I’m So Jealous You Get To See ‘The Simpsons’ Monorail Song For The First Time

Bustle's I'm So Jealous series is dedicated to the books, TV shows, movies, podcasts, and more that super fans are so jealous someone else gets to experience for the first time. In this installment, Danielle Burgos writes about the classic Simpsons musical number, The Monorail Song.

As someone barely falls into the millennial generation, I was the perfect audience for The Simpsons' first decade on television. As a result, there's nothing I love more than endlessly re-quoting my favorite moments to a barely tolerant audience. And I'm so jealous of anyone experiencing the Monorail song from The Simpsons for the first time, because it's a quintessential moment, when the entire town of Springfield gets swept up in a mass-transit musical number.

"Marge Vs. The Monorail" premiered in 1993, but it wasn't until decades later that great moments burnished by reruns and reiteration shone forth as truly polished gems. (Think "Stupid, sexy Flanders.") By then, the show was past its early punk years of anarchic jabs peppered with lower-class melancholy, past its zanier years helmed Conan O'Brian, the very guy who penned this episode, and heading into what many fans term the "zombie Simpsons" phase — a corpse vaguely resembling the thing you used to love — which is where it remains. Ah, too late we realized the perfection that was.

But this isn't lament of a show past its prime, it's a celebration of its apex! From the moment that con-man Lyle Lanley (voiced by the late, great Phil Hartman) tells a packed Town Hall meeting "it's more of a Shelbyville idea," you're only a few short steps to getting as swept up in monorail-fever as the town of Springfield.

I'm extremely adverse to theater, especially musical theater, mostly due to difficulty suspending disbelief. It's not the artists' fault, but I feel disingenuous pretending people on stage are in the 16th century or whatever when they're right there in front of you. Right there! Throw in songs on top of it, and the artifice leaves me completely cold. Yet, somehow when it comes to the same elements in an animated show, everything reconciles. It's probably the double-removal from real life afforded cartoons, or as was told to Homer when he asked if Itchy and Scratchy was going out live:

The Monorail song, and the entire episode really, spoofs 1958 musical The Music Man, about a con-man who swindles small towns into buying band instruments and uniforms that don't exist. It's also a small lesson in infrastructure and the real reason cons work.

Lisa: Why build a monorail in a small town with a centralized population around a town center?

Lanley: I could answer that question for you, but you and I would be the only ones here who would understand the answer. (leans in) And that includes your teacher!

Flattery will get you everywhere, and it's easy to understand how Springfield gets swept up in Lanley's patter when you're experiencing the pure, dumb joy of the full-on musical number/commentary on corruption in political infrastructure yourself. The song also works as meta-commentary on the bizarreness of musical interludes, something I relate to, especially when Marge tries bringing things back to reality.

Marge: "I still think we should have used that money to fix Main Street!"

Homer: "Well you should've written a song, like that guy."

For a show that was still, at the time, freaking out the squarest conservatives — CNBC notes George Bush derided the show just a year before — seeing The Simpsons tackle the extremely square '50s at their squarest and turning it around completely is a delight. And I haven't even gotten into the episode's Leonard Nimoy cameo, Homer's brief stint as monorail captain, or the survey of Springfield's other foolish purchases.

Keep your eyes peeled and ears open: There's a lot to take in, from Abe's cranky query to the incompetent Chief Wiggum's pudding non sequitur. In the 90-second musical moment, nearly every minor Simpsons character gets a chance to shine, even extremely obscure fan favorites Princess Kashmir, Richie Sakai (based on actual Simpsons producer Richard Sakai), and paranoid veteran Herman Hermann.

If you need more Simpsons production numbers: Look for Disney spoofs ("See My Vest"), '60s swing (actually getting Tony Bennett to sing "Capital City," Robert Goulet covering "Jingle Bells, Batman Smells"), truly bizarre pop-culture mashups (Mark Hamill singing "Luke Be A Jedi Tonight", turning German popstar Falco's "Amadeus" into an ode to Planet Of The Apes' "Dr. Zaius"), and Michael Jackson-penned sweetness ("Happy Birthday Lisa").

And if you're overwhelmed by choice and years of history: Choo-choo-choose whichever one you want, you won't be disappointed.