Alyssa Jayne Milano born December 19, 1972. Alyssa Jayne Milano is an American actress and former singer. She is perhaps best known for her roles as Samantha Micelli in the sitcom Who’s the Boss?, Phoebe Halliwell on the supernatural series Charmed or via her new female apparel clothing line Touch. Recently, she has appeared in a recurring role on My Name is Earl as Billie Cunningham. She got her start in acting by starring in the Broadway show Annie.