Character Breakdown

Annie
A tough, street-smart orphan with a big heart. Strong, hopeful, and full of energy.

Molly
The youngest orphan. Sweet, playful, and full of personality.

Kate
Second youngest orphan. Kind, spirited, and part of the group’s mischief.

Tessie
Emotional and dramatic—known as the “crybaby” of the group.

Pepper
The toughest orphan. Bold, feisty, and a natural leader.

July
The quietest orphan. Observant and thoughtful.

Duffy
The oldest orphan. Confident and caring toward the younger girls.

Miss Hannigan
The orphanage matron. Bitter, dramatic, and full of comedic flair.

Grace Farrell
Warbucks’ secretary. Elegant, kind, and always in control.

Rooster Hannigan
Miss Hannigan’s sly, smooth-talking brother and con artist.

Lily St. Regis
Rooster’s flashy, comedic partner in crime.

Oliver Warbucks
A wealthy businessman who is strong, commanding, and eventually warm-hearted.

Sandy
Annie’s loyal stray dog.

Drake & Servants
Warbucks’ household staff. Polished, precise, and supportive.

Apple Seller
A small but memorable role who shows kindness to Annie.

Lt. Ward
A no-nonsense policeman.

Bert Healy
A lively radio show host with a big personality.

Bundles
The friendly laundryman.

President Franklin D. Roosevelt
A confident leader who helps Annie’s story come full circle.

Louis Howe
Roosevelt’s helpful assistant.

Star(s)-to-Be
Glamorous performers featured in “N.Y.C.”

Usherette
A small role with a featured moment.

New Yorkers
A lively ensemble of 1930s city characters—vendors, tourists, workers, and more.