Winona Ryder broke her arm while shooting the scene in which she and Adam Sandler ride bikes down the stairs.
When Babe and Deeds are talking in a restaurant after a fake criminal act set by her, Deeds talks about how Stephen King visited his town, and how one guy lost two hundred pounds after making eye contact with him, a reference to Thinner (1996).
When Babe, pretending to be a school nurse, talks to Longfellow on the phone, she says that a boy named Billy Barty is in her office, sick. This is a tribute to actor Billy Barty, who died in 2000, three months before production started.
When Deeds and Babe get invited over to the table in the restaurant with all the uppity New Yorkers, he tells the opera singer he looks like Mr. French. He says he didn't know who that was and never heard of him. Mr. French, or Giles French, is a character from the television series Family Affair, and was played by Sebastian Cabot.