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Nneena Freelon Takes on Billie Holiday Songbook

Few jazz vocalists have the courage to take on the Billie Holiday songbook. Those songs evoke such deep feelings - many expressing heartache and others extreme loneliness - that many singers steer clear of the challenge. But one performer not only took the challenge, but did so with flying colors on Portrait of a Lady - Sketches of Billie Holiday.

Though many singers regard the late Billie Holiday as a major influence, only the most seasoned record her songs. For jazz vocalist Nnenna Freelon, it was just a matter of time.

Billie Holiday, or "Lady Day," was one of jazz music's most passionate performers, but also one of its most tragic. A star on stage, screen and television, Holiday crumbled under the weight of a turbulent life tainted by troubled marriages, drug and alcohol abuse, and prison time. She was almost penniless when she died of liver disease and heart failure at the age of 44 in 1959.

On the anniversary of Holiday's 90th birthday, Nnenna Freelon wanted to make sure Billie's legacy lived on.

Freelon faced a daunting task sorting through the wealth of Billie Holiday material. In the end, she chose standards often linked with Holiday or songs Holiday wrote. An inspired Freelon even wrote a few tunes of her own like "Only You Will Know."

It's not that Nnenna Freelon is the only one who can tackle a Billie Holiday tribute album. It's that she makes it looks so easy.