Now that Disney+ has made all 30 seasons of The Simpsons available to anyone with $69.99/year in disposable income and the outbreak of coronavirus has made indefinite downtime available to most "non-essential" workers, it’s the perfect time to take an extended trip to Springfield. When The A.V. Club called it “television’s crowning achievement regardless of format,” it wasn’t an understatement.
Out of more than 600 episodes, hundreds of the show’s installments are good, dozens are truly great, a handful are transcendent masterpieces of animation and comedic storytelling, and one or two are significant milestones in television history. With that in mind, here are 10 episodes of The Simpsons that are consistently rewatchable.
10 You Only Move Twice (Season 8, Episode 2)
In season 8’s “You Only Move Twice,” Homer lands a job with a supervillain and moves into an idyllic community that’s not as cushy as it initially seems.
Of all the guest characters that Albert Brooks has voiced on The Simpsons (always credited as “A. Brooks”), Hank Scorpio is arguably the most memorable.
9 Marge Be Not Proud (Season 7, Episode 11)
Although it’s controversial among some fans, the Christmas-themed episode “Marge Be Not Proud” has the perfect blend of laugh-out-loud hilarity and earnest sweetness. Bart steals a video game his parents won’t buy for him, and when he’s found out, Marge is devastated.
The best thing about The Simpsons is that the titular clan feels like a real family, and that’s exemplified brilliantly in “Marge Be Not Proud.”
8 Homer At The Bat (Season 3, Episode 17)
This is perhaps The Simpsons’ best use of celebrity guest stars. There are gags involving iconic baseball players like Wade Boggs and Darryl Strawberry that work whether you’re familiar with them or not. Even viewers for viewers who have never heard of Don Mattingly, Mr. Burns saying “Mattingly, I thought I told you to trim those sideburns!” is hysterical.
This episode doesn’t coast on its guest stars like a lot of later Simpsons episodes — looking at you, “Lisa Goes Gaga”. The focus is still on the Simpson family, with a typical sports-movie narrative involving Homer’s struggle as the softball team’s underdog. Having the team filled with professional baseball legends just complements the central joke of that premise.
7 Mr. Plow (Season 4, Episode 9)
Homer starting a snow plow business and being overshadowed when Barney steals his idea is a simplistic premise, but The Simpsons revels in simplistic storytelling.
The simplicity of a narrative allows the writers to delve deep into the character moments and explore tangential gags.
6 Cape Feare (Season 5, Episode 2)
Following the plot and structure of Martin Scorsese’s Cape Fear remake, “Cape Feare” is the height of the Bart/Sideshow Bob rivalry. Bob gets out of jail and pledges to kill Bart, so the Simpsons are relocated onto a houseboat and Bob follows.
The episode is filled with spectacular jokes, like Bob hitting himself in the face with dozens of rakes and Homer terrifying Bart with his new chainsaw and hockey mask.
5 Lisa’s Substitute (Season 2, Episode 19)
Before The Simpsons veered into absurdist territory, it told relatable stories about everyday situations. In season 2’s “Lisa’s Substitute,” Lisa bonds with a new substitute teacher (played brilliantly by guest star Dustin Hoffman), making Homer jealous.
The relationship forged in this one episode is emotionally charged. The “You are Lisa Simpson” note at the end is one of the show’s most heartwarming moments.
4 Last Exit To Springfield (Season 4, Episode 17)
When Mr. Burns threatens his employees’ dental plan at the same time Lisa needs braces, Homer becomes the head of the labor union and organizes a strike.
In his negotiations with Mr. Burns, Homer accidentally comes off as a “brilliant tactician” and gets his boss to bend to his every whim.
3 Homer’s Enemy (Season 8, Episode 23)
Frank Grimes is arguably the most memorable single-episode characters in Simpsons history. After suffering through endless tragedies in pursuit of a nuclear physics degree, “Grimey” lands a job at the power plant and is disgraced to meet Homer, a slovenly dimwit with a beautiful wife, three great kids, and a career he was handed on a silver platter.
Grimey’s hatred of Homer, paired with his co-workers’ inexplicable affection for Homer, drives him mad to the point of committing suicide. It’s easily one of The Simpsons’ darkest installments, but that’s arguably a good thing.
2 Bart’s Comet (Season 6, Episode 14)
In the first half of this episode, Bart accidentally discovers a comet that’s on a collision course with Earth. In the second half, the townspeople ruminate on their looming demise.
The episode has non-stop hysterical gags — including plenty of Bart/Skinner moments, showcasing one of the show’s funniest dynamics — and it also deals with some universal themes involving the inevitability of death.
1 Marge Vs. The Monorail (Season 4, Episode 12)
No list of the best Simpsons episodes is complete without “Marge vs. the Monorail.” What makes it a popular pick for the show’s best episode is that it perfects all the usual elements that make a Simpsons episode great.
The plot is dense, yet fast-paced; the humor is beautifully bizarre; and the premise is an eclectic mix of obscure reference points that the episode contextualizes with a relatability by focusing on the Simpson family adjusting to the changes it brings.
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