When filming the scene where Deeds beats up Marty, Allen Covert got spun around by Adam Sandler, slipped on the sidewalk and his skull hit the concrete with no protection; he was unconscious for a minute.
When talking to Longfellow on the phone and still pretending to be a school nurse, Babe says that a boy named Billy Barty is in her office sick. This is a tribute to the actor Billy Barty who died in 2000, only three months before production started.
The main helicopter used in the film is a Sikorsky S-92. At the time of production, the S-92 was not an FAA certified aircraft (still under development) and without much of an interior. No cast or film crew were allowed aboard the helicopter during operation, and all interior shots had to be faked.
In the film, Deeds is from a small town called Mandrake Falls, New Hampshire. Though this is a fictional location, Adam Sandler moved to Manchester, New Hampshire at the age of six and lived there all his life until attending college at NYU.
The trivia items below may give away important plot points.
When Babe and Deeds are talking in a bar after a fake criminal act set by her, Deeds talks about how Stephen King visited his town, and how one guy lost 200 pounds after making eye contact with him, a reference to Thinner (1996).
The location in the park with the large fountain where Deeds and Babe share stories and see the firetrucks they eventually follow was previously used for the scene when Kevin McAllister escapes from the "Sticky Bandits" in Home Alone 2: Lost in New York (1992).