Milano began her career at age seven, after her babysitter, without notifying her parents, took her to audition for the touring company that was national in Annie. She was one of four chosen from more than 1500 girls. Milano as well as her mother spent 18 months travelling while she worked on the play. Milano was featured in television commercials, and she played a variety of roles in off-Broadway productions. This included the American musical adaptation Jane Eyre. Milano became acquainted with a friend from Annie when she accompanied her to the New York office of an agent. She started representing Milano. Milano does not believe that being on camera affected her childhood. She has said: "I love my family very much - they've really backed my career. I'm considered to be normal. I must clean my room and help with the cooking. In the month of August 1984, Milano made her film debut in the coming-of-age drama Old Enough, which she described as an "great" way for "starting off on the right foot". It was shown in the Sundance Film Festival where it was awarded the First Prize.
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