At 90, Willie Nelson is still on the road, bringing outlaw country back to the area

In one of his most storied hits, “My Heroes Have Always Been Cowboys,” Willie Nelson takes a prolonged look in the rear-view mirror at a life fading from view like a stretch of desert highway. Far from celebrating the Western imagery the song’s title suggests, the lyrics honors cowboys for “their own brand of misery” and evokes the aged but quietly unrepentant perspective of a drifter “sadly in search of, and one step in back of, themselves and their slow movin’ dreams.”

Though he wrote his first song at the age of seven, Nelson didn’t pen “Heroes.” It was instead composed by a woman, Nashville songsmith Sharon Vaughn (her first hit, in fact.) Nelson wasn’t even the fist country stylist to record it. Longtime musical pal Waylon Jennings beat him to it in 1976. But when Nelson’s ultra-plaintive vocals wrapped around the tune for a version featured in the 1979 film “The Electric Horseman,” everything about the composition — its sentiments and perspective, in particular — was appropriated. Nelson made it sound like the remembrance of one whose life had slipped past the point of redemption — a calm but lost soul, if you will.

The reality of the situation? Nelson was 46 at the time he cut the song and in the midst of the second (or maybe third) in a series of ongoing career renaissances that would revitalize his fanbase and introduce his music to succeeding generations.

The perhaps unintended irony of “Heroes,” introduced by its depiction of a life long ago derailed, is how dissimilar it has proven to be when compared to Nelson’s real-life adventures. The Nelson we know has become an almost mythic figure in American music — a singer, stylist and storyteller who commands a previously unimaginable stylistic reach while seldom, if ever, straying from the contemplative core of his music. He has dabbled in reggae, sung the blues, swung with jazz and collaborated with artists representing multiple genres outside of country. And yet, his sound is unmistakably his own — light, unhurried and profoundly soulful.

Nelson at Riverbend in Cincinnati

On Sunday at Riverbend Music Center in Cincinnati, Nelson, on the road again — and again and again — at age 90, headlines the Outlaw Music Festival. The day-long summit is named after the renegade country genre he and Jennings cultivated in the mid-1970s, but whose stylistic ripple effect is felt throughout country, rock and Americana music to this day.

The event is also a testament to the level of respect Nelson still quietly commands among his many diverse musical disciples. The rotating team of acts supporting him over the four-month-long trek the festival will travel through October includes Robert Plant and Alison Krauss, Tedeschi Trucks Band, Bob Weir, The Avett Brothers, Nathaniel Rateliff and the Nightsweats, Los Lobos, Marcus King, Molly Tuttle and many others.

This weekend’s Cincinnati bill will boast Creedence Clearwater Revival architect John Fogerty, guitarist Warren Haynes’ juggernaut jam band Gov’t Mule, Canadian songsmith Kathleen Edwards, the trippy progressive folk project Particle Kid (which features Nelson’s son, Micah) and 22-year-old country/soul/funk stylist Myron Elkins.

New releases and touring schedule

That Nelson maintains an artistic career at 90 may seem startling. But the real astonishment comes from the level of activity his career still entails. In terms of recordings alone, the amount of output he delivers puts the work ethics of artists half his age – shoot, one-third his age – to shame.

Last week, for instance, saw the debut vinyl release of one of Nelson’s finest late career albums, 1998’s “Teatro” – a stark, atmospheric set produced by Daniel Lanois with minimal but crucial accompaniment by Emmylou Harris, pianist/sister Bobbie Nelson and vanguard jazz pianist Brad Mehldau. Now if someone would please reissue the 2017 CD version of the record that beefed up the original edition with seven extra songs.

Then in September, Nelson will release his first-ever bluegrass album. Ingeniously titled “Bluegrass,” it resets early career classics like “Bloody Mary Morning,” “Yesterday’s Wine” and “On the Road Again” to the acoustic support of such stellar stringmen as Dan Tyminski, Rob Ickes and Barry Bales, among others.

The two releases represent only a trickle within the flood of Nelson music hitting stores of late. The singer’s ongoing partnership with Sony’s Legacy label has produced nearly 20 releases over the past decade — a mix of new and archival recordings, ranging from vintage concert sets to new tribute projects honoring such disparate artists as George Gershwin and Ray Price. Four of those recordings have won Grammys.

Of particular interest in the herd of Legacy recordings is “Live at Budokan 1984,” a concert document previously available only as a now-prehistoric LaserDisc. Aside from presenting Nelson at what was arguably his performance peak as a live act, the record mirrors the stylistic breadth of the shows he presented locally at Rupp Arena on a near-annual basis four decades ago — shows that effortlessly leapfrogged between Kris Kristofferson tunes, American Songbook classics from the multi-platinum selling 1978 album “Stardust” to country outlaw hits from the ’70s (“Blue Eyes Cryin’ in the Rain”) and crossover pop covers from the ’80s (“Always on My Mind.”)

Forgotten pairing with Sinead O’Connor

That level of easygoing but completely credible genre-hopping explains much of Nelson’s unending appeal not only to audiences, but to other artists. At Hollywood Bowl performances last spring honoring Nelson’s latest milestone birthday, the bursting roster of cross-generational guest artists included Dave Matthews, Sheryl Crow, Norah Jones, The Lumineers, Beck, Lyle Lovett and Kentuckian Dwight Yoakam.

Perhaps the celebration’s most curiously ironic moment came near its conclusion when Nelson was joined by another artist seemingly impervious to retirement – Rolling Stone Keith Richards. In what has to be one of the grandest kiss-offs of all time to career mortality, the two performed “Live Forever,” a cornerstone work of the late Texas song stylist Billy Joe Shaver. Fittingly, Nelson had won his 12th and most recent Grammy in February for a recorded version of the song featured on the 2002 Shaver tribute album of the same name.

Nelson’s follower/collaborators have come from our neighborhood, as well. He last performed locally in April 2022 for Lexington native Chris Stapleton’s “A Concert for Kentucky” benefit at Kroger Field. Stapleton had already cemented his fondness for Nelson’s music by recording Gary Nunn’s “Last Thing I Needed First Thing This Morning” for his 2017 “From a Room: Volume 1” album. Wilson popularized the tune on his hit 1991 chart-topper “Always On My Mind.”

But one of Nelson’s most fascinating and artistically revealing collaborations sat dormant for decades – until this summer.

In October 1992, Nelson was part of an all-star concert honoring Bob Dylan when he witnessed another contributing performer getting booed off the stage after deviating from the planned repertoire to voice protest against child abuse and social/racial injustice. Nelson invited the artist to a recording session days later to cut a version of the Peter Gabriel composition “Don’t Give Up.”

The artist in question was Sinead O’Connor, who died July 26 at the age of 56.

Gabriel had written the song from the perspective of a worker devastated by unemployment in Margaret Thatcher-era England with a duet voice, supplied on the original 1986 version by Kate Bush, offering consolation and hope. Nelson brought the tune to America and, in an accompanying video featuring O’Connor, fashioned it to represent the despair of a laid off coal miner.

It’s unfortunate that it took O’Connor’s passing for many of us to refocus on what stands as one of Nelson’s great forgotten triumphs – a performance that cared nothing about which genre it represented or the political profile of the artist he chose to sing with. The song stands, as so much of the music Nelson has made for over six decades, as the work of an American original – unassuming, uncompromising and undeniably soulful.

The Outlaw Music Festival

Featuring: Willie Nelson, John Fogerty, Gov’t Mule, Kathleen Edwards, Particle Kidd and Myron Elkins

When: 3:20 p.m. on Aug. 13, gates open at 2:30 p.m.

Where: Riverbend Music Center in Cincinnati

Tickets: $24.50-$224.75 through ticketmaster.com.