Believe it or not, there is an entire strata of civilians walking among us for whom the word “monorail” does not immediately evoke a steady chant and a simple piano lick.
Through 34 seasons and counting, The Simpsons has outgrown the simple classification of “comedy show” and exists more as an entity exerting its influence over the entirety of entertainment. Comedy fans who grew up in the 1990s likely still remember the channel and time slot when new Simpsons episodes graced the airwaves — as well as the after-school hours when one could catch a rerun of classic episodes like “Last Exit to Springfield” or the aforementioned “Marge vs. The Monorail.”
Still, just as everyone at some point listens to The Beatles for the first time, every comedy fan must, at some point, lose their Simpsons virginity. And, in order to make a future Simpsons fan’s first time special, anyone introducing someone to the series would do best to pick a specific episode that exemplifies the humor and storytelling better than whatever airs Sunday nights on Fox nowadays.
Over in the Simpsons subreddit, the superfans recently debated which episode is the best gateway drug to hook a fan for life. Here are their top picks…
“Itchy & Scratchy Land,” Season 6, Episode 4
For anyone unfamiliar with the family dynamics of the show’s title characters, “Itchy & Scratchy Land” will give them a crash course on how the Simpsons family operates. Bart’s mischief, Homer’s irresponsibility, Lisa’s voice-of-reason-ness and Marge’s Tipper Gore-esque pearl-clutching are all on full display when the clan takes their best vacation ever while battling killer robots.
“Marge vs. The Monorail,” Season 4, Episode 12
Containing arguably the greatest utilization of original music in the show’s early history, “Marge vs. The Monoral” does the best job of blending The Simpsons’ grounded characters with the writes’ ability to, quite literally, go way off the rails. This episode shows Phil Hartman at his absolute best doing his best Harold Hill impression, and the blending of high-stakes drama and sheer pageantry provides the best pure entertainment value of any episode on this list.
“Mr. Plow,” Season 4, Episode 9
This episode can make a Simpsons nonbeliever singing the line, “I’m Mr. Plow, that’s my name! That name again is Mr. Plow,” for the rest of the day in 30 minutes flat. In terms of iconic-jokes-per-minute, there are few episodes that match “Mr. Plow’s” sheer density of memorable punchlines. Also, the episode has some of the best examples of The Simpsons using guest stars to their weirdest potential — how many other shows can say they had Adam West utter a line like, “How come Batman doesn’t dance anymore?”
“Last Exit to Springfield,” Season 4, Episode 17
As one of the most critically acclaimed episodes in Simpsons history, there’s not much new to be said about “Last Exit to Springfield’s” greatness, but if you find a friend who’s never seen it, you vicariously experience it for the first time through them. The episode is as timeless as the struggle between Labor and Capital, and it would introduce the power dynamics at play in Springfield to a new audience better than most. Plus, it actually shows Homer being a good father, which becomes more and more uncommon as the series progresses.
“Lemon of Troy,” Season 6, Episode 24
In recent decades, The Simpsons has moved away from the small-town tribulations that first made us fall in love with the denizens of Springfield in favor of celebrity cameos and crazy, maximalist plot threads. However, The Simpsons is at its best when it concentrates on its emotional core — the acrimony between Springfield and those cousin-lovers over in Shelbyville. Watching the disparate groups of Springfield Elementary band together to reclaim their town’s prized lemon tree gave us some of the most inspiring moments of the series as well as many of its best lines — like, “Wait a minute, there’s a lemon behind that rock!”
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