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Preston Blake started out in his career hoping to be a disc jockey 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. It is found that Blake has a living nephew named Longfellow Deeds (Adam Sandler), who runs a pizzeria in New Hampshire and attempts (unsuccessfully) to write and sell greeting card captions. Deeds is contacted and brought to New York City by attorney and 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 Deeds wanted to meet a girl by saving her, the same way his father had met his mother. Deeds rescues her (as well as mercilessly beating her "robber") 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 (Syosset, New York). 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 is not who she says she is, but Inside Access, in concert with Cedar (fed the truth by the "robber", still suffering from the effects of Deeds "saving" Bennett) reveals it to Deeds first. Heartbroken, and upset, Deeds decides to return home to Mandrake Falls after giving his $40 Billion inheritance to the United Negro College Fund (much to the surprise of the chairman, who has a heart attack). 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. After saving her after she's fallen through the ice over a lake, he rejects her saying he does not really know who she is. 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 not to 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 (at one point he had told Deeds that Blake treated him "like a son"), and the true heir. As a result, Deeds' sale of his shares to Cedar is not legal. Emilio immediately takes control and fires Cedar, as well as the entire top brass at the company, with the exception of Cecil Anderson (Erick Avari), a good-hearted executive who had befriended Deeds (when he asks to remain, Emilio leaves the decision to Deeds, who quickly says yes). Babe reveals herself to Deeds and apologizes for tricking him, and they reconcile and Deeds falls in love again. As they are leaving, Emilio thanks Deeds for his support and asks how he can repay him. Deeds says that nothing is needed save for friendship, considering they are blood relatives. Emilio ends up giving 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.
