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Bailey grew up in Pittsburgh, Pennsylvania as part of a musical family. She started playing the guitar at 13. At first she was primarily interested in rock music and after a few years she heard Wes Montgomery play on the radio and discovered jazz. She attended Berklee College of Music in Boston, where she helped to found the college's first LGBT student group. After college, she taught music in Baltimore before moving to New York City in 1988 to further her career as a performer. She released her first album, Little Misunderstood in 1995. It featured musicians George Colligan, Vince Loving, and Chris Battistone.
In 2001, Bailey released Reunion of Souls with guitarist Chris Bergson, featuring Ashley Turner and Sunny Jain. Stewart Mason of Allmusic called one of the tracks "charming" and one "perfectly sweet" but said that the album was "nothing groundbreaking". This was followed by The Power of 3! in 2002 which contained eight tracks all written by Bailey. Allmusic's Rick Anderson said that each track was "a gem" and "more complex than you'd guess at first listen". Overall he said the album was "highly recommended". Her next album was 2004's Bull's Eye. In 2006, Bailey released her fifth album Live @ the Fat Cat and was a headline act at the Pittsburgh Jazz Festival. Her sixth album, A New Promise is due for release by MCG Jazz on February 2, 2010. She also teaches at Berklee, and at Stanford University's summer workshops.