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.
Studio executives were not enthused with reports that Salma Hayek would be cast in the film, and in a meeting suggested to Adam Sandler that they continue looking until they could get a "less ethnic" actress in the part. Sandler then told them he'd already offered Hayek the role and she'd accepted, adding that he would not consider re-casting the part and warned them not to bring the subject up again.
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.
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.
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 "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's wife Jackie Sandler makes an apperance in the movie when the guys are playing basketball near the end. She plays Tardio's wife. Their two daughters are the real daughters of Adam & Jackie Sandler.
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.
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.
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 t-shirt, University of Rhode Island (hat), Vermont hockey, and Boston University (sweatshirt). He is also seen wearing a Whalers Hockey t-shirt.
Director Dennis Dugan has a cameo during the opening credits as the basketball referee. This is not his first time making a cameo as a referee; he played a football referee in his earlier film, Saving Silverman.
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.
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.