Milano began her career at age 7, when her babysitter, without notifying Milano's parents, took her to an audition for one of the four principal parts in a national touring company of Annie. Milano was one of four selected from more than 1,500 girls. During the course of her work in the play, Milano and her mother were on the road for 18 months. After returning to New York, Milano appeared in television commercials and did several roles in off-Broadway productions, including the first American musical adaptation of Jane Eyre. When accompanying a friend from the Annie production to the office of a New York agent, Milano was introduced to the agent, who began representing her. She does not feel that growing up in front of the camera harmed her childhood and has said: "I love my family very much – they've really backed my career. I consider myself to be normal: I've got to clean my room, and help in the kitchen. "