Milano began her career when she was just seven years old. Her babysitter took her on auditions for Annie the national touring company. From more than 1,500 girls she was among four selected. Milano along with her mother, were traveling as they worked on the show. Milano was featured in television commercials as well as played a range of roles in Off-Broadway productions. This included the American musical adaptation of 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 doesn't think growing up in front of a camera has hurt her in the past. I'm a normal person. I must clean my house and assist with the cooking. Milano's debut film was Old Enough, a coming-of-age drama. She described it as an "great method" to "start out." The film was screened in the Sundance Film Festival where it was awarded the First Prize.
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