15 Essential Episodes of The Simpsons

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Where to Begin with The Simpsons

Cape Feare
Sideshow Bob comes for Bart. Fox, Screencap via Simpsons Wiki

I believe every episode of The Simpsons is worth watching, but if you somehow have never seen any and you're just starting to watch now, these are the must-see episodes. If you start with these essential Simpsons episodes, either when they run on FXX or if you get the DVDs, these will show you why The Simpsons are so brilliant they have lasted since 1989. These episodes are examples of The Simpsons working on multiple levels, doing many things in a single story. Or, some can simply be a large collection of iconic Simpsons moments. I’m sure I left out some greats, and we’ll get to them too, but these are the episodes you can talk to any Simpsons fan about and we’ll all know what you’re talking about.  Once you watch these, you’ll need to see more! Luckily you have 600+ to choose from.

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Mr. Plow (Season 4, Episode 9)

Mr. Plow
"Call Mr. Plow, that's the name. The name again is Mr. Plow.". Fox, Screencap via AVClub

The Mr. Plow jingle is what everyone remembers decades later. “Call Mr. Plow, that’s the name. The name again is Mr. Plow.” Homer would go on to have many more outlandish jobs outside the nuclear power plant but everyone remembers him driving a snow plow. Then Barney steals his thunder with a bigger plow, Plow King, and launches attack ads on Homer. There’s a great montage where Homer plows several locations only to have much worse than snow hit them, and Marge gets frisky when she sees the Mr. Plow jacket. You’ll see that jacket again in later episodes.  

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Stark Raving Dad (Season 3, Episode 1)

Michael Jackson with Bart and Lisa
"Lisa it's your birthday, Happy birthday, Lisa". Fox, screencap via AV Club

Everyone remembers this as the Michael Jackson episode, and that’s a very good reason to remember it, but “Stark Raving Dad” has something to say too. Homer is committed to a mental institution for wearing a pink shirt instead of the standard white. It’s only because the shirt was washed with Bart’s red hat, but what a clear statement about enforcing conformity. In the  institution, Homer meets a man who says he’s Michael Jackson (Jackson, using an alias), and Homer doesn’t know any better. So when he comes home promising to bring MJ with him, the town is disappointed. But the fake Jackson helps Bart compose a birthday song for Lisa, and the classic “Lisa It’s Your Birthday” is born.  

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Itchy and Scratchy Land (Season 6, Episode 4)

Itchy Lot
"Remember, we're in the Itchy lot.". Fox, Screencap via Reddit

Real families go to Disneyland, but in Springfield the big theme park is based on their favorite violent cartoon, Itchy and Scratchy. So ensues a vicious satire of what theme parks had come to represent in the ‘90s, and could probably stand an update today. From the non-helpful parking reminders to the Westworld-style animatronic robot uprising and the Disneyland-esque underground tunnels, “Itchy and Scratchy Land” feels our pain. 

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Who Shot Mr. Burns? (Season 6, Episode 25/Season 7, Episode 1)

Who Shot Mr. Burns?
Who Shot Mr. Burns?. Fox, Screencap via AV Club

This two-parter was a landmark for The Simpsons. Not only did they get to spoof the TV classic “Who Shot J.R.” mystery from Dallas, but they got to engage the viewers in a summer-long mystery and finally give Mr. Burns some consequences for all the horrible things he’s done. The resolution of the mystery still provokes debate today, and in later episodes, Lisa would say that Smithers would’ve made a lot more sense than Maggie. Spoiler Alert: Burns lives, by the way. 

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Lisa Vs. Malibu Stacy (Season 5, Episode 14)

Lisa Lionheart Doll
Lisa Lionheart reaches exactly one little girl. Fox, Screencap via Frinkiac

Lisa makes a stand for feminism and The Simpsons skewer the toy industry when a talking edition of the fake Barbie clone only says demeaning things like “Don’t ask me, I’m just a girl.” Lisa finds the creator of Malibu Stacy and creates her own empowering doll, but feminism is no match for the mass marketing of Malibu Stacy. This episode came out when the hoopla about Barbie’s unrealistic appearance was just starting to be voiced, and look how long it took for Mattel to create alternate Barbies. The Simpsons were ahead of the curve on that, but still knew enough to show that any victory was likely small and fleeting. Lisa still fights the good fight today. 

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Marge Vs. The Monorail (Season 4, Episode 12)

The Springfield Monorail
The Springfield Monorail. Fox, Screencap via Genius.com

This episode is mostly memorable for the monorail song, led by huckster Lyle Lanley (Phil Hartman). Conan O’Brien wrote this episode and later performed the monorail song at the Hollywood Bowl, that’s how big it is. But this episode also opens with Homer doing the Flintstones opening! It concludes with guest star Leonard Nimoy riding the disastrous monorail with Homer conducting. At the red carpet opening, you also get to see a broken down Lurlene Lumpkin, sans the voice of Beverly D’Angelo. 

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Deep Space Homer (Season 5, Episode 15)

Homer in Space
"They'll clog the instruments!". Fox, Screencap via Simpsons World

Among the many outlandish jobs Homer has taken part time, the most outlandish is probably astronaut. NASA decides to send a regular joe up into space to get the public caring about space travel again. Homer competes with Barney for the position, and eventually gets it by default. This gives The Simpsons a chance to spoof The Right Stuff and 2001 while letting Homer bumble around in zero gravity. To show you how far The Simpsons can take a random joke, when an ant farm gets lose, newscaster Kent Brockman infers that space ants are coming to enslave humanity. He does an entire editorial on the spot complete with graphics and the conclusion: “I for one welcome our insect overlords.” 

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Lisa the Vegetarian (Season 7, Episode 5)

Meat and You: Partners in Freedom
Troy McClure hosts a meat propaganda video. Fox, Screencap via Frinkiac

This was a landmark episode because it involved a permanent character development. Lisa has remained a vegetarian ever since, but in tackling this philosophy, The Simpsons used every satirical trick they knew. The Troy McClure hosted meat propaganda film is classic spin, framing cows as the enemy and eating meat as a patriotic duty. “Bovine University” is still hilarious. Lisa imagines the animals’ feelings but gets a bit confused about their voices, and we see her imagine where hot dogs come from. The family peer pressuring her with a “You don’t win friends with salad” conga line is a lighthearted way to show how hard it is to stick to one’s principles. This episode landed the major guest stars Paul and Linda McCartney to teach Lisa about vegetarianism, and the story is they insisted that if they were to do the episode, Lisa had to remain a vegetarian. They probably didn’t know this mandate would last 20 more seasons. Read a full review of this episode.

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Cape Feare (Season 5, Episode 2)

Sideshow Bob in Cape Feare
Sideshow Bob steps on a rake, a lot. Fox, Screencap via TheSimpsonsShow.net

It’s become a tradition to have Sideshow Bob return to get revenge on Bart for catching him trying to frame Krusty in season one. This was Kelsey Grammer’s third appearance as Bob and it’s the one against which all his other appearances must be measured. In case the cleverly added E at the end fooled you, this is indeed a spoof of Cape Fear, with Sideshow Bob in the De Niro role. Strapping himself under the car doesn’t go as well for Bob, and this episode has the most epic “stepping on a rake” sequence. Somehow it ends with a musical number.

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The Itchy & Scratchy & Poochy Show

RIP Poochy
Poochy's unceremonious departure. Fox, Screencap via Tstoaddicts.com

Already in the eighth season, The Simpsons tackled the issue of long running shows growing stale and clueless network notes trying to hip it up. Trying to revitalize the Itchy and Scratchy Show, the network adds a new character, Poochy, a hip, street, rapping dog with the voice of Homer. Poochy is aggressively everything focus groups say they want with no artistic integrity. Ultimately, Poochy is killed off from the show in the most hilariously unceremonious way possible!

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Lisa's Wedding (Season 6, Episode 19)

Lisa's Wedding
Lisa sees her future wedding. Fox, screencap via Nerdhistory101.blogspot.com

A carnival psychic shows Lisa her future, in which she falls in love with a handsome Brit whose proper upbringing clashes with the crude and crass Simpsons. At the time this episode was aired in 1995, the future they were looking at was only the year 2010, but nobody’s counting real time at The Simpsons. Their spoof of future technology is still hilarious with holograms and robots. It’s also become a recurring trend for The Simpsons to look forward as often as it looks back. Season 27 featured the episode Barthood, which took 12 years of Bart’s life like the movie Boyhood. Seeing Lisa and Bart as adults are great extensions of their character, and seeing Lisa find love is a rare treat. They even mock the rom-com formula of Lisa hating Hugh, only to have him win her over. It’s really about getting Lisa to understand Homer in the present.

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Homer the Great (Season 6, Episode 12)

The Stonecutters
Homer joins the Stonecutters. Fox, screencap via Learnawesome.com

Homer is invited to join the elite secret society of The Stonecutters, and he almost blows it before they discover he is their chosen one. Homer reaps the benefits of privilege, but despite his instance that “everything lasts forever,” this too must come to the end. You don’t need to know about The Freemasons to get the joke, but it certainly helps. Any society that deems Homer their leader is doomed to fail, as Homer abuses his power in hilarious ways. The Stonecutter theme song is one of the classic Simpsons songs, which also reveals they rig Oscar night and made Steve Guttenberg a star. This is The Simpsons saying something about privilege and power, while mocking the institutions behind the scenes and giving Homer a comeuppance.  

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You Only Move Twice (Season 8, Episode 2)

James Bont
Hank Scorpio threatens James Bont. Fox, Screencap via Simpsons Wikia

Homer gets a new job at a very progressive factory run by Hank Scorpio (Albert Brooks), who turns out to be a Bond villain. Homer never quite puts that together but he helps Scorpio capture and kill “James Bont” and foil the American forces trying to stop Scorpio’s terrorism. Taking the Simpsons out of their element gives the show a great opportunity to show what’s so great about their routine. Marge’s self-sufficient kitchen gives her anxiety. Bart can’t clown around without the mediocrity of the public school system. Lisa may no be the nature girl she hoped she was when she discovers her allergies. But it’s Homer’s episode, and the way all the James Bond stuff just happens in the background (as a vehicle for Homer to realize he misses Springfield) is classic Simpsons.

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Bart Sells His Soul (Season 7, Episode 4)

Alf Pogs
"Remember Alf? He's back, in pog form.". Fox, Screencap via Alf Wikia

This episode is as ridiculous as you would imagine an eight-year-old selling his soul to be. Where it becomes transcendent is that The Simpsons make that genuine and emotional. When Bart gets in trouble for swapping the church hymns for “Inna Gadda Da Vida,” he sells his soul to Milhouse for $5. Bart quickly becomes a believer when he feels himself missing something, when old pranks don’t work anymore. The Simpsons never forgets that this episode is just about recovering a piece of hastily scribbled on paper, and even has a minor character point that out. But Lisa understands it’s a metaphor, even if Bart doesn’t. Meanwhile, a subplot about Moe turning his bar into a family restaurant is equally hilarious, making this a perfect Simpsons episode. Read a full review of this episode.

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El Viaje Mysterioso Del Nuestro Homero (Season 8, Episode 9)

El Viaje Mysterioso del Nuestro Homero
Homer looks for his soul mate. Fox, screencap via Bestepisodeever.wordpress.com

This is my favorite episode of The Simpsons ever because it breaks structural rules, goes into philosophical territory and goes in depth with the characters. Homer eats a hallucinogenic chili pepper at a chili cook-off and goes on a vision quest to find his true soul mate. Normally the first act of a Simpsons episode is a random, tangentially related sketch at best, and the rest of the episode has to tell a more traditional story. In this episode, each act escalates and builds off the last, with the hallucination stemming from Homer upsetting Marge at the cook-off and the final act dealing with Homer realizing of course Marge is still his soul mate. The visual gags of the hallucination know no limits since it’s not real, and Homer’s coyote spirit guide (voice of Johnny Cash) even comes back to be no help at all once he wakes up. Homer’s emotional phone call to GBM is my favorite, and there’s even a fun Batman reference.