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The full Nelson 

In honour of this week’s Halifax show, Sandy MacDonald offers up a look at the 50-year career of Willie Nelson.

If Hollywood wanted an archetypal rags to riches storyline, it would be hard-pressed to conceive a more sweeping character than Willie Nelson—singer, hit songwriter, actor, outlaw, author, spiritualist, pot advocate and music industry survivor.

Rooted in the rich traditions of country music, blues, swing jazz and Tin Pan Alley show tunes, Nelson’s music has never failed, in more than 50 years, to find an appreciative audience. His warm weathered voice sings straight into your heart. His plucky guitar style on Trigger, his battered Martin gut-string, is as distinctive as BB King’s signature tone. Nelson’s confessional songwriting style has created some of the most memorable songs of the last 40 years—“Crazy,” “Hello Walls,” “Night Life,” “On the Road Again,” “Funny How Time Slips Away.”

But what defines Nelson is his relentless pursuit of the far edge of his music, always looking beyond the barren flatlands of northeast Texas for greener musical pastures.

Nelson was born in the midst of the Great Depression in hard-scrabble Abbott, Texas, population still about 300. His parents had uprooted from Arkansas in the late ’20s, escaping the fields of shoe-top cotton that offered little beyond an aching back and a few pennies a cotton sack.

When Willie was just six months old, his teenage parents split up and kept right on moving, leaving him and his older sister Bobbie (who still plays piano in his band) to be raised by their grandparents.

He learned the guitar quickly and began performing around Abbott, leaning into a career as a musician in the rough Texas honkytonks. All the while, he was writing. Poems on scraps of bar napkins, bits of melody turned into song.

The inevitable move to Nashville in 1960 landed Nelson in a shared mobile home in Dunn’s Trailer Court while his wife and kids stayed behind in Texas. He was finally in Music City, and it didn’t take long for his songs to start catching the right ears.

Major country stars began recording and releasing his songs—Faron Young topped the country charts with “Hello Walls,” selling two million copies; Ray Price hit with “Night Life,” Billy Walker released “Funny How Time Slips Away” and then Patsy Cline scored with “Crazy.” All four singles broke the country top 20, while Nelson was making $25 a day playing bass in Price’s band.

He was, however, still struggling to be heard. Maybe it was his nasally voice, or writing beyond the standard three-chord structure or his around-the-beat, jazz-inflected phrasing, but Nashville was slow to accept Willie Nelson as a mainstream star.

“Even though I was writing a country song, I wasn’t singing it on the traditional way,” says Nelson in his 1988 autobiography. “Not that I couldn’t. I just wanted to phrase it the way I felt like phrasing it…I could put more emotion in my lyrics if I phrase in a more conversational, relaxed way.”

Frustrated with the entrenched Nashville scene, Nelson moved his operations to liberal Austin in 1971—just the place for the pot-puffing cowboy to lay down a foundation. Life was finally making sense, anchoring a raw new country sound with his old pals Waylon Jennings, Merle Haggard, Tompall Glazer and Billy Joe Shaver—a raggedy crowd of musicians dubbed the Outlaws.

Nelson has stayed in the public eye via his movie projects and frequent genre-bending duets, from Kid Rock and Toots Hibberts to Merle Haggard and Julio Eglesias. He’s comfortable recording new music with Rob Thomas and Lucinda Williams or loving tributes to Americana pioneers Bob Wills, Lefty Frizzell and Townes Van Zandt.

Like Johnny Cash, Merle Haggard and Dolly Parton, Willie’s career has aged well. His latest recording project, released this week, is a tribute to country songwriting legend Cindy Walker. At an age when most road-worn musicians are either dead or getting ready for the big dirt sleep, Nelson continues to create and perform. Maybe it’s his long-held belief in reincarnation; that we embody a part of the “great spirit.” Willie simply calls himself “a troubadour going down the road, learning my lesson in this life so I will know better next time.”

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