Marty Bronson (Jonathan Pryce) who raises his son and daughter on his own has to sell his homey motel to clever Barry Nottingham (Richard Griffiths) who promises to make Marty's son manager, when he's grown up and has proven himself. Nottingham pulls down the motel to raise a pricey hotel. Although grown up, Marty's son Skeeter Bronson (Adam Sandler) works as a janitor and general servant, but unlikely as it seems, he still dreams of becoming the manager. When Nottingham announces a brand-new gigantic hotel project, he makes his future son-in-law, base Kendall (Guy Pierce), manager, shattering Skeeter's dream. At the same time Skeeter's sister Wendy (Courtney Cox) has to leave town for a job interview and asks him to alternate looking after her two children Patrick (Jonathan Morgan Heit) and Bobbi (Laura Ann Kesling) with Wendy's responsible-minded colleague Jill (Keri Russell). He doesn't get along with either Jill or the children, but his being easy going loosens them all up and once he starts telling his bedtime stories, the children grow fond of him and begin to bring in their ideas about how the stories should go. When the stories turn out to become true in real life, Skeeter tries to maneuver the stories into a direction which will make his dream come true, too.
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