– Annie is a tough streetwise urchin who is, nevertheless; vulnerable when she thinks she might lose what has become most important to her: a newfound "family" who loves her. Throughout the show she shows independent, needy, maternal, and hopeful qualities. Although she is at times aggressive or crafty, there is no doubt that Annie is a friendly and caring child.

– Miss Hannigan is the evil orphanage matron. Her distaste for her job and the children is obvious in every line she speaks, every song she sings, and every move she makes. She is predictable and funny in her ridiculous, cruel ways.

– A powerful, self-assured billionaire who always has his mind on business. While sometime gruff and abrupt he has a kind heart. At first he is awkwardly affectionate toward Annie, but he soon finds himself completely charmed by her.

– She is the beautiful and loyal private secretary to Oliver Warbucks. Grace is mature, calm, and classy. She is businesslike when dealing with Miss Hannigan and Warbucks, yet maternal toward Annie.

– Miss Hannigan's despicable brother. Rooster is flashy and self-assured. His "moves" are as smooth as a gambler’s, sly, and deceiving. Rooster must have a convincing New York and Southern accent.

– Lily is Rooster’s airhead girlfriend. She is always distracted, although she manages to pick up on any conversation involving money. Lily must have a convincing New York accent.

 - The toughest girl in the orphanage.

Oliver Warbucks’ domestic staff. Their presence, posture, and speech is proper and fastidious. Their heads are always held high, with pleasant, yet guarded emotions.

- The President of the United States of America.

- President Roosevelt's assistant.