I first saw country music legend Willie Nelson perform in 2001 at the Zellwood Corn Festival in rural Central Florida. Admission was $11, which included all-you-can-eat ears of sweet corn, a greasy paper bag full of boiled peanuts and a beer ticket.

With only a few hundred middle-aged and elderly spectators scattered in front of the stage, I got a front-row listen as Nelson and his backing band, The Family, romped through 40 years of songs I’d grown up listening to on my grandfather’s record player. Afterward, Willie and crew hung around to chat with fans and sign autographs. My grandfather was never happier than when I presented him with a John Hancock-ed copy of Willie’s 1975 album The Red Headed Stranger — and never more jealous than when I told him I got to shake the bearded, braided man’s hand.

In 2014, a ticket to see the 81-year-old Nelson will set you back $60 to $120 — and plunking down $200-plus for a VIP package won’t even secure you the chance to say hello after the show. So what happened in the intervening 13 years to transform Willie from grinning folk hero of The Greatest Generation and its Baby Boomer offspring to living, breathing embodiment of American cool, out of reach of the common man?

The answer is wrapped in a confluence of factors. Marijuana’s a big one — Willie’s always been an unabashed toker, and mainstream acceptance of weed has never been higher. And what better way to spread awareness than with a loveable old guy who agitates for drug reform while proudly boasting to Larry King that he’s smoked every day for decades?

Yet Willie’s outsized celebrity detracts from the fact that his songs stand as some of the finest ever written. Before the 1970s, no one had successfully mixed country’s down-home poetry with jazz’s offbeat timing, swing’s refined elegance and folk’s traditionalist clarity. It took Nelson decades to refine such an aesthetic.

Orphaned shortly after birth, Willie Hugh Nelson wrote his first song at age 7, joined his first band at age 10 and quit picking cotton at age 13 to play local concert halls.After high school, he joined the Air Force, sold encyclopedias in Fort Worth, trimmed trees in Waco, washed dishes in Springfield, DJed a radio show in Vancouver and taught guitar lessons in Houston before landing in Nashville. He scored a few songwriting hits for bigger stars — namely, Patsy Cline’s career-defining 1962 smash “Crazy” — and toured as a bassist for honky-tonk hero Ray Price. But Nelson struggled to define himself as a solo artist, even after RCA Records signed him to a $10,000-a-year contract.

By 1970, he’d squandered most of his royalties on unprofitable tours, saw his Tennessee ranch burn to the ground and watched two marriages disintegrate in the space of eight years. Which helps to explain why, in 1972, Nelson paid $14,000 to get out of his RCA contract so he could “retire” to the sleepy Central Texas burg of Austin.

His timing was impeccable, though, as the city and its outlaw country scene were just taking off. In a year’s time, Nelson went from outcast to multiplatinum superstar — at age 40, no less. In the 1970s and ’80s, he delivered 15 No. 1 albums, a mythological concept record, odes to Broadway and Tin Pan Alley, and wildly successful collaborations with Merle Haggard, Waylon Jennings, Johnny Cash and Kris Kristofferson. As The Highwaymen, Nelson and the other three musicians defined the term supergroup.

Nelson’s fall from such grace was inevitable — and the low point came in 1990, when the IRS seized most of his assets, claiming he owed $32 million in back taxes. (His accountants apparently forgot to file for years).

The decade’s rapidly shifting musical tastes forced Willie into a comfortably wealthy oblivion; he played to adoring crowds 200 nights a week, even as not a single one of his 1990s albums cracked the Billboard Top 10.

The decade wasn’t a total wash, though; Nelson was inducted into the Country Music Hall of Fame in 1993 and received Kennedy Center Honors in 1998. But there’s still something about the 2000s and 2010s that has served as a cataclysmic moment for Willie, à la Austin circa 1972. Statues have been erected in his honor. Honorary doctorates have been endowed in his name. His business empire has mushroomed to include truck stops, biodiesel companies, whiskey and Sirius XM radio stations.

Yet the man understands his own mortality; in 2012, he implored critics and fans to “Roll Me Up and Smoke Me When I Die.” Miraculously, the herb hasn’t affected his voice, just as carpal tunnel syndrome hasn’t affected his sparse, spacious guitar-playing. To this day, no one has replicated Willie’s lackadaisical cadence, cracked vulnerability, and ability to sing and play perfectly behind the beat.

In his hands, a seemingly simplistic standard like “On the Road Again” or “Blue Eyes Crying in the Rain” becomes something raw, something timeless, something moving. “I don’t mind playing the hits,” he told Rolling Stone last year, addressing complaints that his “set lists haven’t changed much since the Carter administration.” “I’m glad I got ’em.”

We can all learn something from Willie Nelson — from his song titles, from his lyrics, from his laid-back approach to life and from his unflappable work ethic (dude still performs 150 nights a year at the age of 81).

As you prep for Willie’s May 18 performance at St. Augustine Amphitheatre, study up on these 10 essential life lessons we’ve drawn from Willie’s long, storied career — with more than 40 millions records sold in the U.S. alone, a book called The Tao of Willie and a bustling business empire, nobody does plain-spoken success better than The Red Headed Stranger.

1. “Mammas, don’t let your babies grow up to be cowboys.”
We hear that the job market is collapsing, wages are depressed and room for growth is nonexistent. Still, there’s just something about the way that Willie Nelson and Waylon Jennings imbued Ed Bruce’s 1976 song with such sad-eyed yearning (“’Cause they’ll never stay home/And they’re always alone/Even with someone they love”). Nearly 40 years later, the track resonates even more in our increasingly digitized world: Who doesn’t long for a simpler life dominated by “smoky old pool rooms and clear mountain mornings/Little warm puppies and children and girls of the night”?

2. Even the mellowest among us can have a nasty temper.
Like Willie sings on 1975’s “The Red Headed Stranger,” “Don’t cross him, don’t boss him/He’s wild in his sorrow/He’s ridin’ and hidin’ his pain/Don’t fight him/Don’t spite him/Just wait till tomorrow/Maybe he’ll ride on again.” Apparently, Willie’s easygoing public demeanor hides a private mean streak that’s attributable to his Irish and Cherokee heritage and upbringing. As his current wife, Annie, told Rolling Stone in 2013, “You can see his pupils dilate and his eyes get kind of black [when he gets mad]. Pretty much everybody who knows him knows that that is not a good sign.”

3. If at first you don’t succeed, try, try again.
Today, all we see is the millionaire with the most bangin’ tour bus known to man and neighbors in Owen Wilson and Woody Harrelson. But back in the 1950s, when Willie went by his middle name, Hugh, he supported his first wife and three children as a scrappy jack-of-all-trades working any job he could anywhere he could find one, while tentatively pursuing life as a singer and songwriter. He sold some of his earliest hits for other artists for $50 a pop, and the day-in, day-out drudgery of the music business motivated Willie to retire twice, in the late ’50s and early ’70s. But both times, friends urged him to keep on keepin’ on, and it wasn’t until 1975 that Willie scored his first No. 1 single and album — at age 42. Even more impressive? The fact that his 1978 album Stardust remained on the country charts for 540 consecutive weeks — more than 10 years.

4.“Still is still moving to me.”
Willie has written some of the finest rambling songs in country music history. The entire Red Headed Stranger album celebrates the life of a mythical drifter, while 1980’s “On the Road Again” is the quintessential diary of life on tour (we dare you not to sing along when Willie joyfully intones, “The life I love is makin’ music with my friends”). But there’s something about the upbeat instrumental haunt of 1993’s “Still is Still Moving to Me,” written to honor the Navy’s Blue Angels flight demonstration pilots, that feels like the ultimate testament to perpetual motion: “I swim like a fish in the sea all the time/But if that’s what it takes to be free I don’t mind.”

5. When the government tries to screw you, screw ’em right back, and then laugh at the situation.
When Willie Nelson was slapped with tens of millions of dollars in back tax penalties by the IRS in the 1980s, the lifelong outlaw didn’t roll over. He fought the eventual $6 million settlement for seven years; sued his former accounting firm, Price Waterhouse, for $45 million in damages; recorded an album called The IRS Tapes: Who’ll Buy My Memories?; had his daughter hide Dad’s prized guitar, a beat-up old Martin acoustic he named Trigger, from repo men; saw charitable foundations and aspiring Willie Nelson museums buy much of his personal memorabilia; and watched as the very farm activists he’d helped with Farm Aid either dissuaded investors from purchasing any of Willie’s land at auction or purchased it themselves to hold until the musician could eventually buy it back. “A lot was bought by the Willie Nelson Showcase, the golf course and studio didn’t sell, and my daughter’s home was bought by farmers,” Willie told People magazine in 1991. “The things that did sell were just things. So actually, I haven’t lost anything.”

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october, 2021