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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?Even though she scored platinum in Japan, Milano had no interest to pursue a music career in the United States: "I'm not interested in crossing over.
She returned to the theater in 1991, producing and starring in a Los Angeles production of Butterflies Are Free from December 26, 1991, to January 19, 1992.She is known for her roles as Samantha Micelli in Who's the Boss?, Jennifer Mancini in Melrose Place, Phoebe Halliwell in Charmed, Billie Cunningham in My Name is Earl, Savannah "Savi" Davis in Mistresses, Renata Murphy in Wet Hot American Summer: 10 Years Later, and Coralee Armstrong in Insatiable.She welcomed the cancellation of the series, as she was ready to move on to other roles and enthusiastic to "showcase" what she was able to do.Looking back on eight years of playing the same role, Milano commented, "Creatively, it's been very frustrating. I changed her wardrobe, cut her hair, anything to give her new life." and finally tried to shed her "nice girl" image by appearing nude in several erotic films targeted at adults, such as Embrace of the Vampire, Deadly Sins and Poison Ivy II: Lily.
Via: Milano is currently a host and judge on Project Runway: All Stars and had a fairly major role in My Name Is Earl, playing Billie Cunningham the former criminal who married Earl.