"Don't threaten me with love, baby, let's just go walking in the rain" (Billie Holiday)

A lot of ink has been spilled covering the lives of history's most influential figures, but how much of the forest is lost for the trees? In Charles River Editors' American Legends series, listeners can get caught up to speed on the lives of America's most important men and women in the time it takes to finish a commute, while learning interesting facts long forgotten or never known.

If Billie Holiday wanted to become a jazz singer, she chose the best of all eras in which to attempt it. A wave of great jazz and jazz/pop crossover artists swept over the United States from the 1920s through the 1950s, generating a golden age for the genre. This wondrous jazz era represented both black and white master artists, men, women, vocalists, and instrumentalists, and Billie Holiday has stood the test of time as well as any of them, despite struggling with an environment that easily could have doomed such aspirations.

Emerging from such a powerful group of talented vocalists was not easy. The woman who has come to represent a model of great, instinctive jazz singing came from nowhere, had nothing, and virtually had no one who was truly helpful in her background. She was raw and untrained, but went forward, regardless, with limited and quirky vocal gifts, the likes of which had never been heard in the highest circles of jazz. This especially was true among women, where perfection of phrasing and a smooth style of delivery stood as the unspoken guidelines of vocal success. No female counterpart of Louis Armstrong, one of Holiday's idols, was ever going to survive in the female jazz world for long, except perhaps as a novelty.