Top 10 Worst Pre-2000 The Simpsons Episodes

The Top Ten

  1. The Principal and the Pauper (1997)

    It was a genuinely funny episode. However, it showed huge disregard for a well-developed character who was loved because of the way he was.

    This episode destroyed Skinner, basically saying that he was never real.

    Ahh yes... THAT ONE! This episode is two big middle fingers to the canon that the great cartoonist Matt Groening created with his brain of steel and his supersized heart and funny bone.

    Ohh... Skinner really didn't do all that stuff in Vietnam! He's the imposter among us!

    To be honest, Sgt. Skinner does have a point. Principal Skinner essentially commits identity theft, but the town of Springfield is 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.

  2. Another Simpsons Clip Show (1994)

    At least possibly the best thing is we found out what happened to Mindy, even if it was harsh: "She hit the bottle and lost her job."

    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 three times a season where Homer and Marge are "on the rocks" and their marriage is put into jeopardy? Then 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. My Sister, My Sitter (1997)

    My issue with this is the premise of an eight-year-old babysitter. No one wanted an eight-year-old babysitter at first until she helped Flanders, and even Ned was unsure at first.

    To quote Lisa, Why hasn't anyone called? Lisa is upset sitting by the telephone. To quote Marge, Maybe people don't want an eight-year-old baby-sitter, honey. Parents need to be sure their sitter can handle anything that might happen. That's why they hire teenagers. To quote Ned Flanders, Well, I don't know, Lisa. You're awfully young, and the boys can be a handful. Todd's been pinching everyone lately.

    It's funny, but it's also not as clever as other episodes in classic Simpsons.

    Bart and Lisa seem to be unlikable characters in this episode, which kind of bothers me.

  6. Homerpalooza (1996)

    Outdated Apple joke.

    The kids insulting Homer's music.

    Homer feels uncool.

    Censorship of record shop "Suicide Notes" and Otto's drug gags.

    Did you understand why everyone was offended by the Rastafarian hat?

    Dumb freak show act.

    "With it." A timeless warning that pretty much every generation will have to face as they grow older and face how society evolves.

    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 the 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 notably, The Smashing Pumpkins.

  7. A Milhouse Divided (1996)

    Voted because I'm tired of this episode being referenced every single time someone mentions "American Gladiators" on Reddit.

    Is this ridiculous episode from a show that was already past its prime, even when it first aired, seriously all anyone remembers about AG? That is sad.

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

    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.

  8. Lisa vs. Malibu Stacy (1994)

    This is just a parody of "SJWs" complaining about a talking Barbie doll in the early '90s. They ignored girls with dyscalculia. regarding the quote "Math class is tough," how about fractions, long division, algebra, trigonometry, geometry, and calculus?

    This is arguably the forefather episode of when Lisa changed from "Girl Genius" to "The Writer's Poorly Disguised SJW Viewpoints," as it involves Lisa criticizing Malibu Stacy dolls for being "sexist" and wanting to make a doll that's more "politically correct."

    Several moments do save the episode, 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.

    Just like When Flanders Failed, it had several of its Ink and Paint done in America, which clearly shows that it was handled by another team of inexperienced Korean animators. The same animation problems, like the linework, are visible here.

    But the episode is good for the idea of having the 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.

    He only agreed to appear if his then-wife could also appear so they could hawk their line of vegetarian alternatives.

    11. The Newcomers
  11. ?

    Viva Ned Flanders (1999)

    This was just stupid, I mean, come on, Homer and Ned getting drunk and unconsciously marrying someone else. This episode disrespected both Marge and Maude hugely.

    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.

  12. ?

    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.

    13. The Contenders

  13. 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 have at least made this episode slightly less of a dud. But they didn't.

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

  14. Lisa the Iconoclast (1996)

    With more and more scrutiny being placed on historical figures (except the ones 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.

  15. The Itchy & Scratchy & Poochie Show (1997)

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

  16. 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.

  17. Miracle on Evergreen Terrace (1997)

    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."

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

    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.

  18. Homer Badman (1994)

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

  19. Itchy & Scratchy & Marge (1990)

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

  20. When Flanders Failed (1991)

    The plot is good, and the episode does have its fair share of funny gags and emotional moments, but the animation is comparable to DiC in how stupid it looks.

    The animation was made by Korean animators who were only starting their careers, and it clearly shows. The number of retakes made it one of the few episodes to have some Ink and Paint done in America.

  21. 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. It was still a funny moment though.

  22. Bart's Dog Gets an "F" (1991)

  23. All Singing, All Dancing (1998)

    It's a clip show, so it is automatically subpar. Even worse, it was released the same year as a line of Simpsons VHS tapes.

  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 was too depressing for the show. It clearly showed too much depression. Not a really good classic episode. Sorry, just my opinion.

  26. Homer at the Bat (1992)

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