New York City during the Depression. Annie (Annie Jackson) lives in an orphanage run by the ill-tempered, heavy drinking Miss Hannigan (Tami Rae Weiss). Like the rest of the children, Annie doesn't like the orphanage and hates Miss Hannigan. When Annie is chosen to spend the Christmas holidays with the wealthy industrialist Oliver Warbucks (David Riley), Miss Hannigan is infuriated that Annie will be spending the holidays in the lap of luxury. Warbucks is charmed by Annie's spunk and good spirits and is eager to adopt her, but Annie is convinced that one day her real parents will come back to claim her. Warbucks loves her enough to offer a fifty thousand dollar reward in the search for her folks. That's when Miss Hannigan's con-artist brother Rooster (Jacob Hustvet ) and his floozy girlfriend Lily (Anna Booman), concoct a scheme to pose as Annie's long lost parents. Along the way Annie befriends a mutt named Sandy (Cassidy Woods) and even President Franklin Delano Roosevelt (Bob Pitel).

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