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

15. The Principal & The Pauper


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.

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