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There’s something about the singer-songwriter, the self-contained musical artist whose compositions succeed largely on the strength of his or her imagination. When determining our top 20, we considered both solo artists, and singers who were the primary songwriters for their bands. -Nicholas Pell
11. Willie Nelson
Willie Nelson’s lovable iconoclasm was born of Depression-era Texas, his parents’ whiskey-fueled wanderlust, and the moral rectitude of the grandmother who raised him. Across his long career – ’60s jukebox naïveté, earnest ’70s outlaw country (“You can’t make a record if you ain’t got nothin’ to say”), singalong ’80s chart toppers (“On the Road Again,” “Always on My Mind”), and even oddities like Countryman, his 2005 reggae foray – the strengths of Nelson’s songwriting are constant: honesty, humor, and an unflinching subversive edge. – Theis Duelund