15 Worst Episodes Of The Simpsons (And What They Represent)

The Simpsons has been on the slide for a long, long while. Punching down on it isn’t even fun; it’s agreed by pretty much everyone that it’s a shadow of its former self. There’s too many terrible episodes to even count.

Despite the title, this isn’t so much a definitive worst episodes ever (that’s too subjective anyway) but more a look at fifteen episodes which, more than any other, are emblematic of the downfall.

Not only is it important that these episodes aren’t funny and have terrible narratives (though that’s true across the board), but that they fundamentally represent where, when and why The Simpsons went so wrong.

If you love the characters, go in with low expectations and think of modern episodes as being more of a spin off/reboot of the Golden Era, Season 30 is still watchable, although it does occasionally punch you in the gut for being stupid enough to stick around.

With over 650 episodes, you could easily find 100 stinkers, so there’s a lot of great (or rather, poor) candidates which didn’t make the cut. These though are not only bad episodes, they strike at the very heart of why The Simpsons is a husk of its former self.

What It Represents: The start of the decline.

The Principal & The Pauper is the one and only Golden Age episode on this list, and while there’s plenty of arguments to be made that it’s not inside the worst fifteen, it represents the first time The Simpsons really took their eye off the ball.

Laugh wise, no, it’s probably not in the worst fifteen. There’s possibly fifteen worse than it across Seasons 29 & 30 alone. But this isn’t about just kicking the show when it’s down. Instead, we need to explore just why it fell down in the first place.

Apart from some teething problems in the first couple of seasons, The Principal & The Pauper was the first negatively received episode of the show. Even Harry Shearer, who plays Skinner (as well as Smithers, Flanders, Burns etc) , has been a vocal critic of the episode.

Shearer claimed it ‘tossed [Skinner’s development] in the trashcan for no good reason’, then showrunner Bill Oakley considers it his most controversial episode, and even Matt Groening called it ‘a mistake’ in an interview with Rolling Stone.

The Principal & The Pauper was a grim warning of things to come.