Originally, this episode was going to have a song with Patty and Selma called "We Love to Smoke," but it was cut for time. The song is available on the season eight DVD set and on the Go Simpsonic with The Simpsons album.
One of the scenes from this episode is used in Filp Flap Big Brown House, during the prologue of Dancing Workers Song.
This episode is a parody of Mary Poppins, particularly the 1964 musical 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 auditionees 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 possible reference to the 1993 film Addams Family Values when Wednesday and Pugsley scare off all the nanny auditionees.
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.
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.
Krusty's show is called Krusty Komedy Klassics, yet Krusty performs new material.
The tree that Grampa crashed into at the end of the episode isn't usually in the Simpsons front yard.
When Shary Bobbins gets drunk in the living room, she has on a blue dress. When the family comes over to comfort her, she's in her black dress she wore when she first arrived.
According to the audio commentary, when Marge, Lisa and Bart sang this part: "But we're happy just the way we are", Homer was not singing. That's because Al Jean and Mike Reiss forgot to record Homer. "The show must go on." - David Silverman, Supervising Director.