Top Simpsons Episodes Written by Oakley & Weinstein

Bill Oakley and Josh Weinstein were not only writers for The Simpsons, but the showrunners of seasons 7 and 8 which is a high point in the show where it was assumed to be nearing its end.  They made it their mission to deliver episodes that pushed the boundaries of what the show was capable of conceptually, while still remaining true to what the show established itself as roughly around season 3.  One of the most innovative and influential shows of all time that had already prided itself from experimenting with the form of sitcom had now reached the point of experimenting with none other than the show itself.

Their contribution to the show as executive producers was a high wire act of seeing how far the rubberband of The Simpsons universe can stretch as they pumped out episodes that played with format, formula in storytelling, and even took characters, whether secondary or main, and explored them to a greater extent so late into the show’s lifecycle, oftentimes turning them on their heads, or allowing them to change beyond the confines of a single episode.  They managed to do all of this while still maintaining the heart and nuanced qualities that made the characters and universe of the show so outstanding to begin with.  To this day, season 7 and 8 are hailed as part of the classic run of the show, and in my opinion, is the last showrunning era before the show began to decline based from its own standards.  Each of those seasons are also some of the greatest seasons of comedy on television, period.

The work I’m familiar with outside of The Simpsons is Josh Weinstein’s solo credit as a writer on later Futurama episodes, but most prominently they are both the creators of 1999’s Mission Hill which was an adult animated sitcom on the WB that only lasted one season, despite its high critical acclaim.  They are also set to write for Matt Groening’s new Netflix series Disenchantment, an adult animated sitcom that tackles the medieval fantasy genre which is set to air sometime in 2018.

Before all of that though, they were plain Simpsons writers so for fun, here’s every Simpsons episode that Oakley & Weinstein wrote as a writing pair, ranked.  Again, it’s what they wrote, not the episodes from their time as showrunners.  I will try to sum up to the best of my ability what makes each one stand out to me.  Some entries I was disciplined to keep short and sweet, while others I might have more to say about.  Regardless, I love them all.  Enjoy!

10. “Lady Bouvier’s Lover” (Season 5)

A risk taken towards the end of season 5 in terms of alienating the 18-49 demographic, by having a plot that focuses on Abe and Marge’s mother, Jacqueline, and the not-so-budding elderly romance between them, which eventually gets intercepted by Mr. Burns.  “Lady Bouvier’s Lover” is brimming with old film and tv nods, spanning from Charlie Chaplin’s 1925 film, The Gold Rush to Jimmy Durante’s work of the 1950’s.  The episode is paced rather patiently (for an episode in David Mirkin’s showrunning era) which helps create this desperately mellow tone to a story that explores the loneliness of getting older and the roadblocks that exist from allowing us to become closer with one another. The most memorable moment of the episode is its tip of the hat to The Graduate (1967) with a more raw, not-so-ideal outcome which results in an ending that is ironically satisfying and serene.  It’s also interesting how an entire story that brings Abe, Jacqueline, and Burns to the forefront, unravels from the juxtaposition of celebrating Maggie’s birthday in the first act.

9. “Marge Gets a Job” (Season 4)

“Marge Gets a Job” is an episode that is pretty loose when it comes to its humor, ranging from humbly conventional to delightfully inventive, ultimately resulting in a pretty charming half hour.  Getting Marge to work at the Nuclear Power Plant and exploring the social dynamic between her and Homer, as well as the larger development of Mr. Burns’ infatuation with Marge proves to make for a compelling A story.  The B story with Bart avoiding his test is something that was admitted by Oakley & Weinstein to be an idea haphazardly thrown together.  Personally, I like it.  It uses “The Boy Who Cried Wolf” motif to such blatant, literal extent (whereas other shows would try to be subtle about it) to the point of absolute silliness in the context of its narrative, and it works.

8. “Marge in Chains” (Season 4)

“Marge in Chains” is an impressively cohesive outing when it comes to kicking the show off with a seemingly unrelated Osaka Flu runner which builds to Marge’s rather ambiguous crime in the stress of taking care of her sick family.  The manner in which this episode sticks to one focused main plot throughout, while being flexible enough to exercise Phil Hartman’s comedic stylings in the courtroom as Lionel Hutz, as well as playing on the drama of Marge’s character getting thrown away, not shying away from committing to that idea to the very end, and showing her absence in exaggeration from various core perspectives makes for some grade A material.  A statue of Jimmy Carter with Marge’s doo being used as a tetherball pole, played to the presidential theme “Hail to the Chief” is one of the most bizarre lasting images to go out on, yet it somehow sums the entire episode up perfectly in the midst of all its absurdity, albeit organically unfolded premise.

7. “Grampa vs. Sexual Inadequacy” (Season 6)

This is an episode that manages to intertwine the conflict of sexual shortcomings in the bedroom between husband and wife (Homer and Marge) with the shaky relationship between a father and son (Grampa and Homer), and is unafraid in the awkwardness of such combined subject matter.  “Grampa vs. Sexual Inadequacy” possesses a sharp, snappy wit and is a half hour where Abe holds the miracle tonic to cure Homer and Marge’s sex life, but in the process opens up a can of worms not just on Homer’s relationship with his dad, but for his own role as one.  Meanwhile, as miracle sex tonic is being sold to nearly every adult in Springfield, the kids get swallowed up in their own theories of what the adults are up to, which becomes less about government conspiracy and more on the fun of the kids’ innocence and naivete and how it brings them together, regardless of how increasingly insane they become as the episode progresses.  Many characters butt heads in this episode, yet it makes for an endearing installment.  Only The Simpsons can have an ending with Homer and Abe on fire, rolling around on the grass, and have it play ironically for laughs while still being a sincere, heartwarming moment shared between them.

6. “Lisa vs. Malibu Stacy” (Season 5)

I’ve always admired this episode due to its hot topic of sexism vs. commercialism where the former becomes validated as long as the latter garners successful results, and how this is all spearheaded by the young Lisa Simpson who sees this for what it is without any veil of traditionalism that seems to lull society into making light of such an issue.  Most importantly, like the best episodes that explore politics, it tackles the subject head-on, traversing the conflict for what it is without strong-arming you or using the story as a tool for the message but instead uses the message as a tool for the story.  It’s an episode that ends in a mock-victory and allows you to sit and reflect on the unchanging, unresolved nature of the overall problem.  “Lisa vs. Malibu Stacy” has you root for Lisa’s undying determination to bring a more rounded take on a celebrated doll of perpetuated stereotype, but also takes fun in sticking true to every other characters’ indifference towards this matter and Lisa, the underdog problem solver.

As for the subplot, it intermittently crosses with the main plot thematically, especially when Grampa and Lisa commiserate over the lack of attention they receive due to their opposing age gap.  You may notice by now that Oakley & Weinstein are big fans of Grampa stories or ‘old-timey’ humor in general, and this one in particular makes for a sweet and bright display of that.  It’s always enjoyable to watch Grampa maneuver stubbornly, yet optimistically through Springfield in the quest for relevance.  In the end, both plots deal with how advertising makes an impression and reflects on how we act, although sometimes to a staggeringly inaccurate degree.  Grampa won over the crowd of seniors as he realizes the initial commercial that kick-started his supposed solution did not provide an answer that pertains to what he’s actually going through.  At the same time, Lisa ends up losing to the crowd of young girls who will continue to be swept up in the commercialism of Malibu Stacy.  It’s all about the escape from the generalizations (or marginalizations) society puts you in, and the necessary tact of execution that needs to occur in order to convince people of the real problem, being something that’s never too late to achieve.  The narrative sounds so busy on paper, but it’s delivered so elegantly and with such a brilliant sense of humor.

5. “$pringfield” (Season 5)

Immediately “$pringfield” sets itself up by delving into the town’s past as a thriving safe haven of opportunity and intrigue.   There’s a hustle and bustling energy to it that is soon met with its current state of decay and financial strain.  Mr. Burns, who is not immune to the the town’s current predicament piggybacks on Skinner’s more noble notion of legalized gambling and before you know it the town becomes subject to a lifestyle of freewheeling sleaze and debauchery.  As soon as we’re introduced to the Mr. Burns Casino, there’s a colossal shift in mood which becomes much more dark, strange, and disconnected.  The best thing that the episode does with such a backdrop, besides allowing it to be an unstoppable vacuum for the characters to fall into, is to take advantage of the varied, surrealistic comedy you can get from such a place.  The gag rate in this episode is on rapid fire as it jumps from scene to scene, smashed together almost like a sketch show that follows several threads of story.  It’s not operating to a formula you can really peg down yet nothing filler is being showcased and everything somehow is still properly paced.  Homer takes on the role of an incompetent blackjack dealer who everybody benefits from, Mr. Burns becomes a germaphobic recluse to the point of insanity as he monitors the casino, and Bart starts his own casino in the treehouse (even tricking Robert Goulet to attend).  Even little snippets of Abe taking too long at the craps table or Otto punching out a persistent greeter Gerry Cooney become unwasted comedic material in this exclusive one-time setting.

The most surprising and pressing storyline which becomes the core conflict is the gambling addiction that develops in Marge (which is a trait that’s seldom referred to in future episodes) and how the family and ultimately Lisa ends up suffering due to Marge’s oblivious neglect.  It’s unnerving and kind of heartbreaking as Lisa fails to get efficient help on her school project when Marge promised she would.  For a half hour that serves as a vehicle primarily for the comedic hijinks of the townspeople, Mr. Burns, Homer, Bart, etc., it still manages to tell an honest story for the family.  And not only does Marge never get home in time to help Lisa (a resolution that’s hilariously resolved by Skinner awarding her for clearly not having any help from a parent, despite the fact that Homer gave his best effort), but the episode ends just due to the fact that Homer confronts Marge on her gambling problem.  The show doesn’t need to give a resolution to her somehow overcoming it, because 1) that wasn’t the point of the episode, and 2) that’s not how life works anyway.  One of my favorite things in The Simpsons is how it never feels required to tie a neat little bow for an ending.  It can deliver the best storytelling in sitcom, but if push comes to shove, comedy many times takes precedent, and because of that, the show during its best years is a pioneer to the form in offering something different and unique every week.

4. “Sideshow Bob Roberts” (Season 6)

Even with “Sideshow Bob Roberts'” resolution leaning more on the convenient side, I can’t deny the highs the episode reaches in terms of its consistency and rate for intelligent satire (political or otherwise), dramatic build-up in story, the pure cinema to the animation direction, and of course Kelsey Grammer’s performance as Bob.  Back in the days when the writers didn’t need to depend on Bob’s homicidal urge to kill Bart Simpson, each episode before season 12’s “Day of the Jackanapes” offered something original, and in this case Bob is running for mayor which offers an epic, high-stakes playground of comic mischief.

I love how the show always includes a recap to who Sideshow Bob is without feeling like a big monkey-wrench was thrown to interrupt the flow of the script.  Instead it’s always done with theatrical sensation which helps set a necessary tone, while still using humor to precede and/or undercut it (“Oh…SideSHOW Bob!” – Homer).  The reveal of Bob’s voice on the radio as he rants to Birch Barlow plays as a neat ‘aha!’ introduction, and the smashcut to his current incarceration is a well-executed physical reveal.  Mayor Quimby’s echoed monologue of Bob’s granted release being pasted over the scene of the prison gates opening as Bob walks towards the screen ala Cape Fear is something I find more cinematically effective than the scene from the actual film.  The slow, eerie push-in to the establishing shot of Republican Headquarters is also one of my favorite exercises of tension and mood used in the show.

First and foremost though, the episode is thriving on laughs, and it succeeds ten-fold, such as Abe’s ramblings of owning the first radio in Springfield where the only broadcast is Edison reciting the alphabet, everyone at Republican HQ assuming the new mayor is a water cooler, or Birch Barlow setting Bob up for his thoughts on what Les Wynan has to say.  It feels like such an injustice to list funny moments, because for every one clumsily called attention to, I’m dismissing another five in the process.  Overall this is a Sideshow Bob show jam-packed with so much quality material, it needed to cut out the opening title sequence.  It stands the test of time for being an absurdist, political thrill ride despite how increasingly bizarre said climate for America today has become.

3. “Bart vs. Australia” (Season 6)

I don’t think anyone else could have made this episode up.  Not for lack of talent, but the key elements that keep this episode glued together are so absurd and obscure, the odds are astronomical in replicating it.  For one, it launches right out of the gate by taking something specifically learned and seemingly tedious knowledge as the coriolis effect, and turns it into a fun and inspired device to fuel sibling competition between Bart and Lisa.  Not only is it an important catalyst to spark the major conflict to the episode, but it also plays a hilariously subtle role throughout and surprisingly to the episode’s conclusion.  Then you have the target of Australia as a source for comedy.  Usually when other shows take relentless cracks at another country or place, it might be cooked up due to some heated political issue that’s going on or hones in on a certain satire that holds some bearing.  “Bart vs. Australia” however, is one of those rare examples that amps the riffing of a country up to 11 with either intentional exaggerations or just flat-out unapologetic inaccuracies, and it’s all the more remarkable for it.  Bart is the villain of this episode but his punishment is too bizarre for us not to root for him and the good ol’ U.S. of A to drag Australia through the mud.  The entire sequence in the courtroom is just peak comical genius.

2. “Sweet Seymour Skinner’s Baadasssss Song” (Season 5)

The series’ 100th episode is a down-to-earth, focused plot that takes advantage of Principal Skinner as a supporting character by respectfully highlighting his underlying humanity when he’s fired from Springfield Elementary and showcases his relationship with Bart from a completely different perspective, as well as sheds further light on his military background.  It’s a seamless balance of thoughtfully delivered story with punch after punch of smart, biting jokes from beginning to end.  The first act with Santa’s Little Helper being brought in for ‘show and tell’ (“I knew the dog before he came to class” – Milhouse)  and getting trapped in the air ducts is one of my favorite first acts in sitcom.  It’s just a treasure trove of elevated energy from the opening of The Wonder Years parody, to the lovable SLH stealing the show from Martin’s geode, to a greased up Willie tobogganing through the vents, all the way up to Skinner’s final hiccup as an act break.  To follow, you get the hilarious twist with the terrifying, no-nonsense Leopold introducing Ned Flanders as Skinner’s replacement, which in turn uses Ned to the highest possible potential before concluding his temporary stint as principal with Superintendent Chalmers’ classic quote, “God has no place within these walls! Just like facts have no place within organized religion!”

When it comes to emotion, the climax to me is provided with two, successive key moments.  The first is Skinner walking by the school at night before becoming enveloped with self-reflection as the educator that impacts the children’s lives whether they knew it or not, and vice-versa.  The next is the moment Bart shows up to his house to learn Skinner has re-enlisted in the United States Army.  I think the twinge I get from that is the shot of the letter itself that Agnes leaves Bart, which is written so formally, and presented with such surrender and weight to the point where it feels absolutely real.  This is the one episode where the cat and mouse between Skinner and Bart is stripped away and we witness a deeper bond formed between the two that otherwise can’t exist if things return to normal, which is a conflict in itself that pushes the viewer up against the wall.  It’s a special chemistry that is proven from here on out to exist under the surface.  The next chronological episode of season 5, “The Boy Who Knew Too Much”, however,  will remind the audience why ‘Skinner vs. Bart’ is a wonderfully iconic rivalry that has just as equal benefits.  Other than that, they’ll always have the laundromat.


1. “Who Shot Mr. Burns? (Part One)” (Season 6) & “Who Shot Mr. Burns? (Part Two)” (Season 7)

Spoilers to anyone who’s been living under a rock for the past 20 years.

I know I’m cheating for the sake of this list by including parts one and two together for the #1 spot, but I find it hard to talk about one without the other.  I would certainly advise to watch them together.  On its own though, Part One is my #1 pick regardless for best episode concocted by Bill and Josh.  Part Two is in an unfair position to be judged in my opinion because it’s meant to be falling action from the sheer intensity that Part One masterfully builds upon, although it still manages to explore the actual mystery to its fullest.  If I was to place Part Two somewhere on this list, it still would rank somewhere towards the top.  Sure, if Part Two came on tv, you can watch it standalone and still enjoy it (as if from Krusty’s perspective returning from Reno after six weeks) because you will still feel the repercussions and increased temperature that Part One sets up, but at the end of the day Part One is completely accessible and it’s borderline silly to not watch them together properly, as intended.

“Who Shot Mr. Burns?” is something I hold in high regard simply due to how much is being achieved at once.  As one of my favorite two-parters in sitcom alone, it transcends The Simpsons Movie (2007) for me in terms of being a celebratory climax to what the first 8 seasons and overall show excels best at.  Not only is Mr. Burns at his most destructive and evil than he’s ever been or ever will be, but it finally brings a longtime running gag of Burns never remembering Homer’s name and turns it into something very personal that will help drive the larger story at hand to peak, epic proportions. Other than that, it’s one of the most carefully crafted mysteries that takes advantage of its limited running time by rewarding you with a plethora of freeze-framed subliminal hints and thematic imagery.  So much thought went into the mysteries’ use of logical and technical clues to the point where it’s almost creepy how elaborate it is.  Beyond character M.O’s, the time on the clocks/sun dial and subtle visual information being shown in the background leading to the M.S/W.S theory still blows my mind in how many possible suspects still remain. The answer to the mystery is all there but only to the most keen viewer/fan who can think in and outside the box.  To this day, I’m still discovering more from clues in the episode’s layout.  On top of that, for an episode that sounds so complicated from a narrative and technical perspective, it’s effortless in being extraordinarily funny in nearly every scene.

Many characters come full circle during this episode and have their own threads of story that become painted into a corner by the time the shooter is revealed.  Whether you consider it a cop-out or not, Maggie as Mr. Burns’ shooter still changes the perspective of how you view the two of those characters being in the same room together in future episodes.  It’s forever iconic.  It’s also interesting how it almost plays like a bookend to David Mirkin’s showrunning era when you consider season 5’s aforementioned “Rosebud” which is an episode nearing the start of season 5 where Burns and Maggie cross paths over childhood teddy bear Bobo.  The bond that’s shared between them at “Rosebud’s” end compared to what transpires between them offscreen in the season 6 finale makes for a jarring contrast.  And the way Homer’s more internal conflict of getting on Burns’ radar culminates in him not only being one of the most likely, definitive suspects, but a payoff in humor as Burns can only seem to repeat his name upon waking from his hospital bed in the second part.  Even if Maggie was a safer (yet earned) choice for the shooter, it doesn’t take away from the dramatic payoff of Homer’s mind losing a circuit as he pulls the gun on a recovering Mr. Burns in front of the entire town.  For the portion of the audience that may have been disappointed with the mystery’s outcome, I still think it’s a scene that’s a widely overlooked substitute of giving the audience something darker as it serves as an incredibly shocking moment to push Homer to that point.

Chief Wiggum, who’s tasked with a case that’s perhaps too difficult for him to crack still ends up displaying a surprising amount of competence amidst his stupidity in the effort of solving it.  Lisa too, who’s desperate to take a stab at the case and later rectify her dad of the accusations against him, manages to prove successful in getting one step closer to the truth.  The breakdown of Smithers after being fired and the wedge that’s driven between him and Burns is also a series first, especially as he develops into one of the lead suspects.  Grampa, who’s retirement home was destroyed, gets good mileage from the story as a recurring red herring up until the very end.  It’s nice to see Abe get a bit of a spotlight in the last episode Oakley & Weinstein ever wrote, considering how much fun and favorability they’ve always held towards his character from the start.

Part One alone has an unnerving energy to it from the very beginning.  You can feel that something’s up about this episode as it feels on edge from the moment Skinner discovers the death of the class gerbil Superdude, and through the acceleration of the plot as soon as Willie strikes oil.  Even the bright, quickly paced sequence of Burns and staff going through the process of sending the parcel to Pete Porter in Pasadena establishes the classic, unmatched comedic swiftness that “Who Shot Mr. Burns? (Parts One & Two)” is about to undertake.  By the time the drama in Springfield accumulates from the aftermath of Burns’ Slant-Drilling Co., you almost forget that this is also ‘the one where he blocks out the sun’, a demonstration in the very surreal flexibility the show is capable of without breaking the constructs it abides to.  Smithers puts it best:

Dr. Colossus is an obscure callback to his brief mention in “Lisa vs. Malibu Stacy”.  Leopold, another character conceived by Bill and Josh from “Sweet Seymour Skinner’s Baadasssss Song” is also showcased here.  In fact, there’s a number of celebrated dig-ups like Principal Dondelinger or Dave Shutton throughout both parts that helps provide a sense of scope and nostalgia for the world of Springfield (along with the candy box recap for Burns’ relation to Maggie, Bart, and SLH) as shit begins to escalate.  Even Shelbyville, which was already recently delved into a few episodes prior in Season 6’s “Lemon of Troy” gets hilariously referenced as the entire town gets crushed when Springfield’s residents tear down Burn’s sun blocking machine.

I don’t know whether the #1 entry in this list is extra long due to the covering of a two-part episode, whether I’m just passionate in my appreciation for it, or if I just don’t know how to end this write-up, but overall “Who Shot Mr. Burns? (Part One)” and “Who Shot Mr. Burns? (Part Two)” are both among the series’ best and a testament to why I love the show in general.  Bill Oakley and Josh Weinstein are among my favorite writer-pairings for a half hour comedy, so I figured it would be fun writing exercise to share my thoughts on their work.  While it’s still wise to consider what showrunners Al Jean & Mike Reiss, and David Mirkin contributed to Oakley & Weinstein’s scripts, you could still feel how quickly they mastered their craft when you watch these 11 episodes in chronological order.  Keep in mind, my ranking of these episodes are just my opinion, which is always subject to change.  Anyway, what do you think?  Do you have a favorite? How would you rank these episodes?

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