8. Gregg Allman
Born in Nashville, the epicenter of country music, Gregg Allman incorporated all types of rock 'n roll into The Allman Brothers Band's music. Country, blues, psychedelic, and Southern rock all conflated to create an original sound that was hugely popular as soon as the nation got a chance to hear it. Gregg was definitely the trippiest looking country singer out there, but he was a certified rockstar and thus could do whatever the fuck he wanted. This included marrying Cher and dressing so kooky that the extra "g" in his name most definitely stood for gangster.