“I’m an unapologetic lefty, but I don’t think we’re perfect,” Earle says. “And I think that we’ve obviously forgotten how to communicate with working people, or we wouldn’t be in the position that we’re in right now.” Credit: Danny Clinch

Two weeks before embarking on his 50 Years of Songs and Stories tour, Steve Earle was performing onstage at Nashville’s famed Grand Ole Opry.

After finishing a song, country star Vince Gill unexpectedly walked out onstage and presented Earle with a Grand Ole Opry 100th-anniversary guitar strap, which Earle gratefully accepted.

It was a nice surprise, to be sure, but nothing compared to what was about to come next.

Gill began to walk offstage, while Earle put the strap to his guitar and stepped up to the mic. It was at that moment that Gill stopped in mid-stride, turned to Earle, and told him that the commemorative strap was made to be worn only by Hall of Fame inductees — and Earle had now joined their ranks.

“It was one of the biggest moments of my life,” said Earle, who fought back tears as he accepted the invitation.

It had been a long time coming.

“They would not let me near their place for years,” recalled the veteran singer-songwriter, who along with his contemporaries like Dwight Yoakam, Maria McKee and Dave Alvin, played a pivotal role in taking country music in new directions — in Earle’s case, a rocking sound that didn’t sit well with the mainstream country establishment.

“The people I’m closest to that are members of the Opry are Vince, Marty Stuart and Emmylou Harris,” said Earle, who’d joined Gill in an Opry tribute to Duane Eddy two weeks earlier. “The three of us have known each other for years. In fact, the first time I got on the Opry, I came as Emmylou’s guest.”

Fresh off that honor, Earle will perform at San Antonio’s Charline McCombs Empire Theatre on Sunday, July 13. As with the rest of the shows on his 50 Years of Songs and Stories tour, he’ll be performing a solo acoustic set.

Even though the tour is a solo showcase, recent years have found Earle in full collaborative spirit.

Willie Nelson, Johnny Bush, and Miranda Lambert are all featured on his So You Wannabe an Outlaw album. He joined forces with Jason Isbell, The War and Treaty, Rosanne Cash and the Nitty Gritty Dirt Band for a remake of Bob Dylan’s “The Times They Are A-Changin’.”

And this past April, The Waterboys recruited Earle to sing the lead vocal on “Kansas,” the first single from the group’s latest album, Life, Death and Dennis Hopper.

“There are only a few bands that I ever wanted to be in,” Earle said with fanboy enthusiasm. “Like I wanted to be in the Beatles, in NRBQ, in the Rolling Stones maybe, and the Waterboys. So I’m kind of a Waterboy for a minute, and I’m pretty proud of that.”

Earle, who grew up in San Antonio, had been living in Nashville for more than a decade before releasing his 1986 debut album Guitar Town and its 1987 followup Exit O.

“I was just trying to make credible country records,” Earle said of the two albums, which earned considerable praise from critics.

But not everyone at his label shared that enthusiasm.

“And then, of course, Copperhead Road sealed the deal,” Earle said of his 1988 rock-leaning breakthrough album and title song, which crossed over in a big way. “It was never played on country radio back then, but it is now. It’s also played in country nightclubs for people to dance to. But back then, things were different.”

In the years since, numerous genre labels have been affixed to Earle’s music. It’s been called outlaw country and alt-country, new traditional and heartland rock, protest music and Americana.

And that’s not all. Earle’s three Grammys are all in the Contemporary Folk categories. He’s also earned seven nominations for Best Solo Rock Performance, Best American Roots Song, Best Bluegrass Album and the list goes on.

All of which gives Earle a lot to work with on his current tour, as he draws upon a career-spanning selection of songs and the stories behind them.

A number of those songs can be found on his 2024 album Alone Again (Live). It’s a testament to his talents as a songwriter and performer that such a wide variety of styles can be translated into a solo acoustic format without sacrificing any of their power.

Earle has also written his fair share of political songs. Among them is “Christmas in Washington” with its poignant chorus: “Come back, Woody Guthrie / Come back to us now / Tear your eyes from paradise / And rise again somehow.”

He’s also covered “Deportee,” a heart-wrenching ballad that is at least as timely now as it was when Guthrie wrote it back in the 1940s. And earlier this year, he encored with “This Land Is Your Land,” a song whose melody Guthrie borrowed from a Carter Family song, which was a common practice in those days.

“As far as I know, Woody never wrote a single melody in his career,’’ Earle said. “He borrowed all of his melodies. But at the time, that was what folk singers did. Bob Dylan didn’t have original melodies until he started writing songs like ‘Mr. Tambourine Man.’ Even the song that changed everything, ‘A Hard Rain Is Gonna Fall,’ that melody is from an old English folk song.”

Like those artists, Earle has never shied away from social commentary, whether it’s in his songs, interviews or onstage. He’s played numerous benefits for the American Civil Liberties Union, while always maintaining a level of respect for people whose views may differ from his own.

“I’m an unapologetic lefty, but I don’t think we’re perfect,” he said. “And I think that we’ve obviously forgotten how to communicate with working people, or we wouldn’t be in the position that we’re in right now.”

That can also be a lesson for songwriters, which is one of the things Earle learned from his friend and mentor Townes Van Zandt.

“With the political songs I write, I learned a long time ago to make characters, and then let characters say it for you,” Earle said. “Because it becomes more about them and less about you if you do that. Pretty important. But, you know, I still write more songs about girls than I do about anything else.”

$48-$182, 7 p.m. Sunday, July 13, Charline McCombs Empire Theatre, 226 N. St. Mary’s St., (210) 226-5700, majesticempire.com.

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This article appears in Jun 26 – Jul 9, 2025.