Annie, a 10 year old orphan living in New York City during the Great Depression, finds herself whisked into a whirlwind adventure that involves a hard hearted billionaire, his doting secretary, and a dog who finds close kinship with the cherry haired little lady. Unfortunately, her good luck becomes threatened by the curmudgeon matron Miss Hannigan and her shifty conman brother Rooster and his pickpocket girlfriend Lily St. Regis.