Milano began her career as a child when she was seven years old. Her babysitter took her on auditions for Annie the national touring company. From more than 1,500 girls, she was among the four selected. During the course of her work in the play, Milano and her mother were traveling for the duration of 18 months. After returning to New York, Milano appeared in commercials for television as well as in a variety of roles in off-Broadway productions which included the very premiere American musical adaptation of Jane Eyre. Milano was introduced to a former friend of Annie as she was escorting her to the New York office of an agent. She started representing Milano. Milano doesn't think growing up in front of a camera has hurt her childhood. I'm considered to be normal. I need to tidy my home and help in the kitchen. In the month of August 1984, Milano made her film debut in the drama about coming of age Old Enough, which she remembered as an "great" way for "starting off on the right foot". The film was screened in the Sundance Film Festival where it was awarded the First Prize.
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