When Willie Nelson became the only country artist to win two Grammy Awards during the Feb. 5 ceremony, he was in the middle of texts with producer Buddy Cannon.

Nelson didn’t give the trophies much thought.

“All he wanted to talk about was the next record,” Cannon says.

That hunger is present at a time in Nelson’s career that’s remarkable, and likely unprecedented, among country acts. Fewer than 1 in 5 people live to age 90, according to the Social Security actuarial table, and as Nelson proceeds one day at a time toward a two-day celebration of the milestone April 29-30 at the historic Hollywood Bowl, he is doing so with an impressive level of activity. 

The two Grammys arrived just a few months after Me and Paul — a book about his late drummer, Paul English, co-written with David Ritz — and shortly after he received a nomination for the Rock & Roll Hall of Fame. A BIC commercial with Snoop Dogg and Martha Stewart aired during the Super Bowl, and Nelson is prepping the March 3 release of I Don’t Know a Thing About Love, a 10-song collection of material penned by late songwriter Harlan Howard. That next record he was focused on during the Grammys is bluegrass recordings of songs from his own catalog; it will likely be released later in 2023. 

The Hollywood Bowl weekend, dubbed Long Story Short: Willie Nelson 90, has a stacked lineup of well-wishers: Chris Stapleton, Beck, Leon Bridges, Kacey Musgraves, Miranda Lambert, Rosanne Cash, Neil Young, Tom Jones and The Chicks, to name a few. And Nelson has his usual array of standard concerts on the calendar before that event.

“It’s something that people half his age would have a hard time keeping up with,” says CAA senior music agent Brian Greenbaum, who has booked Nelson’s shows since 2010.

Nelson, of course, has never been one to approach life quite like anyone else. His trademark braids and bandana set him apart visually from the rest of his peers. So did his grainy timbre, his unpredictable phrasing and the twangy resonance of Trigger, a beat-up guitar that provides a vehicle for improvised solos that are simultaneously adventurous and reassuring. 

In a crowded business where it’s challenging for artists to carve out an identifiable lane of their own, Nelson managed to brand himself so well that he can enter any scenario and maintain his individuality.

“It gives us more leeway to think outside the box with Willie,” Greenbaum says. “He is such a multigenre artist, so you can tour Willie with a straight-ahead country artist, but you could also tour Willie with Bob Dylan, which we’ve done. And you can present him with some young up-and-coming artists like we’ve done with the Avett Brothers and a bunch of other artists in that vein.”

Part of what makes Nelson so appealing as an artist is his embrace of his story. Like Frank Sinatra, Ray Charles, Johnny Cash or Tony Bennett, he has aged gracefully under the glare of the spotlight. Instead of attempting to mask his experience, he wears it with an admirable authenticity. Both of his Grammy-winning entries at the recent ceremony — best country album A Beautiful Time and best country solo performance “Live Forever,” pulled from a tribute album to late singer-songwriter Billy Joe Shaver — are frank examinations of mortality. Beautiful Time ranges from the inspirational “Leave You With a Smile” to the humorous “I Don’t Go to Funerals,” with Nelson acting as an aspirational guide through a difficult topic. And that’s part of his brand, too.

“I’ve had the opportunity to meet the Dalai Lama and to meet Bishop Desmond Tutu,” says Bill Silva, who booked the Hollywood Bowl concerts as a principal in events company Live Nation-Hewitt Silva, in association with Blackbird Presents. “These guys are different than people you meet every day. They vibrate a little differently. And I would put Willie in that same category.”

Nelson is in that company because he approaches the world with such a laid-back attitude. Many observers credit that to marijuana, and there is likely some truth to that. But there’s a philosophical component to that stance, too. Nelson embodies it in person, and he brings it to the stage, where he has a jazz-like propensity for creating setlists and interpreting solos on the fly.

“He’s always in the moment,” says Sheryl Crow drummer Fred Eltringham, who has played on at least five of Nelson’s albums and sat in with the band when one of Nelson’s road musicians got COVID-19. “When you see him live, even if people perceive it as sort of a mess, he’s in it. And it’s not a mess. They’re just having fun.”

It’s a reason why the Rock & Roll Hall of Fame nomination makes sense. It came as a surprise to some, but others who assumed he was already a member viewed it as an overdue honor. 

“I don’t think there are too many artists that are as punk rock as Willie Nelson, as far as just embodying the things that rock’n’roll is supposed to be,” Legacy vp of marketing Zach Hochkeppel says. “It seems like he kind of does it a lot better than most of the folks in the building.”

For now, Nelson is focused on that bluegrass album, recording it in his own way with Cannon overseeing the process. Nelson isn’t there when they cut the tracks — Cannon or studio singer John Wesley Ryles provides a reference vocal for an A-list band of gypsies that has seen enough Nelson shows or listened to enough of his records that they can anticipate the kind of arrangements that work for him.

Nelson adds his lead vocal and Trigger, at a later date, rarely performing more than three takes before he moves on. He’s so attuned to the song that even though he approaches it with a unique stylistic voice, he typically delivers the material with humility and a touch of reverence.

“It’s just like a strong magnet,” Cannon says. “It makes me listen to the song closer.”

That’s all part of what makes Nelson so remarkable in the current moment. He finds himself in a swirl of activity 25 years after most of his former contemporaries have retired, and he continues to do what he’s always done, focused on the project in front of him. The 90th birthday concerts will get here soon enough, and so will the Rock Hall’s May induction announcement.

Says Hochkeppel: “I don’t think that’s something that Willie himself is going to lose sleep over either way.”

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