There might be many contenders for The Simpsons' “Worst. Episode. Ever” crown, but the real low point came when the creators made everyone in Springfield into hateful villains. Since it began back in 1989, The Simpsons has never been afraid of dark, cynical humor or sharp social satire, but the show usually also knows to never go too far into pure nihilism. Since its first episode, the series has been an anarchic subversion of family sitcoms that has featured jokes about Barney’s evident alcoholism or Homer’s uncontrollable temper.
The Simpsons didn't pull its punches when it came to mocking the saccharine image of happy families or picket-fence Americana that was expected from network comedies of the time either. However, even The Simpsons usually avoided getting too dark, which is what led to the show’s true low point with season 18’s "The Boys of Bummer".
Unlike most contenders for worst episode, it’s not immediately obvious why Simpsons' viewers hate "The Boys of Bummer" so much, and have done so since it debuted shortly before the release of 2007's The Simpsons Movie. This episode sees Springfield gang up against and bully Bart to the brink of suicide when he misses an easy baseball play, and in the process, the episode depicts the entire town as cruel, spiteful people.
This is the sort of dark, South Park-style joke that the comparatively light-hearted Simpsons has rarely used, as it’s so downbeat and grim that few find it amusing. Unlike the majority of hated Simpsons episodes, "The Boys of Bummer" is not a post-season 20 offering. It doesn’t feature an out-of-place, fawning celebrity cameo like "The Musk Who Fell To Earth" or "Lisa Goes Gaga," and it’s not an epoch-defining moment like "Saddlesore Galactica's" self-referential surrealism or "The Principal and the Pauper"’s blatant rewriting of canon. Despite its terrible reputation the episode even centers around baseball, the theme of the classic Simpsons' episode "Homer At The Bat." So why is "The Boys of Bummer" so widely hated?
The same theme of the town being filled with horrible people also showed up at the tail end of “Miracle On Evergreen Terrace,” but there, their greed and cruelty aren’t the main focus. In contrast, the collective awfulness of Springfield is unavoidably front-and-center in "The Boys of Bummer," which is what led to most fans disowning the episode entirely and branding it even worse than The Simpsons' many embarrassing celebrity cameos or smug self-aware plots.