Luck favors the prepared, as they say, and young Jason Isbell was ready. He had honed his skills as a songwriter and guitar player since he started playing the mandolin back when his hands were too small to wrap around a guitar neck. He would sit alone in his bedroom for days on end, isolated and insulated from his parents' arguing, tearing through the classics. Playing local bars before he was even a teenager, and the Grand Ole Opry by 16, he went off to college but, famously, never completed his degree for want of a single required health studies class. By his early 20s, he returned to his home in the Shoals of Alabama, an obscure corner of the country that produced some of the greatest R&B in the universe, where he found work writing for FAME Studios.

Then, at the age of 22, his moment arrived. A member of the Drive-By Truckers, a band that had returned to its home in the Shoals to play a breakthrough house concert for Spin magazine, failed to show up for the gig. As a result, Isbell got a rapid field promotion onto the stage. He joined the band for the show and then departed on tour with the band for the next six years. Isbell may have been a young adult, but he looked more like a doughy high school sophomore, especially among the more grizzled members of a hard touring band.

The group he joined in 2001, the raucous, punk infused, careening-toward-the-ditch band, the Truckers, had just released its epic masterpiece, Southern Rock Opera, a whirlwind of Southern rock, punk and gothic hell — literally. In one song, the devil sports a George Wallace sticker on the bumper of his Cadillac. Spin, reviewing Isbell's first show with the Truckers, called them "alt country's rockingest neo-rednecks" who delivered "poetry among the wreckage."

So began the wild years of Isbell's young adulthood, a fiery, creative period that delivered him to two ends. One, he quickly revealed his genius for empathetic portraiture, painting alienated, lost souls and revealing entire worlds in precise drops of telling detail. Two, he lost sight of himself in a haze of booze.

Not long after Isbell joined the Truckers, he penned three incredible songs in rapid succession. "Decoration Day," a dark, rocking examination of intergenerational violence based on his own family's lore, proved to be so good that the band named their next album after the cut. "Outfit" still stands as an Isbell crowd favorite, encapsulating, in his father's voice, warnings about succumbing neither to the dire fate of working-class entrapment ("don't let me catch you in Kendale with a bucket of wealthy man's paint") nor the perils of a musician's life on the road ("don't tell 'em you're bigger than Jesus, don't give it away.") Then there was "TVA," a meditation on three generations and the meanings of the New Deal, the Wilson Dam and the time when "Roosevelt let us all work for an honest day's pay."

Just a few years after joining the tour, Isbell confessed his identification with the weary and dying musicians of The Band in "Danko/Manuel." Its slow-running bass pacing out the brutality of road life, he sings, "Got to sinkin' in the place where I once stood / Now I ain't livin' like I should." Then came the aching "Goddamn Lonely Love," a tight study in killing sentiment with alcohol. "I'll take two of what you're having / And I'll take all of what you got / To kill this ... goddamn lonely love." Under the sway of his own addiction, he began to lose touch and say stupid things on stage. The other Truckers asked him to leave. "Some people get drunk and become kind of sweet," Patterson Hood, one of the leaders of the Truckers, told The New York Times Magazine a decade ago. "Jason wasn't one of those people."

Walking across East Nashville earlier this month to meet Isbell, I am thinking about how the dreams of more than one singer-songwriter ended in this part of town. Isbell released a few post-Truckers albums that showed glimmers of promise but lacked voice and focus. That might have been it for him. But his friends and his future wife, Amanda Shires, helped him into rehab, which he paid for by taking out a bank loan. As I approach our meeting, it is the young Jason Isbell that drifts through my mind. The one before the drinking took over, before the rehab, and before he took control of himself and released some of the best records of his generation.

When I reach his manager's bright and breezy home, I find Isbell is in the front room, Sharpie in hand, signing vinyl copies of his fantastic new album, Weathervanes. He chats up the staff as he moves down the makeshift assembly line, scrawling what might generously be regarded as his signature in the upper left corner of each record sleeve. Spirited, smart and kind, Isbell does authenticity unnervingly well. I'm already feeling the presence of a musician who'd rather lay it on the line now than dance around to keep up with his own web of B.S. later.

Sincerity, his trademark, serves him well, but sometimes his persona feels a bit more learned than natural. In person, his mannerisms remind me of his 2015 cut "24 Frames," in which he self-consciously trains himself in the day-to day requirements of being a good person: "And this is how you make yourself worthy of the love that she gave to you back when you didn't own a beautiful thing." So many of his songs are about an outsider peering in, searching for an opening into how the world works, and wondering about his place in it all. Along the way, he has extended an open invitation to his fans to share the journey.

This is a time of anniversaries. Last year he marked his 10th year of sobriety with the addition of another hashmark tattoo, inscribing on his body a commitment to himself and his family, now tallied in two tidy sets of five. It's on the inside of his forearm, just where he'd see it if he reached for a drink.

Ten years ago this month, Isbell released Southeastern, a payoff for that sobriety and the crystallization of his immense talent. The cover image alone — a crisp, tightly focused, black-and-white portrait of a man who had spent too much time appearing blurry, bloated and stumbling for another pull on a bottle of Jack — promised something new and fresh. Here was a person no longer lost in the quagmire of the Southern gothic or the grip of addiction. He looked more like a pin-striped professional bluesman with a fresh haircut staring straight into the camera with some truth to tell.

Isbell's voice, once a bit reedy under the strain of youth and booze, became resonant and rich, freeing his solid gold north Alabama accent and its inescapable trace of ache and tenderness. Southeastern opens with a deeply personal and sharply honed meditation on recovery, surrender and living with the pain that one has caused another. "Cover me up, and know you're enough, to use me for good," he sings, in a bid to trade the dominion of addiction for the shelter of love. Vulnerable, direct, hopeful and cataclysmic, the song is so intimate that it can still deliver his wife back to the raw pain of that moment. To this day, when he sings the lines, "I sobered up, I swore off that stuff, forever this time," he gets a supportive round of applause from his loyal audience. The pace, clarity and vulnerability of the entire album remains riveting, and, a decade later, the opening chords of Southeastern still pull the listener in for what seems a fresh fight for the soul of a man.

Amanda Shires married Isbell just days after the completion of Southeastern. Instrumental in his sobriety, she took a gamble on a man with a "heart like a rebuilt part," as he says in one of the album's best cuts, "Traveling Alone." Shires, an immensely talented violinist from Lubbock, Texas, has a successful solo career and plays with the supergroup The Highwomen. She also plays with Isbell's band, the 400 Unit, a group that rivals Springsteen's old E Street Band for the virtuosity of its individual members, its connection to place and its cohesion. Together, Amanda and Jason have become the heart of hope and authenticity in the Nashville scene. Today Isbell is riding high with a new album, a collection of Grammys and Americana Music Awards, a revealing new HBO documentary, a custom signature series Isbell Telecaster, a role in a forthcoming Scorsese film and a relentless national tour schedule.

I talk through this history with Isbell, and ask, "What holds this story together? What's the Jason Isbell arc?"

"If there's a theme to all of it," he says, "it's like you settle on this meaning of life, and it's arbitrary. Pick one and stick with it, because it's as valuable as any of them. For me, it is the work of understanding yourself and improving yourself. If I did that today, it was a good day. And if I didn't, I'll try again tomorrow." He believes, above all, in work. "It's work, just do the work, and the rewards will come." My mind jumps to Camus' The Myth of Sisyphus. "Each atom of that stone, each mineral flake of that night-filled mountain, in itself, forms a world," Camus writes. "The struggle itself toward the heights is enough to fill a man's heart."

Yet Isbell's existentialism is more than rolling stones uphill. His project, he says, is "trying to connect with other people. Trying to connect with the time that I was in. Trying to connect with myself has been a theme since the beginning."

Connecting with the present is more difficult than it might seem. His work — artistic, emotional, social and now ever more political — contains a unique deployment of history, one in which time is as likely to fold back upon itself as go forward, and all things are, indeed, interconnected. The burdened cycles of "Children of Children," the feisty older woman who just wants to ride in "Hudson Commodore" or life after the closing of the mines in "Cumberland Gap," show people struggling with historical circumstance. Even the cosmic love song "If We Were Vampires" transcends genre by pegging love to the foreshadowing of loss, the finality of human time. On the new album, the haunting "White Beretta" has a man talking to both his younger self and his memory of the woman he failed to help enough when she needed an abortion. It is the biggest gut punch on the album.

Throughout Weathervanes, new narratives twist back upon old, blending perspectives, voices and Isbell's own past and present. It juxtaposes deep concern for the next generation, his daughter's generation, with what he calls the "the old assignments," songs that contain more than a whiff of the old Truckers-era themes. There's the opioid addiction of the Dylanesque, John Prine-influenced blue collar character in "King of Oklahoma"; the thumping rocker with a rising chorus about survivor guilt after the death of a friend, "When We Were Close"; and the irresistible hook of "Cast Iron Skillet," which vivisects a series of Southern aphorisms and the received wisdom that might not be much in the way of wisdom at all. Throughout, he asks what remains real and current about voices from the past, and when do the old patterns keep us from seeing love and other truths that should be "simple as a weathervane."

"I always felt like I was not living in the current day," he explains, but "in a different time altogether." His personal space-time continuum is a kaleidoscope of anachronisms. Isbell's is not a linear kind of history. It is more like wandering through a museum in which the rooms have been rearranged, the ages shuffled. His upbringing in Green Hill, Ala., near the renowned studios of Muscle Shoals, may have been in the '80s, he explains, but it felt more like the mid-'60s. His grandparents, who played an important role in raising him, were Holiness Church of God Pentecostals; that meant a pre-industrial life with long dresses, no makeup and no medicines. His grandmother still cooked on a wood stove, and animals were raised, slaughtered and eaten.

In jarring juxtaposition with his grandparents' asceticism, Isbell loved the movies, and soaked up popular music like Prince, Crowded House, Squeeze and 'Til Tuesday. Further complicating the picture, his parents were pretty much kids themselves, 17 and 19 years old, when he was born, and there were five generations of family members surviving on his mother's side. All that, and he'd been a Robert Johnson fan since he was 9 years old. Eventually he discovered the likes of Otis Redding and Aretha Franklin recorded right down the road from him in the legendary local studios. "That blew my mind," he explained. "It was what helped me not be racist."

History and Jason Isbell did get on the same page until the 1990s, when he and grunge were happening at the same time. Finally, he felt, "what I liked was current." That page was the return of innovative rock guitar, which he loved, but even then he remained a bit of a time traveler. He was so much younger than the rest of the Truckers that Patterson Hood, one of the group's leaders, had attended high school with Isbell's mother. While young Patterson fled Alabama for the punk scene in Athens, young Jason got hired to write for FAME studios and ended up working with Patterson's father, legendary studio bassist David Hood. He then brought history full circle, delivering some of the musical precision of Muscle Shoals into the Truckers' shaggy sound. "Musically," Isbell reflects, "I was more like Patterson's father's generation, and more like the musicianship of Dave Hood."

How Jason Isbell became a guitar player is a more than twice-told tale, but I want to know how he learned to write, with the narrative economy of the best short story authors and with some of the most tightly conceived lines in the business. He cites early exposure to a panoply of literary and lyrical influences, some random, some contemporary, some distinctly anachronistic. His mother loved John Prine and John Hiatt, he says, and his dad liked Merle Haggard and Willie Nelson. There was also plenty of "bonehead" arena rock around the house — a genre he still loves for its clear statements of the obvious. His obsessive personality, which he notes would later become addictive, had him tearing through books at a "freakishly early" age. He devoured all the Tolkien and Madeleine L'Engle type books, and then began to sneak his mother's Stephen King and Dean Koontz novels.

The Bible stands above all else in training Isbell in the craft of story. Every night he had to read and understand a passage, in a self-inflicted assignment. Otherwise, he knew he was going to hell. If he could not prove his ability to read, and comprehend, a King James Bible passage, he felt the real danger "of burning forever with a pitchfork in my ass." From such pressure, he believes, came comprehension, metaphor, allegory and all the rest of the concepts of traditional western storytelling. Nightly cramming to avoid a lifetime in hell may "not the most psychologically healthy thing," he reflects, but "you can very easily trace an unintended formalist reading of each of these songs" to the Bible.

Despite being raised in such fire and brimstone, Isbell feels blessed to have been surrounded by men who listened and who nurtured, and who were often in relationships with strong women. When we spoke, Isbell was a week back from his grandfather's funeral. He had "a sensitivity to him that was palpable and contagious," he notes. "I was lucky enough to have examples of a nontoxic form of masculinity from early on."

"I used to want to be a real man / I don't know what that even means," Isbell sings in the 2017 song "Hope the High Road," written after the election of Donald Trump. That song put a blunt point on the artist's often more nuanced explorations of masculinity. If you think you were born to be "some sort of man," he tells me, then you need to "figure out a way to do it that contributes to society rather than scaring the s*** out of everybody." The toxic stuff going on today is "putting all of us at risk."

In a cut off the new album, "Middle of the Morning," Isbell documents his incomplete strides in his own sense of masculinity. "Yes I've tried," he howls, "to be grateful for my devils, and call them by their names / But I'm tired / And by the middle of the morning, I need someone to blame." Seemingly caged by the pandemic, there is danger in the air. "I know you're scared of me, I can see it in your face." But his character is at least trying, and he notes without defensiveness one reason why the effort hurts: "I ain't used to this ... I was raised to be a strong and silent Southern man."

The debate on both the right and left about the problems with men, especially in areas of economic decline, ring hollow to Isbell. "What's masculine about earning a living and feeding your family? Nothing. That's not feminine, that's not masculine. That's: If you see something that needs doing, you do it." Today, manhood is lost in a peculiar kind of consumerism, he argues. "That was a capitalist trick, too, to sell products, to sell tools, and trucks, and guns." He is particularly bewildered by the trap of guns. He thinks of his family back in Alabama. "They spent so much f****** money — you know how many members of my family are broke with a gun safe full of guns they could sell and pay their mortgage for months?" In "Save the World," an eerie Weathervane track about a school shooting, clearly suggestive of Uvalde, Isbell sings, "something's drowning out the light." In his fear and fatigue, his character fights his own desire to shrink his world to keep it safe.

As moving as Isbell's portraits of troubled masculinity are, I wonder if his characters, in their turmoil, might drift toward the easy answers of the right. When the radical right enters the conversation, Isbell slumps, takes a hit from his vape pen, and explains quickly and clearly that he sees two audiences for his work. The first is those fans and critics who appreciate not only his music but the glimpses he offers into worlds they might not otherwise know, let alone be able to feel. His songs deny any kind of facile liberalism. The lives of Isbell's compelling characters are messy, real and leave little room for pat answers.

His second audience is white, blue-collar Americans whose lives resemble those of his characters. With them, his project is to "separate what they believe from what they actually see happening." In his stories, floating, as he says, between fiction and nonfiction, he tries to get very specific. "I see that you are suffering in this way," he wants to communicate; "I see that you're alienated in this way; what, pray tell, could be one of the reasons for that?" Simply by acknowledging their lives and asking, "how is that working out for you?" he feels he can get them to pull back and consider the futility of tribalist rage. "The argument" (how many popular musicians speak in arguments?) is: "Can you at least, for a minute, consider that you might not be right about these things?"

I accept the rough dichotomy in his audience and take note that he offers no simple answers to either. But I proffer a rejoinder. Isn't he doing much better on one side of this equation than the other? "Well," he chides, "the choir needs to be doing a better job, too."

Isbell's search for place and connection and his rejection of rigid categories includes his choice of genre. "I think of myself as a guy with a rock band," he declares. For this Shoals artist, rock is about cultural mixing, and too much of country is about exclusion. Despite all the Nashville trappings, the varieties of Southern-ness and the relentlessly applied label "Americana" (almost exclusively applied to white acts), he chooses rock and roll. Rock has fewer of what he calls the "scary historical connotations" of country, and it maintains the most latitude and the fewest restrictions on style. Rock, he says, allows you to "sound like almost anything you want." Rock is expansive and, at its core, it contains the idea, however grossly incomplete, of an integrated American vision.

Isbell has long stated that some music can be poisonous to the soul, and he includes mainstream commercial country in that category. He derides it as little more than a jukebox of mass-produced whiteness. "It's like they have taken this parody of Southern-ness and made that the standard and run with it. And the songs are so formulaic, and predictable, and pandering, and it's just awful." As he sings in the rock-driven "White Man's World," from 2017, "Mama wants to change that Nashville sound, but they're never gonna let her." In 2020, when the Country Music Association failed to recognize the passing of the heroes of their wing of the genre, John Prine, Billy Joe Shaver and Jerry Jeff Walker, Isbell and Shires turned in their lifelong membership cards.

When it comes to the vacuity of mainstream country, one might be tempted to say the fans are driving the market and getting what they demand, but Isbell is quick to finger the industry. "I think it's intentional," he remarks. "I think it's capitalism." To make capitalism even remotely humane, "you have to stop doing the wrong thing for five seconds," he says, and figure out alternatives that have more integrity. He hates the use of the term "recording artist" since so "many are not artists." When it comes to making hits, "they're going by their research their lackeys have done, finding out what sounds and what words will sell the most records. And that's not art. Art is making something because you think it has to exist."

He is not naïve, though, about the ways the system has rewarded his work. Far from his shifts sleeping in the back of the slovenly painter's van owned by the Truckers, he now enjoys three tour buses and a semi-truck and trailer hauling the gear of the 400 Unit. And of course his own economic success lets him indulge an almost talismanic drive to collect and play storied, vintage gear. "I wouldn't have a 1959 Les Paul if it weren't for good ol' capitalism," he notes of a rather extreme recent indulgence. But artists need to find ways of making capitalism work for them, he explains, not just end up as a servant to crass commercial interest. "I feel like there's a way to do it that is not unfair, that's not being dishonest with people ... that has more longevity."

In 2019, the establishment country star Morgan Wallen, a guy who was on his way to shattering chart records while singlehandedly trying to make the mullet cool again, recorded Isbell's trademark song, "Cover Me Up." Wallen's fans greeted his slick version, along with an extended narrative video, with tremendous acclaim. It has become a Morgan Wallen song to more people than it is an Isbell song, despite Wallen's generous acknowledgement of Isbell in his live introductions. Isbell is fine with that. It's how things work, and Wallen didn't do a bad job with it. But then Wallen got into trouble for using a racial slur and running around unmasked at a frat party during COVID, actions for which he had to apologize publicly.

When Wallen was criticized for his behavior, sales of his album soared, a sort of MAGA revenge on the woke. Contemplating the fact that his song was selling because of a racist backlash, Isbell was suddenly overtaken by what he described as "maniacal laughter." Anyone who follows his Twitter account knows Isbell can be a bit devilish. He sat back and watched sales go up. A couple of weeks after the frenzy peaked, he announced that all of his royalties from the Wallen cover would go to the Nashville NAACP. He had, indeed, figured out how to make the system work.

"It's not Morgan Wallen we should be talking about," Isbell reflects. You know, it's: Why are these people in these positions, with this kind of platform, making this kind of money, selling these kinds of records to everybody? Why? There's so many people in line behind him who might be more gifted, harder working, less likely to pull some crazy bulls*** cuz maybe they just don't have it in 'em. Or maybe they're just Black."

Freedom looms large in Jason Isbell's 10-year arc since recovery and Southeastern but not necessarily in a rock and roll way. "It's like that Kristofferson line, the f****** greatest line ever written in a country song. 'Freedom's just another word for nothing left to lose.' " Contemplating again the profundity of the lyric, he says, "It almost doesn't make sense. Then it hits you again, and you go, 'Goddamn, man, that is exactly right.' " Freedom, and the idea of endless opportunity, is a trap. "What are we doing with it?" he rhetorically asks the American people. "You talk about it so much, you fight for it, you pray for it, and what are you going to do with it? Sit on your ass and drink sodas? That's what you do with your freedoms. Is that it? Is that all? Is that what you were screaming about this whole time?"

That version of American freedom, in many ways, is the opposite of the connection Isbell has been working on. He is in fact, looking for things to cherish, things he might just be invested in enough to be afraid to lose. His new album sticks the arc of connection well. Musically, it highlights the spontaneity of the 400 Unit's play, Isbell's effort to capture the sound of an intimate live show, and offers tribute to his many musical forebears. Slightly older this time around, his characters hold the wisdom of reflecting honestly on the past even when it feels like grief or regret, show concern for the next generation even when the future feels like too much for one person to sustain. And it is; that's why we need to know we need each other, a message both personal and political.

The live shows are where connections are revealed, and that, too, is no accident. Isbell's sense of authenticity places him in a reciprocal relation to his audience. "I told my agent 20 years ago, maybe 15 years ago, that I want to be big enough to play the arenas, but I don't want to do it. I want to play three nights, four nights in the theater," he says. Both the sound and the sense of intimacy ring truer — "People feel like you are a human being" — in the small venues. "Some people don't want to be seen as a human being, but I like it. I like that because people will trust you, they'll root for you, they won't turn their back on you."

Authenticity and connection may be Isbell's brand, but they're also a daring survival strategy. Trapping his public self in such a way that absolute legibility is the only way forward, he leaves little space for dishonesty and no place to hide from himself. Isbell lays himself bare as if leaning on the world to help him keep his commitments to sobriety, to family and to his artistry.

In return, he gives us an updated vision of the artist's role in society, one that seems singularly appropriate in its opposition to our cultural moment of performing "reality." Isbell's honesty, even if shaped by the imperative of survival, brings the demons into the conversation. And that's right where we can keep an eye on them.

Jefferson Cowie received the 2023 Pulitzer Prize in History for his latest book, Freedom's Dominion: A Saga of White Resistance to Federal Power. He teaches at Vanderbilt University where he holds the James G. Stahlman Chair in American history.

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