Originally, Adam Sandler wrote and was set to release this movie in the mid-1990s with actor Chris Farley in the role now played by Kevin James. However, Farley's tragic passing in 1997 halted production plans and the film was shelved for more than a decade.
Kevin James' character, Eric Lamansoff, was also mentioned in another Adam Sandler movie; The Wedding Singer (1998), as a neighbor of Robbie Hart (Adam Sandler) during the scene where Robbie and Julia are negotiating prices for wedding pictures.
The lake rope swing scene was added at the last second during filming. Adam Sandler told the story of how it happened to him and it was decided to include the scene in the movie. It was then decided it would be funnier if it happened to Kevin James' character.
The "flashback" basketball game was filmed at the Huntington St. YMCA in Boston. It was filmed on a 95-degree August day in a non air-conditioned gym while all of the extras in the stands were dressed in the material of the day - polyester. So, if everyone in the stands appears to be melting, that is why. Adam Sandler was on set with Dennis Dugan and they both guided the team and the cheerleaders during the 15 hour shoot.
Adam Sandler took a break from filming to be the guest speaker at the 2010 Graduation of his Alma Mater (Manchester Central High School) in Manchester, New Hampshire. His niece was a member of the graduating class.
Kevin James' character name "Eric Lamansoff" is also mentioned in Adam Sandlers other movie "Click" as a the CEO who kills himself followed by David Hasselhoff's character telling Adam Sandler's now obese character that he's the new CEO.
Adam Sandler wears a different New England area college shirt or hat in nearly every scene. The colleges that Sandler can be spotted wearing are University of Connecticut (hat), University of Massachusetts (t-shirt), Harvard (t-shirt) with a University of New Hampshire hat, University of Rhode Island (hat), and Boston University (sweatshirt). He is also seen wearing a Whalers Hockey t-shirt.
Director Dennis Dugan directed his ex-wife Joyce Van Patten in this movie. Just like depicted in her character Gloria's relationship with Rob Schneider, also Van Patten is older than Dugan. Though, their age difference (11 years) is not quite as significant as that of the movie characters.
An environmentally aware production, all 250 cast and crew were issued with their own water bottles which they used throughout filming, cutting down on the number of plastic disposable water bottles usually used throughout a film's production.
An early scene where the 5 male leads all sit in chairs outside the lakehouse in sunshine was actually extremely cold. External heaters were placed out of shot so the actors - who were all dressed in t-shirts and shorts - could warm themselves in between takes.
The ponies you see during the 4th of July Carnival scene are in real life Disco (brown one with white socks), TJ (fat brown and white one), Tigger (little brown and white one) and Double-Up (white one). They live at Hunter's Haven Farm in Groveland MA.