Good Girls Gone Bad: Alyssa Milano in the 90s

Alyssa Milano starred on the family-friendly TV series 'Who's the Boss' from 1984 to 1992. As Sam, Milano was a smart-mouthed but straight-laced teen, and the only trouble she ever got into was the typical family sitcom kind. But after the show ended, Milano was having trouble finding interesting roles for herself on film, which led her to believe that she should try and shed that good girl image and go for something a little more daring. In 1993, Milano landed a role as Amy Fisher in 'Casualties of Love: The Long Island Lolita Story,' followed by sexy turns in 'Embrace of the Vampire,' 'Poison Ivy II: Lily,' and 'Fear,' among others. She even negotiated her own nudity clause in her contract to ensure that she had full control over her nude scenes, and while those movies weren't particularly classy, her attitude worked because she's still finding work in film and television to this day.