Alright, for my 2nd pick, from the Blues category...
Howlin' Wolf - Moanin' at the Moon
Quote:
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Unlike many other blues musicians, after he left his impoverished childhood to begin a musical career, Howlin' Wolf was always financially successful. Having already achieved a measure of success in Memphis, he described himself as "the onliest one to drive himself up from the Delta" to Chicago, which he did, in his own car on the Blues Highway and with four thousand dollars in his pocket, a rare distinction for a black blues man of the time. In his early career, this was the result of his musical popularity and his ability to avoid the pitfalls of alcohol, gambling, and the various dangers inherent in what are vaguely described as "loose women", to which so many of his peers fell prey. Though functionally illiterate into his 40s, Burnett eventually returned to school, first to earn a G.E.D., and later to study accounting and other business courses aimed to help his business career.
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http://en.wikipedia.org/wiki/Howlin%27_Wolf
What a legend. Listening to this guy was such a key component in my education in rock and roll. Just listening to him, you can detect his influence in so many present artists. Awesome stage presence and by all accounts, a pretty decent guy. This guy was Tom Waits before Tom Waits was Tom Waits.