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The 50 Best Willie Nelson Songs

The country icon is always there to get us through, and here are his essential moments

Willie Nelson

BOB RIHA, JR./GETTY IMAGES

Willie Nelson songs are essential to the fabric of American music. Whether the Abbott, Texas, native wrote them himself or interpreted the tunes of others with his idiosyncratic singing style, songs like “Crazy,” “Night Life,” “On the Road Again,” “Blue Eyes Crying in the Rain,” and “Georgia on My Mind” are all uniquely Willie. And, remarkably — seven decades into his career — he’s still adding to the country canon, from lighthearted weed anthems like “Roll Me Up and Smoke Me When I Die” to the dissertation on navigating grief “Something You Get Through.”

Now 92, the outlaw-country pioneer continues to tour, record, and release new albums. The most recent, this year’s Oh What a Beautiful World, pays homage to the songwriting of Rodney Crowell and underscores Nelson’s gift as a song stylist. He is, arguably, not only the voice of country music, but of the country itself — a comforting troubadour and north star for a genre and a nation, both of which often stray from the path. But that’s all right. Willie’s there to see us through, even now.

He is Pancho to Haggard’s Lefty. He is Shotgun Willie. He is the Red Headed Stranger. He is Willie Nelson. And these are his 50 essential songs.

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5

‘Night Life’

It’s no coincidence that rock & rollers like B.B. King and David Lee Roth have all taken their own stabs at “Night Life.” A salute to the wee small hours, the song fires twin barrels of sad-eyed storytelling and six-string riffage, creating a call-and-response between Nelson’s late-night observations (“Listen to the blues they’re playing!”) and the guitar parts that follow. Credit for those mid-song riffs goes to Paul Buskirk, who bought the song from a perpetually cash-strapped Nelson for $150 and joined him on the original recording in 1960. Even so, Nelson was the song’s main architect, and he’d rarely built such a sturdy bridge between his vocal and instrumental chops before.

4

‘Crazy’

Nelson had originally hoped Grand Ole Opry member Bill Walker would record “Crazy,” but Walker deemed the song too feminine. So Nelson pitched it to Patsy Cline, whose 1961 recording of “Crazy” became one of the defining ballads of the 20th century. One year later, Nelson released his own version, singing the song in a voice untarnished by age or pot smoke. It’s one of the earliest examples of his unique, unpredictable phrasing, with each word landing somewhere before or after the actual beat. Cline took a different approach, smoothing out the imprecision she’d heard on Nelson’s demo in favor of steady, controlled vocals. For a song about heartache, though, Nelson’s is perhaps the more effective performance, delivered with the halting hesitancy of someone who’s coming to grips with his own craziness.

3

‘On the Road Again’

There’s something delightfully crude about the fact that Nelson wrote one of his biggest, and signature, hits on the back of a doggie bag. “On the Road Again” was conceived, spur of the moment in the middle of a flight, as the theme song for Honeysuckle Rose, the 1980 film about an outlaw country singer who didn’t quite make it to the top, starring Nelson himself. The film may have been an alternate reality to his own life, but the song was quintessential to the real thing, a jaunty, singalong travelogue tailor-made for awards galas and commercial placements. Which is apt, because no song celebrates Nelson’s band-of-gypsies love affair with life on the road and making music with his friends more simply than this one.

2

‘Mammas Don’t Let Your Babies Grow Up to Be Cowboys’

For all the hit songs that Nelson wrote for other people over the years, it’s hard to think of a song written by someone else that could be as perfectly suited for him as “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.” The song had already charted with its author, Ed Bruce, and been covered by Chris LeDoux before Nelson and Waylon Jennings tackled it on 1978’s Waylon & Willie – but all other versions were relegated to footnotes once they’d touched it. (Even the Chipmunks’, whose parody was inspired by Nelson and Jennings’ definitive reading.) The Lone Star belt buckles and smoky old pool rooms fit in perfectly with the outlaw country mystique, but it’s the delivery that sells it: You get the feeling that Jennings is that dark, distant cowboy, but Nelson’s warm, airy contrast gives the song the wry, knowing wink that it needs.

1

‘Blue Eyes Crying in the Rain’

Fred Rose wrote it in the Forties, and everyone from Roy Acuff to Hank Williams took a shot at it, but the true purpose of “Blues Eyes Crying in the Rain” was to finally launch a long-striving, industry-beleaguered, 42-year-old Willie Nelson into orbit as the stark, startling centerpiece of his 1975 smash, Red Headed Stranger. Michael Streissguth’s 2013 study Outlaw: Waylon, Willie, Kris, and the Renegades of Nashville has a great scene where skittish label suits, fearful that the album “sounds like it was recorded in Willie’s kitchen,” frantically arrange a press listening session at Nashville hot spot the Exit/In, and then marvel as “Blue Eyes” triggers a standing ovation. “Nobody was more shocked than we were,” then-CBS Records President Rick Blackburn once conceded. “It didn’t have … the bells and whistles. It wasn’t the way you went about making a record in Nashville in those days.” Result: his first country Number One.