Willie Nelson

Before assuming his frayed, pony-tailed persona and long before the superstardom he snared in the '70s, Willie Nelson was just another strait-laced, short-haired Nashville tunesmith cranking out hits for others. His songs — "Crazy," "Funny How Time Slips Away," "Hello Walls," and "Night Life" among them — went on to become country classics, but it wasn't until his groundbreaking album The Red Headed Stranger simultaneously opened the door for crossover country and unplugged attitudes that Nelson himself found a following. Since, he's become something of an elder statesman of the alt-country crowd, launching the outlaw movement with cool cronies like Johnny Cash, Waylon Jennings, and Kris Kristofferson and influencing a new generation of young upstarts like Steve Earle, Uncle Tupelo, and Ryan Adams in the process. On the other hand, Nelson's never been bound to any one genre. He sang standards on Stardust, reaping one of the biggest-selling albums of his career. His improbable duet with Latin legend Julio Iglesias on "All the Girls I've Loved Before" also struck gold. And when he covered the King with a redo of Elvis' "Always on My Mind," his sales soared again. Still, Nelson may be best-known for ancillary events — founding Farm Aid to help America's embattled farmers, his ill-fated encounter with the IRS that cost him nearly $17 million, a penchant for pot, and a never-ending road show famously immortalized in his signature song "On the Road Again."