My first disc, “Little Misunderstood,” was a funk/fusion blowout. I spent a lot of time producing it to fit into that soundscape. At the time, I was living in Baltimore, and playing in a power trio with bassist Gary Grainger and drummer Larry Brite, so the material evolved from that scene. I was pretty fresh out of Berklee then, so my influences were more along Abercrombie, Stem, and Scofield. After moving to NYC in 1996, I really refocused on the jazz guitar sound and style, listening to players like Pete Bernstein, and playing with all of the incredibly swinging drummers here." Her second record was “Reunion of Souls”. It was  a live, jazz guitar date, and a collaboration of sorts with guitarist Chris Bergson, bassist Ashley Turner, and drummer Sunny Jam, Sheryl explains. She adds: " I’ve always loved playing guitar duo and quartet, and all of us had been playing together at different points since we moved to the city, so it was really a celebration of all that creativity. I think it’s a different kind of jazz guitar recording, because it’s about the group interplay and compositions more than two guitarists trying to outdo each other. Chris and I are both unique and different, and I think our styles complement each other and search out the music, not just the chops. Frank Forte wrote a really accurate and beautiful review of the disc for JJG. " But the best of her recordings is the most recent one "BULL'S EYE", a jazz masterpiece, a musical virtuosity which enriches the world of contemporary American music. In addition to composing, performing and recording, Professor Bailey teaches at Berklee school of music. In 1992, she began teaching jazz at Townson University in Baltimore, Maryland. Then, Berklee snitched her. Her alliance with Garzone did help her get the job. At Berklee, Sheryl the "professor" commenced to develop her own curriculum. And that’s how “Chord Rules” evolved.  Sheryl could  identify herself with "the student’s academic head-space, but being a working/traveling artist, I try to cut through the non-practical swirl and get down to the fundamentals—what it’s REALLY like to play jazz professionally. We focus on the basics of the instrument and of jazz improvisation. " as she told the media.

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