Louis Armstrong once claimed that “Every time I close my eyes blowing that trumpet of mine-I look right in the heart of good old New Orleans...It has given me something to live for.” This statement conjures an image which most anyone familiar with jazz music can recall: Armstrong clutching his trumpet forcefully, his eyes closed in a manner that distances him from his physical surroundings in favor of a perfect harmony between the man and his instrument. As Armstrong alludes to in this remark, this connection also speaks to the enduring influence of his New Orleans background, which informed his musical style and indeed continued to live on through his music. In 1956, Duke Ellington was featured on the cover of Time Magazine after a bravura performance at the Newport Jazz Festival that summer. This remains one of his most iconic achievements, and a landmark for jazz music as a whole (only four jazz musicians were ever displayed on the cover of Time). At the same time, however, this recognition stands as one of the prevailing ironies of Ellington's career, as he was deep into the latter stages of his performing life by this point. While those two men became jazz's most famous performers, others rose as legendary singers. 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 was well represented by both black and white master artists, men, women, vocalists, and instrumentalists, and Billie Holiday has stood the test of time as well as any, despite struggling with an environment that easily could have doomed such aspirations.