Top 10 Worst Pre-2000 The Simpsons Episodes

The Top Ten
1 The Principal and the Pauper (1997)

To be honest, Sgt Skinner does have a point. Principal Skinner essentially commits identity theft, but the town of Springfield are willing to let it slide, just because they like him better.
It's no wonder why most people like to pretend this episode never happened.

That episode was when the show officially "jumped the shark".

2 Another Simpsons Clip Show (1994)

This episode is the pinnacle of bad Simpsons content, the other three clip shows in the classic era at least had a framing device - the first was via an April Fool's prank, the third was hosted by Troy McClure (and was the only great one of the four), and the fourth is basically a Simpsons musical showcase, but this one is just... Hey, remember all the times that romance was shown? It could've been done a lot better, like at a wedding anniversary, BUT NOOOO! IT HAD TO JUST COME OUT OF NOWHERE!

3 Secrets of a Successful Marriage (1994)

You know that episode that nowadays pops up like 3 times a season where Homer and Marge are "on the rocks" and their marriage puts into jeopardy, than surprise! Another forefather episode... This introduces the idea that Marge's hair color is really gray, which is basically warping canon, as Marge's father had blue hair, and it's heavily implied Marge's twin sisters (Patty and Selma) got gray hair from chain smoking. Overall, not a good episode.

4 Burns, Baby Burns (1996)

How can you make a Mr. Burns episode forgettable? Simple, use the old, tired trope of "Kid is opposite of his old man/woman" as a plot device. This is also one of the very few classic Simpsons episodes to not have a famous internet meme... Gee, I wonder why? Also, if Burns graduated in 1914, shouldn't he be dead?

It was just a Rodney Dangerfield movie disguised as a "Simpsons" episode.

5 Homerpalooza (1996)

Another forefather of the idea that "The Simpsons are insane, so we can do anything with the characters", this episode has Homer Simpson realize that his music he grew up with isn't considered "cool" anymore, so he takes Bart and Lisa to Hullabalooza (a parody of Lollapalooza) wearing a Rastafarian hat, which the GenXers and Homer's kids both get embarrassed by. The one saving grace is several rock bands appearing in the episode, most notable, The Smashing Pumpkins.

Now Smashing Pumpkins, Sonic Youth, and Cypress Hill are "dinosaur music".

6 My Sister, My Sitter (1997)

This episode is infamous for being cruel, you know when your parents are at the store or at another sibling's sports game on a weekend and you are left with the "annoying older sibling" figure who of course, is being annoying? This is one of the few times I can relate to Lisa in the series, as Bart is at his worst.

My issue with this is the premise of an eight year old babysitter

7 A Milhouse Divided (1996)

Not only was the "character development" of Mr. and Mrs. van Houten not for the better, but once their new personalities were established this became yet another "Homer and Marge have a marital crisis" episode.

This episode was garbage. It felt like a buildup to something that never really hit the spot, just like a whole lotta 21st century episodes.

I know a lot of people will disagree with this, but having Kirk and Luanne go from merely being Milhouse's parents (until this episode they didn't even have first names) to Yet Another Adult Male Loser and Yet Another Catty (censored) in a cast that was already swarming with both character types was *not* a good thing.

8 Lisa vs. Malibu Stacy (1994)

This is arguably the forefather episode of when Lisa changed to "Girl Genius" to "The Writer's Poorly Disguised SJW Viewpoints", as it involves Lisa criticizing Malibu Stacey dolls for being "sexist", and wanting to make a doll that's more "politically correct". Several moments do save the episodes, mainly the appearances of Krusty the Clown and Waylon Smithers being funny, at the end, it shows what seems to be a subtle "Get woke, go broke" message, as the kids (and Smithers) buy the Malibu Stacy dolls anyway.

9 The Simpsons Spin-Off Showcase (1997)

I honestly am a fan of the episode, but I can see why others aren't. For one thing, this episode feels like a middle finger to the audience at points, plus, just like When Flanders Failed, it had several of it's Ink & Paint done in America, which clearly shows that it was handled by another team of crappy Korean amateurs, the same animation problems, like the linework, are visible here. But the episode is good for the idea of having Simpsons in a format more along the lines of MAD Cartoon Network.

10 Lisa the Vegetarian (1995)

Not only was this an early appearance of Lisa the Insufferable Liberal, but they made her that way solely to get Paul McCartney (the last then-living Beatle who hadn't appeared on the show) to make a guest appearance. And he only agreed to appear if his then-wife could also appear so they could hawk their line of vegetarian alternatives.

The Contenders
11 The Itchy & Scratchy & Poochie Show (1997)

This is an early example of the show becoming diegetically self-aware, which has only gotten worse since.

12 Lisa the Skeptic (1997)

Lisa outright said "Come on, who wants to complain with me?". A clear sign of how much her character had devolved.

13 Lisa the Iconoclast (1996)

With more and more scrutiny being placed on historical figures (except the one who happened to be black, indigenous, and/or female) these days, this episode is now even more painful to sit through.

I enjoyed this episode except it has a flaw at the end, which makes sense.

14 Homer vs. the 18th Amendment (1997)

Maybe if they'd gotten Robert Stack (he was alive at the time) to voice the Eliot Ness ripoff, it might've at least made this episode slightly less of a dud. But they didn't.

Proof that the writers were out ideas even then. Prohibition 80 years too late? And just so they could riff "The Untouchables"? Really?

15 Miracle on Evergreen Terrace (1997)

It was fine and had some charm at first, but then, it gotten worse over time, especially at the end. That's why I absolutely despise the ending of the episode so much. Such a strange episode.

I know this is only the third Christmas episode (they simply re-aired the first episode, which also happened to be the first Christmas episode, every year until the show entered syndication circa season 7), but it's still one of the absolute worst of the so-called "golden era".

When you end with a negative score on "Jeopardy", you simply lose the game. You don't owe the show anything. Alex Trebek of all people should have known that.

16 When Flanders Failed (1991)

The plot is good, and the episode does have it's fair share of funny gags and emotional moments, but the animation is comparable to DiC on how stupid it looks. The animation was made by Korean animators who were only starting their careers, and it clearly shows. The amount of retakes made it one of the few episodes to have some Ink & Paint done in America.

17 Homer Badman (1994)

With "cancel culture" at an all-time high nowadays, this episode can be downright painful to watch.

18 Itchy & Scratchy & Marge (1990)

Like "Homer Badman", it's painful to watch in light of "cancel culture" being rampant.

19 Hurricane Neddy (1996)

We'll start off (If you have the alternate list option enabled on the site, I don't), with Hurricane Neddy, an episode that is good, but has one fatal flaw, it basically was the forefather to "Oh, Springfield can have anything happen to it". A lot of the episode is built on insanity, and oh yeah... There's a Jay Sherman cameo that makes no sense.

If there was any character I felt bad for in this episode, it was Lenny. He didn't do anything wrong, yet Ned Flanders just snapped at him and assumed he was a jerk, for no reason (was still a funny moment though).

20 All Singing, All Dancing (1998)
21 The Two Mrs. Nahasapeemapetilons (1997)

Technically Manjula first appeared in the episode where Apu was revealed to be an illegal immigrant, but this was where her status as a recurring character was cemented. This in turn led to the episode where Apu tried way too hard on Valentine's Day and of course the octuplets.

22 Bart's Dog Gets an 'F' (1991)
23 Viva Ned Flanders (1999)

Can't believe this one wasn't on here already! It introduced Homer and Ned's "Vegas wives", two of the worst, most unnecessary additions to "Simpsons" canon.

24 The War of the Simpsons (1991)

This was actually the forefather of the "marriage crisis" cliche, as it came before "Secrets of a Successful Marriage".

25 Like Father, Like Clown (1991)

Man, I just thought this episode is too depressing for the show. It clearly showed too much depression. Not a really good classic episode. Sorry, just my opinion.

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