TV – The Top 15 episodes of The Simpsons (Part 2)

There are countless good episodes of “The Simpsons”. From Homer failing miserably at his attempts to build a Barbeque, to Ned and Homer’s rivalry reaching such a point that they force their sons to fight it out in a game of mini-golf, “The Simpsons” is more than a meaningless animated laugh.

Nearly all the early episodes – many of the listed are from Seasons 2-10 – convey a special message.

But, if I had to pick 15 that I’d watch over and over again, these would probably be the ones I pick.

So, let’s see which episodes made the cut.

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NUMBER 10: Rosebud (Season 5, Episode 4)

"As easy as taking candy from a baby."

“As easy as taking candy from a baby.”

He loved that bear.

Rosebud is the story of Mr. Burns’ childhood affection for his bear Bobo. But after losing sight of his bear for only a short while, he leaves his home without it, and realizes he may never see it again. Bobo goes through a whole lot of trouble in the next few decades, and eventually ends up being excavated and identically put in a bag of ice, to be shipped to the Kwik-E-Mart. Bart finds the raggedy old bear, and gives it to Maggie. The story then expands on the feud between Burns and Maggie for ownership of the bear.

Oh, how we can all relate to the theme of never wanting to let go. Rosebud does this perfectly, and executes first-class dramatic irony multiple times; Maggie never wanting to let go of the bear much like Burns, Burns leaving the bear as a child to go live with a “twisted, loveless billionaire” – the very thing he becomes in later life, among other things too.

It’s unreal how the writers make you feel for a seemingly loveless, world-hating old geezer like they do. Rosebud is an emotional rollercoaster that you won’t want too forget. It may even make you cry.

Not me though. I’m stone.

NUMBER 9: The Boy Who Knew Too Much (Season 5, Episode 20)

*shivers in his boots*

*shivers in his boots*

By now, I hope you’ve realized that Season 5 is my favourite season.

The Boy Who Knew Too Much, a sort of adjustment to Mark Twain’s “Huckleberry Finn”, details Bart’s hectic day when he decides to skip school. After just escaping Principal Skinner’s grasp, he arrives at Quimby Manor, and witnesses an important event. The event leads to one of Springfield’s biggest ever trials, and even though Bart knows the man on question is innocent, confessing would mean Skinner would nail him for skipping school.

It’s your classic moral dilemma, and a good one at that. I mean, anything taken from real life and put in a Simpsons world is good, right?. I think that’s a fair statement. Things play out beautifully in the story, and the episode as a whole makes you think. Would you take a risk like skipping school? And would you confess?

Ever heard of Freddy Quimby? Ever joked about French people saying “chowder”? Ever wanted to know how bad-ass Seymour Skinner can really be? Then watch this episode.

NUMBER 8: Funeral for a Fiend (Season 19, Episode 8)

Just as mad as each other.

Just as mad as each other.

It’s all apart of the plan.

Funeral for a Fiend starts out normally. Simpsons going out to buy TiVo. Seems normal enough, right? NO. WRONG.

It’s another fantastically planned Sideshow Bob scheme. Unusually, he plans to kill the whole family instead of just Bart – a trait this episode can definitely call it’s own. But Bob fails in his plan, and is accidentally killed. Though after his death, Bart still believes he is alive. His theory remains unproven, until Lisa steps in. Then the genius of the episode unravels.

This is easily the latest episode on the list, but it doesn’t run from the origins of the show. Sideshow Bob’s whole plan is simply brilliant, and so close to fantastically executed. But the way his plan is unraveled by Lisa is equally brilliant. There’s an element of cunning seeping from both sides of the fight in Funeral for a Fiend.

NUMBER 7: Sweet Seymour Skinner’s Baadasssss Song (Season 5, Episode 19)



The Simpsons’ 100th episode. But the chalkboard said “I will not celebrate meaningless milestones”. So there. Get over it.

After Bart decides to bring his dog, Santa’s Little Helper, to school for show & tell, it eventuates to a point where Superintendent Chalmers has no choice but to fire Principal Skinner. It leaves Bart feeling understandably guilty, and he tries to connect with Skinner outside of school as a way of feeling better about himself.

The plot of Sweet Seymour Skinner’s Baadasssss Song is the most important part of the whole thing, though it does feature fantastic humour. One thing leads to another so fluently, it’s incredible. Then everything ties in with each other too. It’s well written, like many Simpsons episodes. But there’s a nagging sense of “what if” that it brings about. What if Bart and Seymour were actually friends? What if Ned stayed as Principal?

The writers ingeniously bring a likability to Skinner, who beforehand was a little soulless. It depicts him as a meaningless man without the school, shown beautifully in the scene where as he walks past the school, Skinner cries. Even though all ends well, it does a great job of bringing the two “enemies” – Bart and Skinner – together, only for them to part, but not before they realize just how close they had become.

NUMBER 6: ‘Round Springfield (Season 6, Episode 22)

So sad.

So sad.

‘Round Springfield, an exploration of the profound effect a person who you barely know can have on you, is a truly gut-wrenching piece of television.

Revisiting the story of Bleeding Gums Murphy, this episode does more than enhance the relationship between Lisa and Bleeding Gums. It takes it that extra step. It makes it special. It establishes Lisa’s love – the saxophone – as a shared love between the two, more so than the previous Bleeding Gums episode. This episode is all about one person’s impact on you even though you’d forgotten about them for some time beforehand – much like Rosebud.

Bleeding Gums’ death is completely heartbreaking. The relationship between himself and Lisa crumbles at the very word from the nurse who tells Lisa what she never wanted to hear. How he died is unclear, but not important. What is important is that he’ll never be forgotten; not by Lisa, and not by me. Lisa’s rendition of “Jazzman” while looking up at Bleeding Gums’ face in the clouds is nothing short of heart-stopping. The emotion is insane.

Oh, and anything Lionel Hutz says in this episode is gold. It rivals only that of Kent Brockman in “Deep Space Homer” for the best writing for one character in one episode. Hilarious.

I’ll admit. This episode has made me cry before.

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Follow me on Twitter (@ElroyRosenberg), on Instagram (gooserosenberg), and on Facebook (/TheSilverScreener)


4 responses to “TV – The Top 15 episodes of The Simpsons (Part 2)

  1. Pingback: Reading Digest: Missing Canadian Edition | Dead Homer Society

  2. Why no Halloween episodes?

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