Born in Boston, Lily Holbrook studied music and art at a local art college near the late nineties, but it was performing that seemed to be her goal. When not studying, Holbrook could often be found busking in subway corridors throughout Boston. Shy and slightly nervous during her initial performances, she received a lot of positive feedback from people passing by. Other spots she would play included Newbury Street, Quincy Market and Harvard Square. Gaining confidence through these gigs enabled Holbrook to get gigs at various venues in Boston, including The Middle East and TT The Bears. Gaining a small but loyal following, Holbrook was praised by Mary Lou Lord as a great talent. Holbrook also participated in the Women's Independent Music Show in Boston. In 1999, she entered the studio to work on her debut album. In 2000, Holbrook released Running From The Sky, an album dedicated to Christopher Holbrook. Her melancholic style and folk rock approach has often drawn comparisons to Jewel.