Duke of Earle

Ask Steve Earle his thoughts on contemporary country music and he'll tell you he doesn't think about it at all. And whatever you do, don't call him a country singer. "I'm a songwriter," says Earle. "I'm interested in a lot of things, and my music reflects that." Since his 1986 debut album, Guitar Town, Earle, now 45, has been a reminder that country music—and its tales of broken hearts, life on the road, running from your demons and the law—is as vital an American art form as any other. And Earle knows a few things about demons and the law. After spending three weeks in jail in 1994 for drug possession, Earle came out clean and sober, rolled up his sleeves, and got back to work. Releasing five albums since—including this year's eclectic Transcendental Blues—Earle is already considered one of the greats of the genre. "Thinking about one's legacy is like reading your own press. I do it sometimes, but I find it unhealthy." So while there's a chance he won't be reading this, there's no chance his legacy isn't firmly established.

DANA BROWN