Simpsons Post #1: The Fifteen Most Essential Simpsons Episodes of All Time — DIRECTOR’S CUT!

Bart and God
The Simpsons movie is coming up this week, so I guess this is a good time as any to revisit some of my older articles, as well as composing new thoughts about Our Favorite Family (or OFF, as the online Simpsons fans call them). I’m in no hurry to watch the movie. In fact, I’ll probably skip it. It hold no interest since I haven’t seen The Simpsons in five years. And, frankly, a Futurama movie, given the bigger budget for special effects, would be far more compelling.

Also, I’m getting close to burnt-out on movies this year. So far, I’ve seen Spider-Man 3, Pirates 3, Fantastic Four 2, Ocean’s 13, Transformers, and Live Free or Die Hard. I also promised my girlfriend that I’d watch Hairspray with her, so I’m getting close to critical mass on movie-viewing.

However, The Simpsons also represent a major cultural milestone, for myself and for its millions of fans. So rather than dismissing the series due to the last dismal seasons and the money-grab movie, rather I’ll look back at the series and reminisce over why we loved it in the first place. This article first appeared on I’m reprinting it here for posterity with some added comments, dated some 4 years later. Enjoy!



“D’oh!” — Homer Simpson

I’m the kind of guy who thinks about The Simpsons 24/7/365.

Don’t believe me? I just did a rant about the Seattle monorail in a speech class because the damn “Monorail Song” was stuck in my mind. When I heard about the new GMC Canyon truck, I mused, “Why not go all the way and name it a Canyonero?” And, currently, I’m trying to end our Christmas program with the choir closing their eyes, pouting their lips, and humming “Hark the Herald Angels Sing”. OK, so that’s really from “A Charlie Brown Christmas”, but the Simpsons fans among you know my real inspiration: the closing scene of “Treehouse of Horror IV”.

That’s why I’m cut to the heart when something like Season 14 comes along. Let’s recount last year’s “wacky” adventures: Homer goes to rock and roll fantasy camp! Marge abuses steroids! Bart finds out he was a child star, and he moves out! Ugh.

I could argue that the series has gotten stale, and that it needs to die mercifully… but I won’t. The Simpsons, somehow, always recovers from these doldrums. Time, too, can turn initially mediocre episodes into beloved classics. (Thank you, syndication!) After all, Season 9 was no tournament of roses either, but The Simpsons got back their mojo, plowed ahead, and made episodes as delicious and addicting as Tomacco.

(Ed. note: I can’t believe I wrote “delicious and addicting as Tomacco.” Ugh. However, looking back, I haven’t seen any of the latest episodes, even in syndication. The last few seasons really did kill my passion for the Simpsons. The lackluster plots were only part of it. It became apparent that the writers had no idea how to handle the characters. Everyone mentions how Homer got dumber. But how about bonehead moves like having Ned Flanders — you know, the conservative Christian stereotype who wanted to baptize Maggie to save her from eternal damnation — sleep with a Hollywood starlet, just to do some Notting Hill reference? How about splitting up Edna Krabappel and Principal Skinner because she was jonesin’ for the Comic Book Guy, of all people? And the new characters, like Cookie Kwan, the crazy cat lady, and Lindsey Nagel, were somehow even less than one-dimensional.)

Sooo... Bart is dead?

Besides, the internet is an unrepentant mistress. Hasty negative criticism can never be taken back. Worse, you end up looking like an insufferable geek. Check out this expose on obsessive Simpsons fans at

So instead, I present to you a list of favorite episodes. These are the shows that will cause me to drop everything I’m holding — casting them to the ground to fracture into several pieces, even — if that episode is on syndication.

Shall we begin?

Ratings guide: (5-Whoo-hoo!; 3-Increase my killing powers, eh?; 1-Patty and Selma…nekkid)

Rook’s 15 Essential Simpsons Shows:

1. Best Episode Based on a Jimmy Stewart Movie: “Bart of Darkness”

“Listen, Ned Flanders murdered his wife!”

“But why? She’s such a fox…. I mean, what’s on Fox tonight? Something ribald, no doubt.” — Bart and Homer

(Ed. note: I admit, I picked this episode mainly to get that quote in. I love that quote. And seriously, the entire Simpsons franchise is driven by quotable quotes.)

There are many great Bart episodes, and many of them have tidy little morals. This is not one of them. The family gets a pool, but, wouldn’t you know it, Bart breaks his leg on the first day. Things fall into place for Bart’s descent into madness (a.k.a. “Heart of Darkness,” natch.) The phone menu Police Department Resc-U-Phone, which has an option listed for “regicide”; Classic Krusty, featuring AFL/CIO Chairman George Meany; Stratego; and a play featuring Viceroy Fizzlebottom. And he’s convinced that Flanders is a mur-diddly-urderer! Rating: 4/5

2. Best Halloween Special: “Treehouse of Horror IV”

Have all the doughnuts in the world!!!

“Ah, guten tag! Would you care for a bite of my Vengelerstrasse bar? I also have a bag of marzipan Joy Joys.” — Uter

The “Treehouse of Horror” episodes are not only among the best Simpsons episodes ever aired, they’re also the best sci-fi/horror parodies around. Picking a favorite ToH is like picking a favorite Jelly Belly. So, plunging my hand into the bag, I pick out a random selection: “Treehouse of Horror IV”. We begin with “The Devil and Homer Simpson”, where Homer tastes the Forbidden Doughnut and, as retribution, must stand trial before a Jury of the Damned — which includes the starting lineup of the evil 1976 Philadelphia Flyers! Brrrr. The second segment, “Terror at Five and A Half Feet”, remakes the classic Twilight Zone episode about a jittery passenger, a gremlin, and a pre-licked stick of flavor wax. Brrrr! “Bart Simpson’s Dracula” proves, once and for all, that if Dracula’s Castle wasn’t equipped with a washer, dryer, and Super Fun Happy Slide, it should have been. Rating: 5/5

3. Best Hallucination about Confectionery: “Burns Verkaufen der Kraftwerk”

“Oooh, the Germans are mad at me. I’m so scared! Oooh, the Germans! Uh oh, the Germans are going to get me!” — Mr. Burns

The Springfield Nuclear Plant is purchased by a German firm. The new owners hold a performance review for Homer Simpson. To calm down his nerves, they tell him that Germany is the Land of Chocolate. Now if Germany really isn’t some magic land where you can take a bite out of a yipping chocolate dog, I don’t want to hear about it. Rating: 4.5/5

(Ed. Note: Earlier this year, I did get a chance to visit Berlin. There’s a nice shop there that has giant chocolate molds of the Reichstag and the Brandenberg Gate. It took the utmost discipline not to bust out in Simpsons quotes right then and there.)

4. Best Sports-Themed Episode: “Lisa on Ice”

“That’s very nice, Dad, but it’s wrong for you to reward violent competitive behavior. However, I will sit up front with you if it’s a fatherly gesture of love.”

“OK, hon…. Sucker! Competitive violence, that’s why you’re here!” — Lisa and Homer

Apu discovers Lisa’s hidden talent: after years of dodging Bart, Lisa has developed the keen reflexes of a goalie. But when Bart is the star player of the opposing team, their sibling rivalry erupts into violence! Which child will win Homer’s love? Naturally there’s an ending so sickly sweet that the upset spectators set fire to the hockey arena. Excellent. I’m from Detroit, by the way, so naturally any hockey episode is going to be high up on my list. Rating: 4/5

5. Most Romantic Episode between Bart and a Teacher: “Bart the Lover”

“Bart, you’re the closest thing to a man in my life. And that’s so depressing, I think I’m going to cry.” — Edna Krabappel

Bart fools his teacher, Edna Krabappel, into thinking she’s being wooed by a handsome fellow named Woodrow. It’s really a picture of Red Wings Hall of Famer Gordie Howe. Did I tell you that I’m from Detroit? This episode includes, for better or for worse, a scene where Edna poses in a revealing negligee. Rating: 4.5/5

Mmmm... Gordie Howe

6. Best Portrayal of Historical Figures: “Mountain of Madness”

“Stand back! I have powers! … Political powers!” — Homer

Maybe I’m all alone here, but I think there’s a primal urge inside all of us that wants to see Abe Lincoln, Mao Tse Tung, and Ghandi fight hand-to-hand combat with an army of Nazi snowmen. Rating: 4/5

7. Best Episode from the First Season: “Bart the General”

“Contrary to what you’ve just seen, war is neither glamorous nor fun. There are no winners, only losers. There are no good wars, with the following exceptions: The American Revolution, World War II, and the Star Wars Trilogy.” — Bart Simpson

There are only two ways to watch an episode from the first Simpsons season: kicking and screaming. The show suffered from uneven animation, and underdeveloped cast of characters, and Bart-centric stories. Ugh. “Bart the General” was one of the few good episodes. Bart gets into trouble with the local bully, Nelson. He gets help from two military nuts: Grandpa Simpson and Herman, the one-armed guy who runs the gun shop. The duo school Bart in the art of war and, together, they coordinate a tactical hit to end Nelson’s reign of terror. Rating: 3/5

8. Best Song: The Stonecutters’ Song, “Homer the Great”

“These people look deep within my soul and assign me a number based on the order in which I joined.” — Homer

Homer joins the super-secret Stonecutters organization. Well, relatively super-secret; it seems every man in town has a membership. But with the extensive club perks, who could blame them? Secret underground freeways, free rollerblades for work, and, best of all, a snazzy theme song! “The Stonecutters’ Song”, also known as the “We Do” song, explains many of the mysteries in life. Who rigs every Oscar night? We do! We do! Rating: 4.5/5

(Ed. Note: In retrospect the episode wasn’t that great. Yet the song is wonderful. Yes, it beats out the “Planet of the Apes” musical.)

9. Sexiest Guest Voice: Michelle Pfeiffer, “The Last Temptation of Homer”

“Foul temptress. I’ll bet she thinks Ziggy’s gotten too preachy too!” — Homer

No woman, other than Marge, got Homer’s motor running more than the red-headed Jezebel, Mindy. Listen, when you need spiritual intervention from Colonel Klink, you know you’re in trouble. I tend to agree with a comment my roommate once said, “If I were in Homer’s place, I’d just jump in the sack!” Warning: episode also contains disturbing yet hilarious scene of Barney Gumble in a bikini. Rating: 5/5

(Ed. Note: I read somewhere that Ren and Stimpy creator John Kricfalusi complained that new shows, like the Simpsons and South Park, made it impossible for new cartoons to show sexy women. Apparently he was not familiar with Mindy Simmons. Svelte, red-head, voiced by Michelle Pfeiffer… how can you go wrong?

Mmmmm.... Mindy Simmons....

10. Best Peek into the Future: “Lisa’s Wedding”

You know, Fox turned into a hardcore sex channel so gradually, I didn’t even notice. Yeesh!” — Marge

Since this is a cartoon, the Simpsons family never ages. However, if they did age, I’d want them to turn into the characters from “Lisa’s Wedding”. Especially Maggie. A teenage hellion with the voice of an angel … and Homer’s table manners? Something tells me there’s brilliant future in store for this youth. Rating: 5/5

11. The Episode That Got Better With Time: “Who Shot Mr. Burns?”

“No jury in the world’s going to convict a baby. Mmm… maybe Texas.” — Chief Wiggum

When the second part of this episode first aired, about twenty of my college dorm mates gathered around a small TV in the student lounge. I predicted, correctly, that the shooter would be either the stupidest or the most unlikely choice. When they revealed that it was Maggie, I felt vindicated and disappointed. Now, though, the initial shock is behind us, and I can finally appreciate the weird Lynchian touches. By that, I do mean that weird dream sequence with Lisa and the burning card. Rating: 4/5

12. Best of Homer’s Side Occupations: “Guess Who’s Coming to Criticize Dinner?”

“This éclair is over one million calories. Twenty-five pounds of butter per square inch. Covered with chocolate so dark that light cannot escape its surface.” — French Chef

You’d think that Homer, the man who once devoured an entire bag of flour when no other food was available, would be a perfect food critic. Unfortunately, he caves in to peer pressure from his fellow reviewers, and he writes negative reviews to appease them. Disgruntled restaurant owners try to off him with a deadly pastry. Wait a minute… negative reviews can kill you? Eh heh… I’d better give this one a 5/5.

(Ed. Note: This is one from the later seasons — at least from my perspective — that I really liked., went posting a favorite Homer job, listed the episode when he became an astronaut. It was gleefully funny, especially when Homer broke out his Planet of the Apes monologue but … seriously, that had to be the most unlikely job for him to have. Astronaut? I pinpoint that as the exact moment the series began it’s long slip into Family Guy-style absurdity. And, yes, I know Family Guy wasn’t out yet. Still….)

13. Quirkiest Episode: “Trilogy of Error”

“So, what are we doing? A lengthening, or a widening?” — Dr. Nick

The day starts of as a typical day in the Simpsons household: Bart and Milhouse discover a cave full of firecrackers, Lisa invents a grammar speaking robot, and Marge accidentally chops off Homer’s thumb. OK, so perhaps this is an incredibly strange day, even by The Simpsons standards. We follow the story in an interesting manner: each act is viewed from a different character’s viewpoint. Unexplained events that happen in the first act are neatly tied at the end. It’s a tough trick to pull off, but the writers do it and manage to make it funny. Besides, this episode has Fat Tony. Fat Tony! Rating: 4/5

(Ed. Note: I included this mainly to have an episode from the later seasons, but I would gladly rewatch this one. It’s too bad that, when the show’s in syndication, I’d have to wade through several sub-par episodes before getting to this one.)

14. Best Sideshow Bob Episode: “Cape Feare”

“Oh, I’ll stay away from your son, all right. Stay away… forever! Wait a minute, that’s no good.” — Sideshow Bob

Was the controversial rake sequence an inspired bit of slapstick comedy … or a brutal manifestation of Chinese water torture? Who cares? It’s a Sideshow Bob episode! The Simpsons, under a witness protection program, are briefly renamed the Thompsons. Wackiness ensues. But best of all are the Gilbert & Sullivan references. From the Simpson family version of “Three Little Maids” to the climactic one-man performance of the HMS Pinafore, this episode proves that any show can be greatly improved through silly British opera. Rating: 5/5

15. Best Episode Ever: “Rosebud”

“It’s chock full of … heady goodness.” — Apu

Rock fans will remember this episode for the appearance of the one of the most welcome set of guest voices: the Ramones. Homer fans will remember fondly of the scene where Homer exposes his big, fat can. And many will remember “Rosebud,” a Citizen Kane parody where Mr. Burns pines for a stuffed teddy named Bobo, as the best Simpsons episode of all time. And they would all be right. But me, I’ll remember this episode mainly for the sixty-four slices of American cheese. Rating: 5/5

(Ed. Note: And four years later, it’s still my favorite episode.)

And finally, I bring you the episode that can only be called the “Worst Episode Ever”. My nominee would be the “All Singing, All Dancing” clip show (Rating: 1/5). I’ll stick around for the beginning spot where Clint Eastwood and Lees Van Cleef literally paint the wagon red, but you can only watch rehashed song-and-dance segments for so long before you lose interest due to the lack of a good story. Click.

Time to paint the wagon.

(Ed. Note: Oddly enough, in the review of Paint Your Wagon — the real Clint Eastwood movie — in the’s My Year of Flops feature, Nathan Rabin mentions that nowadays, “Paint Your Wagon” is best known not for the musical, but for this animated segment at the beginning of the Simpsons clip show. Such is the power of the Simpsons that even the “Worst Episode Ever” still has and incredibly far reaching cultural impact. At least among adults under 35, anyway.)

Hence, I raise my champagne glass to the yellow, four-fingered family and wish for many more years of The Simpsons to come. Fifteen cheers for fifteenth seasons! If this list proves anything, it shows that the Simpsons were funny, are funny, and will always be funny. So help me Homer.

You can be sure, on November 2, 2003, that I’ll be parked with my seat on the living room couch for the beginning of the new season. Bring on “Treehouse of Horror XIV”!

(Ed. Note: Sadly, a highly disappointing episode. It’s the one that had Homer as a Grim Reaper, a Frankenstein parody, and the one where Bart and Milhouse stop time. This had to be the first Treehouse where I fell asleep… sometime in the middle of “Frinkenstein.” This may have been the pinnacle of my Simpsons fandom, and there was no where to go but down.)


6 thoughts on “Simpsons Post #1: The Fifteen Most Essential Simpsons Episodes of All Time — DIRECTOR’S CUT!

  1. The Astronaut episode was awesome! I didn’t care if it wasn’t plausible…cause it was hilarious…but that’s just me.

  2. Recently I saw an episode in which Lisa was failing gym class so she was sent to a gymnastics coach. There she met two girls who were in college. Lisa posed as a college student & they became friends. One evening they all went to a night club to hear a poetry reading…and that’s where I need help!!
    I cannot remember what the poet read onstage. It was something like ‘the impossible poem’. Lisa said the name of it as soon as the poet started reading.
    It is driving me crazy as if it is a real book (poem) I would love to read it!!
    Can anyone please help me with this????

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