Milano was born in New York City, the daughter of Italian-American parents Lin, a former fashion designer and talent manager, and Thomas M. Milano, a film music editor and a well-known boating enthusiast. She has a younger brother, Cory (born in 1982), who is also an actor, but has more recently started a band, called Chloroform Days, in which he is the lead singer. Milano was born in Brooklyn but grew up in Staten Island, New York and was raised Catholic. She began her career at the age of eight when she won a part in an open audition for a national tour of Annie. She appeared in television commercials and off-Broadway productions. At the age of eleven, she earned her first major role in the TV 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, Tony Micelli. When Milano won the role, her family relocated from Staten Island to Hollywood. She produced a teen workout video