The late, great Guy Clark didn’t invite just anyone to coffee in his Nashville basement workshop. But if you were lucky enough to get the call, as did disciples like Lyle Lovett, Steve Earle, and Robert Earl Keen, you quickly learned the drill: Clark would ask you to play a song. If he didn’t like it, he’d say, “Play another one. What else you got?”

Jack Ingram, who dropped in on the Monahans native a few times a year, always had to play a second song. That was fine by him; earning a private audience with one of his idols was enough. But two years ago, Ingram played Clark something he’d been working on, a tune called “All Over Again.” Maybe Clark, who battled lymphoma, diabetes, and heart disease in his waning years, related to the line “It’s funny how dying is just living, we all do it one day at a time.” Or maybe he simply admired the universality of a song about fading without regrets, about how so many of us would happily make the same mistakes, live through the same pain, all over again. “When I finished, he just looked at me and said, ‘Good work,’ ” says Ingram. “That’s what Guy said when he dug a song. Those are the words every songwriter I know lives for, would kill for. It was one of those times I was grateful for how hard I’ve been on myself. It was validation.”

Another instance of validation came in May, when Ingram played the song at Clark’s private wake, which took place at the Santa Fe home of his old friend Terry Allen. A guitar was passed around, and Lovett, Earle, Keen, Vince Gill, Joe Ely, Rodney Crowell, Emmylou Harris, and a few others played the tunes they’d written that Clark liked best. Ingram was buoyed by the fact that in a room full of his heroes he could pull out a song that had earned a gold star from their hero. This was especially true because he knew that some people—perhaps turned off by his vapid top-ten country hits “Wherever You Are” and “Barefoot and Crazy”—had never thought he belonged in that august company. “I’m hyperaware that there are people quick to dismiss me as a country frat rocker, mainstream ass shaker, or wannabe Guy Clark,” Ingram says. “I’ve been all three. But nobody can say I didn’t put in my ten thousand hours, that I didn’t do the work. You can’t just pick up the guitar and try to do what I do. At twenty, that’s impossible. And at forty-five, you can’t take it away from me.”

That lightning-fast switch from self-doubt to braggadocio is classic Ingram. During every stage of his career, he’s shown the swagger of a prizefighter, the naked ambition of a tech entrepreneur. But press him on why he slips into big talk so often, and he admits that all the fightin’ words are a tool he uses to psych himself up for battle. “If you think I sound like an egomaniac, I’m good with that,” he says. “Because the worst thing you could ever say is that I could’ve been a contender but was too afraid to say I wanted it. That’s the thing that wakes me up at night. What if I got scared that people might think I’m delusional and I stopped pushing? What if I got embarrassed or got cold feet? I’d have nothing.”

Over the years, the intense pressure Ingram has put on himself has manifested in an equally manic work ethic. For much of his career, he logged upward of two hundred dates a year. In the same week he’ll headline a dance hall, play a big-dollar corporate gig, and then fly out for a weekend filled with festival sets. And despite all the smack talk, he’s built a reputation as one of country music’s most approachable stars; after each show, he’ll stay at the merchandise booth for hours signing autographs and chatting up fans. Radio programmers have a soft spot for him too: they respect how hard he’s worked at cracking their playlists and how in a heartbeat he’ll get on a plane and play their charity events. Ingram has seen his determination pay off in other ways. Willie is a friend and an admirer. Kristofferson too. And in Nashville, he’s built alliances with a new generation of songwriters, like Dierks Bentley, Miranda Lambert, Eric Church, and Kacey Musgraves.

The through line of most of his career has been a sense that there’s a war going on for the soul of country music and that he’s one of its righteous soldiers. Anyone who’s been to a Jack Ingram gig will remember the ritualistic part of his show when he addresses the crowd with a bit of church-revival banter over an instrumental break. His words are precisely crafted to elevate him over whatever flavor of the day is defining country music at the moment. “I’m Jack Ingram and I play country music,” he says. “It’s not that kind of country music. It’s this kind of country music. My name is Jack Ingram. And I play country music.”

Of course, that insistence obscures a queasier reality: for much of his career, Ingram has allowed himself to fall into the trap of playing that kind of country music. In 2005 he signed to Big Machine Records, which is home to Taylor Swift and helmed by Scott Borchetta, widely regarded as Nashville’s most powerful record executive. With Big Machine, Ingram scored a Billboard number one country single, “Wherever You Are,” and won Top New Male Vocalist at the 2008 Academy of Country Music Awards. Mostly, though, the two studio albums he recorded for the label were dominated by slick, shiny swings-for-the-fences written by A-list Nashville songwriters. His growing reluctance to cut those kinds of tunes—and, he says, Borchetta’s indifference to the songs Ingram was writing himself—led him and the label to part ways in 2011. “Borchetta, bless his heart—and I love him for what he did for my career—is unwilling to fail,” Ingram says. “And it’s been tremendously successful for him, and was, for a little while, for me. But great music only happens when the artist is willing to lay it all out there and fall on his face.”

Leaving the major-label system has allowed Ingram to follow his muse wherever it takes him. “I had a record in my head that I couldn’t shake,” he says. “And it’s a record that meant shoving commercial aspirations to the backseat.”

That record is Midnight Motel, his first new set in seven years and his inaugural album for the revered folk label Rounder Records. By design, it’s the most intensely personal record of his career. Ingram wrote or co-wrote nine of its eleven songs, mostly after midnight in his Austin home studio or in motel rooms across the country. To further reflect the midnight vibe, the arrangements are sparse, and every track was recorded live in a candlelit room at Austin’s Arlyn Studios with top-tier session players, including Bob Dylan guitarist Charlie Sexton and longtime Neil Young drummer Chad Cromwell.

And indeed, there’s a nocturnal bleakness enveloping Midnight Motel; almost every song is about weighing the things you did to hurt someone and the things you’ll have to do to win him or her back. Even on a first listen, it’s easy to hear how much of the seven years between records Ingram has spent laboring on these songs, working over each tightly wound line for maximum impact. This sounds like a record made by someone freed of the pressure to create hits and driven to write a set of songs he wouldn’t be embarrassed to play for Guy Clark. Fittingly, one track, “Nothing to Fix,” sounds like a not-so-thinly-veiled summation of his time at Big Machine: “Don’t try to sell what you wouldn’t buy . . . Don’t write a song that you wouldn’t sing. The only thing wrong is everything.”

Ironically, if Midnight Motel represents Ingram’s post-Nashville reset, playing ball in Nashville was itself something of an attempt to distance himself from the cottage business he’d built for himself in Texas. Ingram, who grew up in the Houston-area suburb The Woodlands, didn’t sing professionally or even pick up the guitar till his freshman year at Southern Methodist University, in 1989. After buying a pawnshop acoustic and the tabs for Willie Nelson’s greatest hits on a whim, he began writing his own songs within weeks. Open mics led to regular gigs at college bars in Dallas and Fort Worth, where the audiences were made up of his peers. And before long, he was playing fraternity houses and college pubs across the state. By 1996 he’d sold over 30,000 albums independently and could fill one-thousand-seat rooms throughout Texas. For better or worse, Ingram was the progenitor of what would become the “Texas country scene,” a subgenre fueled mostly by songs about beer and, for the artists, profitable beer sponsorships. Business was good: despite a primarily regional focus, Ingram was soon earning in the mid six figures. But artistically, he found it unfulfilling. “I always suspected that I had an audience that didn’t really like who I was ultimately going to be,” he says. “They were there for the party.

“That’s where it gets a little strange for me,” he continues. “You want to lump me in with everybody playing that scene? I can’t control that. But I was also very aware that it wasn’t cool to tell people why I thought that was offensive. So I just told myself, ‘I don’t know how long it’s going to take, but when I’m done I’ll either have failed to reach my goals or I will reach them—and they won’t care that I got my start playing frat country.’ I figured, if you want to come at me because of the early audiences I played for, I’ll take it till I’m great. And at that point, it’ll be a footnote.”

Still, Ingram’s been around too long to believe that one record is going to change anyone’s perception of him. In fact, he’s already completed a subtly more commercial follow-up to Midnight Motel, which he hopes will deliver songs to country radio with his dignity intact. It’s a few shades louder and more upbeat than Midnight Motel, though Ingram’s not sure how much those distinctions matter anymore. Instead of living song to song or record to record, he says he’s considering a bigger picture. He keeps coming back to a question Clark once asked Rodney Crowell: “Do you wanna be a star or an artist?”

“The punch line is that an artist can be both,” Ingram says, working himself up into his grandstanding mode. “And the path to artistry is one hundred percent authenticity. If I’m going to have a career that lasts the next thirty years, it’s going to be because these records are authentic. Whether they’re hits or not will be collateral. I just have to ask, ‘What’s the best I have to give? What’s my best take on the kind of music I make?’ If I do that, I think I still have every chance in the world to be great.”