The town of Mandrake Falls will never be the same again, especially after their town hero, Longfellow Deeds (Adam Sandler) gets a visit from a couple of New York big shots. Preston Blake is a media magnate who enjoys living on the edge, after a climbing accident that left him frozen like a statue, his company was now going to be passed on to his nephew, Longfellow. The younger Deeds is a simple guy who owns a pizzeria, and tries his hand at creating Hallmark cards. As the world wonders who will replace the eighty something year old media magnate, news organizations try to scoop each other.
In any corporate environment, the one who has control of the most shares gets to call the shots, and Chuck Cedar (Peter Gallagher) has plans to be that person. In the mean time, Babe Bennett (Winona Ryder) is trying to get back in the good graces of her editor and concocts a plan to get close to Longfellow in order to get his story. The two are developing a relationship that ends up exploding when her secret is exposed to Longfellow, before Babe has a chance to come clean on her own. With his faith in humankind shattered, Longfellow chooses to return to Mandrake, where he donates his 40 billion to the United Negro College Fund.
After learning that Cedar has plans to sell the company and cause a great deal of employees to end up on the unemployment line, Longfellow decides to put a stop to it, returning to New York with one share to his name. At the shareholders meeting, Longfellow manages to salvage the votes that would have sold the company, and convinced everyone that selling was a bad idea. It is discovered that the butler (Emilio) is the illegitimate son and the rightful heir to the inheritance. Joining the cast are Erick Avari (Cecil Anderson), Steve Buscemi (Crazy Eyes) and Allen Covert as Marty.