After returning to New York, she appeared in television commercials and did several roles in off-Broadway productions, including the first American musical adaptation of Jane Eyre.
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.She said the nude appearances taught her to begin requiring a nudity clause in her contracts giving her "full control" over all her nude scenes.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.Since Milano is from the same hometown as NFL Network's Rich Eisen, she revealed some of her family's connections with the Giants.
On March 24, 2009, her book on her baseball fandom, Safe At Home: Confessions of a Baseball Fanatic, was released.
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.
Milano's albums, which she described as "bubblegum pop", scored platinum in the country, though she later showed her discontent in 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 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.