Every Time The Simpons REALLY Killed Characters
10. Shary Bobbins
Perhaps one of the early warning signs that a show is suffering from creative fatigue is when the dreaded 'musical episode' comes out to play.
Musical numbers had been a big part of The Simpson's DNA since the early days, but season eight's 'Simpsoncalifragilisticexpiala(Annoyed Grunt)cious' was the first time the show went the whole-hog on show-tunes.
For the most part, it's a solid episode and introduced us to Shary Bobbins, the British nanny that attempts to whip the Simpson family into shape and save Marge's hair from falling out.
Despite a couple of small victories, Shary ultimately fails in her mission. Try as they might, the Simpsons simply cannot change and they come to realise that they're happy just the way they are, even in spite of their numerous flaws. Realising that they're right, Shary takes to the skies in order to help another family in need. The Simpsons wave goodbye and turn their backs to her, with Lisa pondering on whether or not they'll ever see her again.
Just as Homer reassures her that they will, Shary is completely eviscerated by a passing jet engine - which whilst absolutely hilarious, caps this episode off in an unusually macabre manner.