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Milano's albums, which she described as "bubblegum pop", scored platinum in the country, though she later criticised their musical quality.
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".
She and Holly Marie Combs became producers for the show during season four.In a 1995 interview, she explained her motivation for some explicit scenes in Embrace of the Vampire: "I'm not going to say that I was manipulated into doing things that I didn't want to do.I did it because it was a woman director and I felt protected.Milano auditioned as Tony Danza's daughter on the sitcom Who's the Boss?After winning the part, she and her family moved to Los Angeles, where the show was produced. and the first American musical adaptation of Jane Eyre.
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She produced a teen workout video, Teen Steam, and achieved some fame outside the US with her music career, which lasted until the early 1990s.