Adam Sandler's wife, Jackie Sandler, played the waitress in the bar that gets Julian (Cole and Dylan Sprouse) a root beer. This started the tradition of having her cameo in almost every Adam Sandler film.
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.
Making over $163 million domestically, this was Adam Sandler's most successful movie until the animated Hotel Transylvania 2 (2015) made over $169 million in 2015. It's still his most successful live-action movie.
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 little called Diver Dan. Diver Dan can be seen briefly in the intro scenes of another Dennis Dugan film, Problem Child (1990).
Adam Sandler and Jackie Sandler (née Titon) met on the set of this movie. They went on to get married in 2003 and have two children together.