Willie Nelson

Prior to assuming the frayed-ponytail persona, and long before the superstardom he snared in the Seventies, 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 not until his groundbreaking 1986 album, The Red Headed Stranger, opened the door for both crossover country and unplugged attitudes, did Nelson find a following. Since then, he has become something of an elder statesman of the alt-country crowd, recognized for launching the outlaw country movement alongside cool cronies like Johnny Cash, Waylon Jennings, and Kris Kristofferson. In the process, Nelson has influenced a new generation of young upstarts like Steve Earle, Uncle Tupelo, and Ryan Adams. But at the same time, Nelson has 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 Elvis's "Always on My Mind," his sales soared again. Still, Nelson may be best known for ancillary events — Farm Aid concerts to help America's embattled farmers, an 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."