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The 10 Best Simpsons Episodes

Naming the ten best episodes is a daunting task. But here goes!


Bart Gets an F

Season 2, Episode 1

Bart may be an underachiever and proud of it, but the highest-rated Simpsons episode is about Bart taking a sober-eyed look at failure and struggling mightily against it. When the school psychiatrist suggests that he be held back, Bart learns to study properly with Martin Prince and prays to God for a snow day so that he can get a little extra time before the exam. Unsurprisingly, when Bart is about to duck outside with his sled, it’s Lisa who talks him into studying by appealing to Bart’s morals. Rarely have kids on TV been portrayed with so much complexity. 


Three Men and a Comic Book

Season 2, Episode 21

This episode marks the first appearance of Comic Book Guy. The story of Bart, Milhouse, and Martin buying a comic book together becomes a high-stakes melodrama to which every 80s and 90s kid who ever spent three figures on a comic book can relate. 


Homer at the Bat

Season 3, Episode 17

This may have been a dull episode had Mr. Burns’ ringers – professional baseball players all – not fallen victim to nine separate misfortunes. Ken Griffey Jr. came down with gigantism because of dubious nerve tonic, Roger Clemens ended up hypnotized and acting like a chicken, and poor Ozzie Smith vanished right off the face of the earth. 


Marge vs. the Monorail

Season 4, Episode 12

Conan O’Brien (yes, that Conan O’Brien) wrote this episode gave us the first great cast song and dance number, which says something for a show with so many great songs. It also ended with Leonard Nimoy teleporting away, marking the first time the Simpsons truly broke with reality. 


Last Exit to Springfield

Season 4, Episode 17

We don’t know if anyone has calculated the number of jokes per minute of the Simpsons, but if they did, “Last Exit to Springfield” would have a pretty high number. In this episode we see a young Mr. Burns with his grandfather at his atom-smashing factory, a thousand monkeys at a thousand typewriters telling us that it was the best of times and the “blurst” of times, the Big Book of British Smiles, a robot uprising in Alf Clausen’s “The Land of Chocolate”, and Burns embracing his inner Ahab. Oh, and if you yell the words dental plan at nearly any bar, someone is likely to reply with “Lisa needs braces!” 


Cape Feare

Season 5, Episode 2

The best appearance of Sideshow Bob, bar none. It’s also the best appearance of rakes, his old arch enemy. And what other villain could sing H.M.S Pinafore in its entirety? 


And Maggie Makes Three

Season 6, Episode 13

Why are there no pictures of Maggie around the house? Because Homer has them all at work, strategically blocking part of the special demotivational plaque, which initially reads: “Don’t Forget, You’re Here Forever”. But with Maggie’s help, it says: “Do It For Her”.


Lisa the Iconoclast 

Season 7, Episode 16

The entire town may think that Jebediah Springfield has a noble spirit, but Lisa knows that isn’t true. She knows that he’s actually a pirate who fought with founding father George Washington, and she has proof. But she also learns that the truth can make you unpopular and even make your mother turn against you, and that sometimes it’s okay to let people have their idealized – but less than honest – heroes. 


Homer’s Enemy

Season 8, Episode 23

How would a real person react to Homer Simpson? Probably exactly the way Frank Grimes does. Grimes (or Grimy, as he prefers) lived a hard life, mainly in an apartment above a bowling alley and below another bowling alley.  When he saves Homer from accidentally drinking acid but ends up getting berated by Burns for ruining his valuable wall and spilling his priceless acid, Grimes becomes every one of us who has ever had to cover an inept co-worker. 


Behind the Laughter

Season 11, Episode 22

In this episode, The Simpsons turned its sharp, satirical gaze right back on itself and acknowledged that “The Principal and the Pauper” was a mistake. Even though The Simpsons was a show that won tremendous respect, they indulged in every rock ‘n’ roll cliché along the way. Thankfully, Willie Nelson helps them patch everything together. They even got the actual Behind the Music narrator, Jim Forbes, making all those weird metaphors and similes work.

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Posted on:
June, 3 2020



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