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Age has not slowed Willie Nelson, who has released more than 50 albums since 2000.

Larry Busacca/Getty Images

It’s A Long Story: My Life
Willie Nelson, with David Ritz
Little, Brown and Co.
400 pages

A little over a decade ago, I bought myself an acoustic guitar. Not knowing much about guitars (my playing ability is roughly equal to that drunk guy who knows only John Lennon's Imagine), I ultimately chose the one I did because a) it was cheap, and b) it was a nylon-string classical model, which reminded me of Trigger, the guitar Willie Nelson has been playing since the early 1970s. The one responsible for the sweeter-than-sucrose solo on Blue Eyes Crying in the Rain, from Nelson's career-making 1975 album Red Headed Stranger. The one that sports a jagged hole the size of a bookmark.

Nelson's famously decrepit guitar is a perfect match for the legendary singer-songwriter – not just because it, too, looks as though it has been to hell and back, but because it is an unlikely country music icon. Classical guitars simply don't work for country; they lack twang. Nelson, a firm believer in doing whatever feels right at the time, started playing Trigger in the late 1960s after his previous guitar broke, and has been playing it ever since, twanglessness be damned.

From the evidence of his new memoir, It's a Long Story (published just a few weeks after his 82nd birthday), Nelson has been operating with the exact same mix of fatalism and a stubborn disregard for conventions since he was a kid growing up in rural Texas in the 1930s and 40s. In his own leisurely, highly selective telling, Nelson comes across as someone constitutionally unable to go about things the usual ways, always either stumbling upon a road less travelled or stubbornly forging one of his own. That doing so appears to have led to failure almost as often as it has to success doesn't seem to bother him too much.

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As a child, Nelson listened to Louis Armstrong and Frank Sinatra with the same avidity as he did early giants of country music such as Bob Wills, Ernest Tubb, and Roy Acuff, seeing them all as existing on the same musical continuum. (It's not a coincidence that one of Nelson's best-selling albums of all time, 1978's Stardust, is a seemingly left-field collection of jazz standards.) He decided early on that music would be his vocation: He amassed enough songs for a Willie Nelson songbook and was playing guitar with a Czech polka band before he hit middle school. Later, he worked as a radio DJ around the country, though the early-morning slots clashed with his night job as a struggling singer-songwriter. He also became a father for the first of seven times and a husband to the first of his four wives. (One of the conventions he frequently ignored was monogamy; in the book, he quotes an old saying about the dearth of moral conscience in erect penises.)

For years, Nelson tried everything he could to sell his songs, at one point even offering a band leader the full rights to a dozen of his tunes – including Crazy, arguably his greatest – for $10 apiece. Then, almost out of nowhere, his song Hello Walls (which he'd written in less than an hour, sitting in a bare garage) became a million-seller for Faron Young in 1961. Shortly thereafter, Crazy did the same for Patsy Cline and Nelson became a sought-after songwriter-for-hire.

It took another decade and a half for Nelson to become a star in his own right. The way he was (unsuccessfully) packaged and sold by Nashville bigwigs early on is an enduring source of bitterness and pushed him to take control of his own sound. After cannily demanding contracts that gave him total artistic control, he recorded a handful of unembellished, raw-sounding albums that have become modern classics: Shotgun Willie, Phases and Stages and especially the aforementioned Red Headed Stranger among them. Decades before Rick Rubin gave Johnny Cash a second career as a stripped-down elder statesman, Nelson was reinventing himself – and modern country music – by ditching what he calls here "the requisite sweeteners – heavy string sections and heavenly choirs that were supposedly making my music more palatable."

Since that artistic and commercial peak, Nelson has musically zigged and zagged with almost willfully perverse abandon. Not even the notorious IRS bust that nearly bankrupted him in the early nineties did much to slow down his output – Nelson has released more than 50 albums of one kind or another since 2000, including a collection of duets with Merle Haggard due out next month. Many of those albums are forgettable, some even regrettable (though even his reggae album, 2005's Countryman, has its moments), but the sheer variety and bulk of his discography makes Nelson the hardest-working pothead alive.

It's a Long Story has a similarly restless feel to it. Nelson spends a lot of time on a few topics close to his heart – the blues, his marriages, the natural world, the mystical/pedestrian art of songwriting, weed – but he prefers to move through big chunks of time by way of anecdotes than really grapple with his past. This isn't Nelson's first memoir rodeo: in addition to 1988's Willie: An Autobiography, he has put out slim volumes of memories and musings with titles such as Roll Me Up and Smoke Me When I Die and The Tao of Willie. Strangely, the new book uses the battle with the IRS as its dramatic lynchpin, though that whole drama was pretty much over and done with by 1993. And despite the existence of that earlier autobiography, It's a Long Story mostly skims over Nelson's post-1970s career. (Ever the iconoclast, he does pause to give his cautious blessing to digital file-sharing.) Despite repeated assertions that he is happier now than ever, I would've loved to dig deeper into his current state of mind.

It's a Long Story is pretty much what Nelson fans have come to expect from the man: a piece of work that is soulful, goofy, profane, heartfelt, tossed off, a little sloppy around the edges and deeply idiosyncratic. Exactly like country music played on a classical guitar with a hole in it.

Nathan Whitlock is a writer and editor in Toronto. His novel Congratulations On Everything will be published in 2016. He still plays that guitar.

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