Conan O’Brien.  SNL writer.  Simpsons writer.  Late night talk show host.  Here I present you with the three solo-credit episodes that Conan wrote for The Simpsons, ranked.  The #1 choice was actually physically in the process of being written as Conan learned that David Letterman would need a replacement on “Late Night”.  Any Simpsons writer will tell you that Conan was destined to perform for a studio audience as he would be telling jokes and putting on a show for everyone in the writers room 24/7 without them ever asking for it.  Even if the janitor walked by as Conan worked late at night in his office, he would follow the man down the hallway just to perform some more!  You can tune into TBS and watch him on Conan currently on its 7th year running.  Enjoy!

 

3. “New Kid on the Block” (Season 4)

“New Kid on the Block” bids farewell to the seldom seen, crabby elder couple (Mr. and Mrs. Winfield) who lived on Evergreen Terrace and introduces new neighbors Ruth Powers (who will become a recurring character, most prominently known for season 5’s brilliant “Marge on the Lam”) and young teenage daughter Laura Powers voiced by Sara Gilbert (Roseanne).  Ruth is a newly divorced single mother.  Very no-nonsense yet easy-going who is looking to get back into the dating game, or in the very least to casually grab a beer at Moes and effortlessly ease herself into Springfield’s universe.  Laura is her polite daughter (which she cheekily and optimistically owes to a painful upbringing) who owns up to a sense of wit and edge that Bart will eventually become absolutely enamored by.  One of  the many great aspects to The Simpsons is that beyond the regulars, they have a deep bench of extraordinary one or two-time characters which become instantly three-dimensional, layered and more human than most live-action characters in sitcom.

The most impressive thing being achieved in this episode, especially coming from Conan, is how specifically nuanced it is in tackling an honest story of a 10 year old boy’s first crush.  The manner in which the episode establishes Laura Powers as a more mature, positive role-model and a well-intended, genuine friend to Bart, only for him to be gutted (as shown below) when he learns of the misguided, rebellious passion she harbors for Bart’s school bully, Jimbo Jones, is daringly crushing.  Bart’s innocent kid fantasy of having Laura babysit him doesn’t shy away from becoming a nightmare as Jimbo (or ‘Dr. Tongue’) comes over to “study”.  The earlier moment of her mocking Kearney and Dolph in the beginning of the episode leads Bart to believe Laura is special, which makes it all the more disappointing to him when she reveals to have taken a strong, shallow liking to the one bully who was absent from the initial scene presented above.

It’s unforgivingly conflicting territory, yet what I love is that Laura is not an antagonist out to hurt Bart and what makes her character great to begin with, isn’t being sacrificed.  She’s just as much an innocent kid/teenager who’s also just naturally trying to maneuver the terrain that comes with growing up and ultimately (without taking pity upon him) she still considers the incredible chemistry and uniquely platonic relationship with Bart to be very important.  It’s a very in-depth, carefully executed story that although is tough from Bart’s perspective, still remains quite endearing and sweet throughout. It concludes in the most satisfying, yet extremely unconventional circumstance by taking Bart’s long-running prank phone calls to Moe and using it as an important story-point to frame Jimbo.  After Laura witnesses her boyfriend’s cowardice when begging to not be murdered by Moe (something of which is hilariously unfair to be judged for) , she realizes Bart was right about him all along.  It’s a happy ending appropriately summed up by Bart: “As usual, a knife-wielding maniac has shown us the way.”

In order for the babysitting aspect to work in the main plot, Homer and Marge needed to be out of the house, so we end up with a more lighthearted and humor-driven subplot that involves Homer getting kicked out of The Frying Dutchman, the all-you-can-eat seafood restaurant.  It introduces the now long-time Springfield resident, Captain McCallister (aka ‘The Sea Captain’), an original Conan creation, while also giving the late, great Phil Hartman a chance to stretch his comedic legs as Lionel Hutz.

2. “Marge vs. The Monorail” (Season 4)

The monorail episode is without a doubt one of the more notorious installments the show ever produced and one that is most highly associated with Conan to this day.  It opened the floodgates to the absolute bizarre and holds the early secret to what made The Simpsons able to do whatever the hell it wants week to week without ripping the fabric of space-time within the original qualitative run of the show.  However, it was met with criticism by the nerdiest of the nerds who knew how to use the internet back in 1993, and to be fair, there was reasonable cause for concern, even among the writing staff and cast back when the episode had been produced.

For one, the story in certain parts makes no sense whatsoever.  In fact, for an episode with such a high concept premise, there’s really no complex story going on at all, but instead is 22 minutes of a runaway gags and allowing the characters to just naturally react to the absurdity that takes place.  A show that in the first two seasons had taken the archaic portrayal of the American nuclear family and flipped it on its head, as well as successfully mastering the traditional humanist sitcom genre in general (brushing shoulders with Cheers, The Cosby Show, etc.), was now doing a disaster movie story with wacky, surrealistic humor.  A risky move for any primetime animated show that’s trying to stand apart from ‘just a cartoon’, let alone one that influenced the ones you see today.  In short, “Marge vs. The Monorail” is a fun and epic gag-driven extravaganza with a basic through-line technique to make it all work, being…

F*$# the story!

The humor of this episode derives solely from the fact that the story isn’t being taken seriously.  There’s no reason for Marge to have some great revelation that Lyle Lanley is a scamming trickster because it’s obvious as soon as he makes his classic ‘song and dance’ pitch at town hall.  It’s hysterical though that the one clue that does tip her off about him is when she comes across his notebook left out in the open which consists of obvious, overly-specific drawings of him leaving for Tahiti with wads of cash while the monorail crashes and burns with people screaming in agony.  It makes no sense how an angry mob knows that Lanley is on a plane making a spontaneous, brief layover in North Haverbrook, let alone calling out his specific seat number from the ground, but it’s funny.  This is an episode that proved that as long as you keep your characters intact and have a lot of great jokes in the bag, then you can get away with any loose, wacky premise.  It’s something that will easily fail if you can’t maintain those elements, which later Simpsons and other tv shows will find out the hard way.

For me, like many great Simpsons episodes, the actual story that’s going on is purely conceptual.  It all boils down to the Simpsons universe being at odds with itself.  The monorail is the episode itself, being this unusual and unstoppably surreal event, while Lyle Lanley is the episode’s writer (strikingly similar-looking to Conan) who has cut corners and structured the episode with an intentionally careless logic, but man is he lovable, funny and great at performance (thanks to the always brilliant Phil Hartman) in order to allow him to get away with it.  That leaves North Haverbrook and Springfield to represent the polarization within the audience.  For the former, the train or episode ended up in complete disaster (a clear failure) and we’re satisfied as Lanley at least gets his comeuppance for being responsible, yet for Springfield, we get to enjoy all the characters’ antics throughout as they endure the wrath of the show being pushed to the limit.  We root for them as they attempt to apply logical solutions to an illogical problem.

Sebastian Cobb’s final idea is to find an anchor of some sort.  Something that can bring the monorail to a stop, and thus the episode back down to earth.  This conclusion works on so many levels.  The manner in which Homer creates an anchor is a compromise between inspired (letter ‘M’ on the side of train) and convenient as he retrieves a rope from a random never-before-seen (and never seen again) cowboy spinning a lasso.  This results in this “anchor” being successful in stopping the train, but doing the opposite of its intention as it becomes an opportunity for more over-the-top, surreal gags like the world’s tallest tree falling on the birthplace of Jebediah Springfield followed by a nonsensical explosion, or an abstract joke of conjoined twins getting cut in half, and even Leonard Nimoy beaming himself out of the episode claiming “my work is done here”.

The anchor ripping across the street could have easily used the many potholes that were previously established on Main St. as the thing to hook on to, bringing the episode into a full circle but that would have been antithetical to what “Marge vs. The Monorail” offered best.  Entertainment derived from nonsense.  Therefore, the episode invites deus ex machina by letting a random giant donut be the thing that saves the day.  A simple symbol of joyous imperfection, casual enjoyment and the celebrated laziness of modern America that our leading conductor Homer resonates with strictly through the heart of his character.  While there were a handful of episodes from season 3 onward that already began challenging the flexibility of what the show can do creatively, “Monorail” is one that certainly blew the door wide open.

 

1. “Homer Goes to College” (Season 5)

“Homer Goes to College” vs. “Marge vs. the Monorail” is a toss-up, but I chose to go with the former as my #1 due to its clever, grounded premise that in turn is inventive with the conventions of episodic storytelling within the half-hour format, and personally edges to belt the most laughs out of me.  After Homer is deemed unqualified as safety inspector by the Nuclear Regulatory Commission, he is given the chance to get himself up to speed by taking a college course in Nuclear Physics.  Simple enough idea, but what makes it great is how Homer approaches the situation with a cliched, stereotypical perspective of college life (perfectly showcased below), ala Animal House or knock-off movies of the like.

In reality, the dean is super cool and laid back, the professor is well-meaning and reasonably helpful, and all the students are sincere in getting their education.  Homer however is completely oblivious to this throughout and applies a rebellious and juvenile stance to the entire experience.  It’s an absolutely hilarious and subtle satire on campus life that doesn’t rely on the softball material of portraying it as an ultra politically correct atmosphere like you see a lot more recently in shows today.  And yet, “Homer Goes to College” manages to paint Homer in an obviously misguided light while somehow still allowing the observational jabs towards the college’s culture to feel rightly deserved.

This is one of the more jerkier episodes for Homer in the classic era (which becomes a very dangerous, recurring trait for his character during Mike Scully’s time as showrunner in seasons 9-12), but he’s still lovable here and put to good use as he’s completely unaware of how destructive his behavior is by continuing to entertain his innocently out-of-touch ‘school sucks’ outlook.  I can’t stress enough how much I die of laughter when Homer apologizes to the dean for his ‘running him over with his car’ prank (which was something he never even planned to do) or how some unrelated children’s hospital won’t be built now just because Homer swiped six cinder blocks from a construction site in order to have a cool, makeshift bookcase for his “dorm”.

The episode becomes more about Homer ironically becoming friends with nerds to help engage in his zany schemes (nerd: “why does it have to be zany?”) and then ultimately attempting to redeem himself when they end up getting expelled.  By the time the issue is resolved lulling you into feeling the episode has concluded, you forget the whole point of Homer in college to begin with is so he could keep his job.  It’s what makes this following scene so perfect:

This is one of the many reasons why I love The Simpsons.  With the meat of the plot over and done with, the episode is tasked in the final remaining minutes to wrap things up, so instead of using the usual sitcom tropes to accomplish that, the writers (and namely Conan in this instance) encourage themselves to take this as an opportunity to defy audience expectations and stick it to the status quo.  After this, the nerds suggest that they change the grade with a computer, despite the moral implications it will raise, but Homer is completely indifferent and does it anyway.

Marge: “An A+! How did you do it?”

Homer: “Heh-heh, let’s just say I had help from a little magic box.”

Marge: “You changed you grade with a computer?”

Homer: “D’oh!”

Finally, with close to 30 seconds left, Homer tries to clumsily determine the lesson learned in all of this to no success and just when you think the show is going to let Homer’s sloth and ignorance triumph, he’s advised by Marge that if he is to set a perfect example for his children, he’ll go back and retake that test.  It’s all you need to feel satisfied in terms of the characters staying true to themselves without feeling required to tie a neat bow on an ending before the credits roll, while also being a fine demonstration of the show knowing how to balance ironic comedic edge with a sense of taste and sincerity.  In its best years the show is unafraid to do either simply because it knows how to do both very well.

Anyway, those are the three episodes Conan wrote solo (sorry “Treehouse of Horror IV”).  Coincidentally, my rankings match the chronological order in which they aired.  They’re all great and I wouldn’t bat an eye at anyone who ranks them differently.  Go watch them now!