At the beginning of her career, Milano was known mainly for her role on Who's the Boss? (1984-1992). She tried to shed her "nice girl" image by appearing in several films targeted at adults, such as Casualties of Love: The Long Island Lolita Story (1992), Embrace of the Vampire (1994), Confessions of a Sorority Girl (1994), Deadly Sins (1995), and Poison Ivy II: Lily (1995), where she starred opposite Johnathon Schaech and Xander Berkley. She gained more mainstream success in TV as Jennifer Mancini on Melrose Place (1997-1998), Meg Winston in Spin City and most notably as Phoebe Halliwell on Charmed (1998-2006). Both Milano and close friend Holly Marie Combs became producers for Charmed during the show's fifth season. She also played the role of Eva Savelot in MCI's 1-800-COLLECT commercials. In 2007, Milano filmed a pilot for ABC entitled Reinventing the Wheelers. The series was not picked up for the 2007-2008 season, but instead, Milano appeared in ten episodes of the show My Name