8. Billie Holiday

There's so much going on in this picture. Isn't that the most photogenic dog you've ever seen? Do you think it looks happy or sad? And why is there a pineapple on the table? We'll never know, but it all appears to have been very funny to Billie Holiday. The First Lady of Jazz looks very much at ease in this environment.

Massively influential in the jazz and pop singing scene, Holiday's career spanned three decades and spawned a staggering number of hit albums and singles. It was no surprise when at the peak of her fame she transcended into the movie industry, too. Her star never really waned, and she was still one of the most in-demand performers in the world when she sadly passed away at age 44 in 1959.

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