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The Simpsons: what’s there to say apart from the fact that the show is a cultural juggernaut?

It buffed up the careers and resumes of many prominent folks like Conan O’Brien, it gave VOs like Dan Castellaneta, Yeardley Smith, and Tress Macneille stable paychecks, and it spawned a clone of suburban life animated comedy imitators and duplicators from the likes of Mike Judge and Seth McFarlane. And of course, it made Matt Groening a household name in the realm of witty satirical comedies.

So yeah, it’s part of our lives for us pop culture junkies. And we’re going to pay tribute to it by listing out my personal favourite episodes that I rewatch time and again. Also, that Disenchanted Netflix show is coming out this week so what better time to do a feature on a Matt Groening creation than to be timely about it?

Just some ground rules:

  • The best Simpsons episodes are either heavy on comedy and punchlines with a small emphasis on plot, or a good balance of heartfelt story moments and funny bits.
  • I’m only covering the first 10 seasons because the rest of the show can go die in a dumpster fire, as far as I’m concerned.

Here they are, in no particular order. Remember, this is my personal list so take all your arguments and nitpicks on the comments box/Facebook.

Homer At The Bat (Season 3)

Basically, Homer and his nuclear power plant baseball team are doing great in the inter-factory tournaments. But because Mr. Burns made a deal with a Shelbyville power plant CEO, he was forced to hire current baseball pros masquerading as his power plant workers.

One of the few star-studded episodes worth a damn, this one features then-current top baseball players Daryl Strawberry, Ozzy Smith, and Wade Boggs. This being a Simpsons episode, the pros experienced separate and hilarious misfortunes.

Best of all, it showcases a nice character moment where Homer has to try hard to surpass the best of the best, no matter how unfavourable the odds can become.

Bart Gets Famous (Season 5)

After becoming Krusty the Klown’s assistant and getting sick of it, he walks out and causes an accidental havoc, punctuated with his supposed catchphrase “I didn’t do it”. He became an overnight success.

A life lesson about fame and how it is fleeting, through the lens of Springfield and the Simpsons. It also mocks catch-phrase-based humour too, but really the real lesson here is knowing how far you can go while being a one-trick pony.

Oh, and this gag is still pretty ace.

Sideshow Bob Roberts (Season 6)

If you want to see a hilarious take on the infamous Watergate Scandal complete with equal jabs at Republicans and Democrat parties in the US, look no further than this Sideshow Bob-focused episode.

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Our favourite Simpsons antagonist and avid Bart hater gets sprung out of jail for political reasons and ends up becoming the mayor of Springfield. This means hell for the Simpsons since Bob has a huge vendetta against Bart. The payoff of the episode is genius and it plays off Bob’s theatrical nature which ended up being his biggest weakness.

Sideshow Bob’s Last Gleaming (Season 7)

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To be frank, picking just one Sideshow Bob episode as a “must watch” is pretty tough. But this episode had all the 60s nuclear war movie parodies and an R. Lee Ermey guest VO I can get by.

From the airstrip hostage bit to the final chase scene which will leave your sides splitting, I really can’t find a dud moment in this episode, save for the supposed nuclear bomb in the episode’s location.

Deep Space Homer (Season 5)

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Homer wants to prove himself to his family, so he signed up to be an astronaut for a NASA program that’s looking for ordinary people to boost interest in their space programs. Of course, nothing goes right since Homer’s involved. Essentially this premise writes itself but every punchline and comedic bit just flows well, especially when you factor in the 2001: A Space Odyssey nods.

This episode also has the best clips and scenes: Barney getting buffed before falling prey to his vice, James Taylor, Homer’s potato chip-eating spree in zero gravity, and obviously Kent Brockman’s allegiance switch on-air.

You Only Move Twice (Season 8)

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This simple story about the Simpsons family relocating to a new area due to Homer’s new job boils down to its biggest star: Hank Scorpio. Who knew that a one-note James Bond villain archetype-slash supportive boss can make this episode a highlight?

Albert Brooks lends his voice to the theatrical dual-natured boss to great effect, and the James Bond gags and supervillain lair tropes just keep piling up while the patriarch of the Simpsons remains oblivious to all of it.

Who Shot Mr Burns, Parts 1 & 2 (Season 6 & 7)

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Mr. Burns becomes a bigger dick than usual and angers the whole of Springfield. But this time he gets what is coming to him. This is part murder-mystery and part lore-building. It’s got a lovely Tito Puente bit, and some classic gags and lines that involves baby, candy, and Homer’s arc where he attempts to get Mr Burns to remember his name.

Most of all, the two-parter is built like a solvable mystery with so many of the townsfolk being suspects who have motives to axe the most-hated man in Springfield. Of course, it pulls off a 180 degree swerve that knocked our socks off. Remember; there was no Google or Youtube at the time.

Homer The Heretic (Season 4)

Homer skips church one day and it ended up being one of the best experiences of his life. This incurred the wrath of God, some funny bits with Ned Flanders, and even Homer trying to start his own religion which all ends up in literal flames.

This episode features a nice commentary on religion and faith through Homer-centric antics.   It’s not punchline and gag-heavy like the other episodes on this list, but it comes across as thoughtful and genuine. Plus, when the community firefighters help Homer out, we get this gem of a quote:

Ned: Homer, God didn’t set your house on fire.

Reverend Lovejoy: No, but He was working in the hearts of your friends and neighbors when they came to your aid, be they Christian [Ned], Jew [Krusty], or miscellaneous [Apu].

Apu: Hindu! There are 700 million of us.

Reverend Lovejoy: Aw, that’s super.

Marge vs. The Monorail (Season 4)

This episode is about salesman Lyle Lanley (voiced by the late Phil Hartman) who pitched his idea for a monorail in Springfield, and everyone bought it hook line and sinker. Except for Marge, who wanted the Springfield government to get Main Street fixed.

Everyone remembers the monorail song and the Leonard Nimoy cameo, but really this episode has all the right ingredients: a funny subplot regarding Homer being a monorail conductor and how he saved the day, the fast-talking Lyle Lanley, and Marge saving the day despite Springfield not on board with her ideas and all.

Besides, with an opening like this, you know this episode’s going to be a fan favourite hands-down.

Last Exit To Springfield (Season 4)

Homer leads a union as he and his Springfield Nuclear Power Plant co-workers go on strike. All because he does not want his dental plan sacrificed. Basically, this is the battle of wills and wit between him and Mr Burns, but obviously, there isn’t any wit on Homer’s side.

But still, even the biggest of dimwits need to make a stand, even if it’s something like a family-owned dental plan. This episode takes the cake by featuring pop culture references, absurd jokes, middle-class angst, and family drama.

Lisa On Ice (Season 6)

After Lisa finds out that she has an innate talent for hockey goalkeeping, a rivalry between her and Bart is formed. This one’s a sweet yet comedic attempt at a Lisa and Bart-centric episode that brings the best of the Simpsons: family drama played out in comedic fashion via iconic scenes like the one below:

This episode has a few touching moments in-between its slapstick nonsense to hammer on its point home: blood is thicker than water, or at least the ice rink of the Springfield hockey stadium.

Lisa’s Substitute (Season 2)

Lisa gets a substitute teacher after Miss Hoover is diagnosed with Lyme disease. Said teacher is Mr. Bergstrom (voiced by Dustin Hoffman) who is basically everything she wanted in a teacher, right down to the point where she crushes on him.

Of course, he had to leave and there’s a subplot about Homer not being a good male role model for her, but there’s a touching bit around the third act:

Bergstrom: Whenever you feel like you’re alone, and there’s nobody you can rely on, this is all you need to know.”

He hands here a note that reads: “You are Lisa Simpson.”

Here’s some trivia for you: this early Simpsons episode was directed by Rich Moore who is responsible for hit Disney films Wreck-It Ralph and Zootopia.

Homer Badman (Season 6)

Homer gets framed for being an ass-grabber after he dropped a babysitter home. It was generally a misunderstanding (Homer was actually grabbing a Venus de Milo gummy candy), but the media spun it out of control. As a result, he’s hounded and painted as a bad person 24/7 by TV channels and reporters in Springfield.

This episode is a clear satire on the media and television, portraying them as parasites trying to get ratings for the next big thing at the expense of someone or something with no moral code whatsoever.

Bart Gets An “F” (Season 2)

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Before the Simpsons family were in a position where they could do no wrong and didn’t have any stakes in what they do, we have this early episode where it had some drama. Less comedic and more touching, we feel for Bart despite the fact that he tries hard to not repeat the fourth grade.

Episodes like these are a good reminder that the writers for the show always flesh out the headlining family. They’re not one-dimensional jokes and catchphrases; “Bart Gets An “F”” is proof that you can add depth to your merchandisable 90s icons. With characters like these, it’s no surprise that the first 10 seasons of The Simpsons can stand the test of time even with some of its outdated gags.

Bart Sells His Soul (Season 7)

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After so many seasons, the writing and production team can boast about balancing emotional pathos and structured slapstick in their long-running series. This Bart-centric episode is one such example; it’s about Bart selling his soul to his friend Millhouse and the repercussions that follow. His dog doesn’t recognize him, he doesn’t laugh at an Itchy & Scratchy episode, and other strange things occur including an awesome street accident gag that doesn’t give you room to breathe.

Naturally, he’s desperate to get it back and this third act is where you see the emotional bits pop up to cap the entire episode. It also makes us wonder if the concept of an afterlife and souls are worth believing in.

There is also a subplot involving Moe and the rebranding of his bar. It’s funny especially when you see Moe crack due to stress, but the breadwinner is still Bart’s story.

Homer’s Enemy (Season 8)

And we cap it off with the darker episode of the whole series. The episode is about new Springfield Power Plant employee Frank Grimes who had to work his hardest to get to the top. He has the “pleasure” of working alongside Homer Simpson, Lenny, and Carl. Obviously, a serious guy like Frank is shocked that Homer’s incompetence earns him so much merit and a loving family, which paints him as public enemy number one in Frank’s eyes.

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As funny as this episode is, it does make you think: how the heck do these kinds of people get away with what they do while the hard workers don’t? Surely in real life, we have that one colleague who is less qualified for a high position but ends up there for years regardless. Does meritocracy truly exist in practice?

The episode doesn’t really answer that but tells its side of a story where you draw your own conclusions to it while ending things on a comical yet dark note. That’s for the best; the good kind of TV shows let you think about these sort of questions and situations. It’s a funny and morbid way of looking at the kind of real-life predicament where not all rewards are distributed fair and just.

And those are my picks! Yes, there are a ton of other great Simpsons episodes out there. Let us know your favourites on this list (or off the list) via Facebook or our website.

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