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/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 both 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 makes a reference to Julian about dealing with a missing tooth while holding Julian, "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 in fact Adam Sandler's best friend in real life.
The most successful movie of Adam Sandler's career making over $163 million domestically until the animated sequel Hotel Transylvania 2 (2015) making over $169 million in 2015. It's still his most successful live action movie.
Julian, Sonny and the delivery guy, while on the couch watching t.v., they were watching an episode of Columbo (1971). Dennis Dugan, this film's director, played a detective on an episode ('76) of "Columbo".
In the beginning of the movie Sonny takes Julian to a bar called the Blarney Stone. There is a popular bar in Syracuse called the Blarney Stone which is where the characters went to law school which is referenced a couple times throughout the movie.
Footage from the hockey game Sonny is watching when Julian asks to change the channel to the kangaroo show is a January 10th, 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.