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Earle is touring in support of his latest album, 'So You Wanna Be an Outlaw,' which he sees as a stylistic return to where he started as a brash, young neo-outlaw in the shadow of mentors such as Waylon Jennings, Townes Van Zandt, and Wille Nelson, who duets with Earle on the album's catchy title track.

CONTRIBUTED: WARNER BROS. RECORDS - Steve Earle eschewed the mainstream country music stardom he achieved in the mid-1980s for a prolific and respected career as an Americana-oriented singer/songwriter with a broad fan base. He'll visit Portland's Revolution Hall on Monday night, Aug. 14. In most aspects of his life and career, Steve Earle comes across as the maverick's maverick — a musician for whom taking risks and flying by the seat of his pants seem as second-nature as strumming a G chord.

When it comes to presenting his songs in concert, however, the Texas-bred singer/songwriter/guitarist likes to find songs that work together in a certain order — and stick to 'em.

"I have a soft spot for the crew guys, and they go crazy when you change things a lot," he explains in a phone interview from Boulder, Colo. "My encores change, but the main set is pretty static … Look, it's a form of theater. You want to create a direct connection with the audience. When you find jokes that work, you tell 'em again. You find stories that work, you tell 'em again.

While he appreciates the spontaneity of fellow musical veterans like Bruce Springsteen and the Grateful Dead whose setlists can turn on a dime, Earle, 62, admits it takes an ensemble more well-seasoned than his current version of the Dukes to pull tunes from deep within his repertoire.

"I've had a few more personnel changes," he says. "We're in a learning curve. It's kinda like rebuilding a baseball team."

Earle will bring the team and his ever-growing songbook to Portland for a performance at Revolution Hall on Monday, Aug. 14, at 8 p.m. The Mastersons will open the show, which is now sold out.

Earle is touring in support of his latest album, "So You Wanna Be an Outlaw," which he sees as a stylistic return to where he started as a brash, young neo-outlaw in the shadow of mentors such as Waylon Jennings, Townes Van Zandt, and Wille Nelson, who duets with Earle on the album's catchy title track.

"It's basically reconnecting to the moment, back when I thought I'd get a record deal in 1975 when I was 20," he says. "That window closed. I had to kinda come in the back door."

It took Earle another 10 years of scuffling and hustling before he landed a major-label Nashville record deal.

"I did the DIY, punk rock deal," he says of the period that saw him running with bands like Jason and the Scorchers. "I carried the lacquers for their first album to the plating plant."

In 1986, the 31-year-old immediately hit pay dirt with "Guitar Town," a No. 1 country album and its upbeat, top 10 title track. Marketed as a "neo-traditionalist" with a more literal — and rockier — edge than peers such as Dwight Yoakam and Randy Travis, Earle quickly shed Nashville hitmaker trappings for the darker territory of "Copperhead Road." That 1987 album started Earle on the genre-bending, though Americana-oriented path he remains on today. He admits seeing some rays of hope in today's pop-ified version of country.

"I think the girls are doing a better job of it than the guys in the songwriting department, aside from (people like) Chris Stapleton," he says. "I love Miranda Lambert's last record."

Though in Nashville often, Earle, whose singing and songwriting son Justin Townes now calls Portland home, maintains New York City as his primary place of residence.

"I've been there 12 years. Yeah, it's the center of the universe. I need the juice," he says. "Also there's major-league baseball and theater. I like to see a lot."

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