When Deeds inherits controlling interest in a media corporation from his deceased uncle, he’s quickly besieged by opportunists gunning for their piece of the pie. When Babe, a television tabloid reporter posing as an innocent smalltown girl, is sent to do an expose on Deeds, she instead feels herself falling in love.

Preston Blake started out in his career hoping to be a television broadcaster as a young man, slowly working his way up through the ranks to found Blake Media, a corporation running hundreds of television and radio stations and with 50 thousand employees. After Blake freezes to death at the summit of Mount Everest with a triumphant smile on his face, a search for his heir begins.

When it is found that he has a living nephew named Longfellow Deeds who runs a pizzeria in New Hampshire, Deeds is contacted and brought to New York City by attorney & businessman Chuck Cedar (Peter Gallagher). Plans are made for Deeds to sell his shares in the company to Cedar and return home $40 billion richer, but he must remain in New York for a few days as all the legal details are worked out.

The story is major news, and reporter Babe Bennett (Winona Ryder), who works for a tabloid show called Inside Access, has a friend pretend to steal her purse in sight of Deeds, because their research indicated Deed wanted to meet a girl by saving her, the same way his father had met his mother. Deeds rescues her and she continues to go out with him under the disguise of Pam Dawson, a school nurse from Winchestertonfieldville, Iowa (a town she made up on the spot when asked where she was from, which later turns out to be a real place).

Though Pam initially hopes to just get a good story on the new heir, she eventually falls for the unfailingly kind-hearted Deeds, and decides to tell him that she’s not who she says she is, but Inside Access reveals it to Deeds first. Heartbroken, and upset, Deeds decides to return home to Mandrake Falls after giving all the money he inherits to the United Negro College Fund. After returning to Mandrake Falls, he learns from Crazy Eyes (Steve Buscemi) that Chuck Cedar intends to sell off the company, which will cause thousands of people to lose their jobs. Babe visits Deeds in Mandrake Falls and tries to win him back. He rejects her saying he doesn’t really know who she is, apart from being a small-town girl from Iowa in the big city of New York.

At a shareholders meeting, Cedar has everyone convinced to sell the company, until Deeds (who has bought a single share) arrives and manages to convince everyone to not sell. But Cedar has control of a majority of the shares and the sale is approved. Babe arrives, and reveals that Blake’s butler, Emilio (John Turturro), is Preston Blake’s illegitimate son, and the true heir, as his mother, then Preston’s housekeeper who was looking after the house, had sex with him, presumably resulting in their son’s birth. This makes sense, as Emilio mentions that his mother died while giving birth, and Preston never mentioned about his real father during the forty years he lived there.

As Emilio is the true heir, Deeds’ sale of his shares to Cedar is not legal. Emilio immediately takes control and fires Cedar, among others. Babe reveals herself to Deeds and apologizes for tricking him, and they reconcile and Deeds falls in love again. As they’re leaving, Emilio gives Deeds a billion dollars, some of which Deeds spends on Corvettes for the entire town, and he returns to Mandrake Falls with his new wife Babe, where he learns that Hallmark Cards has bought one of his cards, the one he wrote for Babe.

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