She became much like my daughter." The series established Milano as a teen idol, and provided her opportunities for other roles. Her education was split between school and an on-set tutor with whom Milano would work for three hours a day. At age 12, Milano co-starred in "Commando" as Jenny Matrix, the daughter of John Matrix (Arnold Schwarzenegger). On stage, she starred in "Tender Offer", a one-act play written by Wendy Wasserstein, "All Night Long" by American playwright John O'Keefe, and the first American musical adaptation of "Jane Eyre". 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. A few years later this film was shown in Japan, prompting a producer to offer Milano a five-album record deal. Milano's albums, which she described as "bubblegum pop", scored platinum in the country, though she later criticised 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". Milano starred in two 1988 television films, "Crash Course" and "Dance 'til Dawn". Both projects allowed her to work alongside close personal friend Brian Bloom who worked with his brother Scott with her in episodes of "Who's the Boss"; this working camaraderie would later expand in 1993 when Milano made a cameo appearance in Bloom's film "The Webbers". She produced a teen workout video, "Teen Steam", and achieved some fame outside the US with her music career, which lasted until the early 1990s. 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." Simultaneously, she wrote a weekly column called "From Alyssa, with love" for the teen magazine "Teen Machine". Milano played a teenage prostitute in the 1992 independent film "Where the Day Takes You". The film, which focuses on a group of young runaway and homeless teenagers, was shot on and around Hollywood Boulevard. and was met with positive critical reception.