Alyssa Jayne Milano (born December 18, 1972) is an American actress and former singer. Her acting career began after she appeared in the Broadway show Annie. Her childhood role as Samantha Micelli in the sitcom Who's the Boss? made her famous, and an eight-year stint as Phoebe Halliwell on the supernatural series Charmed brought her a new round of fame. She also starred on the ABC series Romantically Challenged as Rebecca Thomas.
Milano began her career at age eight after winning a role in an open audition for a national tour of Annie. She was one of the four picked out of an audition with over 1500 girls. She appeared in television commercials and off-Broadway productions.
At age 11, she won her first major role in the television show, Who's the Boss?, alongside Tony Danza, Judith Light, Danny Pintauro, and Katherine Helmond. She starred as Samantha Micelli, the daughter of Danza's character. After Milano won the role, she and her father relocated from Staten Island to Hollywood. The rest of the family followed a year later, because her mother was initially unwilling to give up her home life "for a show that wasn't a guarantee." Although born and raised in Brooklyn, Milano had trouble getting this accent, because she worked to lose it to land more roles in the theater, including in a stage adaption of Jane Eyre.
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, when she starred in and produced a Los Angeles production of Butterflies Are Free.
In 1985, Milano was in the film Commando as Jenny Matrix, daughter of John Matrix (Arnold Schwarzenegger). Appearing at age 12 in an R-rated action film, Milano admitted she was sometimes "freaked out" by the weapons on set. A few years later this film was shown in Japan, prompting a producer to offer Milano a five-album record deal.
By the late 1980s, Milano was established as a teen idol,[3] appearing in made-for-television teen films such as Crash Course and Dance 'til Dawn (both 1988). Both projects allowed her to work alongside close personal friend Brian Bloom. Bloom and his brother Scott worked with Milano in episodes of Who's the Boss. This working comradere would later expand in 1993 when Milano guest starred in Brian's series The Webbers. She produced a teen workout video in 1988 called Teen Steam and achieved some fame outside the USA with her music career, which lasted until the early 1990s. In 1991, Milano wanted to quit acting to pursue an academic career, but was unable to gain release from her contract.
When her role on Who's the Boss ended in 1992, Milano feared having trouble to obtaining other roles, aware of the fate of many grown-up child stars in that period. Nevertheless, she was excited when she found out the show was cancelled, being ready "to move on." Milano 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 (1993), Embrace of the Vampire (1994), Deadly Sins (1995), and Poison Ivy II: Lily (1996), where she starred opposite Johnathon Schaech and Xander Berkeley.
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