Longfellow Deeds (ADAM SANDLER) is an unassuming pizzeria owner in the little town of Mandrake Falls where he gets along with everyone, including his workers, Murph (PETER DANTE) and Jan (CONCHATA FERRELL), and customers such as Crazy Eyes (STEVE BUSCEMI), a bug-eyed sort with a penchant for odd pizza topping combinations. Always taking the time to say hello or help out those in need, Deeds' big dream in life is that one day, Hallmark will buy one of his greeting card poems.
While waiting for that to happen, Deeds gets a visit from Chuck Cedar (PETER GALLAGHER) and Cecil Anderson (ERICK AVARI), the CEO and legal counsel of Blake Media respectively. It seems that Deeds is the only living heir to owner Preston Blake (HARVE PRESNELL) who recently passed away and left 49% of his company - roughly worth $40 billion - to him.
Soon, Deeds travels to Manhattan to oversee his inheritance and meets Emilio Lopez (JOHN TURTURRO), his late great uncle's butler. He also meets small town school nurse Pam Dawson (WINONA RYDER), completely unaware that she's really TV producer Babe Bennett.
She's working undercover for a tabloid TV program called "Inside Access" and her sleazy boss and host of the program, Mac McGrath (JARED HARRIS), wants her and fellow worker Marty (ALLEN COVERT) to beat out the rest of the media swarm and get the inside scoop on Deeds.
As Deeds inevitably begins falling for Babe who begins to have second thoughts about her ruse when she sees that he's the real deal, he doesn't notice that Cedar is plotting to wrest control of the company from him. From that point on, Deeds must decide whether fame and fortune are worth the price of his integrity and better sense.