5. Killing Maude Flanders
Strictly speaking this episode wasn't just a cheap grab for ratings by randomly killing off a regular character. Maggie Roswell, the original voice of Maude Flanders left the show in 1999 because of a pay dispute and it was decided that it would be easier to kill the character off, rather than replace the actor. That said, if the death of a regular character just happened to lead to an increase in ratings, then so much the better for everybody. For many, Maude Flanders death marks something of a turning point for the Simpsons. It arrived during the Simpsons decline from their late 90s peak and would be followed by five seasons known as the "Dark Ages" where the show is considered it's most woeful. It also came during a season of similarly ridiculous plots such as Apu having eight children and the Simpson buying another horse and racing it against an army of goblins. So yeah things were getting a little desperate in those days.