Although she attempted to start a music career with two country-flavored albums, it was acting that continued to keep her employed, and in 2002 she landed a co-starring role in the hit CBS television series Still Standing. With what little time she had to spare, Olstead began performing with a local jazz/swing band around Hollywood, singing an array of standards with a voice that sounded far more mature than her age. It wasn't long before her musicality caught the attention of famed producer David Foster (Celine Dion, Natalie Cole), and a major-label record deal soon followed. Olstead released her self-titled collection of jazz and pop standards in May 2004, while continuing her work on Still Standing. In 2005, Olstead performed at the Live 8 festival in Berlin, and the following year her sophomore album, Skylark, came out. ~ Aaron Latham, All Music Guide