When millionaire Preston Blake meets his demise while scaling Mount Everest, the future of his news corporation, Blake Media, hangs in the balance. Enter Chuck Cedar, Blake's ambitious second-in-command, who sees an opportunity to sell the company, disregarding the livelihoods of its 50,000 employees. However, hope arises with the news of Blake’s long-lost nephew, Longfellow Deeds. Cedar swiftly sets out to convince Deeds to relinquish control of the company.
It turns out that Deeds, an affable small-town man, works in a local pizzeria alongside his friend Jan in New Hampshire. Although he is somewhat naïve, his kind-hearted and easygoing temperament becomes evident. Cedar manipulates Deeds into selling his stake in Blake Media for a staggering $40 billion, although it requires Deeds to spend some time in New York to finalize the legalities. Upon arriving in the city, Deeds quickly makes his presence felt; he bonds with the staff, notably the butler Lopez, and even delivers a solid punch to an arrogant football star. His clumsy but amusing exploits lead to unintended consequences, including a bizarre incident where he accidentally disrupts his uncle’s funeral.
Deeds's captivating antics attract the attention of a savvy reporter, Babe Bennett, who decides to go undercover to get closer to him. Pretending to be a victim of a mugging, Babe stages an act in front of Deeds. In a heroic move, Deeds punches out her partner, Marty, and his bravery sparks a romance between the two, with Babe pretending to be Pam Dawson, a nurse from Iowa. Together, they navigate a series of comical adventures, but Babe grows to genuinely love Deeds amidst her own fabrications.
When Deeds eventually uncovers the truth about Babe's deception, orchestrated by Cedar, it devastates him. The realization of his naïveté regarding urban life weighs heavily on Deeds as he relinquishes hold of the company and retreats back to his hometown.
Cedar, now free to push his agenda, organizes a shareholders' meeting to finalize the sale. However, Babe's journey of redemption leads her to Mandrake Falls, where she confronts Jan in a catfight before unintentionally plunging into an icy river. Deeds saves her, yet the rift from her earlier lies remains. As she grapples with her feelings, she discovers an intriguing detail in Preston Blake's diary…and she realizes that she must act to save Deeds’s legacy.
During a pivotal shareholders meeting, Deeds unexpectedly arrives, having become a shareholder himself through a single share purchase. He delivers an impassioned speech that reignites the shareholders' childhood aspirations and dreams, but Cedar maintains majority control, pushing the sale forward. Just when all seems lost, Babe produces a revelation from Blake's diary: it discloses an affair that indicates Blake has a son. This revelation nullifies Cedar's majority claim, as the real heir turns out to be Lopez.
With Lopez now in charge, he promptly dismisses Cedar, paving the way for restoration. In the end, as Deeds returns home to continue his life as a pizzeria worker, he has truly found success in love—marrying Babe, gifting Corvettes to his friends, and having his whimsical poetry published worldwide.
