Yeah, we all know The Simpsons. It’s a cultural behemoth and has either depicted (or predicted) most of pop-culture in its 700-plus episode lifetime. Name a celebrity and they have probably made a guest appearance, name a circumstance or film and The Simpsons will have at least referenced it. The series really isn’t what it used to be. The characters themselves are husks and parodies of what they used to be, and the storylines have devolved into unoriginal, crass, 24-minute reels of forced celebrity cameos, cheap humour, and unimaginative attempts to depict the ever-increasingly commercially driven modern lifestyle.
Here, I want to reminisce about five episodes which are the very best of what the series used to be – when their political commentary was apt and candid, and their cameos were genuinely funny and endearing. These are episodes which have aged well – just as prescient and smile-inducing as they were when they originally aired.
'Brother from Another Series' - Season 8: Episode 16
From the opening scene of Krusty the Clown playing a Folsom Prison Blues style gig in Springfield prison, to the brilliant interactions between the hillbilly workmen on the dam and the Terwilliger brothers, it is brilliant. It’s also the best Sideshow Bob episode. Voiced by the marvellous Kelsey Grammar, Sideshow Bob is one of the series' best villains. But this episode also introduced us to Bob’s brother, Cecil, voiced by David Hyde Pierce. The real Simpsons magic in this episode is from the fact that Pierce and Grammar also portrayed the Crane Brothers in sitcom Frasier, and the episode doesn’t skimp on the reference there.
This episode is also proof that the Simpsons characters are not one-dimensional: Sideshow Bob is actually a hero in this episode, saving Bart and Lisa from his evil brother’s attempt to blow them up inside a dam, and Homer’s parenting is thankfully as feckless and funny as ever. Many characters in this episode shine but most of all it’s the Frasier-esque antics of the Terwilliger brothers that really make it a joy to watch.
'The Mysterious Voyage of Homer' - Season 8: Episode 9
Season eight of The Simpsons definitely contained a lot of gems, and this episode is a classic, but one which is very different to ‘Brother from Another Series’. Country music legend Johnny Cash voices a mystical talking coyote that Homer encounters on a red-hot chilli induced out of body experience, sparking a mystical journey and a search for self-meaning.
This episode partially explores the relationship of Homer and Marge, who are of course soulmates but whose marriage does stagnate occasionally throughout the series, only to be rekindled in heartfelt and even realistic scenarios. This displays that The Simpsons creators can produce more than easy comedy – turning their pens to well-thought-out short stories and even romance.
'22 Short Films About Springfield' - Season 7: Episode 21
Another episode from the series’ golden age. This one has one of the biggest meme legacies of the show. Famed for the Skinners' and Chalmers' steamed hams skit amongst other shorts, this episode also shows just how much The Simpsons has changed since its glory days and how influential it has been to the wider world.
The episode starts with Bart and Milhouse on a bridge above a busy Springfield road, spitting on cars with a sincerity that the show crafts almost too easily. “Milhouse, do you ever think about the people in those cars?” asks Bart. “I try not to; it makes it harder to spit on ‘em” responds his blue-haired sidekick. Bart goes on: “sometimes I wonder about all the people in this town, do you think anything interesting ever happens to ‘em? I mean, there must be thousands of great stories out there….”. And there you have it, a Simpsons episode that proves how such a vast and zany crowd of characters can be utilised to great effect but also how the town of Springfield used to be a treasure trove of TV wonder.
'Treehouse of Horror VII' - Season 8: Episode 1
Yep, another one from season eight. Most of the Treehouse of Horror episodes are goodies but this one is the definitive example of The Simpsons’ sharp political satire and the creativity of its writers.
There are a few iconic moments in this episode: who could forget Bart’s ‘evil’ twin Hugo who lives in the Simpsons' attic, subsisting off fish heads and seeking to re-attach himself to Bart. More hilarious is the attempt of aliens Kang and Kodos to run for president, where we get the classic lines upon Homer's successful attempt to reveal that the two aliens are the ones running for president. “It’s true, we are aliens! But what are you going to do about it, it’s a two-party system, you have to vote for one of us!” With that the citizens of America become enslaved by their alien president. Do you still think The Simpsons is a harmless comedy?
'How I Spent My Strummer Vacation' - Season 14: Episode 2
Despite harking from the era when The Simpsons got worse with every season, this episode is a bit of an exception. Why? Well, with Mick Jagger, Keith Richards, Elvis Costello, Tom Petty, and Lenny Kravitz making excellent cameo appearances when Homer is enrolled on a rock 'n' roll summer camp, this episode is just perfect for demonstrating how The Simpsons can be watched by all. It also raises questions about how we view these influential artists in a society where their public image is paramount.
This episode also deals with Homer’s relationship with his family. We can recognise that as a character, despite his numerous faults and his haplessness, he is fundamentally a hard-working family man who has disregarded his dreams to make a living for Marge and the kids. As an episode, it is watertight, and is proof of how cameos can be made to work despite them being overdone nowadays.