a lesser degree—the conversation Homer instigates at the plant with writing on his hand.

Like most great Simpsons episodes, “The Last Temptation of Homer” has a hilarious subplot. In this episode, it is Bart’s turn toward dweebdom thanks to the corrective glasses, shoes, and salve he has to wear to school for two weeks. This subplot provides one of my favorite exchanges between Bart and Milhouse when the two chums are in school and Bart sees his reflection in Milhouse’s glasses and says, “Ugh, I’m a nerd,” then Milhouse sees himself reflected in Bart’s nerdy glasses and says, “Ugh, so am I!”

Other great strokes in this episode include the moments Homer and Mindy share in Capital City and, of course, the classic “Hubba Hubba” moment the hotel bellhop has not once but twice.



6) Lisa the Vegetarian – Season 7
This episode has a terrific beginning with the Simpsons visit to a petting zoo. It has a Simpsons classic with every piece of meat—including a live worm—speaking to Lisa in a little lamb’s voice. It has a classic Troy McClure promo with The Meat Council’s film on how meat is made; The Simpsons version of the food chain:

It also has Homer’s BBBQ invitation, a hilarious homage to Pink Floyd’s Animals album cover when Homer’s pig is seen flying past the nuclear power plant. And it has a cameo by Paul and Linda McCartney! To boot, the ending has a message of accepting one another when Homer and Lisa decide to put their differences aside. A great, great episode.

7) Duffless – Season 4
An excellent episode from beginning to end, one that centers on Homer, one of the greatest TV characters of all-time. The main plot involves Homer sneaking out of work to go to the Duff Brewery with Barney while the subplot revolves around Lisa using Bart for a fiendish science project after he ruins her plans to end world hunger by growing a ginormous tomato. It has so many classic moments: Homer’s interior monologue-gone-wrong about his Duff Brewery plans; the slow-motion sequence of Bart throwing Lisa’s giant tomato on Principal Skinner’s butt; and it has my absolute favorite Troy McClure promo when he narrates a grisly, fucked-up driver’s education film. It has a classic Simpsons moment with Homer singing his ode to beer:



and the sequence near the end when Homer is remorselessly tempted to drink beer.

“Duffless” ends on a sweet note with Homer picking a bike ride with Marge over going to Moe’s.

8) Burns’ Heir – Season 5
What would a top-10 Simpsons list be without an episode that features Montgomery Burns? Years ago I listened to a few Simpsons episode commentary and was a little surprised to hear the writers say that Mr. Burns was their favorite character to write dialogue for. But now that seems like such a “Well duh” moment because he has the most unique verbosity of all the Simpsons characters. Even Lisa can’t pull off using the word “rapscallion” like Monty can in this episode.

“Rosebud” and “A Star is Burns” are terrific episodes but I think this is overall the best one that features Mr. Burns. It has the classic auditions scene (“I specifically said no geeks!”) in the first third of the episode that graded as an A+ for me (the only other episode in which the beginning segment graded so high was the “Marge vs. the Monorail” episode).

Though the episode centers on Bart’s evolving relationship with Mr. Burns, Homer has some of his best lines in any Simpsons episodes: his advice on never trying in life, his line to Bart in front of Mr. Burns: “Bart, get over to the mansion and open up all the windows. We want to get the old people smell out before we move in,” and his line about “lurking in the bushes outside Chef Boy-Ar-Dee's house.” Aaaaaah, I laugh just thinking about them.

Besides the auditions scene, “Burns’ Heir” has the scene where Bart drives a race car through Santa’s Village and a classic scene near the end of the episode where Mr. Burns has actors impersonate the Simpsons family. And the whole brainwashing of Hans Moleman into Bart is pretty funny, too.

9) Deep Space Homer – Season 5
For me, it was between this episode and another Homer-centric episode, “Mr. Plow,” but I picked this one because of the power of its classic scenes. “Deep Space Homer” has classic Simpsons lore with his whimsical potato chip-eating sequence to Strauss’ “Blue Danube”:



Kent Brockman’s ridiculously hilarious turn toward accepting Planet Earth’s “new insect overlords,” and it has a funny cameo from the usually gentle and boring James Taylor. Buzz Aldrin has a couple of zingers, too (“Second comes right after first!” and “Careful, they’re ruffled!”) And it has one of the nastiest Itchy & Scratchy episodes. The wit and genius of The Simpsons creators is on full display in this episode. And since I’m a huge Stanley Kubrick fan, they get double brownie points for the usage of “The Blue Danube” and the parody of 2001: A Space Odyssey’s transition from a flying bone to a spaceship with the final seconds of the episode.



10) Krusty Gets Kancelled – Season 4
Since we’ve arrived to my final selection, let me preface by telling you who my favorite Simpsons characters are. They are (mostly in order): Homer, Mr. Burns, Lisa, Sideshow Bob, Bart, Moe Szyslak (I love asshole characters, what can I say), Martin (“Look fellas, the first snapdragon of the season.”), Nelson (his haha’s are almost always impeccably timed for laughs), and Krusty the Clown. This episode features Krusty while seamlessly incorporating several guest voices such as Bette Midler, (Sideshow) Luke Perry, The Red Hot Chili Peppers and Johnny Carson. “Krusty Gets Kancelled” also has the one and only appearance of Gabbo which ensues in lots of gags: Krusty’s attempt at ventriloquism; the replacement of The Itchy & Scratchy Show for Worker & Parasite;



Gabbo’s prank call to Krusty, and Gabbo and Kent Brockman’s “S.O.B.” faux pas. From beginning to end, Krusty’s fall and comeback is a great watch.


Honorable Mentions:
Mr. Plow – Season 4
Rosebud – Season 5
And Maggie Makes Three – Season 6
Bart the Daredevil – Season 2
Mother Simpson – Season 7
Lisa’s Rival – Season 6
Marge vs. the Monorail – Season 4
Three Men and a Comic Book – Season 2
Saturdays of Thunder – Season 3


So what do you think of my list? I'd love to hear your thoughts and comments. Thank you!