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Willie Nelson: 20 Essential Songs

From the signature ballad he wrote for Patsy Cline to his love letter to life on the road

When Willie Nelson released his 2016 tribute album to the Gershwin brothers, he was showing his reverence for the Great American Songbook. But the fact is that Nelson’s own works deserve a volume or two. The Texas native has written some of music’s most important titles, from “Crazy,” made famous by Patsy Cline, to “Funny How Times Slips Away,” covered by Elvis Presley.

And then there are the songs with which he has become synonymous, thanks to his charmingly eccentric vocal delivery. It’s impossible to hear a Willie Nelson performance and not identify it as such. Whether he was crooning Countrypolitan fare in the Sixties – his 1962 debut album …And Then I Wrote is remarkable for its wealth of enduring songs – or busting down doors with Waylon Jennings in the Seventies, Nelson was always making waves with that unmistakable voice.

“All of a sudden, we were outlaws,” Nelson told Rolling Stone in 2014, reflecting on the country music rebellion he was credited with launching. “I thought it was the funniest thing in the world. And I tried not to disappoint ’em!”

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“Pretty Paper” (1964)

Originally a hit for Roy Orbison in 1963, “Pretty Paper” was inspired by a vendor outside a department store in Fort Worth, Texas. An amputee with no legs who peddled paper and pencils for a living, Nelson suddenly recalled the man a few months before Christmas, and put the memory to music. “He had a way of crying out those words – ‘Pretty paper! Pretty paper! – that broke my heart,” Nelson wrote in his autobiography It’s a Long Story. Nelson recorded the song himself, produced by Chet Atkins, in 1964, and then again as the title track for his 1979 Christmas album. Stripped of the Orbison sheen, Nelson made it a sweet and simple Southern waltz, anchored by some of his most aching, pristine vocals: his tender vibrato as he sings the word “ribbons” is enough to warm even the most calloused of holiday hearts. 

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“Funny How Time Slips Away” (1962)

One of Nelson’s earliest songs, “Funny How Time Slips Away” was written during the same week as “Crazy” and “Night Life.” Nearly a half-dozen artists have turned the song into a Top 40 hit since then, including soul artist Joe Hinton, rockabilly singer Narvel Felts and teen idol Jimmy Elledge. Even so, Nelson’s own delivery always packed the biggest punch, with lines like “It’s been so long. . .but it seems now that it was only yesterday” taking on new meaning as Nelson grew older, outliving close friends like Merle Haggard and Waylon Jennings along the way. Originally a ballad about a short-lived relationship, it’s grown into something bigger: a textbook example of the sort of ageless songwriting that exists long past its maker.

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