- Annie, The spunky, optimistic orphan who's looking for her birth parents. (age range 9-14)
- Oliver "Daddy" Warbucks, Billionaire businessman who opens his home, and finally opens his heart, to Annie. (age range 35-55)
- Grace Farrell, Oliver Warbucks' faithful secretary, who loves Annie from the start. (age range 20-40)
- Miss Agatha Hannigan, The orphanage matron, disillusioned, she hates children. (age range 30-50)
- Daniel "Rooster" Hannigan, Miss Hannigan's younger brother, a convict who escaped jail so he can rob his sister and plot to kidnap Annie. (age range 20-40)
- Drake, The butler at the Warbucks Mansion; a good friend to Grace, Annie and Daddy Warbucks. (age range 25-50)
- Lily St. Regis, Rooster's girlfriend, an egotistical gold digger. She and Rooster pose as Annie's "parents" so they can fool Warbucks and get their hands on the $50,000 reward. (age range 20-40)
- Franklin D. Roosevelt, President of the United States, he aids Daddy Warbucks in the search for Annie's parents. Upon meeting Annie, he is inspired to make a new deal and restore America's economy. (age range 40-60)
- Orphans, Annie's friends at the orphanage. (girls; age range 8-14)
- Louis Brandeis, Associate Justice of the U.S. Supreme Court, he is called upon to assist in Annie's adoption.
- Bert Healy, Radio announcer who agrees to broadcast Annie's search for her parents.
- The Boylan Sisters, Singers on the Bert Healy Show who hope to be famous someday.
- Star-To-Be, An upcoming Broadway Star, who sings a solo in N.Y.C.
- Sandy, An abandoned mixed–breed dog that, once Annie rescues him, becomes her companion and pet.
- Orphans include girls ages 8-14, some of whom have lines, and others who are in the Orphan Ensemble.
- We will cast a Dance Ensemble to be featured in several production numbers.
- We will also cast an ensemble of all ages who will portray various roles including citizens of New York City, radio performers, FDR's cabinet members, Warbucks' servants, residents of Hooverville, and more.