The Cherrywoods are a middle-aged couple who run an orphanage. Mr. Cherrywood tells the orphans a story about the Care Bears and Care-a-Lot, their home in the clouds. In the story, Friend Bear and Secret Bear travel looking for people to cheer up. They meet Kim and Jason, two lonely orphaned children, who lost their parents in a car accident. Friend Bear and Secret Bear introduce themselves and remind the children of their ambitions, but neither of them are interested.
Oopsy, Cheer, Funshine, Share, and Grumpy are building WooHoo World, Care-a-lot's amusement park. Everyone has a job on the building of the park and Oopsy's job is painting the tracks of the Funderbolt ride. He had completed one part of the tracks but realized that he was stuck. Suddenly, he slips into the paint and rides down the whole ride by himself. Cheer, Share, Funshine and Oopsy decided to try the Funderbolt ride. After the ride, Oopsy stumbles and makes a chain reaction with plenty of disaster on the way that leaves Grumpy and the others wondering if they can fix Oopsy's disaster in time for the grand opening. Oopsy feels guilty for his actions and he wants to help his friends. Funshine recommends that Oopsy place the placing signs all around Care-a-Lot, this keeps Oopsy from causing any more trouble. Cheer gives Oopsy a special whistle in case he needs her help.