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Jazz singer Melissa Walker briefly considered a career in law after graduating from Brown University, but instead launched a career as a vocalist in Washington, D.C., in 1990. There in 1993, she produced her own first album, Little Wishes, which she sold at her performances. She moved to the New York area and studied with Norman Simmons. In 1997, she signed to Enja Records and recorded May I Feel, which was released in Germany. She expanded her performing range, employing her own group and appearing with the Lincoln Center Jazz Orchestra, directed by Wynton Marsalis. The 1999 release of Moment of Truth marked her commercial U.S. album debut; two years later came I Saw the Sky.