3. Waylon Jennings
Alongside Willie Nelson, Waylon Jennings was the OG outlaw singer. No one else embodied the fast living of country music's rebel lifestyle more so than Jennings. His signature long hair and beard (unheard of in Nashville in the early '70s) and black leather vest were symbols of his rebellion and spoke to a new audience of country: the youth who were disaffected by the failed utopia of the '60s.