While filming, The Waterboy (1998) came out and was a huge success. Noticing the box-office, Sony sent a memo to the set, letting the production team and Adam Sandler know that they had extra money to film or expand scenes they felt were lacking. This allowed smaller characters played by Rob Schneider and Steve Buscemi to have greater roles.
The "Scuba Steve" action figure in this movie is a fictional doll made up by Adam Sandler. "Scuba Steve" is based on a doll that Adam Sandler owned when he was a child, called Diver Dan. Diver Dan can be seen briefly in the intro scenes of another Dennis Dugan film, Problem Child (1990).
Cole Sprouse and Dylan Sprouse (Julian) lost baby teeth during production and had to be fitted with temporary replacements. Dylan Sprouse's tooth fell out in the middle of a take. Near the end of the movie, just after entering Hooters for his birthday, Sonny (Adam Sandler) makes a reference to Julian about dealing with a missing tooth while holding him, "Hey, You! Still missin' that tooth?").
Near the beginning of the movie when Sonny (Adam Sandler) is arguing with his girlfriend, she makes the comment that "the delivery guy is like your best friend." Rob Schneider, who plays the delivery guy, is Adam Sandler's best friend in real-life.
The most successful movie of Adam Sandler's career, making over one hundred sixty-three million dollars domestically until the animated sequel Hotel Transylvania 2 (2015) made over one hundred sixty-nine million dollars in 2015. It's still his most successful live-action movie.
Julian (Cole and Dylan Sprouse), Sonny (Adam Sandler), and the delivery guy (Rob Schneider), while on the couch watching television, they were watching an episode of Columbo (1971). Director Dennis Dugan played a detective on a 1976 episode of that show.
Footage from the hockey game Sonny is watching when Julian asks to change the channel to the kangaroo show is a January 10, 1999 match-up between the Tampa Bay Lightning and New York Rangers at Madison Square Garden. The game never went into overtime as depicted in the film, as the Rangers won 5-2 in regulation.
During the court scene, Sonny's (Adam Sandler's) father Lenny (Joseph Bologna), while questioning his son's ability as a parent, mentions that he found a bag of marijuana in Sonny's dresser drawer as a kid. Lenny then proceeds to make an example of his son's dishonest nature by mentioning that Sonny tried to tell him they were just pencil shavings. This particular situation was a plot device on Adam Sandler's first comedy album "They're All Gonna Laugh At You" (1993), specifically the track "I'm So Wasted" where a man (Rob Schneider) compliments the quality of a bag of weed he bought from his buddy (Sandler) who reveals that the bag of weed was really just a bag of pencil shavings.
The New York Rangers jersey worn by Tommy is that of Adam Graves, a forward who played on the team from 1992 to 2001. Despite having the alternate captain emblem on the chest, The letters G & S were digitally removed from the back nameplate as the producers wanted to avoid paying licensing rights to the National Hockey League Players Association for the use of Graves' name.
At the beginning of the movie, Sonny (Adam Sandler) takes Julian (Cole and Dylan Sprouse) to a bar called the Blarney Stone. There is a popular bar in Syracuse, New York called the Blarney Stone, which is where the characters went to law school which is referenced a couple times throughout the movie.
Originally Cody Gifford who was eight-years-old at the time was in mind for the role of Julian, his mother Kathie Lee Gifford refused the role after reading the screenplay and was quoted as saying, "I told my agent to tell Adam, whom I like, that Cody pees at home, not on walls."