Ilya S. Savenok, Getty Images The sad news came across late Wednesday afternoon…
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16. Waylon Jennings
An originator of "outlaw music," Jennings was the craziest of the rebellious, longhaired country singers who went against the Nashville establishment in the early '70s. By that time he had already been roommates with notorious pill-popper Johnny Cash, and his hard-partying ways only intensified with time. Soon, Jennings had traded pills for a $1,500-a-day cocaine habit, which he finally kicked in 1984. "I did more drugs than anybody you ever saw in your life," he said. Miraculously, he lived until 2002, when he died in his sleep at 64.