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Throughout its history an impressive roster of singers have performed with the Opera Company of Boston ( OCB ).

Even from the beginning years at the Donnelly, Caldwell was able to attract first rate artists, most notably Beverly Sills and Joan Sutherland, to the company's roster.

She also had an eye for emerging talent with singers like James Billings getting their start with the company.

Other notable singers to have sung in OCB productions include Eunice Alberts, John Alexander, Richard Cassilly, Plácido Domingo, Donald Gramm, Marilyn Horne, Eva Likova, Elaine Malbin, Eva Marton, Sherrill Milnes, Magda Olivero, Renata Tebaldi, Norman Treigle, Shirley Verrett, Anja Silja, and Jon Vickers among many others.