Trama

A sweet-natured small-town guy inherits a controlling stake in a media conglomerate and begins to do business his way.

When small-town pizzeria owner and poet Longfellow Deeds inherits $40 billion from his deceased uncle, he quickly begins rolling in a different kind of dough. Moving to the big city, he is besieged by opportunists all gunning for their piece of the pie. Babe, a television tabloid reporter, poses as an innocent small-town girl to do an exposé on Deeds, but his sincere naiveté has Babe falling in love with him instead. Ultimately, Deeds comes to find that money truly has the power to change things, but it doesn't necessarily need to change him.—Sujit R. Varma

Preston Blake (Harve Presnell) 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 50,000 employees. The 82 years old Blake is attempting to summit Everest when a severe blizzard hits the mountain. His team strongly advises Blake to turn back, but Blake is adamant to keep pushing for the summit. Blake decides to summit alone, when his entire support team abandons him and returns to base camp. Blake freezes to death at the summit of Mount Everest, & a search for his heir begins. Blake's dead body is air lifted from the top of mount Everest by helicopter. Blake has a 49% stake in the media empire, valued at $ 40 billion.

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, hoping they might be accepted by Hallmark. Deeds is very down to Earth and is very well integrated as part of his community. He makes his own Pizza deliveries when the regular delivery guy calls in sick. His friends include Murph (Peter Dante) and Jan (Conchata Ferrell) who work at the Pizzeria with Deeds.

Deeds is contacted and brought to New York City by attorney and businessman Chuck Cedar (Peter Gallagher). Deeds is flown to New York City in a helicopter and the whole town comes to see him off at the airfield. In New York he meets various Blake staff members, including well-meaning general counsel Cecil Anderson. He also meets Blake's longtime butler Emilio Lopez, who saw Blake as a father figure and quickly befriends Deeds. 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. Cedar grows to despise Deeds and secretly wants to break up Blake Media.

The story is major news, and reporter Babe Bennett (Winona Ryder) works for a tabloid show called Inside Access. Mac McGrath (Jared Harris) is the dishonest Australian head of Inside Access and wants the inside story on Deeds at all costs. Babe is flat broke and Mac is about to fire her, so she needs the Deeds story desperately.

Babe has her lecherous co-worker Marty (Allen Covert) pretend to steal her purse in front of Deeds so he can "save her". She does this because their research indicated Deeds wanted to meet a girl by saving her, the same way his father had met his mother. Unfortunately, however, Deeds beats Marty senseless. Deeds rescues her and she goes 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 in Syosset, New York.

Though Pam initially hopes to just get a good story on the new heir, she eventually falls for the unfailingly kind Deeds and decides to tell him that she is not who she says she is. Deeds writes her a poem and manages to find a real "Winchestertonfieldville, Iowa," to which he takes her on a surprise trip.

Cedar is fed the truth by the "robber", still suffering from the effects of Deeds "saving" Bennett. Inside Access, in concert with Cedar reveals the truth to Deeds first. Heartbroken, and upset, Deeds decides to return home to Mandrake Falls after giving $40 Billion of his money he inherits to the United African American 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 follows Deeds to Mandrake Falls to win him back, getting into a massive brawl with Jan, who is furious at Babe for hurting her friend. Jan realizes Babe really cares for Deeds and tells her where to find him. While approaching Deeds, Babe falls through the ice of a frozen lake. Deeds hears her cries and saves her from drowning, breaking the ice with his foot, which was rendered rock-hard from a childhood frostbite injury. Despite Babe's pleas for forgiveness, he rejects her, and she sadly returns to 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 not to sell. But Cedar has control of a majority of the shares and the sale is approved. Babe suddenly arrives, having stolen and studied Blake's personal diary. The diary reveals that forty years earlier, Blake had a brief romance with his maid, Consuela, Emilio's (John Turturro) late mother who died while giving birth to him nine months later. Thus, Emilio is Blake's illegitimate son and the true heir to his stake in the company.

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 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 all he wants is his friendship. Emilio ends up giving Deeds a billion dollars, some of which Deeds spends on Corvettes for the entire town though "Crazy Eyes" immediately crashes his.

Deeds and Babe reconcile and return to Mandrake Falls, where she now works alongside him and Jan at the pizzeria. The poem Deeds wrote for Babe is accepted by Hallmark and becomes a popular greeting card.