[1] Charleston was born in Chicago,[2] and grew up in the Hyde Park neighborhood, the only daughter of an English professor father and voice teacher/singer mother.
During her time off from journalism, she studied jazz singing with Peter Eldridge of New York Voices, and began performing in Greenwich Village.
Her third album, In My Life, had a special promotion with Virgin Megastore, which sold it with an exclusive live DVD.
[3] Paul Newman and Joanne Woodward were among her neighbors; she considers them role models for raising her family.
Her father hosts a classical music program for Philadelphia radio, and her brother plays percussion with the New York Philharmonic.