Listen to this track by original country music outlaw, singer-songwriter, and everyone’s favourite Americana octogenarian Willie Nelson. It’s “I Never Cared For You”, a song dating back to his days as a Nashville hitslinger in the 1960s, here re-imagined as a single as taken from 1998’s Teatro.

The song appeared on an early live album in 1966 (Live Country Music Concert) and again in 1982 as a part of a joint double album with Dolly Parton, Kris Kristofferson, and Brenda Lee called The Winning Hand. But, on the Daniel Lanois-produced Teatro, it shines as a high-point in his career during a time when country music artists of his vintage and calibre were taking an opportunity to simplify their approaches in the wake of younger artists garnering all of the attention of the country music establishment. Part of what this meant was going back to the things that made them singular artists in the first place, unshackling themselves from the demands of that same establishment that had written them off as being outdated.

But Nelson had made a point of making a nuisance of himself where this fickle establishment was concerned from the very beginning in any case.  And how so?

Where the country music industry was concerned, Willie Nelson had always ridden off of the trail. After penning many country hits with a publishing deal in Nashville (including Patsy Cline’s “Crazy”), by the time the ’60s were over, he embarked on a solo career would be characterized by concept albums and recordings of American songbook standards that no other artist in his particular musicial neighbourhood had ever considered. Even the way he looked seemed to run contrary to the staid and conservative nature of modern country music. There’s a reason he was one of the figureheads of the outlaw movement. And he carries that level of artistically motivated disregard for musical ghettos here on this song, and on a few fronts.

First, this song is a reflection for Nelson’s feel for poetry, away from the  more linear narratives of standard country songwriting. Those opening lines about the sun being “filled with ice and giving no warmth at all”, and the stars being “raindrops looking for a place to fall” just shimmer with vivid imagery, and written at a time when writing lyrics for popular music in this way was just beginning. This song approaches the subject of love, longing, and regret from an opposite direction than expected; filled with beauty and sadness all at once.

Second, Nelson’s nylon-stringed guitarwork with the help of his battered and heavily autographed N-20 Martin classical guitar appropriately and affectionately called “Trigger” reveals him to be an instrumentalist of great depth and lyricism. The instrument itself is proven to be both an extension and a reflection of the artist who’s wielded it for over half of his life.

Third, this song borrows from several musical traditions, seamlessly incorporating country, pop, and tejano, and all with a jazzy kind of feel that binds it all together, derived from Nelson’s awe of Django Reinhardt. This loosely makes it roots music. But, nothing that could be readily marketed under any one stylistic banner other than “Willie Nelson”, maybe.

Part of his success comes in who he works with in order to get these results. In this case, producer Daniel Lanois lends a spacious sense of atmosphere matched with backing vocals from Americana legend in her own right Emmylou Harris, Bobbie Nelson (Willie’s sister!) on piano, and stalwart Nelson sideman harmonica player Mickey Raphael completing the sonic palette. Maybe the x-factor in all of this had to do with where the record was created; an old movie theatre in Oxnard California that is pictured on the cover that imbues it with a sense of history, and tradition. Even if this hooks into some traditional folk forms, it’s unconventional. That’s how Willie Nelson rolls. Yet despite its fluidity and even its stylistic contraditions, his music is made for listeners.

That’s what his kicking against the pricks (no doubt sometimes in more than one sense of that term …) when it comes to following the rules of country music has always been about; welcoming listeners in by any means necessary.

As I write this, Willie Nelson is 80 years old and going strong. So is Trigger! Learn more about both of them at Willie Nelson.com.

Enjoy!