Olstead was born in Kingwood, Texas, to Christopher Eric Olstead and Rebecca Lynn Jeffries. Olstead is of Norwegian ancestry. As a child actress, she made films and commercials from age eight onwards. She also attended Centre Stage theatrical school and is mentioned on their website\'s list of alumni.\n', '

From 2002 to 2006, she appeared in the TV sitcom Still Standing as middle sister Lauren Miller. Olstead was presented with the Young Artist Award for Best Performance in a TV Series (Comedy) - Supporting Young Actress for Still Standing in 2002. She also had a small part in the 2004 film 13 Going on 30. She co-starred in the ABC Family series The Secret Life of the American Teenager, about fifteen-year-old Amy Juergens\'s struggle through her unexpected pregnancy and how it affected her peers. Olstead played the character Madison Cooperstein, one of Amy\'s best friends.\n', '

In 2004, Olstead released a self-titled album of jazz songs and pop standards for Warner Bros. Records to good reviews. Since her previous releases had limited distribution, this album was considered her official debut. She subsequently performed in Berlin during the Live 8 concert on July 2, 2005.\n', '

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