In the late 1940s, we meet Hunt Shelton (Nicolas Coster), a prosperous businessman alongside his pretentious and expectant wife, Binky (Deborah Rush). Their journey leads them deep into the woods of West Virginia as they search for a friend's vacation hideout. Just when things take a stressful turn, Binky unexpectedly goes into labor, prompting an urgent rush to the small town of Jupiter Hollow and its local hospital— a private establishment meant solely for the employees of the local industry, Hollowmade Furniture. In a moment of spontaneity, Hunt decides to purchase the company right then and there, and amid the pandemonium, Binky gives birth to identical twin daughters. Concurrently, a local hillbilly woman, Iona Ratliff (played by Patricia Gaul), also arrives at the hospital to welcome her own twin girls. An elderly, near-sighted nurse, caught in the mix of chaos, mistakenly switches the babies, leading to a pair of mixed-up births. Hunt proposes the names Rose and Sadie for his daughters, inspired by his great-aunts. The idea reaches Garth (J.C. Quinn), Iona's husband, who has suddenly found himself responsible for eight children, and he opts to use the same names for his newborn daughters.
Fast forward to 1988—over forty years later—where we encounter Rose (Lily Tomlin) and Sadie Shelton (Bette Midler), who are now the ambitious co-owners of their late father's company, Moramax. This bustling corporation contrasts sharply with Sadie's ruthless demeanor as she treats her employees and her spoiled son, Jason (Seth Green), with the same contempt her father once did. Rose, however, finds herself caught between aspirations and a whimsical desire for a tranquil country life with her commitment-shy boyfriend, Dr. Jay Marshall (Michael Gross). In an effort to rework their business strategy, Sadie proposes the sale of Hollowmade, but discovers she must first secure the consent of company stockholders.
Confidence dripping from her tone, Sadie insists to the board members that the residents of Jupiter Hollow are on board with the sale. However, Rose Ratliff, now serving as the forewoman at Hollowmade, sends a potent letter informing Moramax of her intent to protest the meeting in New York City. Torn between loyalty and ambition, Sadie Ratliff decides to accompany her sister Rose as they leap into the unknown and chase the allure of city life. Meanwhile, Graham Sherbourne (Edward Herrmann), an employee at Moramax, is alerted to Rose's letter—signed only with the letter “R”—and is dispatched to locate the Ratliffs and prevent any potential disruption at the stockholder's assembly.
On the fateful day the Ratliff sisters arrive in New York City, Sadie and Rose Shelton head to the airport to meet an interested buyer for Hollowmade, the Italian entrepreneur Fabio Alberici (Michele Placido). However, a hilarious mix-up occurs when Alberici mistakenly boards the same limousine as the Ratliffs, who assume they have been sent a ride courtesy of Graham. The luxurious vehicle whisks them off to the iconic Plaza Hotel, where the two rural women are entranced by its opulence. In stark contrast, the Shelton sisters struggle to find cash for a cab fare, compelling them to navigate the subway to return to the hotel. When they finally arrive at the Plaza, they are dismayed to discover that the suite they typically occupy has been given away, forcing them to settle for a smaller room.
As the evening unfolds, Sadie Shelton encounters Mr. Alberici in the hotel elevator. Unable to discern him as anything but a predatory stranger, she swiftly rejects his advances—only to feel profound embarrassment when she realizes his identity moments later. Meanwhile, Sadie Ratliff eagerly delves into the city's vibrancy, encountering Jason, her sister’s son, along with Michael, her ex-husband, and Dr. Jay, much to their astonishment as they witness her unexpectedly cheerful demeanor.
That night, Sadie Ratliff receives a mysterious envelope filled with cash, tagged from someone named "Sly," not realizing it is a bribe from Alberici intended for Sadie Shelton. Amidst this chaos, Jay Marshall heads to the Plaza to propose to Rose Shelton. However, he mistakenly stumbles upon Rose Ratliff, who believes him to be “Sly” and brushes aside his engagement ring, mistakenly thinking it is an additional bribe, though she can't help but feel flattered.
Across West Virginia, Roone Dimmick (Fred Ward), Rose Ratliff's longtime boyfriend and an enthusiastic miniature-golfer, finds himself heartbroken when he learns of Rose's trip to New York City without a word. Determined to win her back, he hops on a bus to the city and mistakenly embraces Rose Shelton upon his arrival at the Plaza. Alarmed, she seeks assistance from Graham Sherbourne, who mistakenly believes Roone is the "R. Ratliff" that they are on the lookout for. During dinner, Roone candidly shares his criticisms of city life, inadvertently tapping into Rose's concealed yearnings for a more rustic existence.
In the hotel lobby, Sadie Ratliff unexpectedly crosses paths with Michael, enchanted by the woman he thinks is his reformed ex-wife. Following a lively flurry of conversation, they set a lunch date for the next day, ending with a kiss that leaves her smiling. As the night deepens, Sadie Shelton finally seals the deal with Mr. Alberici, marking the completion of their business transaction. However, things take an intriguing turn when Graham detains Roone in his suite, only to unfurl the truth that the Ratliffs are sisters.
The following morning, a determined Rose Ratliff and Sadie Ratliff enjoy breakfast in the hotel dining room, strategizing their protest for the upcoming stockholders meeting. A bit of chaos ensues when Sadie deliberately spills syrup on her jacket, using the mishap as the perfect excuse to splurge on a new stylish outfit at the hotel shop. However, the moment she leaves to change, Sadie Shelton takes over her spot at the table. Rose, expressing her disdain for Sadie Shelton's austere gray ensemble, persuades her to swap it for the eye-catching polka-dotted dress she had just spotted.
As they prepare for the imminent meeting in the hotel conference room, fate finally intertwines the lives of the four women in the lobby’s restroom, where they realize they’ve been long-separated sisters who were switched at birth—both red-haired Sadies belonging to the Shelton lineage and both brunette Roses hailing from the Ratliff side. Despite this shocking revelation, a determined Sadie Shelton still plans to proceed with the business sale, urging her newfound sister for support. Yet, Sadie Ratliff can’t allow the obliteration of her hometown to happen and assists the two Roses in locking Sadie Shelton in a janitor's closet to thwart the deal.
While Rose Ratliff monitors the entangled Sadie Shelton, Sadie Ratliff boldly impersonates her New York counterpart, stepping into the shareholder meeting with a commanding presence. However, as nerves take over and her assertive demeanor begins to falter, Rose Shelton instances that all the preparations have brought them to this point, stepping in to complete the speech and sway the stockholders' decision in favor of canceling the sale.
After the meeting, the four sisters reconvene in the lobby, greeted by their respective partners in utter astonishment upon learning about the two distinct pairs of sisters. As they exit the Plaza, Sadie Shelton and Mr. Alberici depart in his limousine for a planned yacht vacation. In a heartwarming twist, Sadie Ratliff chooses to remain in the city with Michael, departing in a taxi. Meanwhile, Jay invites Rose Ratliff out for coffee, and they wander away, with Rose beaming in the knowledge that she has safeguarded her hometown. Conclusively, Rose Shelton finds herself relishing a romantic carriage ride with Roone, as the two plan for a bright future in the countryside.
In a whimsical wrap-up, a homeless man (Leo Burmester) lingering outside the Plaza Hotel throughout the film, witnessing the comings and goings of the sisters, encounters his own doppelgänger when a sharply dressed businessman hails a taxi, leaving both men in a state of disbelief. Thus concludes this charming tale of mistaken identities, spirited siblings, and the ties that bind... The End.
