The Story Behind The Best Episode Of The Simpsons, A Conan O'Brien Masterpiece

In 1993's episode of "The Simpsons", Marge vs. the Monorail," corrupt nuclear power plant owner Mr. Burns (Harry Shearer) is exposed for stuffing toxic waste into trees at his local park and thereby giving squirrels eyeball lasers that sprout tentacles and grow tentacles as part of his plan to commit ecological desecration. As punishment, Mr. Burns is fined $3 Million which he just so happens to have in his wallet. Springfield then convenes a Town Meeting to decide how it should be spent. Marge Simpson (Julie Kavner) suggests using their money to repair Main Street, but Lyle Lanley (Phil Hartman), an unknown man with great charm who claims he knows everything, disrupts her plan by performing a "Music Man"-esque musical number to convince Springfield to spend it on building himself a monorail system instead.
Lanley is clearly a con man, peddling substandard monorails to unsuspecting cities before quickly leaving before his low-rent transportation breaks down and causes chaos. When his old targets fail, "Marge vs. the Monorail" was hilarious and odd but came at a time when "The Simpsons" was truly on top form - recently declared by /Film as their favorite episode overall! That is an impressive accomplishment considering this mark was reached nearly 2,145 episodes ago!

"Marge vs. the Monorail" was written by Conan O'Brien while Rich Moore had extensive animation experience and served as director. Vice interviewed both creators in 2020 to gain more insight into its creation process as well as discover where its initial inspiration had originated.

Where did this bizarre concept originate? While a con man defrauding Springfield of millions may make for an interesting "Simpsons" tale, why a monorail? "Marge Vs. the Monorail" appears to have taken inspiration from "The Music Man." Was Conan O'Brien fond of the structure or simply liked how the episode played out? According to showrunner Mike Reiss, O'Brien was still relatively unknown on the show at this time and proposed this entire episode himself. Reiss and co-showrunner Al Jean were skeptical when O'Brien pitched three script ideas during a special writers' retreat hosted by Reiss and Al Jean; they worried that show creator Matt Groening and executive producer James L. Brooks wouldn't approve; in reality they loved what O'Brien presented and Reiss recalls that O'Brien managed to pitch three different ones successfully during that session!

Josh Weinstein recalls O'Brien as being always energetic and "up." Working with Conan was like watching an episode of his show every day in the writers' room; all other writers are hilarious but most tend to remain private and reserved, while Conan was often outgoing and out there.

O'Brien took sole credit for creating "Music Man." According to producer Jeff Martin in Vice's oral history series, O'Brien provided lyrics while it was Martin's responsibility to turn them into songs:

"Conan's original monorail song remains virtually unchanged from my first draft. Back then, my specialty on the show was actually writing tunes to accompany songs; so after writing several, I was assigned the task of setting this particular monorail tune to music - sort of an exuberant rhythmic track that goes: 'Bum! Bum! Bum. Done!'"

Mono - D'oh!
Comparing the fourth season of "The Simpsons" to its initial one reveals an abrupt shift in tone. At first, "The Simpsons" served as a parody of all-American sitcoms; Homer (Dan Castellaneta) began out as an average blue-collar father who worried that his family were also below average and often preoccupied himself with traditional suburban traditions like saying grace at dinner and drinking milkshakes together as a family. But eventually Homer degenerated into an off-beat individual with only vague perception of reality surrounding him; Springfield transformed from being "average all American town" into filthy tilted universe reminiscent of Twilight Zone-esque levels of reality just nearby.

"Marge vs. the Monorail" features an incredible fantasy sequence in which Principal Skinner (Shearer) is attacked by giant mechanical ants - something not typically found in earlier seasons of the show. At the end of this episode, special guest star Leonard Nimoy broke all laws of physics for an unprecedented act on TV; Reiss recalls this shift by noting:

"The show had begun its gradual descent into surrealism. At the end of an episode in which Leonard Nimoy beamed out like in Star Trek, Jeff Martin said he thought: 'Well, that must mean "The Simpsons" has decided it can break physical laws' It wasn't intentional at first; Al Jean and I simply wanted laughs; to achieve that end goal it needed to grow bigger and weirder all of the time."

They followed their hearts, which ultimately lead them down an unusual and unconventional path.

Phil Hartman stands out as an exceptional individual.

According to everyone interviewed for Vice's piece on Phil Hartman, he was an absolute pro - nailing every line on first read and being an absolute delight to work with. Showrunners noted his upbeat nature - often coming across like one of his characters even when not recording booth. While animators took physical cues from Robert Preston's character from "The Music Man," in order to avoid overshadowing Hartman with Lyle Lanley. By the time "Marge Vs the Monorail" premiered he had already made 14 appearances as Lionel Hutz as well as Troy McClure among several other characters as well.

As the article noted, Marge vs. the Monorail was one of the earliest instances where Springfield began emerging as its own character. There may be hundreds of characters on the show, but when all assembled at once it becomes one big ignorant and easily manipulatable mass. Jeff Martin noted this phenomenon.

Mindless groupthink is a common feature on The Simpsons, and I find the monorail episode particularly telling in terms of Springfield mob mentality. While watching this episode, I decided to time it: from Lanley whistling in the back row of an auditorium all the way to everyone marching and singing "Monorail!" on Town Hall steps is just under two minutes, although Harold Hill likely took at least four to whip up River City."

My friends and I ran into trouble.


At the conclusion of "Marge Vs. the Monorail," the monorail breaks down on its inaugural voyage, sending its engines into overdrive and its brakes into failure. As Homer attempts to manage it all from his driver seat, Homer must reach out his window, pull an "M" symbol from its exterior ("M" stands for monorail), and use it as an anchor to slow the vehicle; unfortunately this results in cutting through one of Springfield's oldest trees as well as doing significant other damage.

Rich Moore believes the reason so many viewers relate to "Marge vs. the Monorail," particularly on an aesthetic level, lies with its cinematic elements. There were new settings and scenarios never before seen on "The Simpsons," similar to an Irwin Allen disaster movie of that period; Moore felt this added a level of sophistication to the episode that helped it stand out amongst competitors. Moore had to piece together shots on an extremely tight timeline and was grateful that everything came together so smoothly:

"It was all done through coverage; scenes were shot out of order. As there wasn't much time up front before animation started, guesswork played an integral part. Since there wasn't much preparation time before beginning animation, letting go and trusting that creating these shots will yield something worthwhile was essential to producing worthwhile results at the back end."

"The Simpsons" continued its journey of increasing weirdness after this episode and was consistently hilarious for years afterwards. A common refrain among fans of "The Simpsons" is "it hasn't been good since season [blank]." Everyone can agree, however, that season 4 was one of its finest periods.




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