The 22 Best Simpsons™ Episodes (And The 3 Most Disappointing)

In honor of the twenty-second season premiere in September, I present my personal picks for the 22 best Simpsons episodes…and three episodes that failed to live up to the hype (in honor of the three “seasons” of short subjects on The Tracey Ullman Show):

22. When You Dish Upon A Star – Over the last ten years or so, there’s been a great deal of debate about “Modern Era” showrunners and their over-reliance on cameos by celebrity guest stars to pad out the stories. But this installment proves that in the right hands and with clever material, those cameos can produce pure gold (Oscar gold, even). Ron Howard and the then-married Alec Baldwin and Kim Basinger fit perfectly into the Simpsons universe, and their interactions with their newly-hired personal assistant Homer are instantly quotable. And “Potsie” really steals the show here, as he completely belies his clean-cut image with dynamite fishing, two-fisted drinking action and blatantly ripping off Homer’s “time-traveling robot driving instructor” movie concept.

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21. Bart’s Dog Gets An “F” – For all the great gags and surprise guest apperances (even though Tracey Ullman brings the goods as always), at the very core of this episode is a simple story about a boy and his dog. While there have been many other installments centered around Santa’s Little Helper over the years, there’s never been one better.

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20. The Itchy & Scratchy & Poochie Show – A controversial outing for a number of reasons, and yet what’s often lost (particularly in all the furor over the “You owe them” line) is the fact that this is an hilarious installment (complete with a number of self-aware swipes at the show and the genre itself). Meta-humor is always tricky to pull off effectively even under the best of circumstances, but this episode proves that The Simpsons does it better than most. And honestly, most hardcore Simpsons fans are probably too thin-skinned for their own good anyhow, so an occasional tweaking isn’t necessarily a bad thing.

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19. Who Shot Mr. Burns? (Parts 1 & 2) – The “biggest event in Simpsons history” really hasn’t aged well (anyone still remember Twin Peaks or Tailhook?), but still ranks amongst the show’s best outings. The whole is definitely greater than the sum of its parts, though.

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18. Bart’s Comet – The perennial “D” student accidentally discovers a new heavenly body…which of course is headed on a collision course towards Springfield, sending “America’s Crud Bucket” into a predictable (and highly amusing) panic. The town has rarely looked worse or more collectively incompetent than here, and thus this is one of the best Springfield-centric outings to date.

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17. Lisa’s Wedding – This Emmy®-winning episode doesn’t hold up as well as you’d think, in part because the writers have continually monkeyed with the series timeline and gone to the “wacky future” wellspring far too many times. But there’s no better examination of Lisa’s complicated relationship with her family (Homer in particular) to be found anywhere else in Simpsons canon.

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16. The Last Temptation Of Homer – We’ve seen this type of story on The Simpsons many times before and since, but never done so masterfully. This tale of Homer’s struggle between his love for his wife and his animal attraction towards new plant employee Mindy Simmons (a pitch-perfect performance by Michelle Pfeiffer) could have gone horribly wrong in lesser hands (“That ’90s Show”, anyone?) but thankfully the Season Five team was still capable of conjuring up that delicately-balanced brew of belly laughs and emotional resonance. And of course, as a bonus we get Colonel Klink himself as Homer’s conscience. How can you go wrong?

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15. Blood Feud – While there have been better overall Simpsons episodes, there has never been a better character study than this particular installment. Every performance is pitch-perfect, from Homer’s well-meaning stupidity to Charles Montgomery Burns and his complex mix of arrogance, archaism and obliviousness (a formula that many writers have failed to accurately duplicate). And there are so many quotable gags that it would take far too long to name them all (although Homer impersonating Burns at the post office is a notable standout).

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14. Bart The General – As a general rule, it really isn’t fair to judge Season One episodes against later installments, because the series was still trying to establish itself in the primetime universe and the writers hadn’t yet stumbled upon the winning formula which would propel The Simpsons into the realms of true greatness and worldwide cult status. But those elements were beginning to coalesce here, as Bart confronts Nelson Muntz for the first time and enlist Grandpa’s help to do so. This was the episode (along with “Bart The Genius”) that really put Bart Simpson on the map as a cultural phenomenon during the summer of 1990, although the focus of the series was gradually (and wisely) shifted over to Homer by Season Three.

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13. A Fish Called Selma – These days, an episode focusing on a supporting character is usually a recipe for disaster. But thanks to the talents of Julie Kavner and the sorely-missed Phil Hartman, this hilarious outing stands the test of time and deftly skewers our celebrity-obsessed culture with pinpoint accuracy. And what’s more, there’s geniune emotional growth between Selma Bouvier and Troy McClure, of all people. Who knew? As relevant today as when it first aired.

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12. The Joy Of Sect – It’s The Simpsons vs. The Scientol…er…Movementarians! Although this episode has traces of the elements which would later drag the series down the Road of Mediocrity (Jerkass Homer, out-of-character gags, “wacky” set pieces, overextension of the so-called “rubber-band reality”, and so on), it’s still an enjoyable and hilarious outing with many well-deserved swipes at organized religions of all kinds. And Mr. Burns as The New God is the greatest B-story that never happened.

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11. 22 Short Films About Springfield – The first “genre-bending” outing follows a number of Springfield citizens around during an average day in our favorite town. While the quality of the individual segments varies, it’s “Skinner and The Superintendent” which takes this episode over the top into classic territory. Aurora borealis, indeed.

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10. 24 Minutes – Even the very best of television series tend to run out of creative steam after a lengthy run, and The Simpsons is no exception. While most agree that the “Golden Age” of the show ended somewhere around Season Eight, in truth there have been the occasional bright spots even during the most desolate of seasons. For example, the much-reviled Season Eighteen produced this gem: a spot-on parody of Fox’s action-packed extravaganza 24, complete with a cameo by Kiefer Sutherland himself. Just one hilarious gag after another, even extending into the opening credits.

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9. Last Exit To Springfield – Many people consider this to be the best Simpsons episode ever made. And while it’s very good, there’s a key element missing which separates the true classics from the mere great: heart. As great as the individual gags and Lisa’s protest song were, when compared with other entries on this list (Number One and Two are prime examples) the episode just falls a bit flat. But lack of emotional depth aside, the endless barrage of jokes presented here are indeed among the series’ very best. And while most people cite “Lisa needs braces/Dental plan!” as the episode’s best gag, the “Smartline” segment deserves just as much praise.

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8. Duffless – A shining example of the wisdom of shifting the show’s focus from Bart to Homer, as a concerned Marge convinces her husband to give up alcohol for a month. Dan Castellaneta hits all the right notes as Homer comedically struggles with his newfound sobriety, and Lisa and Bart have a very amusing subplot of their own involving yet another Springfield Elementary School science fair. An oft-overlooked gem of an episode.

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7. Three Men And A Comic Book – Another overlooked gem from Season Two finds Bart, Milhouse and the tragically under-utilized Martin Prince losing their minds and humanity over a rare comic book, Sierra Madre-style. And the fact that apparently no one learns anything from the experience is the icing on the cake and as Simpson-y as it gets.

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6. Behind The Laughter – The Simpsons meets VH1′s Behind The Music. Hilarity ensues. No, really. The best “Modern Era” episode EVER. Nothing else even comes close.

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5. Mother Simpson – The missing piece of the Simpson family puzzle is revealed when presumed-dead Mona Simpson resurfaces after a three-decade absence. Given the unbelievable talents of the main cast, it’s a rare thing indeed for them to be eclipsed by a guest star. But that’s presicely what happens here as Glenn Close gives a tour-de-force performance as Homer’s long-lost mother, and elevates everyone around her in the process. And if the ending doesn’t bring a tear to your eye, then you’re probably not human (or even a robot from the year 2010). Sadly, Mona’s subsequent returns were severely lacking in heart, substance and laughs.

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4. I Love Lisa – These days he’s a walking punchline, but this is Ralph Wiggum’s true moment in the sun. A carefully observed tale of unrequited love and social awkwardness, “I Love Lisa” deftly combines broad humor and pathos as the sublimely pathetic Ralph woos a sympathetic (but uninterested) Lisa after receiving a “pity Valentine” from her. And if that’s not enough, Bart and Milhouse’s reinterpretation of the Lincoln assassination is quite possibly the best standalone gag EVER. Can’t recommend this one highly enough, especially for a Simpsons novice.

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3. Lisa On Ice – The Bart/Lisa dynamic is fertile territory for Simpsons writers, but never have the complexities of sibling rivalries (not to mention youth sports in general) been more expertly examined than in this classic outing. And the ending is as great a representation of what The Simpsons is truly all about as you’ll ever see. And while this episode does feature the Jerkass version of Homer that we’ve grown to know and loathe, his incessant pitting of Bart and Lisa against each other is far more accurate than most parents are willing to admit.

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2. Home Sweet Homediddly-Dum-Doodily – As noted, the very best Simpsons episodes are the ones which combine big laughs with genuine heart and this episode has both in triplicate. A series of innocent misunderstandings lead to Bart, Lisa and Maggie being taken from their parents by the state and placed in foster care…with the Flanders clan. And while there’s plenty of over-the-top gags and one-liners to go around, it’s the carefully observed emotional moments which make this particular installment one of the very best this series has to offer. The fact that you actually CARE about what happens to these goofy-looking ink-and-paper figures is what sets The Simpsons apart from traditional animated fare (and most other situation comedies) and a testament to the hard work that went (and still goes, arguments of declining quality aside) into making the show a global phenomenon. And in an episode full of great performances, Julie Kavner (as Marge) is the real standout here.

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1. Bart Gets An “F” – In 1990, Bart Simpson was being heralded as television’s favorite underachieving bad-boy and the quintessentially cynical symbol of the new decade, and in the Season Two premiere the writers wisely decided to play against that image (and head off the typical “fad backlash” that usually accompanies such phenomena) by revealing the vulerability beneath Bart’s cavalier attitude. Faced with the humiliation of repeating the fourth grade, an increasingly desperate Bart tries to forestall the inevitable and actually applies himself for the first time in his young life. Nancy Cartwright (Bart’s voice actress for the uninitiated) deserves special kudos for her performance here, as she proves her dexterity by seamlessly shifting from comedy to heart-wrenching pathos in the blink of an eye. And try watching the final scene between Bart and Mrs. Krabappel without (at the very least) getting a lump in your throat. Trust me, it’s impossible. Simply the best.

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And just to balance things out:

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3. Trash Of The Titans: Worst 200th episode ever. You’d think that having Steve Martin, U2 and an elaborate Alf Clausen musical number would be enough to make this installment an instant winner…but you’d be wrong. Martin in particular was completely wasted here, playing the straight man to a disturbingly bufoonish Homer. Hindsight being 20/20 and all, “The City Of New York Vs. Homer Simpson” should probably have been the 200th.

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2. Homer’s Enemy – Another idea that sounds great on paper, but is sorely lacking in execution: a normal person from the “real world” trying to deal with the illogical world of Homer Simpson. This episode is more disturbing and needlessly cruel than genuinely amusing, and the final breakdown of Frank Grimes is particularly difficult to watch. A rare exercise in sadism from The Simpsons.

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1. Stark Raving Dad – Possibly the most hyped Simpsons episode ever (behind “Who Shot Mr. Burns?”), this installment doesn’t age well for a number of reasons best left unsaid here. However, the simple truth of the matter is that there’s really not much substance here to begin with. The actual plot is fairly thin, the characterizations are all over the map, there’s not nearly enough satirical bite to counteract the contrived sappiness, and the “birthday song” written by Bart and “Leon Kompowsky” is fairly lousy. Basically, the entire episode was merely an excuse to work with Michael Jackson (who was given creative control, something that no other guest star has had since) and it shows in the final product. This outing actually marked a turning point for the series, as the Groening/Brooks/Simon triumvirate gradually lost power (in part over the writing team’s frustration concerning the early creative direction) while the likes of Al Jean and Mike Reiss began exerting their own influence over the series. And under their guidance, the show finally achieved that much-needed balance of comedy and heart which propelled The Simpsons into the stratosphere.

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TV’s Tim

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