Milano started her career when she was seven years old and her babysitter took her on auditions for Annie the national touring company. She was among four selected from more than 1500 girls. In the course of her role in the play, Milano and her mother were traveling for 18 months. After returning to New York, Milano appeared in commercials for television and was a part of several off-Broadway productions, such as the very first American musical version of Jane Eyre. Milano had a conversation with a pal who was in Annie and was escorted to the New York office by an agent. She started representing Milano. She doesn't believe that being in front of the camera affected her childhood. has said: "I love my family very much - they've really supported my career. I consider myself normal. I must clean my house and assist in the kitchen. "In August 1984, Milano made her film debut on the come-of-age drama Old Enough, which she recalled as a "great" way for "starting off on the right foot". The film was screened at the Sundance Film Festival,[9] where it won First Prize.Milano auditioned to play Tony Danza's daughter on the show "Who's the Boss?" After winning the part, she and her family moved to Los Angeles, where the show was made. It debuted on ABC on September 20 1984. Throughout The Boss?, Milano developed a close relationship with co-star Danza. Danza expressed her feelings about their early years of being together, saying: "She was just a adorable little girl at all times... She became extremely similar to my daughter." Milano was a teen-friendly idol and the series gave her many opportunities to play different roles. Milano's schooling consisted of and a tutor who was on-set with who Milano would work for 3 hours per day.
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