John Plummer (JASON LEE) is a normal guy who's excited by the news that he and his fiancée, Elaine Warner (LESLIE MANN), have finally saved $30,000 meaning that they can get married and buy a house. While John isn't crazy about being related to Elaine's father, Mr. Warner (DENNIS FARINA), who happens to be his boss at a home medical supply store, he loves Elaine and will put up with him.
Then he's reminded of a promise he made long ago to his niece, Noreen (TAMMY BLANCHARD), in front of his trailer trash sister, Patty (MEGAN MULLALLY), that he'd pay for Noreen's college education. Well, it turns out she's been accepted to Harvard and the cost will be in the neighborhood of $30,000.
Unable to tell Elaine of this dilemma, it only gets worse when she uses their money as a down payment on a new house. As a result, John enlists the aid of his goofy friend, Walter "Duff" Duffy (TOM GREEN), a landscaper who comes up with one hair-brained scheme after another of how to get the cash.
Between the two of them, they eventually get involved with Duff's Uncle Jack (SEYMOUR CASSEL), former classmate and current thug David Loach (CHRIS PENN), a lonely man, Mr. Cook (RICHARD JENKINS), who misses his dead wife, and Detective Charles (JOHN C. McGINLEY), a cop who's hot on their trail when their plans turn criminal.