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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.Milano auditioned as Tony Danza's daughter on the sitcom Who's the Boss?In 2005, she was ranked #5 in the "50 Cutest Child Stars — All Grown Up".Milano was briefly married to singer-songwriter Cinjun Tate in 1999; they were divorced later that same year. She has dated a number of professional athletes, including Brad Penny, Carl Pavano, Barry Zito and Russell Martin.
Milano was one of four selected from more than 1,500 girls.
Subsequently, she starred in the children's film The Canterville Ghost, which did not achieve much praise or attention and Variety magazine noted in its review: "Milano as the catalyzing daughter Jennifer adapts to the ghostly Sir Simon without a qualm; that, of course, is the true charm of the story, but Milano doesn't exhibit enough presence to match the droll, charming Gielgud".
Milano starred in two 1988 television films, Crash Course and Dance 'til Dawn.
So at the tender age of seven, with her mother in tow, Alyssa joined the tour as July, one of the orphans.
After 18 months on the road, Alyssa, who had begun to garner a reputation as an energetic and charismatic young actress, left Annie to be featured in off-Broadway productions and television commercials.She is known for her roles as Samantha Micelli in Who's the Boss?