Willie Nelson: The Nonagenarian Red-Headed Stranger Breaks New Ground At 90

Even Willie Nelson himself seems to marvel at the significance of the milestone. “The ‘Big 9-0’,” he muses over the phone with Pollstar, appropriately on the road again on the cusp of another busy year of live performances and more.

“Who’da thought I’d make it?,” he wonders with a laugh that warms across the miles. “I guess you just never know.”

Perhaps in his more notorious “Outlaw” days of being sewed up in bedsheets and beaten with a broomstick, it might have indeed seemed unlikely the famed singer/songwriter/guitarist/what-have-you would hit 90, as he will officially on April 29. But his rabble-rouser days have been left decades behind. Today, Nelson is far better known for his remarkable creative output and zen-like approach to life, some would say powered in no small part by his celebrated love of weed (which, by the way, he’s also turned into a robust business).

He’s also built an incredible live career that’s grossed more than $224 million and sold more than 6 million tickets, according to box office reports submitted to Pollstar dating back to 1981.

As it stands, Nelson’s 90th year will be among his most active, beginning with Long Story Short: Willie Nelson 90, a multi-artist celebration at L.A.’s Hollywood Bowl April 29-30. Announced performers include such artists as Beck, Billy Strings, Bob Weir, Charley Crockett, Chris Stapleton, Edie Brickell, Kacey Musgraves, Leon Bridges, Lukas Nelson, Lyle Lovett, Margo Price, Miranda Lambert, Nathaniel Rateliff, Neil Young, Norah Jones, Orville Peck, Particle Kid, Rosanne Cash, Sheryl Crow, Snoop Dogg, Sturgill Simpson, The Avett Brothers, The Chicks, The Lumineers, Tom Jones, Tyler Childers, Warren Haynes, and Ziggy Marley. Unannounced but expected are artists associated with Nelson as in-studio collaborators or in such live forays as Farm Aid.

Long Story Short is executive produced by frequent Willie collaborators Mark Rothbaum (Nelson’s manager at Mark Rothbaum & Associates) and Keith Wortman (Blackbird Presents), with promoter Bill Silva, longtime agent Brian Greenbaum at CAA, and Brian Smith, Live Nation SVP, California. Rothbaum and Blackbird will also helm Nelson’s summer tour, the “Outlaw Music Festival,” which begins June 23 at Somerset Amphitheater in Wisconsin and will be out all summer with a changing cast that includes such rotating acts as Robert Plant & Alison Krauss, The Avett Brothers, John Fogerty, Nathaniel Rateliff & The Night Sweats, Whiskey Myers, Gov’t Mule, Marcus King, Margo Price, Trampled By Turtles, Molly Tuttle & Golden Highway, Kathleen Edwards, Flatland Cavalry, Kurt Vile And The Violators, Brittney Spencer, Particle Kid, and, of course, headliners Willie Nelson & Family. The tour announced 16 additional dates lasting through Oct. 15.

It’s a busy year for anybody, much less a nonagenarian country legend known for enthusiastic performances and a willingness to hang with artists not even born when Nelson’s songs first graced the country airwaves. Seventy-plus years is a long time to stay busy, it’s pointed out to Nelson.

“Yeah, it is, but I’m looking forward to it,” he says. “It’s gonna be a lot of fun, seeing all the gals and guys come out to help me celebrate the Big 9-0.”

The wide range of artists set to celebrate Nelson this year is reflective of a career that has seen the artist touch virtually every genre at some point or another. After penning a wide range of country standards made hits by others, Nelson broke through to stardom as the vanguard of an “Outlaw Country Music” movement that turned Nashville on its head, most notably with 1975’s sparse classic Red Headed Stranger. Three years later, Stardust, an album of pop standards, went multiplatinum and Nelson’s status as an unpredictable trailblazer who transcends musical boundaries was etched in stone.

Such jarring musical shifts, powered by his off-the-beat vocals and jazzy fretwork, don’t seem jarring at all to Willie. “I just like good music,” he explains. “I grew up playing it all. My sister [Bonnie] and I used to sit on an old piano stool together and just go through the songbooks. We’d play everything from ‘Down Yonder’ to ‘Stardust.’ Just good music.”

If there’s a common thread, it could be described as music people respond to, particularly in a live setting. Nelson doesn’t disagree but adds that musical boundaries were never his thing. “We didn’t really know too much about categories, we just did what we liked,” he says. “I like all kinds of music. I haven’t run into anything yet I didn’t like. Some of it I can’t play, but I like it all.”

Rothbaum, even though he’s been working with Nelson for decades, remains stunned by the breadth of Nelson’s musical diversity. “In history, who was like him?” he wonders. “I mean, Louis [Armstrong], maybe? He played country music. He played jazz. He played blues. He played swing. I’d say Louis Armstrong alone.”

Nelson’s expansive sphere of influences provided Rothbaum and Wortman a broad musical palette to work with as curators of Long Story Short. Describing the process, Wortman calls it a “very thorough and thoughtful approach on a number of levels. Creatively, it has to work, number one. Two, it has to be able to go where Willie’s gone throughout his whole career. Number three, it has to be [artists] that have a real connection. We’re not ones to put people on shows because they have a new record coming out or doing a favor for a manager.”

But the most important factor of all was, “that Willie felt surrounded by people that love him dearly and, on the reciprocal side, have cited him as such a significant influence in their career,” Wortman says. Everyone on the bill is considered a friend of the Family, whether newer artists like Chris Stapleton, Tyler Childers or the Avetts, or seasoned veterans like Tom Jones and Neil Young.

“All with a tethered connection, right?,” says Rothbaum. “You can draw a line, with Willie at the center of it, and define the relationship, define the connection that’s now one. It’s just one significant, broad, comprehensive family, in that you can start with the Nashville cats. You can draw a line to the Texas cats. There’s just so many directions and so many places that Willie takes you, and that’s how the programming naturally led us to all these folks.”

It’s also notable that Nelson and his stellar Family band are known for the ability to jam with virtually any artists that set foot on the stage. Asked what qualities best serve in touring with him, Nelson says, “You’ve got to be a good musician, and be able to play with other folks. It’s really that simple. Most musicians – all the good musicians – know how to do that, when to play and when not to play.”

Such flexibility and “knowing when to play” has led to countless epic jams and unexpected onstage alchemy, whether at Farm Aids, Fourth of July Picnics, or Outlaw shows. Nelson says these moments are not rehearsed. “We just go out and play it and see what happens.”

Nelson’s associations with both Austin and Nashville, as well as numerous other cities, begs the question as to why have the birthday party in L.A. and specifically, the Hollywood Bowl. “Because it’s roughly the equivalent of Willie,” Wortman answers. “It’s venerable and distinguished, and it has entertained us for 90 years, I imagine, and there was no amphitheater like that, and he deserves just that. Everything has to be in keeping with the dignity and respect he’s paid to music, and the Bowl does the same.”

Rothbaum says there were offers from different festivals and venues to host Willie’s 90th: “I represent Willie and Trigger [Nelson’s famed guitar], and the Bowl fits with Willie and Trigger – it’s well-worn in, and it sounds great.”

Tickets were gone “in a matter of minutes,” Wortman says. “We’re filming and recording, and we’re in discussions with a range of networks and streamers. Also, theater companies are looking for theatrical releases, so we’re in conversations with those folks, as well. We want to make sure we mention we have terrific promoter partners in Live Nation and [Andrew] Hewitt and Silva, who have the exclusive on the Bowl, and Mark has a very long history with Bill Silva, who’s been a terrific partner and champion the whole way through.”

In the aftermath of the birthday party, the Live Nation-produced “Outlaw Music Fest” tour continues with some 30 dates planned for 2023, born with the concept of providing a platform for “folks that didn’t quite fit into a box in Nashville, along with other legends like Van Morrison and Neil Young and Robert Plant who felt the joy and the diversity of these kinds of lineups, along with shining a light on emerging artists. How do those folks get a leg up in a place where it’s very difficult to find a home? So, we put that all together and came up with the ‘Outlaw Music Festival’ brand and format, and I’m really proud to say we built it to stand for what Willie stands for, but as a home for all these folks.”

For his part, Nelson seems ready to roll. Asked if he requires anything specific from the venues when he arrives, the artist responds, “No, not really. I just need Trigger plugged in and working, and everything working, and everybody to show up. I just try to play it by ear every night, and it’s been workin’ out for all these years. Nobody really knows what we’re gonna do. One song will bring up another one and another one. I’ve been doing it for so long, the band knows what I’m gonna do.”

Soundchecks? “Naw.”

Though he has written some of the most beloved country classics of all time, and recorded albums that will be played forever, Nelson says it’s still the live thing that gets his juices flowing. “Nothing can compete with a live show, with a live audience, when you’ve got a good band with you,” he states. “That’s as good as it gets.”