Worst Pre-2000 The Simpsons Episodes

The Top Ten
1 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!

2 The Principal and the Pauper (1997)
3 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?

4 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.

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.

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.

7 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.

8 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.

9 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.

10 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.

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