Willie Nelson

Once the butt of jokes from comedians and late-night talk-show hosts for his troubles with the IRS, Willie Nelson remains one of the most beloved figures in American music. Nelson got his start penning songs for better-known artists such as Patsy Cline and Ray Price in the '60s before becoming a bona fide superstar in his own right with a string of crossover hits that included "Blue Eyes Crying in the Rain" and "On the Road Again." Although his long-term appeal may be mysterious to some, Nelson's consistently solid songwriting, good-hearted outlaw image and native charm have allowed him to stay relevant over the years. The iconic troubadour just has a way of giving life's more mundane experiences significance and meaning. All hail the Red Headed Stranger, one of the last true outlaws.