Longfellow Deeds (Adam Sandler) is a sweet, lovable guy leading a simple but happy life in the tiny hamlet of Mandrake Falls, New Hampshire. The popular owner of Deeds' Pizza, the town's only pizzeria, Deeds has become a kind of home-grown celebrity as he entertains his patrons by reciting his offbeat but hilarious greeting card poetry.

Life is good at the small town restaurant until Chuck Cedar (Peter Gallagher), a slick corporate mogul, along with his crony, Anderson (Erick Avari), bring news that Deeds is about to be rolling in a different kind of dough. A long lost relative, Preston Blake (Harve Presnell), has left him an inheritance of $40 billion along with a chain of media outlets, a football team, a basketball team and a private helicopter ready to whisk him off to corporate America.

It's a rags-to-riches story that has local tabloid reporters salivating, and Deeds is quickly swept up into a 24/7 media frenzy. Leading the charge is the beautiful Babe Bennett (Winona Ryder) of T.V.'s "Inside Access," a likable producer working her way up to her dream job at "60 Minutes." Her boss, sleazy "Inside Access" host Mac McGrath (Jared Harris), wants some dirt on Deeds, and it's up to Babe and her colleague Marty (Allen Covert) to forge a devious plan to get it.

After a hero's sendoff in Mandrake Falls, organized by his trusty employees Jan (Conchata Ferrell) and Murph (Peter Dante), Deeds makes a move to Manhattan. In his new Park Avenue digs, he is amused as he listens to his voice echo through the palatial halls and marvels at how his personal butler, Emilio (John Turturro), keeps sneaking up on him to tend to his every need. On his first day on the job at Blake Enterprises, Deeds shakes things up in his own inimitable way. He fires the star quarterback of his football team (to teach him some manners); and he makes the workplace a "hugs only zone." The billionaire's world may look different from the outside, but inside Deeds is still the same small town guy.

What Deeds doesn't know is that conniving Cedar is ready to take the reigns of the Blake empire at any cost. Deeds ultimately discovers what life is all about and has to prove that money changes everything...but not everyone.