One of two films that writer/director Judd Apatow wrote the screenplay for in 1996. The other was The Cable Guy starring Jim Carrey and Matthew Broderick which he fought hard to get credit in a battle with the WGA after rewriting the majority of the script for both Carrey and director Ben Stiller. He still got a producer's credit despite it.
Stay tuned after the film's end credits for a shot of the old Boston Garden being imploded for demolition since both the Boston Celtics basketball team and the Boston Bruins NHL hockey team both moved to the Fleet Center, which was located not far from the old arena for the start of their respective 1995-96 seasons. The film was released towards the end of the regular season and beginning of the playoffs in both sports.
The first film that director Tom DeCerchio accepted after he was fired from Ace Ventura: When Nature Calls by Warner Bros. early in 1995.
Some scenes were shot inside the Boston Garden just before it was scheduled for demolition in the summer of 1995, as the Fleet Center was scheduled to open in September of that year.
The scenes that were shot in the Boston Garden were actually created by the film's production designer Stephen Marsh that was about 90% close to what the old Boston Garden looked like at the time.