Alan Jackson more or less opened his August 31 show at the Minnesota State Fair Grandstand with “Gone Country.”

Less, actually. The 56-year-old country star ran through the chorus of his 1994 hit a handful of times as he waved to fans, but he skipped songwriter Bob McDill’s verses, which side-eye a trio of opportunists (a Long Island-born singer struggling in Vegas, a lefty West Village folkie, and a bill-strapped “serious composer” in L.A.) lured to Nashville by country music’s sudden cultural relevance and commercial appeal. Imagine Bruce Springsteen bounding onstage, belting out the one-line refrain of “Born in the U.S.A.” a dozen times, but ignoring the ironies that drive all the other words in the song.

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The anti-carpetbagger resentment those verses voice is timeless, placeless—today they’d resonate just as strongly in Seattle or San Francisco or Brooklyn or any newly trendy city coping with an influx of careerists cashing in on its cachet. But that ambivalently victorious chorus of “Everybody’s gone country” also captures the blur of anxiety and excitement that surfaces during each of the genre’s periodic booms. As the truest and bluest and honest-est music in the world, country should of course also be the biggest, yet its fragile essence must always be protected from rank strangers. (Or so a certain kind of fan believes.)

In 1994, no one could deliver “Gone Country” more effectively than Alan Jackson. An outlaw wannabe like Travis Tritt—who’d slammed Miley Cyrus’s hunky pa Billy Ray for reducing country music to an “ass-wiggling contest” a couple years earlier—would’ve sneered at those carpetbaggers. A superstar like Garth Brooks couldn’t have stopped himself from blowing up the chorus into the shrill boo-ya of an ungracious winner. Modest and chipper, Jackson softened both the lyric’s ironies and its triumphalism, suggesting that country music rested on a sturdy enough foundation to take in these shady strays and grow from the experience.

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Which is to say that Jackson could pull this song off ’cause he was kind of boring. The inveterate niceness that helped him succeed also kept him from developing a real persona. Jackson was a white hat and a blonde mustache and a fringe jacket and a pleasant voice. He could hardly approach either the moonshine-blinded abandon or the profound hillbilly operatics of his idol, George Jones. He instead followed the narrow trail of George Strait — not the brilliant neo-traditionalist pioneer of the ’80s who knew how to find and fondle a deft lyric, but the increasingly complacent icon of the ’90s who celebrated the consistent reassurance of familiarity.

A new three-disc retrospective of Jackson’s career, Genuine: The Alan Jackson Story (a Walmart exclusive, btw), reminds us that he had his moments in the ’90s—the swinging beat and mild wordplay of “Don’t Rock the Jukebox,” a lively resuscitation of Tom T. Hall’s homey “Little Bitty,” the potently restrained regret of “Someday.” But mostly he sounded like he’d make a better neighbor than he did a star. Not that my highly kickable ass would’ve advanced that opinion to the gal in the Harley crop-top who leapt up on her green plastic chair at the Minnesota State Fair and screamed, “A lot about livin’ and a little ’bout love!” so forcefully during “Chattahoochee” that she nearly toppled into the row in front of her. Jackson’s fans had the best reason of all to like him: He was likable. But only once the second decade of his career began—as documented on disc three of Genuine—did he learn to make likability into an art.

Following the collapse of the Twin Towers, a 9/11 mega-anthem loomed even more inevitably than the bombing of Kandahar. With the efforts of super-famous rockers either premature (Paul McCartney’s “Freedom”) or belated (Springsteen’s “The Rising”), the vacuum soon filled with vague patriotism (Aaron Tippin’s “Where the Stars and Stripes and the Eagle Fly,” Daniel Rodriguez’s “God Bless America”) and even vaguer vagueness (the All-Star Tribute’s “What’s Going On,” capped by a piss-pantsed Fred Durst’s heartfelt message that it’s mean to scare celebrities).

With a warm vocal far more understated than its title, Jackson’s “Where Were You (When the World Stopped Turning)” captured the closest thing to a universal experience that Americans shared on September 11, 2001: We were all uncertain how to react and often surprised by how we did. The song’s Corinthians paraphrase (“Faith, hope and love are some good things He gave us / And the greatest is love”) was a timely appeal to the better angels of our nature; the chorus’s acknowledged inability to distinguish between Iraq and Iran was both candid and humble.

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Suddenly, Jackson’s unflagging ordinariness became his greatest strength. Being polite to your admirers at Country Fan Fest is one thing; advocating mass decency in the face of national disaster and burgeoning fury constituted a genuine public service. Jackson’s hit noted but ultimately turned away from the rage that would later fuel Toby Keith’s “Courtesy of the Red, White and Blue (The Angry American),” with its distressingly accurate presumptions about our national character. At a time when those trumpeting American superiority made the greatest case against themselves, Jackson quietly made our culture seem worth defending.

But the turning point in Jackson’s career wasn’t actually 9/11, though that event made his evolution apparent. It was his father’s death in 2000, which inspired “Drive (For Daddy Gene).” Like most exercises in nostalgia, the song traffics in the sort of memories we like to imagine ourselves having, whether we really have them or not. But Jackson etches his reminiscences of learning to drive in vivid specifics—a secondhand ’75 Johnson with an electric choke and rotten transom, afternoons dumping trash alongside Thigpen Road out of the ’64 Ford flatbed—rather than hinting at some hazy past of a simpler life.

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“Drive” looks to the past and the future simultaneously. In the closing verse, Jackson doesn’t just teach his daughters how to handle a Jeep—he imagines them fondly remembering the experience one day. The song underlines the truth that memories connect us to our elders, and remind us how it feels to have been cared for, so that we can connect as elders ourselves, and care for others.

In St. Paul that August night, I shared a row with a dad and his teen daughter. Beneath the bill of his creased, frumpy ballcap gazed the weary yet alert eyes of a man with strong opinions about proper lawn care; she was an adorable Julie Taylor lookalike in a white dress and jean jacket. They sang along together to “Drive,” and fuck yeah, I cried.

Jackson’s subsequent singles were just as warm and wise. “Work in Progress” traipsed with self-deprecation through clichés about masculinity while begging his wife to be patient; “That’d Be Alright” had kind words for a dangerously un-American future where “everybody everywhere had a lighter load to bear / And a little bigger piece of the pie.” For a minute there, Alan Jackson seemed dang near infallible. Jimmy Buffett helped remind us otherwise.

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We can just be grateful that Jackson duetted with the Parrothead-in-Chief before Kenny Chesney did, and not get too upset that “It’s Five O’Clock Somewhere”—#actually, that’s only true one out of every 60 minutes—is still the biggest hit of Jackson’s career. After all, “My Ding-A-Ling” is Chuck Berry’s only No. 1 single. Just as Nashville had absorbed the soft-rock of the’70s a decade earlier to accommodate middle-aging Boomers, it now flattered the Graying Beachfront Tourist market by conflating resort day-drinking with hell-raising. And at least Jackson followed it up with his finest moment.

From the instant the introductory guitar lays out the melody for our inspection, “Remember When” has a classic feel, and it moves forward with a calm, unrushed assurance matched by Jackson’s vocal. Just where you expect some crappy song-doctored bridge to disrupt the song’s flow, the song instead floats into gentle key change and a laid-back solo. Even the strings stay out of the way.

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“Remember When” is semi-autobiographical, following high school sweethearts from mutual virginity loss through a rocky pass of implied infidelity to parenthood and highly credible promises of golden years to come. Though I’m no fan of the belief that having children brings a troubled couple closer. I don’t deny that it’s a possibility, or, for serious-minded adults, even an opportunity.

Real life is more complicated. Jackson and his wife Denise separated briefly because of his cheating after the birth of their third daughter. As a man and as an artist, Jackson was far from infallible. With “Remember When,” he made something lasting and gorgeous from that fallibility, and as with “Drive (For Daddy Gene),” he celebrated the passage of time as something that give us more than it takes.

Jackson’s most recent album of new material, Angels and Alcohol, debuted in July at No. 2 on the country charts, and has sold around 100,000 copies—a respectable number in 2015. But its uptempo single, “Jim and Jack and Hank” (guess the surnames), stiffed, and the only new song Jackson played at the St. Paul show was the generic honky-tonk number “You Never Know.” His current tour doesn’t even explicitly promote the new release, but instead celebrates his 25-year career—and you know what that sort of marketing says about an artist’s future commercial prospects.

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So it’s not that surprising that Jackson would truncate “Gone Country” today. The old anxieties about how country music has Gone Pop may be more acute than ever, with Taylor Swift’s world domination exceeding Garth’s most megalomaniacal dreams and Florida-Georgia Line making “Achy Breaky Heart” sound like “Take Me Back to Tulsa.” But Jackson is no longer the man to make sense out of this clash of cultures.

Somebody will, though—or at least that’s what Jackson’s music suggests. Just this month, the Nashville establishment itself proffered Chris Stapleton as the genre’s new voice of both tradition and reason. Country music is often saddled with a decline-and-fall narrative, epitomized by the 1985 George Jones song “Who’s Gonna Fill Their Shoes?”: As the myth goes, country will die along with the monumentally talented men (think Merle and Willie and Johnny and Conway) who constructed it. But that never really happens. Modest talents like Alan Jackson will always step up and get the job done, and even if tomorrow’s job might be a little different than yesterday’s, you can still use the skills you learned from the folks who did the work before you. Again and again on Genuine, you can hear Jackson sing about where you find yourself when the world doesn’t stop turning, and how you can keep from losing your footing, even when you’re perched on a county-fair folding chair singing along to a song that makes you wish that the world would never change at all.


The Concourse is Deadspin’s home for culture/food/whatever coverage.Follow us on Twitter.

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Photo by Getty.

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Keith Harris is an immigration attorney who writes about music (mostly) and lives in Minneapolis. Sometimes he tweets @useful_noise.