12 Greatest One-Off Simpsons Characters

Unlike a lot of these characters, we can be sure we won’t be seeing Shary Bobbins again, as her starring episode ends with the Mary Poppins spoof being sucked into an aeroplane propellor, a surprisingly grizzly ending for an otherwise toe tapping musical episode of The Simpsons.

“Simpsoncalifragilisticexpiala(Annoyed Grunt)cious” asks what would happen if a character like Mary Poppins, a being of pure positive energy, were to find herself in the Simpsons universe. The answer: quickly become dispirited and resort to drinking with Barney.

Shary Bobbins leads the family through some of the best songs in the Simpsons canon, with heartwarming songs about alcoholism and laziness. This is Mary Poppins updated for the cynical ‘90s, encouraging negative behaviour so long as it gets you the desired results.

Demonstrating the effort and attention going into this period’s episodes, the character of Shary Bobbins goes beyond the simple gag of a Mary Poppins spoof to actually consider how the character would get on in this world. The answer: not very well.