First appearance: “Simpsoncalifragilisticexpiala(Annoyed Grunt)cious” (Season 8, Episode 13)
Voiced by: Maggie Roswell 

Despite only appearing in one episode, Shary Bobbins has become one of the more notable obscure characters among hardcore fans. She debuts as a thinly-veiled parody of Mary Poppins after becoming a nanny to Bart, Lisa, and Maggie when the stresses of being a housewife leave Marge with PTSD. With a tune in her heart and a saccharine outlook on life, Bobbins attempts to bring peace and harmony into the Simpson household.

Unfortunately for her, she's never met the likes of this dysfunctional family before, and soon turns to alcohol as a way to cope with the misery of the household. In the end, Bobbins is left broken, the kids don’t learn a single lesson, and Marge resigns herself to a life of stress and anxiety. It’s an ending that typifies the nihilistic existence of The Simpsons, and is capped by the terrific sight gag of Bobbins being sucked into a jet engine as she slowly drifts away in her flying umbrella.