I’m sure few people will think I’m overstating things when I say that this is not only one of the greatest episodes of The Simpsons, it’s one of the greatest episodes of any half-hour sitcom ever made. By my weak categorisation, this is one of the major satirical episodes; it begins with Burns being busted for improperly disposing of toxic waste, and the town is convinced to invest the three million dollar fine into a monorail by old-fashioned huckster Lyle Lanley.

(Love the detail that Burns’ fine barely bothers him)

The show has dealt with Homer’s susceptibility to salesmen, and it’s dealt with mob mentality, but this is the first time its combined the two ideas. Lyle is obviously exaggerated for comic effect, but his flashy style and ability to flatter everyone he meets – up to and including Lisa, our usual voice of reason and morality – draws on the same things real life shysters use. You see Lyle tell Lisa only she and him would understand the need for a monorail, and you see the ads promising one weird trick that doctors HATE; we’ve all seen crowds of people trip over each other to praise The New Thing and might as well be chanting ‘monorail’. Part of growing up for me was discovering just how much the world does work like The Simpsons.

It’s the kind of story that Marge, surprisingly, thrives in. She’s not a wet blanket here, she’s a protagonist trying to prevent disaster. It also helps that her squarish details are as perfectly chosen as any of the absurd ones – fixing Main Street is exactly the kind of necessary, boring work I associate with Marge, and it makes sense that the town would spend the money on something way cooler. You strip out the absurdity, the satire, the character work, and what you have is actually a fairly competent disaster story – the town comes into a windfall, Lyle Lanley convinces them to buy a monorail, Marge investigates and discovers disaster is looming, and she has to rush to save the day.
This plot acts as a way to generate absurdity – to illustrate Main Street’s disrepair, we cut to an exploding popcorn van (love the little ‘whoa!’ as the truck falls in), Mr Snrub’s attempt to get his money back is brilliant (“Yes, that will do.”), and my biggest laugh is the most hilariously lazy reason for ‘we’re too late’ I’ve ever seen.

If there are three main parts to The Simpsons – the warm heart, the satirical brain, and the absurdity – then I would suggest it’s the absurdity that had the most influence, on other shows as well as the broader culture, and if any single episode is responsible for that, it’s this one.

Chalkboard Gag: I will not eat things for money.
Couch Gag: The family sit, only for the room to fill with other Springfieldians.
This episode was written by Conan O’Brien and directed by Rich Moore. The episode was inspired by O’Brien seeing a sign that simply said “monorail” and nothing else. I open the floor to comparisons between O’Brien absurdity and Swartzwelder absurdity.

I genuinely don’t understand how “I’ll just amuse myself with these pornographic playing cards,” didn’t enter the vernacular. “I call the big one Bitey,” is Matt Groening’s favourite line of all time.

The episode is partially a parody of The Music Man, with Lyle being a visual reference to Harold Hill. The episode opens with a Flintstones reference. Leonard Nimoy guests as himself, with multiple Star Trek references. A parody of Luke Perry appears. Homer’s conductor uniform inexplicably references Star Wars. Mr Burns is restrainted in court the same way Hannibal Lecter was in Silence of the Lambs.
First Appearances: N/A
Biggest Laugh: