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Hollywood Insider The Simpsons Best Episodes

Photo: ‘The Simpsons’/Fox

The Simpsons is an American staple- it’s as closely associated with the American identity as red, white, and blue, Uncle Sam, and Jersey Shore. I know one of these things is not like the other, but it’s undeniable that all of them are on you, U.S. But, even if it’s hard for us to be proud of The Situation’s abs, at least we can all say that the family of yellow people getting into endless hijinks is something we can all get behind. The Simpsons has been on since 1989. There are over 600 episodes, so it’s going to be a big task to sort through all of them. But someone has to do it, so if it must be me who has to watch hours and hours of one of the world’s funniest sitcoms ever produced, (*sigh*) I guess I’ll have to sacrifice myself.

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Let Us Rank The Simpsons Best Episodes: 

Who shot Mr. Burns? (Part One) (S6E25)

If you thought Mr. Burns was an A-hole before seeing this episode, hold on to your oil reserves. Mr. Burns drills oil near the school, taps into a surplus of taxpayer dollars, and somehow manages to block out the sun. Dr. Evil ain’t got nothing on him. Mr. Burns is one of the most ubiquitous side characters in The Simpsons and the most detestable resident of Springfield. This episode brings that all to a head as Mr. Burns somehow manages to get everyone in Springfield to hate him even more. This episode is so great because it’s one of the first to showcase the larger and richer than life personality that is Mr. Burns. While part two of this episode is great with the police interrogating Maggie and Santa’s Little Helper, my favorite of this duo of episodes is number 1. Pun absolutely intended.

Treehouse of Horror VII “The Thing and I” (S8E1 Segment 1)

I know, I know, Treehouse of Horror V is unanimously considered the best Treehouse of Horror. While Homer turning into Jack Torrance because he has to go without beer for more than five minutes is hilarious, no Treehouse of Horror segment has ever scared me more than “The Thing and I.” Let me start out by saying every Treehouse of Horror is a masterpiece in its own right. Like Beethoven’s Symphony Number 5 or Lou Bega’s “Mambo Number 5,” each Treehouse of Horror is a work of art. But I can’t think of any other segments that kept me up at night to the extent that “The Thing and I” did. After hearing noises coming from the attic, the kids discover Bart has an evil twin their parents have been hiding from them. This segment proves that the writers of The Simpsons are as good at handling horror as they are at comedy. And, unlike the Simpsonian take on The Shining, this segment is an original story. It blows my mind to think that the same show with an alcoholic clown and a Mexican bee as side characters can go this dark.

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Marge vs. The Monorail (S4E12)

“You gotta know the territory,” I make this reference to not only confuse non-Broadway fans but to clue the rest of you in on the fact that this episode is a parody of the classic musical The Music Man. It’s even complete with an arguably unnecessary show-stopping number, and arguably unnecessary show-stopping numbers make up the foundation that Broadway was based on. Marge becomes wary when charming salesman Lyle Lansley sells Springfield on the idea of building a monorail through town. It’s a ridiculous idea, to begin with: I live in a small town like Springfield where everyone either drives or has someone to drive them. There is absolutely no need for a massive automated train running through town. Yet, of course, the townspeople of Springfield are naive enough to buy into it. This episode is a solid parody of one of Broadway’s greatest musicals and goes down in the record books as one of the most hilarious and ridiculous Simpsons episodes.

You Only Move Twice (S8E2)

Sorry Broncos fans, I had to put your least favorite episode on the list. The family uproots itself after Homer is offered a new high paying job by a recruiter in a black van. Red flag number one: if you ever see a black van driving slowly towards you, run away. Come to think of it, if you ever see a black van driving quickly towards you, run away. The general rule of thumb: black vans are evil. When Homer starts his new job, it becomes clear that his new boss is an evil gazillionaire. Like, seize the entire East Coast type of evil. This episode is great because it demonstrates the obliviousness of Homer so clearly. He doesn’t see any of the red flags and there are a lot of them. He threatens the UN in Bond villain fashion and most pictures you will find of him on the internet showcase him brandishing a flamethrower.

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One Fish, Two Fish, Blowfish, Bluefish (S2E11)

There are very few Simpsons episodes that pack the emotional punch that this episode does. After eating what is probably poisonous sushi, Homer is given 24 hours to live. He vows to accomplish every item on his bucket list in those 24 hours. This episode is a perfect balance of sentimentality and the humor The Simpsons is known for. In the same episode we have Homer saying goodbye to his loved ones, he also has to take hours saying goodbye to Grandpa Abe because he’s both hard of hearing and senile. The most emotional moment of the episode comes when the night after getting the news of his impending death, Homer tearfully says goodbye to his sleeping family. Great, now I have to write through tears while finishing this paragraph. The plot twist everyone saw coming happens when Homer wakes up the next morning completely fine. If you’re going to call that a spoiler, there are several hundred episodes left in the series after Homer’s brush with death, so calm down. Everyone knew it was coming.

Lisa’s Wedding (S6E19)

This episode primarily makes this list because it introduces us to the snarkiest fortune teller in history. She specializes in showing failed relationships: a snark-free fortune teller would’ve picked a different major in clairvoyance school. Said fortune-teller shows Lisa the man who will become her first love. Lisa is the most competent member of the Simpson clan, and probably is the only member of the family who can survive on her own. So, it’s surprising that when her future boyfriend decides he hates her family she chooses them over him. It’s a refreshing reminder that though The Simpsons can get a bit absurd at times, it’s a show about family above all.

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Rosebud (S5E4)

Rosebud is the Citizen Kane of Simpsons episodes… Mostly because it’s a parody of Citizen Kane (Sorry, Hollywood Insider requires at least one dad joke per article.) In this episode, we learn that Mr. Burns lost his beloved childhood teddy bear when he was a boy and he becomes desperate to get it back. He’s just a little tyrannical megalomaniac who lost his toy. This is another episode that shows off Burns’ character but in a different light. In Who Shot Mr. Burns, we see him at his most evil, while in this episode we see that behind that drill-oil-right-next-to-where-children-hang-out, there might be something resembling a human inside.

Cape Feare (S5E2)

We’ll call this episode “Sideshow Bob Classic.” While it’s not the first Sideshow Bob episode, it’s the first one that really makes an impression and lets us know that Sideshow Bob is going to be a force to be reckoned with throughout the rest of the series. When Sideshow Bob is released from prison, the Simpsons are put in witness protection for their safety. This episode is the best display of Simpsons slapstick humor. Of course, on the car ride during which Sideshow Bob stows away in the undercarriage of the car, Homer decides it’s his lifelong dream to drive through a field of cacti. And Homer throws boiling hot coffee out the window just to really hammer in the point that Sideshow Bob is in for some bad karma. But the funniest moment of the episode comes when Bart is terrified in bed and Homer barges into the room shouting, “HEY BART, DO YOU WANNA SEE MY NEW HOCKEY MASK AND CHAINSAW” dressed like fat Jason Vorhees.

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Deep Space Homer (S5E15)

I understand that they’ve had to come up with hundreds of ideas for episodes. But when a writer pitches, “Let’s put Homer Simpson in Space,” maybe it’s a good idea to send him home for the day. When NASA realizes the ratings for their TV broadcasts of space launches are low, they decide to send an “average shmoe” into space. And I’m assuming you’re smart enough to figure out who they chose. This episode is Simpsons absurdism at its finest. The show has gotten weird before, but when you have Homer eating chips in Zero-G, you know you either smoked too much weed and should probably go lie down or The Simpsons creators smoked too much weed and pulled out their laptops and started writing.  

Homer’s Enemy (S8E23)

This episode just goes to show that when you mess with the stupid, you get the horns. Not by the stupid’s own volition, of course, the stupid is too stupid to remember where he put the horns in the first place. An unlucky but well-qualified orphan named Frank Grimes gets hired at the Springfield Nuclear Plant. Grimes quickly makes enemies with Homer. He believes Homer has the good life he has because of luck, while Grimes has had to work hard for everything. This episode demonstrates the self-awareness of the show. Homer’s Enemy answers all the plot holes that have existed in the show from the beginning. How did Homer get a job which pays him enough to support his whole family? Luck. How does he hold onto a wife he clearly doesn’t deserve? Luck. How does Homer keep his job despite being clearly incompetent? Luck. This episode has the audience conflicted. Grimes brings up some pretty good points, but, if you’re not team Homer by now, why are you even watching the show. The episode also reminds us why we all love Homer. Homer is shaken by the fact that Grimes doesn’t like him, and so he gets everyone dressed up, invites the poor guy over for dinner, and genuinely makes an effort to be friends. Homer may be an incompetent idiot, but he does try his hardest to be nice to everyone… except Flanders. Flanders sucks.

By Carrie Fishbane


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