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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.
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".
Milano starred in two 1988 television films, Crash Course and Dance 'til Dawn.
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.
I'd much rather have it released where it's appreciated than laughed at." she was noticed by the media, which helped her land the role of Amy Fisher in the high-profile TV movie Casualties of Love: The Long Island Lolita Story, one of three TV films based on Fisher's shooting of Mary Jo Buttafuoco.
Alyssa Milano also had a regular role as Jennifer Mancini in Melrose Place.
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.Incidentally, some of these films would never had been made had Alyssa Milano been allowed to quit acting and continue her studies.In 1991, while still working on Who’s The Boss, she wanted to quit acting and study.Milano began her career at age 7, when her babysitter, without notifying Milano's parents, took her to an audition for one of the four principal parts in a national touring company of Annie.Milano was one of four selected from more than 1,500 girls.