The entire episode is a parody of Mary Poppins, the 1964 Disney film. It shares a similar storyline, parodies its musical numbers and Shary's name itself is wordplay on Mary's.
During the park scene Principal Skinner attempts to sell Jimbo Jones into labor by yelling "Boy for Sale". This is a reference to the musical number in the 1968 musical film Oliver! when Mr. Bumble sells Oliver to the undertaker Mr. Sowerberry after failing to sell Oliver to a blacksmith and a chef.
One of the nanny applicants was a kindly old lady, Homer reacted to this by saying: "Wait Marge I saw Mrs. Doubtfire; this is a man in drag!".
The nannies being rejected one by one is a reference to the 1993 film Addams Family Values when Wednesday and Pugsley scare away all of their potential nannies.
The failed skit that Krusty attempted to do in his Krusty Komedy Klassics, "Mad About Shoe," was a reference to the sitcom Mad About You. He also mentioned a "NYPD Shoe" skit when he learned that the audience didn't like it and warned that it was the same thing, a reference to the show NYPD Blue.
Also in that sequence, when Apu is singing, the area of Shary's white undershirt beneath her bowtie is briefly colored dark like her jacket.
Homer doesn't recognize Kearney as the punk kid who threatened to egg his house if he didn't give him candy (as seen in Season 3's "Treehouse of Horror II") or one of the kids he was going to buy beer for (as seen in "The Springfield Connection").
Although the Treehouse of Horror series is non-canon.
The tree that Grampa crashed into at the end of the episode isn't usually in the Simpsons front yard.
When Shary first announces that her work with the Simpsons is finished, her hair is black instead of brown viewed from the back.
When Shary Bobbins gets drunk in the living room, she is wearing a blue dress. When the family comes over to comfort her, she is wearing her black dress which was seen earlier.
On the "Before They Were Famous" television show, Bleeding Gums Murphy's beard is colored darker than it usually is.
According to the audio commentary, when Marge, Lisa and Bart sang this part: "But we're happy just the way we are", Homer wasn’t singing. That's because Al Jean and Mike Reiss forgot to record Homer. "The show must go on." - David Silverman, Supervising Director.
The Duff Beer label in this episode is light blue with red text instead of the usual red with black text.
Quentin Tarantino wears a shirt with pink designs on it, one of which disappears for a frame.