When Marge started losing her hair due to stress, the Simpson family decided to hire a nanny to help look after the kids. After interviewing several candidates, all of whom Homer chased away, Shary Bobbins arrived, floating down with her umbrella. The family decided that they liked her, so they hired her. Shary immediately got to work with the kids, getting them to help tidy Bart's room, albeit in a half-assed way, through a song and dance ("Cut Every Corner"). This helped her bond with the kids.
Shary Bobbins then took the kids to the park. There, they passed Ned Flanders, Snake Jailbird, and Nelson Muntz, who all knew Shary. They then met up with Groundskeeper Willie, who revealed that he had previously been engaged to Shary Bobbins back in Scotland. Then she got her eyesight back and called off the engagement. Shary and the kids then started flying kites when Mr. Burns came along. Shary let Burns fly a kite and he got struck by lightning, causing his heart to restart. Meanwhile, Marge praised Shary Bobbins because the house was spotless and the kids were occupied.
When Shary Bobbins went to put the children to bed, they wanted another song, which annoyed Shary as she had been singing songs all day. She then sang them "A Boozehound Named Barney," which put them all to sleep. Eventually, Shary decided that she had changed the family for the better and that her work was done. As soon as she left, the entire house descended into chaos, with Homer and Bart fighting, Marge's hair falling out again, and Lisa and Maggie trying to control the situation. Shary said that she would unpack her things as Grampa flew off, as he had Shary's umbrella. Shary then started to get annoyed at the family's attitude, with them all having relapsed into their lazy, selfish selves.
Eventually, the family's attitude toward Shary broke her and she started drinking with Barney, singing "Margaritaville". The Simpsons then told her that they were happy the way things were and that nobody could ever change them. They sang "Happy Just the Way We Are" to demonstrate this. Accepting this, Shary decided to leave again and took her umbrella from Grampa, who was stuck in a tree. Shary then flew off, only to end up going through an airplane engine, killing her.[1]
In a coma dream Bart had, Shary Bobbins appeared as a ghost. She asked Bart to help her get vengeance against all jet engines so she could go to Hell.[4]
When Marge imagined what life would be like if Homer was a fighter pilot, a picture of Shary Bobbins was on the wall of "Heaven's Heroes" in Fighting 799th.[5]
Shary Bobbins is extremely kind and helpful, wanting to fix everyone's problems. She also likes to sing to motivate people. However, she also has a stricter side, as seen when she said what she'd do with Bart if he were caught reading Playdude. Eventually, though, the Simpsons were enough to get to her. She tried to stay happy and kept trying until she broke and began drinking with Barney.
Julie Andrews, who played Mary Poppins in the film, was asked to play the role of Shary Bobbins. However, she was busy with a Broadway musical at the time.[7]
