Two master thieves go at odds with one another as one sets the other up for a crime. The first (Alec Baldwin), a suave pro who does his job and then hides in his own privacy, listening to old jazz records and caring for his ailing dog, Wally. The other (Michael Jai White) is a local gangster with a taste for the finer life, who decides to eliminate the competition. This ignites a war between the two men and their aides. An angry mob boss (David Byrd) and a female police officer (Rebecca De Mornay) try to sort the mess before things get too out of hand.

Henry Roth (Sandler) is a veterinarian living in Hawaii who enjoys the company of vacationing women. He leaves the playboy life behind after he falls for Lucy (Barrymore), who suffers from short-term memory loss. Since she can never remember meeting him, Henry has to romance Lucy every single day and hope that she falls for him.