In 1986, Cassidy was asked by Stonehenge guitarist and high school friend, David Lourim, to lend her voice to his music project, Method Actor. This brought her to Black Pond Studios, where she met recording engineer and bassist Chris Biondo. Biondo helped her find work as a session singer and later introduced her to Al Dale, who would become her manager. She sang back-ups for various acts, from go-go rhythm and blues band Experience Unlimited to rapper E-40. Biondo and Cassidy, who were in a romantic relationship for a time, formed the five-piece "Eva Cassidy Band" with Lenny Williams, Keith Grimes and Raice McLeod in 1990. They began to perform frequently in the Washington area.