When one thinks of jazz vocalists, fewer come to mind quicker than Billie Holiday. Born Eleanora Fagan, Holiday lived a troubled childhood before embarking on a career as a vocalist while still a teenager. She was discovered by famed record producer John Hammond in 1933, who booked her to sing with his other recent star creation, Benny Goodman. In the mid-1930s, Holiday, with help from Hammond and pianist Teddy Wilson, led several classic recording sessions that firmly established her as jazz's top female vocalist.

Holiday sang with several of the top big bands of the 1930s and 1940s before achieving her greatest commercial success in the 1940s. Her career began to take a turn for the worse by the end of the decade, however, as she struggled with drug addiction and ensuing legal problems from said addiction. Her performances during this time period took on a much darker, harsher tone, but are considered nowadays to perhaps be the apex of her career. Sadly, she could never escape the personal demons that chased her her entire life, and she passed away from complications of cirrhosis in 1959.