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Lionel Spalding (Glenn Shadix) and his dog Neil arrive at the prestigious, five-star Majestic Hotel where, due to a prank by Kyle Grant (Eric Lloyd) and his older brother Brian (Graham Sack), an overflowing fountain accidentally drenches him, greatly frustrating the hotel manager and the boys' widowed father Robert (Jason Alexander). He is disappointed with the boys but they are guaranteed a vacation in Barbados afterward, only for the ruthless, haughty hotel owner, Elena Dubrow (Faye Dunaway), to force them to cancel the trip for a third time, due to the upcoming Crystal Ball where one of the guests is revealed to be a critic from the Le Monde Traveller Organization who they hope will reward the Majestic with a sixth star.

At that moment, "Lord" Rutledge (Rupert Everett), a jewel thief whom Mrs. Dubrow believes is the critic, arrives with an orangutan named Dunston, intending to steal the guests' jewelry. Dunston and his deceased brother Samson were both trained in thievery their entire lives, and Dunston has been wanting to escape from Rutledge's poor treatment and life of crime ever since.