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Known popularly as “the divine Sarah” and “Sassy,” Sarah Vaughan was regarded as one of the premier female vocalists of her day. Drawn to music from an early age, she studied piano and sang in her church choir as a youth. When Vaughan was eighteen, she entered an amateur talent contest at Harlem’s Apollo Theater on a dare and won first prize. This success led to frequent invitations to perform alongside the leading figures in contemporary jazz, including Earl “Fatha” Hines, Dizzy Gillespie, and Billy Eckstein. Adept at bebop improvisation, Vaughan possessed a wonderfully versatile voice that complemented a larger jazz ensemble. By 1950—the year in which Josef Breitenbach created this portrait—she was selling upwards of three million records a year. During this period, a poll in Down Beat magazine named her the top female singer for six consecutive years.