It's 1974, and a man named Marty Bronson (narrated by Jonathan Pryce) tells the story of his life as the proprietor of a cozy hotel, managed alongside his two children. His daughter, a serious 12-year-old named Abigail, efficiently oversees the front desk, while his imaginative 10-year-old son, Thomas, seems to contribute little, his boundless creativity failing to aid the hotel in practical matters. Unbeknownst to them, the family business is drowning in debt, prompting Marty to consider selling to an Englishman named Barry Nottingham (Richard Griffiths). However, Marty stipulates that he will only sell if Barry agrees to let his son run the place when he comes of age.
Fast forward to the present day, the once quaint hotel has transformed into a lavish establishment catering to the rich and famous, with Skeeter Bronson (Adam Sandler](/actor/adam-sandler)) now serving as the handyman. When Barry announces the intention to expand and appoints Kendall (Guy Pearce) as the new manager, Skeeter's life takes another twist. One day, after a brief visit to his sister Wendy (Courteney Cox) for his niece's birthday—whom he hasn’t seen in four years—he learns that Wendy's school is facing closure, forcing her to move to Arizona for work. She asks him to babysit her children, Patrick (Jonathan Morgan Heit) and Bobbi (Laura Ann Kesling), which he reluctantly agrees to despite not knowing them well.
After the regular babysitter, Jill (Keri Russell), leaves, Skeeter comforts the kids by reading them a story. Bored by the dull books available, he weaves a tale of a medieval squire named "Sir Fixalot" and his rival "Sir Buttkiss." The children eagerly add their own twists, culminating in a bizarre conclusion where "gumballs rain down" during a celebration.
The following day, while repairing Nottingham's television, Skeeter learns about the hotel's new rock and roll theme. Seizing the chance to compete with Kendall, Skeeter finds his life inexplicably mirroring the fantastical stories he tells the children. The next tale—a Western fantasy—sees him riding a "Ferrari" horse and facing off against villains, echoing the children's vivid additions.
As the story unfolds, Skeeter becomes aware that only the children's spontaneous ideas bring about changes in reality. He struggles to engage them with various plots, culminating in increasingly ridiculous scenarios, such as fighting off a rival in a space-themed adventure. On the final night, amidst the chaos of a birthday party for Nottingham, Skeeter's dreams of competition take an unexpected turn, leading to humiliation and a stern reminder of the stakes at hand.
Faced with the possibility of losing everything, including the school where his sister works, Skeeter is inspired to take a stand. He devises a plan to prevent the demolition and even finds a new location for the school, culminating in a thrilling motorcycle ride with Jill as they manage to save the day. The film concludes with Skeeter marrying Jill and founding a hotel in honor of his late father, leaving his previous rival, Kendall, to serve as a diminished member of his staff.
Through love, adventure, and a touch of magic, Skeeter learns profound lessons about family, responsibility, and the importance of sticking together.